The 15 Sailing Trips in Greece That Earn Their Price

BBQ, Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Sailing, Things to Do in Santorini, Tour Reviews, Tours

Santorini: Catamaran Tour with BBQ Dinner, Drinks, and Music

/ August 8, 2026

1.Catamaran Tour with BBQ Dinner, Drinks, and Music

★★★★★★★★★★4.6 · 5,886 reviews · 5 hours · from $93Our pick

5-hour Santorini catamaran with Red and White Beach swims, BBQ dinner, unlimited white wine, drinks, music, and sunset views.

“I booked this trip for 5 of us. This trip was excellent, the staff were very friendly & helpful. We got to get in the sea at several stops & the food was very good. All 5 of us loved the experience & we’re pleased we booked the sunset trip. I would recommend this Tour.”

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BBQ, Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Drinking Tours, Private Drivers, Sailing, Things to Do in Santorini, Tour Reviews

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

/ August 8, 2026

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

★★★★★★★★★★5.0 · 4,209 reviews · 5 hours (approx.) · from $151.16Top rated

Premium small-group Santorini catamaran with BBQ, open bar, and multiple swim stops, plus sea-level caldera views and optional sunset sail.

“Watching the sunset in Santorini is always beautiful, especially from a Catamaran. On this trip you will get three Swim stops at about 10-15 minutes each x 3. Very nice experience. George was a great guide. The food was delicious and views very nice. This trip also offers transport to and from, which is very convenient. One thing to note, we had 21 people on our boat to give you sense of the crowd. We were thinking it would be 20 or fewer based on the booking description. Overall great experience.”

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BBQ, Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Private Drivers, Sailing, Things to Do in Santorini, Tour Reviews

Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

/ August 8, 2026

3.Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

★★★★★★★★★★5.0 · 3,933 reviews · 5 hours (approx.) · from $114.88

Santorini catamaran cruise with BBQ, wine and drinks, plus swims at Red Beach area, hot springs, and a caldera volcano route.

“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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1-Day Tours, Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Day Trips from Santorini, Drinking Tours, Sailing, Things to Do in Santorini, Tour Reviews, VIP

Santorini: Luxury Catamaran Day Trip with Meal and Open Bar

/ August 8, 2026

4.Luxury Catamaran Day Trip with Meal and Open Bar

★★★★★★★★★★4.8 · 3,678 reviews · 5 - 6 hours · from $129

Sail a luxury Santorini catamaran for swimming in volcanic hot springs, snorkel stops, and a Greek meal with an open bar, at sunset or morning.

“This was one of the highlights of our trip. The boat was very well maintained, the trip was well organized and the food was delicious. We made multiple stops to swim and snorkel And got to know fellow travelers!”

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Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Drinking Tours, Half-Day, Sailing, Things to Do in Santorini, Tour Reviews

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

/ August 8, 2026

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

★★★★★★★★★★5.0 · 2,975 reviews · 5 hours (approx.) · from $133.02

Half-day Santorini catamaran with hotel pickup, Red Beach and hot springs swims, plus BBQ meal and open bar drinks onboard.

“Mika, Kostas, and Bill were phemoniminal! We had such a blast! The food was tasty, the stories and history were memorable, the sense of humor brought everyone on the catamaran together. I have never experienced something like this and 10/10 I reccomend ^_^”

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BBQ, Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Drinking Tours, Sailing, Things to Do in Santorini, Tour Reviews

Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar

/ August 8, 2026

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

★★★★★★★★★★4.8 · 2,822 reviews · 5 hours · from $117

Santorini Gold catamaran from Vlychada with snorkeling, Red and White beaches, volcano hot springs, BBQ and open bar.

“We had a lovely time. The crew were fab! Would have preferred longer swim stops, especially as the third one clashed with the BBQ tea. Had a great day though and would recommend to everyone. Thank you!”

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Boat Tours in Crete, Cruises & Boat Tours, Dia Island Sailing Trips, Sailing, Things to Do in Crete, Tour Reviews

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

/ August 8, 2026

7.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95

Small-group sailing from Heraklion to Dia Island for swimming, snorkeling, SUP, and a Mediterranean meal with unlimited drinks.

“It was amazing experience. Definitely a highlight of my vacation. Mariana and Manos was fun and helpful. Good food and beautiful views.”

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Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Sailing, Santorini Caldera Cruises, Things to Do in Santorini, Tour Reviews

Santorini: Catamaran Caldera Cruise with Meal and Drinks

/ August 8, 2026

8.Catamaran Caldera Cruise with Meal and Drinks

★★★★★★★★★★4.7 · 2,255 reviews · 5 hours · from $70

Santorini catamaran caldera cruise with hotel transfer, snorkeling stops, hot springs, and onboard BBQ plus an open bar, 5 hours from Ammoudi.

“We really enjoyed our day, the food was amazing, and the staff were lovely”

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Boat Tours in Rhodes, Catamaran Trips, Cruises & Boat Tours, Lunch Experiences, Sailing, Things to Do in Rhodes, Tour Reviews

Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks

/ August 8, 2026

9.All-Inclusive Catamaran Cruise with Lunch and Drinks

★★★★★★★★★★4.8 · 2,002 reviews · 6 hours · from $83

All-inclusive Rhodes catamaran cruise with snorkeling bays, Greek buffet lunch, and unlimited wine and beer from noon, 6 hours.

“The crew, the food, the drinks, the whole experience everything was 5 stars, absolutely wonderful day and I would genuinely recommend this trip to anyone! Thankyou so much!”

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Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Sailing, Sunset Cruises in Santorini, Things to Do in Santorini, Tour Reviews

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

/ August 8, 2026

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

★★★★★★★★★★5.0 · 1,694 reviews · 5 hours (approx.) · from $181.39

Small-group Santorini catamaran with Greek meal, open bar, hot springs and Red Beach swim stops, plus optional sunset views.

“What a terrific tour! Everything was great, the staff, the food (pork) and the stops. One of the best things we did in Santorini.”

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Cruises & Boat Tours, Full-Day, Lunch Experiences, Sailing, Things to Do in Milos, Tour Reviews, Tours

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

/ August 8, 2026

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

★★★★★★★★★★4.9 · 1,646 reviews · 10 hours · from $147

Full-day Milos and Polyaigos cruise from Adamas with Kleftiko cave snorkeling, boat-only swims, and lunch and drinks included.

“LOVED this activity! The tour was exceptional with our hosts working diligently to ensure everyone was having a great time (they even provided sea sickness tablets before departure just in case, plus our guide Dora was sooo charming and charismatic). The swimming spots were awesome and sheltered from the wind as much as possible. Food was also excellent. A bit on the expensive side, but worth it for a full day tour with all foods and drinks included.”

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BBQ, Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Sailing, Things to Do in Santorini, Tour Reviews

Santorini: Sailing Catamaran Cruise with BBQ and Drinks

/ August 8, 2026

12.Sailing Catamaran Cruise with BBQ and Drinks

★★★★★★★★★★4.7 · 1,452 reviews · 5 hours · from $117

Santorini catamaran cruise with BBQ, drinks, snorkeling stops, hot springs, guided volcano views, and timed Aegean sunset.

“The most amazing day and experience. The food was amazing Liz. The staff were exceptional would highly recommend.”

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BBQ, Boat Tours in Santorini, Catamaran Trips, Cruises & Boat Tours, Sailing, Things to Do in Santorini, Tour Reviews, Tours

Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks

/ August 8, 2026

13.Catamaran Tour with BBQ Meal and Unlimited Drinks

★★★★★★★★★★4.8 · 1,449 reviews · 5 hours · from $153

5-hour Lagoon 450 catamaran in Santorini with hot springs swim, two beach stops, BBQ and unlimited drinks, plus Oia sunset views.

“We had a great time, the staff were friendly and made the trip fun, the boat was spotless, delicious food and wine. Everything was perfect, from being picked up from the hotel to being dropped off back at the hotel. The highlight was seeing fish while snorkeling and swimming in the sea.”

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