Sailing Tours with Drinks in Greece: 15 Worth the Sea Air

Santorini: Sailing Catamaran Cruise with BBQ and Drinks

1.Santorini: Sailing Catamaran Cruise with BBQ and Drinks

★★★★★★★★★★4.7 · 1,452 reviews · 5 hours · from $117Top of the fleet

You’ll cruise Santorini aboard a luxury catamaran with an English or Greek-speaking crew, stopping at Red Beach, Mesa Pigadia, Palea Kameni, and the hot springs. Expect three swim stops, snorkeling gear, towels, a BBQ, wine, soft drinks, and sunset views. Maria, Neta, and Liz are among the crew members praised for warm, attentive service.

“This was excellent!!!! We wished there was an all day option. The crew on board, our driver, the people answering all my crazy questions on WhatsApp, were fantastic. They were even able accommodate a vegan diet which we were so thankful for as well. This is a top notch company and it shows. For anyone visiting Santorini looking for a great cruise look no further.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

2.Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Lowest fare aboard

Choose a shared half-day sail to Dia Island, a private yacht trip, or a one-hour coastal cruise from Heraklion. The Dia route includes lunch, unlimited water, soft drinks and local wine, plus snorkeling, paddleboards, and optional fishing. Crew members may include Stavroula, Dennis, Mido, or Miso.

“A very choppy crossing to the island. Very well handled by the skipper though The boat was comfortable and safety was well looked after Food was very good. Would have been nice to have beer as an option perhaps Time went very quickly”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

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

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

Spend about five hours sailing from Ammoudi or Athinios, with hotel pickup, swims near the volcano, Red Beach and White Beach, plus a BBQ buffet, Santorinian wine, soft drinks and music. The later departure may include sunset views toward Oia. Expect a lively boat with up to 55 passengers, shade, restrooms and snorkeling gear.

“Not sure this was the right trip for us. Didn't know was a party catamaran. However the company running this do have a more semi private opinion The BBQ was very good, actually enjoyed it and the crew was very good too Just the experience was not enough. A bit more could have been better The snorkeling equipment was not clean”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

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

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

From Gouvia Marina, sail northeast on a small yacht with an English or Greek-speaking skipper. Swim at Barbati and Gialiskari, try a supervised cliff jump, explore a blue cave, and enjoy sandwiches, fruit, and soft drinks. Boats hold up to 12 people, with private trips available. Bring snorkel gear, towels, and sunscreen.

“We absolutely loved this boat trip, very chilled and relaxed and beautiful views, our guide (Ari) was brilliant and fun too😁”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

5.Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

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

Join Sailing Grace for a six-hour cruise from Heraklion to Dia Island. You’ll sail with an English or Greek-speaking crew, hear island legends, swim, snorkel, fish, paddleboard, and eat a Mediterranean meal onboard. Hotel pickup is available, and afternoon departures can include a sunset return.

“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 Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

6.Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

★★★★★★★★★★4.5 · 608 reviews · 6 hours (approx.) · from $145

Spend about six hours sailing from Mykonos to Rhenia and Delos. Swim from the yacht in clear Aegean water, use the free snorkel gear, eat lunch with wine and soft drinks, then tour Delos with a licensed English-speaking guide. The group can reach 35 people, though yacht size and numbers vary.

“Thld was the highlight of our trip--swimming in the Mediterranean Sea with my son. The crew of Chris, Thanos and The Captain (I don't want to butcher his name) was incredibly hospitable with our 3 yr old. The only very minor complaint was the extended 2 hrs stay on Delos given the heat, but that's just Greece. The whine was minor, and my child just hung at the boat. Hopefully you are as lucky as us and we were with 2 other amazing families that we really enjoyed sharing the boat with......the other boat looked miserable based on the demanding and rude guests at check-in (lol & dodged that boat).…”

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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

7.Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 560 reviews · 5 hours (approx.) · from $145Best loved

Spend about five hours on a catamaran sailing Santorini’s caldera, with hotel pickup, swim stops at Red or White Beach, warm volcanic springs, a Greek BBQ, and unlimited beer, wine, and soft drinks. Morning departures leave Vlichada Marina, while afternoon sailings begin near Akrotiri and may include sunset views.

“Great half day event with excellent crew. Definitely must do in Santorini! Two stops for swimming, dinner and sunset - everyhting was just perfect. Me and my kids enjoyed this trip.”

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Dia Sailing Cruise With All-inclusive Meal And Drinks

8.Dia Sailing Cruise With All-inclusive Meal And Drinks

★★★★★★★★★★4.6 · 422 reviews · 5.5 hours · from $76

Sail from Heraklion’s Old Venetian Port to uninhabited Dia Island on a 5.5-hour cruise led by an English-speaking crew. Swim, snorkel, paddleboard, and enjoy pasta with shrimp, Greek salad, fruit, wine, soft drinks, and water. Day and sunset departures are available, with hotel transfers by prior arrangement.

“You know those nights that just feel… perfect? This was one of them. We set sail for Dia Island, hoping for one of those crazy-colorful sunsets. The sun was a little shy, but honestly? It didn’t even matter. The crew was amazing, making us feel so at home, and the food and wine were delicious. It was just one of those magical, simple moments that you never want to end.”

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Naxos: Sailing Cruise with Lunch & Drinks

9.Naxos: Sailing Cruise with Lunch & Drinks

★★★★★★★★★★4.8 · 347 reviews · 2 - 7 hours · from $188

Spend 2 to 7 hours aboard an Actionseaze sailing yacht with captains and crew such as Nikos, Eri, Xarris, Eric, and Harry. Swim and snorkel at weather-chosen stops near Naxos and Paros, eat a Greek lunch, and enjoy wine, beer, fruit, and coffee. The boat usually carries a small group, with private trips available.

“It was a beautiful boat and perfect weather conditions! The crew was sympathetic, the spots well picked and the food fitting. All in all amazing experience.”

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Rethymno: Sailing Catamaran Cruise with Meal & Drinks

10.Rethymno: Sailing Catamaran Cruise with Meal & Drinks

★★★★★★★★★★4.7 · 285 reviews · from $164

Sail from Rethymno Marina aboard DanEri Yachts’ spacious catamaran Karina for 6.5 hours. Expect welcome treats, music, WiFi, a swim stop near Georgioupoli, SUP boards, snorkeling gear, inflatables, a fresh Mediterranean lunch, and unlimited soft drinks, beer, and white wine. Hotel transfers are optional.

“Very happy with the trip, would really recommend! A small inprovement idea would be that it would be great if there was more variety in snacks and drinks. Overall a great experience!”

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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

11.Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 268 reviews · 5 hours (approx.) · from $229

Spend about five hours aboard a small catamaran from Vlychada Marina, with hotel pickup, swimming near Red and White beaches, views of the Venetian Lighthouse and Indian Head Mountain, hot springs at Nea Kameni, and a fresh BBQ lunch with beer, wine, and soft drinks. Day and sunset departures are available.

“Very good team with a very nice and professional crew! Had a great time!”

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Sail the Athenian Coastline on a Catamaran with Meal & Wine

12.Sail the Athenian Coastline on a Catamaran with Meal & Wine

★★★★★★★★★★5.0 · 165 reviews · 5 hours (approx.) · from $163

Spend five hours sailing from Alimos Marina along the Athenian Riviera with a maximum of 12 people. Swim and snorkel near Hydroussa and Vouliagmeni, use the SUP and kayak, and enjoy a freshly cooked Greek lunch. Captains Bill or Chris and hosts including Julia or Claudia provide the sailing and onboard service.

“This was an amazing trip! We will do this again! The Captain and chef was great! They took such great care of us! Everybody talked about how this was the highlight of our trip and we went on a cruise! Imagine a vacation before the vacation!”

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Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

13.Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

★★★★★★★★★★4.5 · 116 reviews · 5 hours (approx.) · from $114

Join Sunfos Alessia Yachting for a five-hour sailing trip from Agios Ioannis to Rhenia. You’ll pass Mykonos beaches, swim from the yacht, use free snorkeling gear, and eat a Greek buffet with wine, beer, and soft drinks. Crew names vary, with Costas, Joanna, Bobi, Foti, and others praised on past departures.

“It was a great excursion. Everyone enjoyed themselves and would certainly do it again. The staff was great as well.”

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Single day Sail boat cruise with swimming, snorkeling, drinks and lunch

14.Single day Sail boat cruise with swimming, snorkeling, drinks and lunch

★★★★★★★★★★5.0 · 68 reviews · from $116

Spend about seven hours aboard Thetis I, sailing from Rhodes Town along the island’s east coast. Captains George, Adonis, and their crew choose scenic bays for swimming and snorkeling, then serve a fresh lunch with water, soft drinks, beer, and wine. The boat carries up to 10 people, making this a calm, personal day on the Aegean.

“Our captain Adonis and hand artimis , were lovely , very helpful and knowledgeable with local history and information of the coves and caves we explored, everything was very relaxed , plenty of beers and soft drinks for all and great food at lunch , would highly recommend, when I return to Rhodes we will call on them again , thanks for a great day”

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Sailing Nafplio | All Inclusive Half-Day Cruise

15.Sailing Nafplio | All Inclusive Half-Day Cruise

★★★★★★★★★★5.0 · 67 reviews · 4 hours 30 minutes (approx.) · from $144

Spend about four and a half hours aboard a small sailing boat from Nafplio, with a maximum of nine people. Pass close to Bourtzi Castle, hear about its past, then swim and snorkel near Romvi Island. Gear, snacks, drinks, and some food are provided, with the cruise returning to the harbor.

“This was easily one of our favourite days on our 2 week holiday. We had the whole boat to ourselves as a group of nine. Easy to find the meeting point with free parking at the port. The 2 staff were really friendly and took us to two lovely secluded areas for swimming and snorkelling. The weather was hot but there was shade if needed on the boat. Drinks and nibbles were perfect! Would definitely recommend!”

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