Greek Islands Sailing Adventure
15 nights/ 16 days

2017 Small Group Departures
May 26-June 10 $3395 (Single Supplement N/A)
Due in Full by February 25, 2017
Price is per person based on double occupancy. Initial deposit is $500 and is payable by credit card. Once submitting your deposit, you’ll receive an invoice for the remaining balance, plus any trip add-ons and extensions. Payments can be made online with a credit card or by mailing a check. Please be aware that a 3% bank transaction fee will be applied to all balances paid by credit card. 
Solo Travelers: We provide roommate matching, so you never have to pay for a single supplement unless you want your own room. Should there be an odd number of men to women, you may be asked to join a triple occupancy room if you are one of the last to join.
Your deposit is fully refundable or transferable


The Cyclades archipelago is comprised of about 220 islands in the Aegean Sea – the most well-known being Mykonos and Santorini. A yacht adventure is the ideal way to experience what many consider to be the world’s most beautiful islands. We’ll have our own private sailing yacht with an experienced crew. There will be plenty of time for hiking, snorkeling, kayaking and relaxing as we explore ancient archaeological sites and taverna-lined harbors. We’ll enjoy breakfast and lunch on the boat daily. Evening meals are a cultural and gastronomical experience on this adventure. We’ll dine at a different island each night and enjoy a wonderful selection of fresh seafood and local cuisine. Don’t forget to try the ouzo!


  • Sail the beautiful Greek Islands from Athens for 14 days on a private 50 foot sailing yacht with an experienced crew and try your hand at sailing, or just relax on deck
  • Enjoy authentic Greek food and fresh seafood in waterfront tavernas
  • Swim and snorkel in the warm Mediterranean waters off the side of the boat and let the waves rock you to sleep each night
  • Star gaze from the deck of our yacht or the shore lined beaches
  • Explore the whitewashed villages of Santorini, the most popular island in Greece, if not the world

Is this trip right for you?

  • As the majority of this trip takes place on a sailing boat, you’ll need to feel comfortable with moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others. You should come prepared in case of the effects of sea sickness.
  • This trip takes place in The Cyclades, or the Ionian islands, which are great for more experienced sailors with plenty of islands to keep you happy and weather that will sometimes keep you on your toes. For those looking for a more relaxing sailing holiday without too much excitement, check out our Greek Ruins and Island Hopping trip
  • A zodiac is often used to transport passengers from the boat to the mainland, with landings taking place at piers (dry landings) as well as on beaches (wet landings). Zodiacs can sometimes be awkward to climb in and out of.
  • This is an adventure on board a real yacht, which means living spaces, cabins, bathrooms and showers need to be shared with other passengers. Sleeping quarters can be quite compact, but you will be spending the majority of your time above board in the open air.
  • Please note that smooth sailing is dependent on the weather, so itinerary changes may occur at the last minute if the weather becomes unfavorable. If any changes are made, you can trust in your knowledgeable skipper to choose an alternative route or activity.
  • Due to the size of the yachts, sound carries easily from one side to the other and can wake your fellow travelers. If you do enjoy a late night out, please keep this in mind when returning to the yacht or possibly consider booking a room in town for the night so you don’t wake other travelers (and more importantly the skipper) upon your return. It’s important to have fun, but also to respect your shipmates who might be sleeping.
  • Summer temperatures in Greece can reach up to 40°C (over 100°F, which can be uncomfortable for those not used to the heat. On the other hand, early in the season (April) many businesses may still be closed and the weather is unpredictable, however you may have some of the major sights of the Greek islands almost to yourself. Please consider the time of the year you wish to travel and your suitability to that season.
  • Due to the current financial situation, banking services in Greece could potentially become limited at short notice. This includes credit card processing services and servicing of ATMs. When travelling through Greece, please ensure you have more than one means of payment with you (cash, debit cards, credit cards etc.). You’ll also need to have sufficient Euros in cash to cover emergencies, unforeseen circumstances and any unexpected delays.
  • In Athens, accommodations on this trip are multi-share. Single travelers will share a room with another traveler of the same sex. If you’d prefer not to share, a single room supplement is available at an additional charge. Also, hotels in Europe often don’t have double beds, but rather two single beds that can be pushed together/ apart.
TRIP LEADER(S) Local Skipper & Assistant
PLACES VISITED Athens, Siros, Mykonos, Paros, Koufonisi, Santorini, Ios, Sifnos, Kithnos
ACTIVITIES Sailing, hiking, kayaking, snorkeling, sightseeing
GROUP SIZE Min. 6 Max. 8 people
PHYSICAL RATING All Ability Levels
2 nights hotel/ 13 nights aboard yacht All meals indicated in the itinerary (B=Breakfast, L= Lunch, D=Dinner)
Fully licensed skipper & crew All transfers listed in the itinerary
On-Board Snorkeling Equipment On-Board Kayaks
Yacht cleaning service Fuel Costs
Marina Fees  Provisions
Airfare to/from Athens (ATH) Airport taxes & excess baggage fees
Travel Insurance Alcoholic beverages & meals not specified
Personal Expenses Gratuities
Optional Activities
2017 Small Group Departures
May 26-June 10 $3395 (Single Supplement N/A)
Due in Full by February 25, 2017
Ready to book? Click the button above to submit your information along with a deposit to secure your spot. Need assistance? Call us at (800) 953-5538 or email and one of our tour consultants will be happy to help.
Not finding what you’re looking for? We can tailor your adventure to fit your travel style, time frame, budget, and interests. From different styles of lodging to your favorite adventure activities, we’ll create the best custom itinerary for you. Feel free to call one of our travel specialists for information on custom trips. Let us plan your next adventure of a lifetime! Contact us today!


Today is arrival day so there are no activities planned. You are free to relax or explore the city. Athens is the historical capital of Europe, with a long history, dating from the first settlement in the Neolithic age, 5th Century BC.  Our hotel will be located near the Acropolis and is surrounded by small art museums, galleries, jewelry museums, cafes and restaurants.

Overnight at Hotel Herodion or similar


Athens to Lavrion Marina (B)

This morning, after checking out of the hotel, we’ll head to the Lavrion Marina where we will leave our bags in the marina office and spend the afternoon exploring this area. Located on the tip of the Attiki Peninsula, the oldest and biggest ancient amphitheater in the country is located here as well as a mysterious giant hole that would be an attraction to Fortians and seekers of unexplained phenomena if they knew about it.

The afternoon is free to do whatever you choose before boarding our yacht at 5:00pm. Upon boarding, we’ll be greeted by our crew who will be with us for the next fourteen days. After unpacking our belongings, we’ll receive a safety briefing in the cockpit followed by a relaxed welcome dinner (not included) at one of the many nearby tavernas, giving you an opportunity to get to know our crew a bit better.

We’ll spend the night on the boat this evening in the marina so that we can depart early in the morning.

–Private transfer from Athens to Lavrion Marina
–Meals: Breakfast

Overnight on the boat at Lavrion Marina


Lavrion to Syros (B, L)

This morning, we’ll depart the marina very early since we have a long day of sailing ahead of us. The journey through the marvelous islands of the Cyclades is illuminated by the blue and white colors of the Aegean. According to ancient myth, it is Poseidon, God of the sea, who created the island complex that is now one of the most famous worldwide. The Cycladic islands charm and challenge all sea lovers. It is within their crystal-clear waters that senses awake to allow travelers to grasp the essence of the islands’ splendor.

We’ll arrive in the afternoon to the island of Syros, the island where Greek tradition and western influence come to a harmonious marriage.  After stepping off the yacht, a visit to both the Catholic and Orthodox cathedrals on their respective hills offers a great view back down to the harbor. The great number of beautiful beaches will delight the sea and sand lovers.

Syros is well-known for its gastronomic peculiarities. Halva pie (a pie made of thyme honey and roasted almonds), loukoumi (a delight made of water, starch and sugar), “loosa” ham, fennel sausages, and the San Mihalis spicy cheese will no doubt satisfy even the most demanding taste buds. In the evening, we’ll enjoy dinner at one of the beautiful garden tavernas.

–Meals: Breakfast & Lunch (on the boat)

Distance from Lavrion to Syros: 46 NM – 9 hours
Overnight on the boat at Syros Island


Syros to Mykonos (B, L)

After breakfast, we’ll motor along the coastline and then set sail to Greece’s most famous cosmopolitan island, a whitewashed paradise in the heart of the Cyclades. According to mythology, Mykonos was formed from the petrified bodies of giants killed by Hercules. It gets its name from the grandson of Apollo, “Mykonos.”

Stroll around its narrow marble streets and admire whitewashed houses with colorful doors and window frames, bougainvillea trees in purple bloom and hidden churches. Soak up the atmosphere along the lively waterfront and admire a fleet of fishing boats casting colorful reflections in the azure waters. One of the most scenic corners of the island is Alefkantra or “Little Venice,” an 18th century district, dominated by grand captains’ mansions with colorful balconies and stylish windows.

While you’re out strolling, don’t be surprised if you come across the official mascot of Mykonos, which is nothing other than a… pelican! Petros the Pelican was found by a fisherman after a storm in 1954, and eventually became the locals’ companion. When he died, the grief for his loss was so deep that a replacement was soon found. In honor of Petros, the locals have established a long tradition of pelicans wandering around the waterfront as an essential part of everyday life. So, whatever you do, don’t forget to take a picture with the successor of the famous pelican Petros!

In the evening, we’ll enjoy a group dinner (not included) at one of the rooftop garden tavernas. Enjoy some local Aegean specialties such as Pepper flavored kopanisti, a soft cheese seasoned with pepper. It is the island’s gastronomic trademark. Try it as a topping on a round rusk spread with grated tomato, a favorite local appetizer. Meat eaters can sample “louzes” (cooked pork filet with spices) and tasty local sausages sprinkled with pepper, and local oregano that has been caressed by the sun and dried in the north wind. To finish off your meal you can sample two exceptionally good local pastries, “amigdalota” (small round cakes with ground almond, rosewater and caster sugar) and honey pie.

If you’re up for it, be sure take advantage of Mykonos’ world renowned party scene.

–Meals: Breakfast & Lunch (on the boat)

Distance from Syros to Mykonos: 25 NM – 5 hours
Overnight on the boat at Mykonos Island


Mykonos (B, L)

Today, enjoy a full day at your leisure in Mykonos, and perhaps try your hand at one of the islands numerous water sports. It is only natural that the “Island of Winds” should attract surfers and sailors from all over the world! There is a great choice of beaches for windsurfing; however, the most secluded ones are considered to be the best. Choose from Korfos, Ftelia, Meyali Ammos and Kalafatis, where surfing lessons are also available. Play beach volleyball at Ayia Anna or try sea parachuting or jet skiing at Elia or Kalafatis.

Diving fans can do a little exciting exploration of the underwater magic of Mykonos. On the island, you can find many well-organized diving centers. Explore the island on a cacique or a boat and discover secluded beaches, or take a boat tour around the nearby islets, which are also ideal fishing spots!

Be sure to hit the rooftop of the Belvedere Hotel to watch the sunset and try their Lychee Mojito. You won’t regret it!

–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Mykonos Island


Mykonos to Paros (B, L)

Unrivalled natural beauty, beaches with crystal clear waters, unrivalled Byzantine footpaths connecting traditional villages and breathtaking landscapes make up the island of Paros, located in the heart of the Cyclades. Parikia, the capital of Paros, is a beautiful Cycladic village with whitewashed cubic houses and impressive neoclassical mansions. A well preserved 13th century Venetian castle stands proudly on a hill at the center of the village offering an amazing view of Parikia. Here, you’ll also find the 6th century church of Panayia Ekatontapyliani, also called Katapoliani. The name “Ekatontapyliani” means the church with 100 gates, one of which is a secret one!

Sun-drenched beaches, like Chirssi Akti, Santa Maria and Pounda, welcome sun-loving visitors who want to enjoy the crystal-clear sea, the sun or even their favorite water sports. You may also choose to discover the island’s stunning beauty by hiking along the “strates,” the trails created by farmers to help them cross the island and transport their goods. It’s like stepping back into history! Alternatively, you can discover the island on horseback. There are two horse-riding centers, one by the sea at Ambelas, and one at Ysterni. Ride around the coast, along the sandy beaches or take a detour inland – a great way for you to discover some of the most beautiful spots on the island.

–Meals: Breakfast and Lunch (on the boat)

Distance from Mykonos to Paros: 25 NM – 5 hours
Overnight on the boat at Paros


Paros to Koufonisi (B, L)

Koufonisia is a small group of two islands, Pano Koufonisi (Upper Koufonisi) and Kato Koufonisi (Lower Koufonisi), that are separated by a narrow strait. They were named Koufonisia (meaning Hollow islands) because of the existing huge caves which gave the impression to pirates who viewed them from a distance that the islands were hollow.

Upon arrival, we’ll motor around the island and admire the sea caves as well as the nearby islets Glaronisi, Prasoura, Voulgari, Tsouloufi, Lazaros and Megali Plaka; all of them have been designated as areas of great natural beauty.

After docking, we’ll see the white windmill which stands at the harbor entrance as if welcoming visitors. Chora is further up, a typical Cyclades village with white-washed houses and picturesque alleys. In the center, you’ll see Agios Georgios church, the island’s patron saint.

Koufonisia is the perfect place to relax on one of the golden sand beaches, swim in one of the small natural pools of turquoise waters, or rent a bicycle and tour the island following the shoreline. Visit the inland area and hike along the paths from Chora to Pano Meria.

For dinner, we’ll feast at one of the local tavernas, the original ‘island way,’ and enjoy seafood fresh from the sea.

–Meals: Breakfast and Lunch (on the boat)

Distance from Paros to Koufonisi: 27 NM – 6 hours
Overnight on the boat at Koufonisi


Koufonisi to Santorini (B, L)

Today will be another full day of sailing as we make our way to Santorini! Santorini is the most popular island in Greece, if not the world. In fact, it’s actually a group of islands consisting of Thira, Thirassia, Aspronissi, Palea and Nea Kameni. It is frequently included among the best destinations in the world. There are few travel destinations that combine beautiful beaches, spectacular scenery, ancient cities, amazing restaurants, some of the world’s best wine, and an active volcano. The entire complex of Santorini islands is still an active volcano and probably the only volcano in the world whose crater is in the sea. The last big eruption occurred 3,600 years ago and what remains today is a submerged volcano and a caldera.

Amazing villages have been constructed on the edge of this caldera, with Cycladic architecture and breathtaking views and sunsets. Fira is the picturesque capital of the island; perched high up on the edge of the Caldera, it looks like a marvelous painting. Fira, together with Oia, Imerovigli and Firostefani, located high above on a cliff, make up the so-called “Caldera’s eyebrow,” the balcony of Santorini, which offers an amazing view of the volcano. Some of the villages are cosmopolitan and some more peaceful, surrounded by vast vineyards, whitewashed cliff-top towns with castles affording amazing views out over the Aegean.

A visit to Santorini is the ultimate gastronomic experience, as the island is a true culinary paradise! Treat your taste buds to some famous traditional products like cherry tomatoes, white egg plants, fava, caper and “hloro tyri,” a special kind of fresh goat cheese found on the island, or why not try some of the exceptional wines produced from grapes grown in the volcanic soil.

–Meals: Breakfast and Lunch (on the boat)

Distance from Koufonisi to Santorini: 46 NM – 9 hours
Overnight on the boat at Santorini


Santorini (B, L)

Today is free to explore the island at your leisure. Whether you choose to participate in water sports or trekking activities, visit museums, shop, or simply relax on the beach, the possibilities are endless!

Santorini is especially known for its natural beauty and is ideal for nature lovers. It offers a lot of amazing paths to do some trekking to view wild, volcanic landscapes to picturesque villages and lovely churches in the countryside. Trekking is a great way to get to know the island in a more special way. There are numerous routes that vary in length and difficulty for anyone to enjoy.

Venture into Santorini’s seaside treasures and enjoy deep blue waters and beaches with white, red or black sand or volcanic pebbles, spectacular rock formations and impressive lunar landscapes.

Take a full-day or half-day kayaking tour, get a birds-eye view of the island by taking a parasailing excursion, explore the island on an ATV, take off on a jet ski, or try a water skiing lesson. Most beaches in Santorini have a water sports center with loads of fun activities to choose from.

–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Santorini


Santorini to Ios (B, L)

Ios or Nios, as the locals call it, is one of the most beautiful islands of the Cyclades, like a flower, as its name “Ion” denotes. According to the ancient tradition, Ios was the homeland of Homer’s mother and the final resting place of the great epic poet.

Upon reaching the island, the village of Hora is enchanting and as pretty-as-a-picture. The snow-white little houses, picturesque arcade-covered alleys, the twelve windmills, churches with arched belfries and light blue domes create a unique residential area. Out of the 365 churches on the island, the most important is Panayia Gremiotissa, standing on Hora’s highest spot. It is built literally on the edge of a cliff, affording an amazing view of the open sea.

A feast of local tastes awaits lucky visitors: chickpea balls, sun-dried picarel, tsimetia (stuffed vegetable marrow flowers), vegetable marrow omelette, dolmadakia using fresh vine leaves from the numerous vineyards where the famed niotiko wine is produced, and goat soup are just a few of the menu items we might find at dinner this evening.

Don’t leave without getting some of the local cheeses like skotiri (soft goat cheese with herbs), local kefalotyri (hard salty yellow cheese) and mizithra (soft white creamy, almost sweet cheese) as well as some of the excellent thyme honey, pastelia (honeyed sesame bars), watermelon confiture, mizithra pie and pomegranate liqueur.

–Meals: Breakfast and Lunch (on the boat)

Distance from Santorini to Ios: 30 NM – 5 hours
Overnight on the boat at Ios


Ios to Sifnos (B, L)

Sifnos, the island of flavors, is the birthplace of several famous poets, such as Ioannis Gryparis, Kleanthis Triantafyllou (or Rampagas) and Aristomenis Provelegios; as well as award-winning chefs like Tselementes. Unique traditional villages, organized and secluded beaches, and 227 churches spread around the island are waiting to be discovered.

Apollonia, the capital town of Sifnos, is built in the shape of an amphitheater over three hills in the center of the island. During your evening walk, be sure to pay a visit to the Folklore Museum at the Hiroon Square (meaning “Square of the Heroes”).

A few kilometers away from the town lies the traditional settlement of Artemonas, famous for its neoclassic mansions and its outstanding panoramic view of the island. Some of the most famous restaurants and patisseries of Sifnos will welcome you here with fresh homemade cookies and hot doughnuts.

The historic settlement of Kastro (meaning “castle”), inhabited since ancient times, is built over the ruins of ancient Sifnos, on an abrupt rock with a breathtaking view of the sea. A beautiful outdoor museum and one of the most picturesque villages on the island, Kastro stands out for its old houses with the wooden balconies, the ancient columns and the narrow courtyards.

Whether cosmopolitan or secluded, all the beaches in Sífnos offer sun-loving tourists azure waters and sun-drenched sandy beaches. Kamáres, the port of the island, is a sandy beach with trees and beach bars; Platís Yialós is the most cosmopolitan and buzzing beach on the island, whereas next to it lies Vathí, a sandy beach with shallow waters and many tavernas where you can enjoy fresh fish. The rocks in Chrisopigí, where also the homonymous Monastery proudly stands, are ideal for diving. If you’d like to rest under a cool shade, head to the next beach which is surrounded by salt water loving trees. If you find yourself in Kástro, follow down the path to “Eptá Mártyres”, and enjoy a leisurely swim or unwind with a book lazing on a sun lounger.

Sifnos is the center of pottery in the Cyclades since the first samples were found here are dated back to the Early Cycladic period. The island’s clay soil in combination with the continuous sunshine resulted in the development of the art of pottery on the island. Throughout the island there are many pottery workshops where you can buy ceramics for domestic use, utensils and decorative items.

In every small taverna or classy restaurant, you can sample some of Sifnos’ exceptional dishes cooked by chefs who know how to tempt our taste buds. When the night falls, set out to discover fancy lounge bars and the hottest nightclubs on the island and dance the night away!

–Meals: Breakfast and Lunch (on the boat)

Distance from Ios to Sifnos: 30 NM – 5 hours
Overnight on the boat at Sifnos


Sifnos to Serifos (B, L)

Serifos Island, with its rugged mining sites, ladened with history, has its own distinct Cycladic flair. The island exudes a calm atmosphere and speaks directly to our senses. The locals have respected the Cycladic architectural tradition by building white and blue houses making the islands towns and villages all the more powerful. There is much to do here including hiking, climbing, mountain biking and diving!

Beach-goers will have plenty of beaches to choose from while visiting Serifos Island; rocky, pebbly, or sandy beaches accompanied by crystal blue waters will satisfy all tastes. Beaches are reached either by car, walking trails or by sea.

Serifos’ cuisine bursts with aromas and flavors! Try delicious meat products such as louzes, syglina (traditional cured pork) and sausages, as well as the islands rich aromatic spices. Taste marathopites and marathotiganites (fennel pies, baked or fried), revythada (traditionally cooked chickpeas) with a local variety of raisins, sun-dried octopus, local cheeses sucha as myzithres and xinomyzithres. Make sure to accompany your meal with the islands local wines.

–Meals: Breakfast and Lunch (on the boat)

Distance from Sifnos to Serifos: 20 NM – 4 hours
Overnight on the boat at Serifos


Serifos to Kythnos (B, L)

Kythnos, also called “Thermia” on the account of its thermal springs, is in the Western Cyclades. It is a surprising island of beautiful beaches, traditional villages, and folding hills punctuated by stone huts and ancient walls. An agricultural island mostly, life is still simple. We’ll arrive at the rustic fishing village of Merihas. The harbor is a safe and quaint place with an open-air fish market, restaurants strung along a sandy beach, an internet cafe and ice cream parlor. To cool off, we’ll have a swim at the tiny little beach just 5-minutes’ walk from the yacht.

The most impressive of the 65 sandy beaches is the island of Kolona, where a lane of sand connects the islet of Ayios Loukas to Kythnos. Low stone fences run for many kilometers on bare Cycladic hills with 350 white country chapels here and there. The typical Cycladic style equally appears in the villages with its cobbled narrow streets, white houses, squares, chapel and windmills. Follow the paths that connect the villages to each other and taste apricots and wild mulberries on the way to Katafyki cave, one of the biggest caves in Greece with beautiful stalactites and stalagmites.

–Meals: Breakfast and Lunch (on the boat)

Distance from Serifos to Kythnos: 24 NM – 5 hours
Overnight on the boat at Kythnos


Kythnos (B, L)

On the northeastern coast of the island, the village of Loutra is famous for its thermal hot springs, which boast healing powers, as well as a rather special archaeologic interest on the island called Maroulas. It is the home to one of the oldest prehistoric Mesolithic archaeological settlements in all of the Cyclades, dating between 9000-8000 BC. The excavations, which ended in 2005, unearthed 30 round spaces that used to be hut floors. 15 tombs, one of which contained a human skeleton and tools made of pyrite, obsidian, and quartz, were found below their stone layers.

After a visit to the archaeological site, why not visit the thermal spa center (optional) and relax in the swimming pool, try a hammam (Turkish bath) or sauna, or get a hydro massage? This modern spa is located on a cliff overlooking the Aegean Sea.

–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Kythnos


Kythnos to Lavrion Marina (B, L)

Today, we’ll make our way back to Athens arriving in the harbor in the afternoon and we’ll say our goodbyes to our crew before disembarking the yacht. We’ll have transportation to take us back to the city for our last night with the group.

–Meals: Breakfast and Lunch (on the boat)
–Transportation to Athens

Distance from Kythnos to Lavrion Marina: 25 NM – 5 hours

Overnight at Hotel Herodion or similar


Athens (B)

Today is departure day and there are no planned activities as we say goodbye to our new friends and head home or to your next destination.

–Meals: Breakfast

Is This Trip Right For You?

Life Onboard a Sailing Yacht Meals Onboard the Yacht
Itinerary Disclaimer Weather/ Seasons in Greece
About the Area We Are Sailing

Essential Trip Information

What to Bring Laundry
Visas and Passports Health and Vaccinations
Travel Insurance Currency and Foreign Exchange
Spending Money Gratuities
Local Time and International Calling Codes Plugs and Adapters
Medical History and Abilities Safety and Security
General Rules

Other Things You Should Know

Yachting Terms Useful Words and Phrases in Greek


This is a sailing trip and you must be comfortable with moving about the boat. Yachts are designed to maximize living area space, so sleeping quarters can be a bit cramped. For solo travelers, there is no single supplement on-board the yacht. You will be paired with a same sex roommate.

Please be aware that this is a sailboat and not a cruise vessel and space on board is tight. You will be sharing a small room with one of your fellow travelers or your travel partner and possibly sharing a bathroom onboard. Some people are not comfortable with the type of close quarter arrangements typically found on sailboats, however if a real sailing experience on a real sailboat is what you are after, then this experience should more than make up for cramped quarters.

You will be spending most of your time above board in the open air (and you may choose to sleep out there as well) and with time on the water comes time in the sun. Remember to pack sun protection, such as sun screen and a hat. Also, be sure to drink plenty of water and keep hydrated.

That said, the adventure and exhilaration of an authentic sailing trip more than makes up for any discomfort. Although the waters are usually calm, it can get rough and choppy, which requires steady sea legs and a sturdy stomach. Please note that smooth sailing is dependent on the weather, so itinerary changes may occur at the last minute if weather becomes unfavorable. If any changes are made, you can rest assured that your experienced skipper will choose the best alternate route or activity.

Due to the size of the yachts, sound carries easily from one side to the other and can wake your fellow travelers. If you do enjoy a late night out, please keep this in mind when returning to the yacht or possibly consider booking a room in town for the night so you don’t wake other travelers (and more importantly the skipper) upon your return. It’s important to have fun, but also to respect your shipmates who might be sleeping.


Two healthy meals are provided aboard the yacht each day. Breakfast is usually self-service and is generally light continental, rather than an American style hot breakfast and may include: fresh fruit, cereals, yogurt, toast, boiled eggs, tea, coffee and juice.

Lunch is usually served in the shaded cockpit anchored in secluded bays and consists of: fresh bread, crackers, spreads and dips (including tzatziki, taramou salata, melanzani salata), various salads: Greek, tuna, egg, coleslaw, potato, rice or pasta, an assortment of cheeses and/or cold cuts as well as olives, capers and bell peppers.

Beverages such as soft drinks, iced tea and water are included and stowed on board. You are advised to bring aboard your own specialty and snack foods, alcohol, mixer drinks and ice.


The information in this trip details document has been compiled with care and is provided in good faith. However, it is subject to change, and does not form a contract between parties. While it is our intention to adhere to the route described, there is a certain amount of flexibility built into the itinerary and on occasion it may be necessary, or desirable to make alterations. The itinerary is brief, as we never know exactly where our journey will take us. Due to our style of travel and the regions we visit, travel can be unpredictable. Occasionally our itineraries change due to weather or other circumstances that are beyond our control. Additionally, any travel times listed are approximations only and subject to vary.


August is the hottest month in Athens with an average temperature of 84 F (29 C) and the coldest is January at 50 F (10 C). The most daily sunshine hours is 12 in July. The wettest month is December with an average of 3.85 inches of rain. The best month to swim in the sea is in August when the average sea temperature is 77 F (25 C).

Low Season (Nov-Mar)

Many hotels, sights and restaurants shut down, especially on islands. Accommodation costs up to 50% less than in high season. Ferry schedules are skeletal. Temperatures drop; Athens and Crete can see snow. Average temperatures range from 45 F (7 C) to 65 F (18 C).

Shoulder Season (April, Sept & Oct)

Accommodation prices can drop by 20%. Temperatures are milder. Internal flights and ferries have reduced schedules. Fewer crowds. Average temperatures range from 54 F (12 C) to 75 F (24 C).

High Season (Easter & May-Aug)

Everything is in full swing and transport is plentiful. Accommodation sometimes cost September is a shoulder season in Greece. Temperatures are typically in the 80’s in Athens and the climate is very dry — think Arizona. Most rain falls between November and February, while rainfall in September is very rare. The weather on the islands is about 10-15 degrees cooler than Athens, and after watching the beautiful sunset, it can get chilly at night (average 63-67 degrees), so bringing a light jacket or sweater and a windbreaker is advised.

For more information, please visit


The Cyclades lie to the southeast of Athens and the Greek mainland and to the east/ southeast of Poros. Unlike the Saronic Gulf, the Cyclades islands are not protected by any mainland. Their position out into the Aegean Sea means they are more exposed to the northerly ‘Meltemi’ wind which very much dominates the Cyclades islands from late July to September. These wind conditions mean sailing the Cyclades islands provides for more invigorating sailing, but might also prove ‘too exciting’ for those looking for something more relaxing.


There is limited space on the yachts. Our advice is to pack as light as possible as you are expected to carry your own luggage. We recommend the use of a duffel bag, soft bag or backpack (whichever you find easiest to carry). Smaller bags with wheels are convenient if your bag has carry straps. Large suitcases or heavy luggage are not recommended. You will also need a day-pack for carrying water, a camera, and other electronics, and extra clothing for day trips exploring the areas we will be visiting. Luggage locks are also recommended.

Packing Checklist


– Passport (with photocopies) & Visa (if required)
– Travel Insurance policy (with photocopies)
– Driver’s License
– Flight Information & Boarding Pass
– Money and credit or debit card (please see the section on Currency & Foreign Exchange)
– Travel packet w/ pre-departure info & itinerary
– Any vaccination certificates

 Clothing and Footwear

– Weather-approriate clothing
– Light fleece top/jacket
– Light windproof/waterproof jacket
– Moisture wicking t-shirts/ tank tops
– Hiking pants/shorts
– Swimwear
– Under garments
– Sunhat (that can be secured if it is windy)
– Sturdy, comfortable walking shoes
– Flip flops/ sandals

Personal Items

– Shampoo, conditioner, soap (biodegradable)
– Toothbrush & Toothpaste
– Razor
– Brush/comb
– Biodegradable laundry soap
– Eyeshades/ earplugs
– Sunglasses
– Sunscreen (biodegradable & waterproof)
– Lip Balm
– Ocean Nasal Moisturizing Spray
– Hand sanitizers/ antibacterial wipes
– Plastic bag for wet items
– Small travel towel
– Beach Towel
– Dry bag
– Headlamp or flashlight
– Camera and extra memory card
– Binoculars (optional)
– Water bottle
– Watch or alarm clock
– Power Adapter (please see the section on Plugs & Adapters)
– Batteries
– Chargers for electronics
– Luggage lock(s)
– Reading/writing material
– First-aid kit (should contain Aspirin, Ibuprofen (for anti-inflamation), Band-Aids, anti-histamines, motion sickness remedy, imodium or similar tablets for mild cases of diarrhea, and re-hydration powder)
– Personal prescription drugs , contact lenses, glasses


Laundry facilities can be found in some harbors. Ask your skipper for the best places. There will be times when you may want to or have to do your own laundry, so we also suggest you bring a biodegradable laundry soap.


All countries require a valid passport (valid for a minimum of 6 months after the date of departure). Contact your local embassy, or consulate for the most up-to-date visa requirements. It’s your responsibility to have the correct travel documentation. Please visit for links to helpful websites.


It is your responsibility to consult with your physician or a travel clinic for up-to-date medical travel information well before departure to find out what vaccinations might be required or recommended for Greece. Also, keep in mind that some heat waves are possible from June to October all over the country. People who are sensitive to seasickness should come prepared.

We recommend that you carry a First-Aid kit and hand sanitizers/ antibacterial wipes as well as any personal medical requirements. Please be aware that sometimes we are in remote areas and away from medical facilities, and for legal reasons, our guides/skippers are prohibited from administering any type of drug.

Please visit for links to helpful websites.


Travel insurance is mandatory to participate on any of our trips. You will not be permitted to join a trip until evidence of travel insurance has been presented. The minimum requirement must provide coverage of $200,000USD for medical expenses including repatriation and emergency rescue. We strongly recommend that the policy also covers personal liability, cancellation, curtailment and loss of luggage and personal effects. Some credit card companies offer travel insurance, but proof of coverage will be required. Contact your provider for details.


In Greece, the only currency accepted is the Euro. As currency exchange rates fluctuate, we ask that you refer to the following website for the most up to date daily exchange rates, or

The most convenient and cheapest way to acquire money is via an Automated Teller Machine (ATM), or Bancomat as they are often referred to. Check with your bank in advance concerning the suitability of your account/ card overseas and any international fees that will be applied.

You can obtain local currencies easily at airports and major train stations, as well as banks and money exchange “kiosko” in all cities, but be sure to bring some extra emergency cash that can be exchanged if the ATM’s are not functioning.

Do not rely on credit or debit cards as your only source of money, a combination of cash and cards is best. Credit cards are not always accepted in stores and restaurants. Change can be difficult to obtain, so try to gain as many small denominations as you can. We do not recommend bringing travelers cheques as they are very difficult to change.

Please be advised that slightly torn notes, notes that have been heavily marked or are faded may be difficult to exchange. It is best to bring notes in fairly good condition, in denomination lower than 100USD (or equivalent).


When it comes to spending money on a trip, every traveler is a little different. You know your spending habits better than we do, so please budget a sensible amount for things like meals not included, drinks, shopping, optional activities and laundry. It’s always better to bring more than you think you’ll need as you don’t want to spoil the trip by constantly feeling short of funds. Also, make sure you’ve read the trip details thoroughly so you know what’s included in the trip price and what isn’t. This should make budgeting a little easier.


If you’re happy with the services provided, a tip – though not compulsory – is appropriate. While it may not be customary to you, it’s of great significance to the people who will take care of you during your travels. The following amounts are based on local considerations. You are always free to tip more or less as you see fit, depending on your perception of service quality and the length of your trip.

Hotels: It is customary to tip the porter/ bellboy around 1 Euro per bag. For your housekeeper, leave around 1 Euro per day on the bedside table before you check out. You can also leave a few Euros as gratuity for the concierge if you received excellent service.

Restaurants:  Local markets and basic restaurants, just leave the loose change. At more upscale restaurants, a suggested gratuity of 5% to 10% of the total bill is suggested.

Taxi’s & Drivers: You won’t always be expected to tip your taxi driver, but it’s up to you. If you do decide to tip your taxi driver, round-up the fare, or leave between 5% and 10%. For a private driver, leave around 20 Euros per day. If they went above and beyond you can always tip more.

Skipper & Crew: Skippers and crew will deliver excellent customer service on your trip, safely sailing and providing meals each day. A suggested gratuity amount per person would be 50-75 Euros ($60-$90) per crew member for 7-nights aboard the yacht.

Tour Guides:  For local activity guides, the suggested gratuity is between 2 and 5 Euros for full or half-day tours.


Greece is on Eastern European Time (GMT +2) and is ten hours ahead of PST and 7 hours ahead of EST in the US.

The country calling code is +30. To call Greece from the US, dial 011 30 + area code and phone #.  to dial the US from Greece, dial 001 + area code and phone #.


power plugs

Greece uses type C, D, E, and F outlets and the voltage is 220 volts/ 50Hz. In the US, we use types A and B, 120 volts/ 60Hz. For using your electronics in Greece, you will need a voltage converter in addition to a plug adapter. Many electronics already have a built-in converter, so all you’ll need to use is one of the adapter plugs. This covers most modern laptops, cell phone chargers, and many other devices, but be sure to read the information on your device to be sure.

While there should be electricity on board the yacht throughout your trip, the voltage is likely to vary widely, from 12V to 220V, and when in port or moored we are dependent on the supply available. Please be aware that the supply may not be sufficient to power some electronic devices all the time and that you may need a voltage adapter or similar (such as portable inverter used in cars). It may be possible to charge devices ashore at restaurants or resorts, however this is not guaranteed.


Our trips bring together people of all ages. It is important that you are aware that, as a minimum, an average level of fitness and mobility is required to undertake any of our trips. Travelers must be able to walk without the aid of another person, climb 3-4 flights of stairs, step on and off small boats, and carry their own luggage. You must inform us at the time of booking if anyone in your party has a disability, medical or behavioral condition which could affect their participation in the trip or other people on the trip.

Travelers with pre-existing medical conditions are required to complete a short medical questionnaire, which must be signed by their physician. This is to ensure that travelers have the necessary fitness and mobility to comfortably complete their chosen adventure. While your group leader and guides work hard to make sure that all our travelers are catered for equally, it is not their responsibility to help individuals who cannot complete the day’s activities unaided.


We recommend that you check your government’s advice for the latest travel information before departure. We also strongly recommend the use of a neck wallet or money belt while traveling, for safe keeping of your passport, credit cards, cash, and other valuable items. Leave your valuable jewelry at home – you won’t need it while traveling. In addition, a lock is recommended for securing your luggage. Only carry with you the money and documentation that you need for the day and always keep an eye on your belongings.

Since you’ll have a lot of free time on the islands, please note that any optional activities you undertake that are not part of the itinerary, are at your own risk. We offer no representations about the safety of the activity or the standard of the operators running them. Please use your own good judgment when selecting an activity in your free time. While most of the cities we will visit are generally safe, there can be risks when wandering through a major city at night and it is our recommendation that you stay in small groups and take taxis to and from restaurants or other night time excursions. We also advise staying away from any protests and demonstrations. Even those that are well intended have the potential to turn violent with no warning.

Adventure activities and water based activities have an element of danger and excitement built into them. We recommend only participating in activities when accompanied by guide(s). We make every reasonable effort to ensure the fun and adventurous element of any of our planned activities, have a balanced approach to safety. Swimming, including snorkeling, is always at your own risk.


Illegal drugs will not be tolerated on any trips. Possessing or using drugs not only contravenes the laws of the land but also puts the rest of the group at risk. Our philosophy of travel is one of respect towards everyone we encounter, and in particular the local people who make the world the special place it is. The exploitation of prostitutes is completely contrary to this philosophy and therefore prohibited. The group organizer has the right to expel any member of the group if drugs are found in their possession or if they use prostitutes.


Here are some technical terms for you to learn before your trip to help you orient yourself with the world of yachting:


Hull: the ‘body’ of the boat
Keel: stabilizing part of the hull under the waterline to prevent capsizing
Deck: upper level of the boat
Cockpit: area in the back where we are operating the boat
Bow: Forward area of the boat
Stern: Backward area of the boat
Helm: steering facility
Helmsman: Person at the helm, not necessarily the skipper
Starboard: right side of the boat looking forward from aft
Port (side): left side of the boat looking forward from aft
Rigg: all fixed equipment standing up above the deck
Mast: vertical massive pole to fix the sails
Boom: horizontal massive pole going backward from the mast
Mainsail: sail at the rear of the mast
Headsail: sail in front of the mast
Fender: sort of ‘bumper’ to avoid damage of the hull when moored
Winch: sort of drum to operate loaded lines or anchor chain
Beaufort: intl. scale for strength of winds, starting with 0 up to 12


Manoeuvre: changing the course of the boat or doing several operations
Tacking: turning the bow through the wind
Gibing: turning the stern through the wind
Round up: turning the boat exactly into the wind to stop moving
Fetch sth.: pulling tight a line
Ease sth.: detaching a line


There are only LINES on a boat, no ropes etc. Most important ones:

Furling lines: to set and take away the sails
Sheets: to adjust the sails during sailing
Mooring lines: connecting the yacht to the peer
Ground lines: fixing the bow when moored ‘stern too’ (the peer)


Figure-eight knot: belongs to the end of certain lines to avoid going by the run
Half hitch: easiest knot to fix a line somewhere, not very strong one
Clove hitch: famous knot to fix various lines like mooring-, fender- etc.
Reef knot: used to connect two lines of same size to each other
Bowline: creating a strong and everlasting loop to a line


We always encourage our travelers to respect the lives of locals and their language by learning a few important words, such as hello, goodbye, please, thank you etc. It may also be helpful for you to download the Google Translate app on your phone along with Greek language to your phone so that it is available offline when you are not in an area with WiFi.

English Greek
Good morning kali̱méra
Good afternoon or evening Kaló apóyevma
Good night Kaliníhta
Thank you sas Efharistó
Hello Geia sas
Sorry sygnómi
How are you? ti kánete?
Pleased to meet you sti̱n ef̱cháristi̱ thési̱ na sas gno̱rísoume
What time is it? Ópoia ó̱ra eínai?
Do you speak English? Miláte angliká?
I don’t understand katalavéno
Cheers/ Good health! iyían
Please speak more slowly Parakaló miláte pyo argá
What is your name? pyó íne to ónomá sas?
My name is______ Me léne______
Where are you from? Apó pu íse?
I’m from_____ íme apó______
How much is this? Póso einai aftó?
Excuse me Me synhoríte
Where is the toilet? pu íne i tualéta?
Do you have change? Echete allagi?


Our sailing vessel is a Beneteau Cyclades 50.5 monohull sloop with 4 double cabins (+ 2 crew quarters) and 3 washrooms. Your chartered yacht will include an experienced skipper and an assistant who will provide two healthy meals aboard the yacht each day. There is no kitty, or deciding who is going to make the meals or wash the dishes!

Note: Images shown are of the make/ model of the yacht we’ll be sailing, not the actual yacht. On occasion, based upon the number of bookings, a different vessel, either larger or smaller, could be used. The service, meals, and itinerary are not changed when a vessel changes.

Greek Islands Sailing Adventure
Marching of the Guards
Swimming in the Mediteranean
Cats of Hydra
Greece sunset
Santorini sunset
lavrion marina

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