Sailing

GREECE

15 Best Sailing In Greece

The Greek classics.

The 15 most popular sailing in Greece, with what each one is really like on the day, who runs it, and what it costs.

15 Best Sailing In Greece

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer - The Red Beach and White Beach photo run (and why it’s actually smart)

1.Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

Most Popular★ 5.0

Small-group catamaran cruise in Santorini with BBQ, open bar, and multiple swim stops including the hot springs near Akrotiri and Thirasia.

“Amazing experience!! Beautiful sunset, great food, and fun swimming. Capitan and crew were so much fun and made sure everyone was having a blast throughout the evening! Must do!!!”

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Santorini: Luxury Catamaran Day Trip with Meal and Open Bar

Santorini: Luxury Catamaran Day Trip with Meal and Open Bar - Snorkel and Swim Stops: What You’ll Do in the Water

2.Santorini: Luxury Catamaran Day Trip with Meal and Open Bar

★ 4.8

Luxury Santorini catamaran with hotel pickup, open bar, Greek lunch, snorkel stops, volcanic hot springs, and sunset views near Oia.

“We loved everything about this cruise The captain and crew were awesome The music played, the dinner on board was excellent and the views of Santorini are unbelievable. Stopped 3 times at some great swimming spots Would definitely recommend this activity”

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

Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar - Santorini volcano and hot springs: your warm-water reality check

Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar

Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar - White Beach views and the Venetian lighthouse from sea level

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

★ 4.8

5-hour Santorini catamaran cruise from Vlychada with snorkel stops, volcano hot springs swim, BBQ, and open wine bar. Hotel pickup.

“omg this is so amazing I can even tell you this is so good so good so good made my day the crew is all rounder constantly in serving and hospitality especially the lady amd other two guy pmg they click pics for you make you feel like home and the food is amazing they…”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Where you meet in Heraklion, and how timing works

5.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

★ 4.8

Small-group sailing from Heraklion to Dia Island with swim, snorkel, SUP, and a Mediterranean meal plus unlimited drinks in 5.5 hours.

“Absolute 5⭐️ all round. From the transfer to the sailing staff on the boat, the food, unlimited drinks, the views.. absolutely nothing to complain about. The staff were very welcoming and friendly and explained everything that was going to happen on the boat. When we got to the island we got a safety briefing before…”

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Santorini: Catamaran Caldera Cruise with Meal and Drinks

Santorini: Catamaran Caldera Cruise with Meal and Drinks - Pickup that actually works: from your hotel to the dock

6.Santorini: Catamaran Caldera Cruise with Meal and Drinks

★ 4.7

A 5-hour Santorini caldera catamaran cruise from Ammoudi with hotel transfer, snorkeling stops, BBQ, and open bar included.

“We done this for our 1 year anniversary It was fantastic, great vibes from the yacht team and great food, the views were amazing they gave us some facts on the places we visited too. We saw the sunset made some new friends too. Would highly recommend ! There was loads of opportunities to swim…”

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Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks

Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks - Sailing vs Power catamaran: choosing the right route for your day

7.Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks

★ 4.8

Rhodes all-inclusive catamaran cruise with snorkeling stops at Anthony Quinn Bay, Ladiko, Kalithea and optional Afandou caves, lunch and drinks.

“There were eight of us on the trip, and we were all very satisfied. The staff were very kind and helpful, the food was delicious, and the places we visited were absolutely beautiful. I highly recommend this experience to anyone who wants to spend a wonderful day on the water.”

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

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Price and value: what $181.39 buys you on the water

Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch - Sarakiniko and Glaronisia: The Volcanic Milos “Book Cover” Moments

9.Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

★ 4.9

A full-day Milos sail from Adamas with boat-only swimming, Kleftiko cave snorkeling, lunch in a wild setting, and Polyaigos water.

“This was an amazing experience! Milos is gorgeous in and of itself but Dora made the day extra fun! The music and food were both great and shout out to captain George! Dora had a fabulous assistant on board helping to serve us as well! The stops were amazing for swimming and sightseeing and Dora…”

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Santorini: Sailing Catamaran Cruise with BBQ and Drinks

Santorini: Sailing Catamaran Cruise with BBQ and Drinks - The morning vs sunset cruise: what changes and why you should care

Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks

Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks - Pickup and Getting to Ammoudi or Vlychada Without Stress

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island time: swimming and snorkeling that you’ll remember

Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ

Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ - Your Sea Route: Coast Views and Real Time to Relax

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

★ 5.0

Luxury catamaran cruise from Athens with hotel pickup, two swim stops, open bar, and a traditional Greek BBQ meal on the Aegean.

“The skipper and mate were wonderful hosts and prepared delicious fun. This is truly a relaxing experience with a small group, where you have time to talk and make friends, especially if you are a solo traveler. If you’re looking for a 1/2 day experience that you will want to book again, this is the…”

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

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Red Beach and White Beach: the real “vacation” part of the day

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

★ 5.0

Sail Santorini’s caldera on a luxury catamaran with hotel transfers, Red and White Beach swims, BBQ, drinks, snorkeling, and a sunset view.

“The trip was great! Good food, vine, beer and soft drinks. Nice and friendly staff. I wish the weather and water would be warmer, but hey its November...I highly recommend to take this tour. Especially sunset one.”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Getting Picked Up: The Santorini Logistics Win

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

★ 4.5

Sunset sailing catamaran in Santorini with hotel pickup, hot springs and beach swims, BBQ, and drinks as you chase Oia sunset views.

“This is a no brainer! BOOK THIS TOUR! Amazing staff, great food, fun environment and beautiful views. Side note, my wife often gets seasick and she felt great the entire time on the catamaran!”

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