Greece · SAILING

15 Sailing Trips in Greece Worth Booking

118 tours  ·  from $57 a head

Good sailing trips fill up weeks ahead and the great ones go first. Below: the 15 to book early, what each includes and how they differ.

Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers - Mesa Pigadia: the first real swim stop
BBQ, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Sailing, 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

Review of Santorini’s 5-hour catamaran cruise with Red and White Beach, hot springs, BBQ, wine, swimming, 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 - Swimming by the volcano and Santorini Hot Springs
Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Half-Day, Sailing, Santorini Tours, Tour Reviews

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

Sail Santorini’s coast on a small catamaran with swimming stops, hot springs, BBQ seafood, open bar, transfers, and sunset views.

“Amazing tour! Everything from start to finish was absolutely perfect. Captain Giannis, Natalie and Alex were phenomenal and gave us the best experience. Would highly recommend!”

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Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar - Red Beach, red cliffs, and Greek meze
BBQ, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Sailing, Santorini Tours, Tour Reviews

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

Sail Santorini’s caldera by catamaran, swim at Red Beach and hot springs, snorkel, enjoy a Greek BBQ, and sip unlimited wine for five hours.

“Great ride with great views and stories. Guides were wonderful. Boat was fun and refreshing. Swimming/snorkeling was very cool! Plenty of fish to see! And food was incredible.”

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

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 to protected Dia Island for swimming, snorkeling, paddleboarding, a Greek meal, drinks, and sunset views.

“Here’s a smoother, more natural version of your text: This was the last day of our trip through Crete, and we ended it in the best way possible. The cruise was incredible, the weather was perfect, and the crew and food were fantastic. It was everything I wanted and more. We were having so much fun that we didn’t even have enough time to try all the activities - which is actually a good thing!”

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Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Hotel pickup is useful, but allow extra time
Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Sailing, Santorini Tours, Tour Reviews

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

Sail Santorini’s caldera, swim at volcanic hot springs, enjoy a Greek meal and open bar, then watch the sunset from a catamaran.

“The whole thing was extremely well coordinated from pick up to drop off. This cruise was one of the biggest highlights of our time in Greece. The crew was amazing and our group was really fun. The swimming was so fun The meal was delicious and the final sunset was simply magical. Thank you for a wonderful memory”

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Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ - What the small boat setting feels like
Athens Tours, BBQ, Catamaran Cruises, Catamaran Cruises in Athens, Cruises & Boat Tours, Sailing, 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

Review of Athens’ luxury catamaran cruise with hotel pickup, swimming stops, Greek BBQ, open bar, snorkeling, and sunset sailing.

“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 - Arriving at Dia and the Gulf of Saint George
Crete Tours, Cruises & Boat Tours, Lunch Experiences, Sailing, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - White Beach, lunch, and the best stretch of swimming
BBQ, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Evening Experiences, Private Drivers, Sailing, 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

Review of Santorini’s 5-hour sunset catamaran cruise with swimming, hot springs, Greek BBQ, unlimited drinks, hotel transfers, and practical tips.

“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 - Boarding the catamaran and setting the tone
BBQ, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Evening Experiences, Sailing, Santorini Tours, Sunset Cruises, Sunset Cruises in Santorini, Tour Reviews

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

Review of Santorini’s 5-hour sunset catamaran cruise with hotel pickup, swimming stops, BBQ, drinks, snorkeling, and Oia sunset views.

“What an absolutely brilliant day we had on this trip! We were looked after from the time the booking was made to the time we came off the boat. We had opportunities to swim in the clear blue sea and saw the most gorgeous sunset! Thank you to everyone on board!”

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Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer - Thirasia and the caldera from sea level
BBQ, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Private Drivers, Sailing, Santorini Tours, Tour Reviews, VIP

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

Half Day Premium Catamaran Cruise in Santorini including Oia - Starting with Red Beach and its volcanic colors
Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Sailing, 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, Thirassia, BBQ, open bar, and sunset views.

“Very good boat experience. We had a nice relaxing time. Did some swimming in the Sea. It was nice and refreshing. The crew was terrific. Lunch was very nice. Swam in the hot springs which were kind of warm here and there. From the description I was under the impression we were walking up to the volcano, snorkeling and walking around the town of Oia. We didn’t snorkel which was okay with me but I was looking forward to. We saw the Volcano but didn’t walk up to it and didn’t stop at red beach either like it was advertised. For those reasons have to give it four stars. It…”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach brings the first clear-water swim
Corfu Tours, Cruises & Boat Tours, Sailing, Tour Reviews

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

Review of Corfu’s small-group sailing trip from Gouvia, with swimming, snorkeling, cliff jumping, blue caves, snacks, and soft drinks.

“The directions given on how to find the yacht were not clear enough. We also had to wait for 3 guests to arrive, they were in wrong place. I found it difficult to get to the correct pier. The trip was really nice, very chilled and relaxed. Our skipper - Thassos was a real character, very knowledgable of area and entertaining, loved the cliff jumping display! He also made us lovely sandwiches and fruit!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - The crossing to Dia Island
Crete Tours, Cruises & Boat Tours, Sailing, 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

Review of Heraklion’s Dia Island sailing cruise, with snorkeling, SUP, a Greek meal, drinks, hotel pickup, and sunset views.

“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 - Rhenia swim stop and clear Aegean water
Catamaran Cruises, Catamaran Cruises in Mykonos, Cruises & Boat Tours, Mykonos Tours, Sailing, Tour Reviews

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

Review of Mykonos catamaran cruise to Rhenia with lunch, drinks, water toys, hotel transfers, and possible Delos views.

“The whole experience was amazing! The catamaran was beautiful, the staff was exceptional, and the scenery breathtaking. The crew gave a history lesson of Delos as we passed by. We then had a stop where we could swim, snorkel, and paddle board in the Aegean Sea. The dinner they prepared on board was absolutely delicious! Would highly recommend this excursion.”

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