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.

“We had an amazing time with our group! The staff is fantastic and very knowledgeable of the area. The food is fresh, boat very clean!”

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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.

“Great day and the food was exceptional. The weather was not the greatest with quite windy conditions but our superb crew adapted and made the most of the day. The sunset was great and overall I can definitely recommend this tour.”

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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

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

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 had a group of seven, the weather could not have been any better. The crew were friendly and helpful. The cruise was fun. Saw a lot of sites. The food was amazing and more than plenty to eat. Enjoyed the sunset tremendously. We drove ourselves. It was a little bit hard to find with…”

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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.

“I recently went on a catamaran cruise, and it was an absolutely wonderful experience. The atmosphere on board was very pleasant, and the people made the trip even more enjoyable. The crew was extremely friendly and attentive, always making sure that everyone felt comfortable and well taken care of. The food was delicious, fresh, and…”

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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.

“it was sooo fun! the itinerary was perfect, a great mix of swimming spots and iconic landmarks. it was very interesting learning about milos too! our host dora was great and the trip was much more fun bc of her. definitely recommend”

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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

10.Santorini: Sailing Catamaran Cruise with BBQ and Drinks

4.7

Sail past Santorini’s Red and White Beaches, snorkel hot springs and the caldera, then enjoy BBQ and drinks on a luxury catamaran.

“I booked this trip at the very last minute, and the team stepped forward in the most awesome ways. First, the woman at the office was very helpful, she quickly arranged transportation after we landed at the airport (they picked us up in 9 minutes!) My friend is 83 years old and walks a little…”

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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

11.Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks

4.8

A small-group Lagoon 450 catamaran cruise with hot-spring swim, two beaches, BBQ and unlimited drinks, and Oia sunset.

“The deckhands and stewardess were all nice and very accommodating. We enjoyed the fact that it was a smaller group of 12 people. The lunch buffet was also surprisingly very good and well put together. Just keep an eye on the weather as we went on a windy day with choppy waters. Some in our…”

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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 sunset cruise was our favorite part of our three days in Santorini. Oia is beautiful but crowded, so spending time in a more relaxed environment with minimal people was great, and every other person on the excursion was polite and friendly. Staff was wonderful, the included food was good and bathrooms and the entire…”

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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.

“The food was yummy and the crew was very hospitable. The swim at the hot springs is only about 20 minutes. There is sulfur in the water which might turn white clothes yellow and tarnish certain jewelry, so be mindful of what you wear. Don’t plan to see much if snorkeling. Just enjoy the views,…”

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