Greece · SAILING

Sailing Trips in Greece: 15 Days Under Canvas

64 tours  ·  from $58 a head

Wind, a small group, and swimming stops that no road reaches. These 15 sailing days are compared on boat size, how many hours the engine stays off, and what the skipper puts on the table at lunch.

Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers - Palea Kameni hot springs require a short swim
BBQ, Boat Tours in Santorini, Catamaran & Sailing Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Sailing, Sailing Trips in Santorini, Santorini Tours, Tour Reviews

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

Sail Santorini’s caldera by catamaran with Red and White Beach views, swimming, hot springs, a Greek BBQ, drinks, and hotel transfers.

“The tour was great! The team is super friendly and wanted you to enjoy the experience. Just one clarification- it is 5 hours including the car ride so the actual boat tour is 3hr ish.”

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Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar - The Venetian Lighthouse and the caldera view
Boat Tours in Santorini, Catamaran & Sailing Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Half-Day, Sailing, Sailing Trips in Santorini, Santorini Tours, Tour Reviews

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

Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar - Starting at Vlychada Marina
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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

Cruise Santorini’s caldera by catamaran, swim at Red Beach and hot springs, snorkel, enjoy a Greek BBQ, and watch the sunset with drinks included.

“The best way to experience Oia sunset! Our guide, host and captain were very nice and made everything memorable as possible. I love the vibe the bring during the tour specially the music part. And the food was delicious!”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why the 14-person limit matters
Boat Tours in Crete, Crete Tours, Cruises & Boat Tours, Sailing, Sailing Trips in Crete, Tour Reviews

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks - Choosing sailing or power catamaran
Boat Tours in Rhodes, Catamaran & Sailing Cruises, Catamaran Cruises in Rhodes, Cruises & Boat Tours, Lunch Experiences, Rhodes Tours, Sailing, Sailing Trips in Rhodes, Tour Reviews

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

Cruise Rhodes’ east coast by catamaran, with three or four swim stops, Greek lunch, unlimited drinks, and snorkel gear included.

“Really amazing trip. Smooth booth ride around the east coast. Really fun and would go again. Food was delicious. Guides and crew were lovely, informative and great people. The swimming stops were super special. We sat on the upper deck and it was perfect, highly recommend getting first on so you can get a great spot on the boat”

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Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Palea Kameni and the warm volcanic pools
Boat Tours in Santorini, Catamaran & Sailing Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Sailing, Sailing Trips in Santorini, Santorini Tours, Tour Reviews

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

Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ - The first swimming stop
Athens Tours, BBQ, Boat Tours in Athens, Catamaran & Sailing Cruises, Catamaran Cruises in Athens, Cruises & Boat Tours, Sailing, Sailing Trips in Athens, Tour Reviews, VIP

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

Sail Athens Riviera waters on a small-group catamaran with hotel pickup, swimming stops, open bar, and a freshly cooked Greek BBQ.

“Really fabulous, tasty food, wine beer and sodas, great crew, beautiful Athens coast, 2 swim stops with snorkel equipment and towels, hotel pick-up drop-off, great communication throughout. Would highly recommend this trip!!”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Saint George Bay and Dia Island
Boat Tours in Crete, Crete Tours, Cruises & Boat Tours, Lunch Experiences, Sailing, Sailing Trips in Crete, Tour Reviews

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

Review of Heraklion’s Dia Island sailing cruise, with snorkeling, lunch, unlimited drinks, yacht comfort, timing, and practical booking tips.

“This activity was amazing, great communication from the get-go, staff were lovely and very knowledgeable, the transport shuttle was on time and quick, the boat and Dia Island were stunning and the food and drinks were great - especially if you like a sweeter white wine!”

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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Red Beach, where volcanic rock meets clear water
BBQ, Boat Tours in Santorini, Catamaran & Sailing Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Evening Experiences, Private Drivers, Private Drivers in Santorini, Sailing, Sailing Trips in Santorini, Santorini Tours, Tour Reviews, VIP

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

Sail Santorini’s caldera at sunset with swims, hot springs, a fresh Greek barbecue, open-bar drinks, hotel transfers, and a small group.

“One of the best experiences we have experienced. The staff were friendly, food was amazing. Live BBQ, music and the vibe. The most beautiful sunset was witnessed. This should be one of the experiences booked when visiting Santorini.”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Sailing beside the volcano and Palea Kameni
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer - Pickup is useful, but plan around the early meeting time
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Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer

Half Day Premium Catamaran Cruise in Santorini including Oia - Red Beach: a quick swim beside rust-colored cliffs
Boat Tours in Santorini, Catamaran & Sailing Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Sailing, Sailing Trips in Santorini, Santorini Tours, Tour Reviews

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

Review of Santorini Star Sailing’s 5-hour catamaran cruise, with Red Beach, hot springs, swimming, BBQ dinner, open bar, and Oia views.

“This is a great way to experience the beauty of Santorini. The crew and other passengers were friendly and helpful. The boat was clean and in great condition and not too crowded to enjoy the experience. We are a family of six with kids ages 10-19 and this was perfect for evreyone...until the sunset. The end of the trip was just too long. We could have started slightly later (by and hour or more) and still had time to stop and swim at the different locations, then see the sunset and head back. We were picked up at 2 and dropped back off after 10, making it a really long…”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Leaving Gouvia Marina for the northeast coast
Boat Tours in Corfu, Catamaran & Sailing Cruises, Catamaran Cruises in Corfu, Corfu Tours, Cruises & Boat Tours, Sailing, Sailing Trips in Corfu, Tour Reviews

Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

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

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

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, a Mediterranean lunch, drinks, and sunset views aboard a small yacht.

“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on board at the harbour and at the island had a chance to try snorkelling and SUP for the first time. Lunch was prepared while we swam and we had plenty of chance to sunbathe without feeling under pressure to do anything to a schedule. The whole experience was so relaxing, we felt like welcomed guests…”

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Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport - Sailing toward Rhenia or Mykonos southern coast
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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

Cruise from Mykonos to Rhenia on a spacious catamaran with lunch, drinks, swim stops, hotel transfers, and views of Delos.

“Such an amazing day! A once in a lifetime experience made even better by Captain Adonis and crew. The boat helped make the experience better because it was huge, modern and super comfortable. There were probably 20 guests and we were all able to spread out comfortably, but still socialize. There were probably 20 guests and we were all able to spread out comfortably, but still socialize. The food was ok. The drinks flowed.”

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The Aegean, the Ionian and everything inland

Start with a coast, a ruin or a kitchen.