11 nights/ 12 days
Athens to Athens

Explore the ancient ruins of Athens, Greece before boarding a yacht for some island hopping in the Saronic Gulf! 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!

2017 Dates: September 14-25 $2795 (Single Supplement N/A)
Trip Leader(s):Stacey
Places Visited:Athens, Aegina, Hydra, Poros, Epidaurus, Santorini
Activities:Sailing, hiking, kayaking, snorkeling, sightseeing
Group Size:Min. 6 Max. 8
Travel Style:Comfort/ Sailing
Physical Rating:All Ability Levels

Ready to book? Please click the button below to BOOK THIS TRIP and submit your information along with a $500 deposit.  Your deposit is fully refundable for 72 hours and always transferable to any of our other trips, or we can hold it for a future trip.

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  • Explore the ancient ruins of the Acropolis
  • Marvel at the ancient theater of Edipaurus
  • Sail the beautiful Saronic Gulf from Athens for 7 nights on a private catamaran 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


Our sailing vessel is a Catamaran Lagoon 420 with 4 double cabins (+2 crew quarters) and 4 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.

Day 1: Athens

Today is arrival day so there are no activities planned. You are free to relax or explore the city. Please arrive at the hotel before 6pm for an important group welcome meeting. After the meeting, you may choose to head out for an optional group dinner and explore Athens by night.

Overnight at Hotel Herodion or similar

Day 2: Athens (B)

This morning we’ll be picked up at our hotel for a tour of Athens including The Acropolis and the new Acropolis Museum. This tour will give you an opportunity to observe the striking contrasts that make Athens such a fascinating city.

Our expert guide will take us to see the Panathenaic Stadium where the first Olympic Games of modern times were held in 1896. We’ll continue past the Prime Minister’s residence, guarded by the Euzones in their colorful uniforms, and then on to the Temple of Olympian Zeus, the Hadrian’s Arch, the Parliament, the memorial to the Unknown Soldier, the Academy, the University, the National Library, and the Constitution Square (Syntagma).

On the Acropolis visit, we’ll explore the Architectural Masterpieces of the Golden Age of Athens: The Propylaea, the Temple of Athena Nike, the Erechtheion and finally “the harmony between material and spirit,” the monument that “puts order in the mind,” the Parthenon.

Continue and visit the place where at last the statues found their home and admire the wonders of the classical era at The New Acropolis Museum.

We’ll return to our hotel around 1:45pm and you’ll have the rest of the day free to explore more of the city.

–Half-Day Athens Sightseeing Tour
–Meals: Breakfast

Overnight at Hotel Herodion or similar

Day 3: Athens/ Kalamaki Marina to Aegina (B)

This morning, you’ll have more free time in Athens before we go to the marina, where you’ll be greeted by our yacht crew. After unpacking our belongings, we’ll receive a safety briefing in the cockpit before we set sail on the Saronic Gulf for approximately 2.5 hours to the island of Aegina, a town full of life and ready to offer unique experiences! We’ll arrive in time for dinner and then possibly enjoy a night swim!

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

Distance from Athens to Aegina: 12 NM – 2.5 hours
Overnight on the boat at Aegina

Day 4: Aegina to Poros (B, L)

This morning, we’ll see the famous Temple of Aphaia (490 BC) by taking a 1.5-hour round-trip hike up an ancient path. Arguably the jewel in the crown of Aegina Island, the temple is a stunning example of ancient architecture set in a beautiful, naturally forested area with sensational views across the island to the sea. After our visit to the temple, we’ll explore the quaint little village overlooking the bay. Aegina boasts the best pistachio nuts in the world and they can be found in the local shops. Enjoy lunch in the cockpit followed by a swim in the crystal-clear waters of the bay.

After lunch, we’ll sail to the nearby island of Poros. When viewed from seaward, Poros is one of the most beautiful towns in Greece — arriving is a great photo opportunity. As Henry Miller describes it, the impression you get upon arrival is that you are sailing down main street. The harbor road is lined with cafes and alive with activity. There are taxis waiting to take you wherever you need to go. After docking, take about a 20-minute walk up to the clock tower for a panoramic view of the sun setting over the majestic Peloponnese Mountains. Upon arriving at the clock tower, you are rewarded with the sights and smells of local Mediterranean bougainvillea, jasmine, cactus, fig and cypress trees.

In the evening, we’ll enjoy dinner at one of the beautiful garden tavernas, where you can try one of the many Greek seafood specialties.

–Hike to Temple of Aphaia
–Meals: Breakfast & Lunch (on the boat)

Distance from Aegina to Poros: 22 NM – 3 hours
Overnight on the boat at Poros Island

Day 5: Poros to Hydra (B, L)

Spend the morning in Poros before departing through the narrow channel between Poros and Spathi. We’ll motor sail along the coastline for an excellent photo opportunity of the built-up terracotta roofed town, passing fishing boats and the bustling harbor. At Bourtzi island, take pictures of the Venetian fort that once defended this narrow passage. Spathi bay’s clear water is good for snorkeling and Mediterranean marine life. Lunch is aboard the yacht anchored at Spathi or upon arrival at Hydra.

A jet setter’s haven, the tiny port of Hydra becomes congested in the summer months with yachts regularly rafting three deep bow to stern. After an exciting tie-up, spend the afternoon wandering the cobbled streets and Venetian laneways of this famous historic port. To cool off, dive in at Hydra’s swimming area – just a five-minute walk from the yachts – or relax at one of the many cafes while watching the donkeys pass by — Hydra’s only mode of transportation. The town has been restored and preserved exactly as it appeared in the 1800’s when its inhabitants built it during a period of prosperity gained from piracy and blockade running. The Hydriotis made a name for themselves during the war for Independence.

In the evening, we’ll enjoy a group dinner at one of the rooftop garden tavernas. Following dinner, great cocktails and dancing can be found at Amalour or Pirate’s bar.

Distance from Poros to Spathi Bay: 6 NM – 1.5 hours
Distance from Spathi Bay to Hydra: 5 NM – 1 hour
Overnight on the boat at Hydra Island

Day 6: Hydra (B, L)

Today, we’ll enjoy another full day in Hydra, and perhaps explore some of the best walking paths and donkey trails in all of Greece.  Hydra is a paradise for hikers! There are twelve hiking routes that will cover Hydra to anyone’s satisfaction.

For a bird’s eye view of the island, a great way to orient yourself, and the best hike for hot months, start with the forest-shaded climb to the Profitis Ilias Monastery – the white compound perched on the highest hill above the town, viewable only while approaching the island. Another option is to hike to the Zourvas Monastery and the lighthouse. This trail is varied in terrain, vistas, and vegetation and offers spectacular views of the town, the farther islands, the mainland, and straight down into expensive walled villas.

Whichever route you choose, the island’s beautiful scenery and rich flora can be enjoyed just about everywhere, be it along the coast, through the meadows or up in the mountains. Many flower species are endemic to the island and found nowhere else.

–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Hydra Island

Day 7: Hydra to Epidaurus (B, L)

This morning, we’ll leave the beautiful island of Hydra and sail to Epidavros for a 2-night stay. Named after Epidaurus, the son of Apollo, the UNESCO World Heritage site of Epidaurus comprises a series of ancient monuments spread over two terraces and surrounded by a preserved natural landscape. Among the monuments of the Sanctuary is the striking Theatre of Epidavros, which is renowned for its perfect architectural proportions and exemplary acoustics. The Theatre, together with the Temples of Artemis and Asklepios (the ancient god of medicine), the Tholos, the Enkoimeterion and the Propylaia, was built to celebrate the power of the healing gods of the Hellenic and Roman worlds, with some structures dating back as far as the 4th century BC. The Sanctuary is the earliest organized sanatorium and is significant for its association with the history of medicine, providing evidence of the transition from belief in divine healing to the science of medicine.

–Ground transportation to Sanctuary at Epidavros
–Entrance Fee at Epidavros
–Meals: Breakfast and Lunch (on the boat)

Distance from Hydra to Epidavros: 36 NM – 5 hours
Overnight on the boat at Epidavros

Day 8: Epidaurus (B, L, D)

Today, we’ll go snorkeling at the Sunken City off Kalymnios beach, just south of Palaia Epidaurus. To get there, we’ll hike a preserved part of an ancient footpath which connected the sanctuary of ancient Epidavros to the ancient Epidavros port. The start of the sunken city is about 50m off-shore and it lies in about 10m of water, although some places are more shallow. You can snorkel over the remains of both square and round buildings of the ancient city.

According to historical information, the ruins that are visible were the ancient Agora of Epidavros. The Agora was located opposite the ancient port that used to be next to Spilia beach, and beneath the ancient Citadel that used to be on top of the Nisi mountain-peninsula. Walls, building foundations, support structures, and enormous pots lie half-buried underwater at 1.5-2.5 meters below sea level, just a few meters off the shore.

This evening, we’ll enjoy a beach BBQ and some Aegean star gazing.

–Snorkeling at the Sunken City
–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Epidavros

Day 9: Epidavros to Athens (B, L)

Today, we’ll make our way back to Athens, making stops along the way to swim and explore.

Arriving back at Alimos Kalamaki Marina in Athens, we’ll celebrate the end of our adventure with a toast in the cockpit and dinner in the marina. We’ll spend one last night on-board before we say goodbye to our crew.


–Meals: Breakfast and Lunch (on the boat)

Distance from Epidavros to Athens: 32 NM – 6 hours
Overnight on the boat in the marina

Day 10: Athens/ Santorini

This morning we’ll pack up our belongings before disembarking the yacht for a very early departure at 5am. We’ll have a mini-bus waiting for us to take us to the airport for our departure to the beautiful island of Santorini!

Santorini is the most popular island in Greece, if not the world. In fact, 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 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.

Our 50-minute flight will have us arriving on the island by approximately 8am. We’ll have transportation to take us to our hotel where we can drop off our bags and then grab breakfast in the nearby village of Oia. Oia is a photogenic town with a maze of small shops, restaurants and cafes, almost all with spectacular views of the rest of the island and the caldera.

After breakfast, spend the morning exploring this quaint village until check-in at the hotel. The main street of Oia has plenty of tourist shops and some pretty nice galleries and bookshops. Follow the walking path along the caldera and walk to the end of the village with the sea on your left until you see signs for the Kastro. Here, you’ll be rewarded with a spectacular view of the caldera and the village of Oia itself as well as a glimpse of the port of Amoudi below. The Kastro is actually an old Venetian castle. As this is a windy area, you’ll notice a number of windmills, some of which have been turned into houses and rental units. Also, don’t miss the Maritime Museum, established in the 1950’s and the nearby Weaving Mill where you can buy woven products as well as traditional canned and bottled agricultural products.

–Private transfer from Alimos Kalamaki Marina to airport
–Domestic flight from Athens to Santorini

Travel time from Athens to Santorini – 50 minutes by plane
Overnight at Atlantida Villas or similar

Day 11: Santorini (B)

Today is free to explore the island of Santorini 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.

Take a full-day or half-day kayaking tour, get a birds-eye view of the island by taking a parasailing excursion, 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

Overnight at Atlantida Villas or similar

Day 12: Santorini/ Athens (B)

This morning, we’ll transfer to the airport, and sadly this will be the end of our adventure in Greece. We’ll depart Santorini at 8:20am for our journey back to Athens.  Please do not book any ongoing travel from Athens before 12pm.

Travel time from Santorini to Athens – 50 minutes by plane

What’s Included?

4 nights (3-4*) hotel/ 7 nights aboard a 50ft yacht
Fully licensed skipper & crew
All meals indicated in the itinerary (B=Breakfast, L= Lunch, D=Dinner)
All transfers listed in the itinerary
On-Board Snorkeling Equipment
On-Board Kayaks
Half-Day Athens Sightseeing Tour
Round-trip airfare from Athens to Santorini
Entrance at Epidovros

What’s Not Included?

International airfare to Athens
Airport taxes & excess baggage fees
Travel Insurance
Alcoholic beverages & meals not specified
Personal expenses
Optional Activities

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.

This is a real 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.

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. Rain or shine, your trusty crew will always be on hand to assist you.

Also, If you do enjoy a late night out, consider booking a hostel 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.


Trip Length
11 nights/ 12 days
Travel Style
Comfort/ Sailing
Physical Rating
All Ability Levels
Starting at $2795