Greece · SAILING

The 15 Sailing Trips in Greece That Earn Their Price

68 tours  ·  from $58 per person

Every trip has one free day too few. These 15 sailing trips earn the slot, priced and timed so the decision takes minutes.

Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers - Mesa Pigadia: The First Swim Stop
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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 $115Our pick

Review of Santorini’s 5-hour catamaran cruise with Red Beach, hot springs, swimming, Greek BBQ, drinks, sunset views, and hotel transfers.

“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 - Red Beach, where red cliffs meet blue water
Boat Trips in Santorini, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Drinking Tours in Santorini, 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 volcanic coast on a five-hour catamaran cruise with swimming, snorkeling, BBQ lunch, open bar, and hotel transfers.

“You get picked up by a nice van and arrive at the boat. The crew were amazing. The boat was amazing, we sat in the front and laid on the nets. The views were amazing. 3 swimming spots, 2 snorkeling and one volcanic hot springs (not super hot but still warm!) The sunset view was incredible. The food was out of this world. plus…. all the beer and wine you want!”

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Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar - Red Beach and the First Swim
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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

Review of Santorini’s Gold Catamaran Cruise, with Red Beach swims, hot springs, snorkeling, BBQ, open bar, and hotel pickup.

“The experience was 10/10. This was one of the excursions we did for our honeymoon. The views were beautiful and food was great. Some things I would love to share for the next group: - One of the stops to swim is near the volcano, they don’t suggest you wear light color swimwear because of sulfur in the water. - Bring a light jacket/sweater for the ride back if you are doing sunset. - They provide everything, water,’sodas, beer, wine, a light app, and dinner. - They have a room downstairs to change too. Ammos, and the crew were amazing. So friendly and genuine.”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why 14 people changes the day
Boat Trips in Crete, Crete Tours, Cruises & Boat Tours, Sailing, Sailing Trips, Sailing Trips in Crete, 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

Review of Crete’s Dia Island sailing cruise from Heraklion, with swimming, snorkeling, paddleboarding, a Greek meal, drinks, and sunset options.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks - Anthony Quinn Bay, clear water and plenty of fish
Boat Trips in Rhodes, Catamaran Cruises, Cruises & Boat Tours, Lunch Experiences, Rhodes Tours, Sailing, Tour Reviews

Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Pickup, marinas, and the real timing
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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

Review of Santorini’s 5-hour catamaran cruise with Greek meal, wine, swims, hot springs, caldera views, and optional sunset.

“What a wonderful evening with the Summer boat crew. They were so kind and fun with everyone on board. The food they cooked for us was amazing. We had six in our group with some other guests, but it felt like a private excursion. The round trip transportation was perfect from our hotel.”

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Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ - First swimming stop, with towels already waiting
Athens Tours, BBQ, Boat Trips in Athens, 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 $206

Review of Athens’ 5-hour luxury catamaran cruise, with hotel pickup, Greek BBQ, open bar, two swim stops, 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 Saint George Bay on Dia Island
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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 from Heraklion to Dia Island for swimming, snorkeling, lunch, unlimited drinks, and relaxed yacht time on Crete’s clear waters.

“I loved the sailing trip and the time we had to swim. The skipper and first mate were friendly and professional. The meal was healthy and delicious. The crew provided a quick safety talk, rules of the vessel, and tips for a successful sailing trip. This was a great afternoon that I was sad to see end.”

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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Red Beach: Santorini’s first swimming stop
BBQ, Boat Trips in Santorini, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Evening Experiences, Private Drivers, Private Drivers in Santorini, Sailing, Sailing Trips, 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

Review of Santorini’s five-hour luxury catamaran cruise with swimming, snorkeling, Greek BBQ, drinks, hot springs, and sunset views.

“Such a fun tour. Swimming in the hot springs was a unique experience and the waters around the island were so clear it. Got to see a lot of fish. The food was also super delicious!”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Passing the volcano and Palea Kameni
BBQ, Boat Trips in Santorini, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Evening Experiences, Sailing, Sailing Trips, Sailing Trips in Santorini, 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 $96

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

“Sunset tour was absolutely amazing. Stopped at a couple of places to snorkel and the water was so clear you could see down 30’. Food was good and plenty of it. Met very nice people and the whole boat had a great time listening to music and dancing. Sunset was fantastic as pretty much all sunsets in Santorini are.”

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Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer - Thirasia and the caldera from sea level
BBQ, Boat Trips in Santorini, Catamaran Cruises, Catamaran Cruises in Santorini, Cruises & Boat Tours, Drinking Tours, Drinking Tours in Santorini, Private Drivers, Private Drivers in Santorini, 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 - Red Beach: a quick first swim
Boat Trips in Santorini, 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 dinner, drinks, and sunset views.

“This is definitely worth the money and half of your day. It’s the perfect way to see the island views that Santorini is so famous for. The foods fresh and yummy. Captain Giomnis, Alexander, Maria, Nefeli were a delight and always made sure you had a bevy in hand. The sunset of course was absolutely gorgeous!”

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

Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - The crossing to Dia Island takes its time
Boat Trips in Crete, Crete Tours, Cruises & Boat Tours, Sailing, Sailing Trips, 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, Greek food, drinks, and sunset views on a six-hour yacht cruise.

“This was a fabulous trip. The staff were very friendly and committed to making sure everyone had a good time. They boat was fantastic and their were enough activities to keen everyone entertained during the cruise. Food was fantastic too. Highly recommend this tour to anyone in Heraklion for the day.”

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Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport - Getting to Agia Anna and Boarding the Catamaran
Boat Trips in Mykonos, 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’ five-hour catamaran cruise to Rhenia, with lunch, drinks, swim stops, water toys, Delos views, and hotel transport.

“We booked a Mykonos Catamaran cruise during our overnight stay on the Virgin Voyages Greek Glow itinerary, and it was absolutely fantastic. From start to finish, the crew was incredibly friendly, welcoming, and accommodating. The entire experience was smooth, relaxing, and truly memorable. We had a wonderful time and would highly recommend this tour to anyone visiting Mykonos!”

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