Greece · SAILING

The 15 Best Sailing Trips in Greece

58 tours  ·  from $58 a head

Every trip has one free day too few. These 15 sailing trips justify the slot, priced and timed so you can decide in minutes and get back to the fun part.

Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers - Mesa Pigadia brings the first swim
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Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

1.Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

★★★★★★★★★★5.0 · 3,933 reviews · 5 hours (approx.) · from $114Our pick

Spend about five hours sailing from Vlychada past Red Beach, White Beach, Mesa Pigadia, the hot springs, and Santorini Volcano. You’ll have swimming and snorkeling time, towels, equipment, hotel transfers, and a Greek BBQ with wine and soft drinks if you choose the food option. Sunset departures add a memorable finish.

“I unfortunately was not able to go on the experience due to a last minute sickness but the customer service is phenomenal! They helped me adjust the booking, were extremely accommodating and were helpful in offering other suggestions for activities during our trip. Nothing but good things to say about them!”

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Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar - Lighthouse views and the approach to the volcano
Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Half-Day, Sailing, Tour Reviews, Tours in Santorini

Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar

2.Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar

★★★★★★★★★★5.0 · 2,975 reviews · 5 hours (approx.) · from $133

Spend about five hours aboard a catamaran from Vlychada Marina, stopping at Red Beach, the hot springs, and Thirassia. Swim, snorkel, eat shrimp, mussels, Greek salad, pasta, and BBQ food, and enjoy local wine and beer. Guides such as Giannis, Natalie, Alex, Mika, Kostas, and Bill are known for lively service and island commentary.

“Have pick-up service, good arrangement, nice food, nice music, well introductions for Santorini. Although the weather wasn’t very well, me and my family still having so much fun.”

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Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar - White Beach, the lighthouse, and volcanic rock
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Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar

3.Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar

★★★★★★★★★★4.8 · 2,822 reviews · 5 hours · from $117

Spend five hours aboard a small Vista Yachting catamaran, with room for about 16 people, visiting Red Beach, White Beach, the Venetian lighthouse, volcanic hot springs, and Mesa Pigadia. You get snorkeling gear, towels, Greek meze, a fresh BBQ, unlimited soft drinks and white wine, an English-speaking guide, and hotel pickup.

“It was great, I’d do it again, especially since it was too cold to swim, so we decided to come back in the summer to do a do-over. Highly recommend!”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - The one-hour sail from Heraklion to Dia
Cruises & Boat Tours, Dia Island Boat Trips, Sailing, Tour Reviews, Tours in Heraklion

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

4.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95

Sail from Heraklion’s Old Venetian Harbour to protected Dia Island on a yacht limited to 14 passengers. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos provide a relaxed day of swimming, snorkeling, paddleboarding, Greek food, unlimited drinks, and optional sunset views.

“Amazing experience!! The food and staff were amazing, the location is stunning, we had the most beautiful day”

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Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks - Sailing or power catamaran: choose by the kind of day you want
Catamaran Cruises, Cruises & Boat Tours, Lunch Experiences, Sailing, Tour Reviews, Tours in Rhodes

Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks

5.All-Inclusive Catamaran Cruise with Lunch and Drinks

★★★★★★★★★★4.8 · 2,002 reviews · 6 hours · from $83

Set out from Mandraki Harbor on a sailing or power catamaran with up to 24 passengers. Swim at Anthony Quinn Bay, Ladiko, Kalithea Springs, and, on the power route, Afandou Caves. The crew serves breakfast snacks, a Greek-style buffet, fruit, wine, beer, and soft drinks throughout the day.

“The first stop we got to swim. It was amazing, crystal clear waters. Floats and snorkels provided. It was excellent. And then the unimaginable happened. Heavy rain which was forecasted swept through. This ruined our day but at no fault of the company. Staff were very good, explaining options. The rain lasted a good 1 and a half hours so the captained had asked us if we wanted to wait it out and he’ll try and get us an extra stop in. We waited it out and the sun finally came out. By this point I had given up hope and got changed. The kids on board though got an…”

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Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Choosing between morning and sunset
Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Sailing, Tour Reviews, Tours in Santorini

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

6.Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

★★★★★★★★★★5.0 · 1,694 reviews · 5 hours (approx.) · from $181

Spend about five hours on a shared Santorini catamaran with hotel pickup, a Greek meal, white wine, Greek beer, sodas, and swim stops at Palea Kameni and Red Beach. Choose a morning or sunset departure. Some luxury sailings pass beneath Oia and Ammoudi Bay, though you stay aboard rather than visiting the town.

“Amazing! They were super friendly, the boat was immaculate, the views were beautiful and the food was delicious. They grilled to order our lunch and had amazing wine and snacks. Would 100% recommend. Loved the music too!”

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Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ - Getting from Athens to Alimos Marina
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Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ

7.Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ

★★★★★★★★★★5.0 · 1,346 reviews · 5 hours (approx.) · from $205

Spend about five hours sailing from Alimos Marina along the Athens Riviera in a catamaran limited to 10 people. Enjoy two swim stops, towels, snorkeling gear, an open bar, and a fresh Greek BBQ with salad, vegetables, shrimp saganaki, and grilled meats. Choose a lunch cruise or sunset dinner, with hotel pickup and return included.

“Beautiful & serene trip. Great captain & first mate and wonderful food❤️ My wife and I had an amazing time.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - The one-hour sail toward Dia Island
Cruises & Boat Tours, Dia Island Boat Trips, Lunch Experiences, Sailing, Tour Reviews, Tours in Crete

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

8.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.9 · 1,287 reviews · from $90

Sail about an hour from Heraklion to Dia Island on a shared or private yacht. Swim and snorkel in Saint George Bay, try fishing, enjoy lunch, fruit, local wine, and soft drinks, then return by sea. Crew members such as Marcos, Vasilis, Alexandra, and Dimitry have helped make these cruises warm and personal, though the crew can vary.

“Great activity. Thoroughly enjoyed and the crew were amazing. Food was excellent, couldn’t have asked for better”

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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - White Beach and a Greek meal cooked on board
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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

9.Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

★★★★★★★★★★5.0 · 1,170 reviews · 5 hours (approx.) · from $133

You’ll sail from Vlychada on a spacious catamaran with a maximum of 20 passengers. Swim at Red and White Beach, visit volcanic hot springs, enjoy a freshly prepared Greek barbecue, and watch the sunset near Oia. Hotel pickup, snorkeling gear, towels, drinks, and return transport are included.

“The entire crew was incredible. This is an amazing way to see Santorini from a different perspective. Nichole was amazing, and prepared an outstanding meal for all of us on board”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Sailing beside the volcano and Palea Kameni
BBQ, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Evening Experiences, Sailing, Sunset Cruises, Sunset Cruises in Santorini, Tour Reviews, Tours in Santorini

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

10.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95

Spend about five hours aboard a catamaran with hotel pickup, swimming stops at the hot springs, Red Beach, and White Beach, plus a BBQ, wine, soft drinks, and music. Captain Sakis and crew members Giannis and Orestis have been praised for their friendly service. Choose the later departure if seeing sunset near Oia matters most.

“Overall it was ok. The food was good along with the views. Music was load and it could’ve been shorter. Those looking for a quiet ride around seeing the sites this is not for you.”

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Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer - Thirasia and the caldera from sea level
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Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer

11.Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer

★★★★★★★★★★5.0 · 1,047 reviews · 5 hours (approx.) · from $169

Sail with Spiridakos Sailing Cruises from Ammoudi Bay or Vlychada Port, stopping at Palea Kameni’s hot springs, Mesa Pigadia, White Beach, and the caldera. Your crew provides towels, snorkeling gear, a buffet of Greek dishes, local wine, beer, and cocktails. Groups are capped at 20, with guides such as Captain Leo, Heleni, and Louis reported on different sailings.

“The scenery. The crew was amazing and the meal great. Would suggest adding a few light snacks during the cruise and a wider selection of alcohol for those of us who are not beer or wine drinkers. Windy day but the crew kept us safe.”

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Half Day Premium Catamaran Cruise in Santorini including Oia - Red Beach and the first swim
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Half Day Premium Catamaran Cruise in Santorini including Oia

12.Half Day Premium Catamaran Cruise in Santorini including Oia

★★★★★★★★★★5.0 · 988 reviews · 5 hours (approx.) · from $193

Sail Santorini’s caldera aboard a small catamaran limited to 18 people. Swim near Red Beach and the volcano, snorkel by Thirassia, enjoy a BBQ dinner and open bar, and see Oia and the Venetian lighthouse from the water. The exact route and timing can change with the cruise schedule.

“It was great. I'm glad. Great memory. Lovely crew. A little bit expensive for what it is anyway. The towels are provided, I had not paid attention I had brought mine.Auto-translated”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Gialiskari: snorkeling, lunch, and the cliff jump
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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

13.Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Set out from Gouvia Marina on a small yacht with a skipper such as Ari or Savvas. Swim at Barbati and Gialiskari, try a supervised cliff jump, explore a blue cave, and enjoy sandwiches, fruit, and soft drinks. Groups are limited to about 12 people, with alcoholic drinks available to buy.

“The boat ride was excellent with Ari! We went to 3 amazing swimming spots! The water was gorgeous and sail boat was perfect!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Dia Island: clear water, rocky hills, and a quiet beach
Cruises & Boat Tours, Dia Island Boat Trips, Sailing, Tour Reviews, Tours in Heraklion

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

14.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Spend six hours sailing from Heraklion to Dia Island with an English- and Greek-speaking crew. Swim, snorkel, fish, paddleboard, hike, and eat a fresh Mediterranean lunch onboard. Hotel pickup is available, and afternoon departures can include a sunset sail back to port.

“FANTASTIC!!! HIGHLY RECOMMENDED!!! the trip to and Dia was an iregular trip(rough sea) ( but very safe) but the interaction with the crew was out of this world! we have spent 3 hrs (or so) by the Island of Dia snorkeling, paddling, diving... drinking. nice company as well beautiful meal plenty drinks Thank you Captain Nick "BARBOSSA" 1ST MATE KRISTINA 1ST MATE IORGU”

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Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport - Passing Delos from the water
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Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport

15.Brand-New Catamaran Cruise with Meal, Drinks & Transport

★★★★★★★★★★5.0 · 777 reviews · 5 hours (approx.) · from $180

Spend about five hours aboard the brand-new Aerial or White Coral catamaran, cruising from Mykonos toward Rhenia and possibly past Delos. Expect a freshly cooked three-course lunch, wine, beer, soft drinks, swimming, snorkeling, and weather-dependent SUP and kayaking. Transfers are available if you submit your pickup details at least 24 hours ahead.

“We had an amazing time on the boat. The staff were really friendly and welcoming. The meal provided was delicious. Thanks for a good time!”

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New in Sailing

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★ 5.0Catamaran Semi Cruise Paros Antiparos includes Food and DrinksFrom $326208 reviews
★ 4.8Spinalonga PM Catamaran Cruise with DinnerFrom $13488 reviews
★ 5.0Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transferFrom $157201 reviews
★ 5.0Island Hopping: Santorini Catamaran Charter Cruise with a skipper136 reviews
★ 5.0Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)From $120197 reviews
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★ 5.0Mykonos Catamaran Private Day Cruise, Full Lunch & Open-barFrom $79684 reviews
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★ 5.0Catamaran Full-Day of Milos and Poliegos With Lunch & BBQFrom $217262 reviews
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