Greek Islands Sailing Adventure

♦ Start: Santorini
♦ Finish: Mykonos

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, and relaxing as we explore ancient archaeological sites and taverna-lined harbors. Watch a host of spectacular sunsets and enjoy mouth-watering local cuisine in the coastal villages seeped in history, mythology, and beauty.


7 nights/ 8 days

Physical Rating



Places Visited

Santorini, Mykonos, Cyclades Islands


  • Sail the beautiful Greek Islands from Athens for 8 days on a private 56-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 sailing 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 and late in the season (April/ October) many businesses may 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.
  • Single travelers will share a cabin with another traveler of the same sex. If you’d prefer not to share, a single room supplement is available at an additional charge. Even better, ask a friend to come along!


Today is arrival day and there will be a group welcome meeting and safety briefing with our crew at 5pm, so please be sure to arrive before then. There will be a bit of time to explore Santorini by night or just enjoy a night cap with your crew mates on the boat. We recommend that you arrive early to spend some time in beautiful 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. 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.

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.


Cyclades Islands (B, L)

As we depart Santorini this morning, we’ll make stops at some other islands in the Cyclades as we make our way to Mykonos. We keep our sailing itineraries flexible to allow for weather and the opportunity to showcase all the hidden gems in this archipelago. While in the Cyclades, a few of the islands we might visit are:


Explore one of the must-see islands in the Cyclades, Folegandros, and the beautiful clifftop city of Hora. Spend some time hiking the trails, taking photos of the classic whitewashed houses decorated with colorful bougainvillea or enjoy a drink or a bite while taking in the view, which is said to be second only to that of Santorini. There are limited things to do in Folegandros, apart from swimming and walking. Time is slow and relaxing on this island. Beaches are beautiful, calm, and uncrowded, which makes it the perfect place to relax.


Upon reaching the island of Ios, 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.

This island is particularly famous for its intense nightlife that attracts mostly young crowds. However, this island is not just about partying. It has many places off the beaten track. Take a scenic 25-minute walk up to the hill of the old town. Visit the tomb of the famous poet Homer or head to the famous Manganari beach on the south side of the island to enjoy the sun and crystal-clear water.

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 you might find. 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.


If you are looking for that perfect Greek island with a balance of beautiful beaches, a sizzling food scene, low-key nightlife, and quaint villages, look no further than Sifnos. Hike along the walking trails with spectacular views of olive groves and wild juniper. The aroma of orange-and-anise biscuits will hit you as you drift down the whitewashed lanes with pockets of sage and oregano in wind-chiseled valleys. Little churches with blue domes on green hills that lead to sandy beaches.

Known as the island of flavors, Sifnos 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.

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 small, locally owned pottery workshops, some of which are open to the public.  Stop and pick up a unique gift to take home.

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!


Located just next to Paros island, Antiparos is great for a day excursion. Explore ancient sites like the Cave of Antiparos, used as a place of worship for the goddess Artemis. Hop on one of the hourly buses to the cave, travel 100m down using the staircase and take in the view of the stalagmites and stalactites. Chora, the capital and only village on Antiparos, is built around a 15th century Venetian castle and is also worth exploring.


Located in the heart of the Aegean Sea, Paros Island is known for its hidden beaches, byzantine footpaths connecting quaint villages and bountiful plant life. The countryside is filled with vineyards, olive groves and fruit trees, while in the spring the scenery is dotted with bursts of color from blooming flowers. Parikia and Naoussa are the main villages of Paros, where most activities are concentrated.

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!

Naoussa is located in a huge bay in the northern part of Paros and is considered to be one of the prettiest villages in the Cyclades.  This village is built amphitheatrically around a picturesque port where colorful fishing boats called caiques moor and remains of a Venetian castle can still be seen.

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.


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 arriving at the island, a white windmill stands at the harbor entrance as if welcoming visitors. 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.


Naxos is the largest island of Cyclades and is located between Paros and Mykonos. According to mythology, this was the nuptial isle of the god Dionysus, god of wine. Plaka, Agios Prokopios, Orkos and Mikri Vigla are among the most beautiful beaches on the island, while the entire coastline is ideal for windsurfing and kitesurfing due to the strong winds that blow here in the afternoon.

A drive inland will bring you to picturesque villages and some interesting stops including the Monastery of Fotodotis in Danakos. The name of this monastery means Christ who give the light and it is found at an altitude of 500m, of top of a hill with a fantastic view to the sea and Donoussa Island. The monastery was originally founded in 6th century AD and legend says it was constructed by a Byzantine princess, after she was saved by the rough sea. The interior of the church has fantastic frescoes dating from the Medieval times.

The Temple of Demeter, near the village of Sangri, is a magnificent temple made of the finest quality of Naxos marble and is believed to date back to the 6th century BC. Some excavations in the area certify that the area was used for religious purposes during the late Mycenean Era. The remains of the ancient temple were discovered by archaeologist Nikolaos Kontoleon in 1949 and excavation works lasted from 1976 to 1995.

Another site to see is the Panagia Drossiani church, meaning Dewy Virgin. It’s the oldest Christian church of Naxos. Located near Moni, it is also considered one of the most important Byzantine churches and is therefore of immense historical significance. It dates back to the end of 6th century AD and if full of rare paintings and offers a beautiful view of the Tragea Valley.

Mount Zas is the tallest mountain of the Cyclades with an altitude of about 1,000m (3280 ft). As you would guess, it’s a popular hiking destination on Naxos.


Mykonos (B, L)

Today, we’ll celebrate our arrival to Mykonos, 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.


Mykonos (B)

Today is departure day. After breakfast, we’ll say goodbye to our crew and new friends as we disembark. We recommend spending extra time in Mykonos after your sailing journey to explore the island 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!


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.

2018 Dates & Pricing

If your dates are flexible, why not join other like-minded Adventure People on an exciting small-group adventure? Below are our set departures for this itinerary. Group trips are perfect for the solo traveler; ideal for friends. All are welcome!

Our custom small-group tours offer the opportunity to feel like you’re exploring a destination with a group of friends — because that’s what they’ll be after your trip! Our groups range in size depending on the destination and the activities but are generally no more than 16 people. The yachts on our sailing trips accommodate 8 people in double cabins, but we often have 2 yachts sailing together.

All Scheduled Departures for 2018:

7 nights/ 8 days
USD $2350
Tour price is per person (excluding flights) and is based on double occupancy.
Due in Full by April 10, 2018
+ Single Supplement $2350 (Optional)

Starts in Santorini:  June 9, 2018
Ends in Mykonos: June 16, 2018

Status: AB (Available to Book)
Trip Leader: Local Skipper & Assistant

7 nights/ 8 days
USD $2350
Tour price is per person (excluding flights) and is based on double occupancy.
Due in Full by June 3, 2018
+ Single Supplement $2350 (Optional)

Starts in Santorini:  September 1, 2018
Ends in Mykonos: September 8, 2018

Status: AB (Available to Book)
Trip Leader: Local Skipper & Assistant

SIGN UP WITH NO RISK Your deposit is fully refundable or transferable

When you travel with us, you’ll become a member of the #AdventurePeopleTravelClub after your first trip and earn discounts on all future trips with us! To learn more, visit

Ready to Book?
Use the booking form to the right and 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.

Gather your favorite people to share this adventure on the dates of your choice.  Pricing available for individuals and 10% discount for groups of 8+!

***Pricing Available Upon Request***

All prices are per person in U.S. dollars based on double occupancy.

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!

Request a Custom Itinerary

7-nights aboard a sailing yacht Fully licensed & experienced skipper & assistant
Port fees, cleaning fees & any other yacht expenses Provisions on-board
On-Board Snorkeling Equipment Prepared breakfast & lunch, as indicated in itinerary
International Airfare to Athens (ATH) Airport taxes and excess baggage fees
Optional Activities Gratuities
Personal Expenses Travel Insurance
Beverages & Meals not specified
Santorini sunset
Swimming in the Mediteranean
Cats of Hydra
Greece sunset
Santorini sunset
lavrion marina
Island hopping on a sailboat
greek islands

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