The 11 Best Sailing Trips

1.Santorini: Catamaran Caldera Cruise with Meal and Drinks

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

Spend five hours aboard a catamaran from Ammoudi Bay, passing the caldera, volcano, hot springs, Aspronisi, lighthouse, and southern beaches. Swim or snorkel at several stops, then enjoy fresh Greek appetizers, BBQ skewers, wine, soft drinks, and music, with hotel transfer available.

“I was hesitant at first to take another catamaran journey on another vacation on another island. I thought once you do one you've done them all. I was COMPLETELY wrong. This is such a unique experience to take in the essence of how beautiful Santorini truly is. Being able to see the South side of the island and see the beauty that exists on the Black, White & Red beaches was surreal. Getting an opportunity to swim/snorkel in the Aegean Sea was breathtaking. And, getting to feel the water temperature difference as we docked by the volcano was awesome. Tack on an authentic Greek barbecue was a good way to…”

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

★★★★★★★★★★5.0 · 1,694 reviews · 5 hours (approx.) · from $181Top rated

Spend about five hours aboard a shared catamaran with a Greek skipper and crew, swimming at Palea Kameni and Red Beach, eating grilled chicken or pork with salads and pasta, and sipping wine or Greek beer. Choose a morning or sunset sailing, with luxury options adding Oia and Ammoudi Bay.

“What an incredible evening!!!! From the moment we got on the boat, the crew was focused on giving us the best experience possible. The boat stopped to let us swim three times and each experience was unique including the volcanic hot springs. The BBQ was delicious including chicken, shrimp, salad, pasta, grape leaves - and they had no issue with my dairy allergy. The evening concluded with a sunset that was simply breathtaking. Thank you to the wonderful crew for giving us this incredible memory. Book this trip immediately!!!”

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3.Lake Taupo: Classical Sailing to the Māori Rock Carvings

★★★★★★★★★★4.8 · 1,275 reviews · 2h 30m · from $35

Set out from Taupō Marina for 2.5 hours aboard Fearless, a classic sailing yacht, or a catamaran when conditions require it. Hear local stories from guides such as Aaron, Liam, or Danny, view the 14-metre Ngātoroirangi carving, swim in clear lake water, and enjoy a complimentary drink.

“We had a wonderful cruise with great captain and crew who gave us their undivided attention because we happened to be the only 2 people booked on our cruise! It was smooth with no wind which meant only one sail was up for a short time, but this didnt spoil the fabulous experience on Lake Taupo. We learnt so much about the lake and also the town”

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4.Ras Mohamed & White Island luxury Yacht Trip Sharm el Sheikh

★★★★★★★★★★4.5 · 997 reviews · from $25Best value

Cruise from Sharm el Sheikh to Ras Mohamed National Park and White Island on a yacht, with two guided snorkeling stops, a buffet lunch, soft drinks, and an optional 15-minute introductory scuba session. Ahmed is one instructor singled out for patient help. Hotel pickup and return are included.

“This tour was amazing. Really well organised and very friendly staff. We had a hotel pickup with good communication, then they took us to the marina and we boarded the yacht. I was with my nephews, one is a baby, and the staff were extremely helpful with them. I tried scRead more”

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5.Santorini: Catamaran Caldera Cruise with Meal and Drinks

★★★★★★★★★★4.8 · 980 reviews · 5 hours · from $112

Spend five hours aboard a luxury catamaran with swimming stops at the Red and White Beaches, the Caldera, and volcanic hot springs. Your crew handles the sailing, snorkeling gear, towels, Greek meal, dessert, and open bar. Choose a daytime outing or sunset cruise from Vlychada.

“Very enjoyable. Family had a great time. We had 3 Dimitris in the boat. ( captain and 2 crews). They all went above and beyond to ensure that we are taken care of. They are always asking us if we need anything. The sunset view was amazing! The music they played while the sun was setting was meaningful and moving. The food could be better but we are here for the experience. Absolutely love this sunset cruise!”

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6.Maori Rock Carvings Eco Sailing Taupo

★★★★★★★★★★5.0 · 758 reviews · from $33

Sail from Taupō with Chris or Pete aboard a small eco-friendly electric yacht, then reach the 14-meter Ngātoroirangi Mine Bay Māori Rock Carvings by water. The 2.5-hour cruise includes lake stories, volcano views, a complimentary drink, and time for a swim in warm weather.

“This trip is a super relaxing and cost effective way to see the beautiful rock carvings on Lake Taupo. Chris is a very engaging captain and host, hugely knowledgeable and passionate (about sailing as much as the lake and Māori culture). If it’s sunny in Taupo, this is a must do.”

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7.Snorkeling trip to Ras Mohamed & The White Island aboard Luxury Yacht

★★★★★★★★★★5.0 · 479 reviews · from $70

You’ll sail from Sharm el Sheikh to Ras Mohamed National Park and White Island on a spacious yacht, with one or two snorkeling stops, a seafood buffet, drinks, hotel transfers, and playful water activities. Bring or rent snorkeling gear, and confirm pickup and any VIP extras before departure.

“The tour we received was not the tour we booked. The initial hotel pick up was late and in doing so we endured a speeding scary ride to the port, including double backing for nearly 40minutes. We specifically booked this tour as it was advertised with an English tour guide, Read more”

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8.Santorini: Caldera Classic Catamaran Cruise w/ Meal & Drinks

★★★★★★★★★★4.8 · 379 reviews · 5 hours · from $123

Cruise Santorini’s caldera for five hours aboard a comfortable catamaran, with stops at Red Beach, White Beach, Mesa Pigadia, and Nea Kameni. Enjoy snorkeling gear, towels, a Greek barbecue, unlimited local wine and soft drinks, and an evening sunset or relaxed morning return.

“I would never have an opportunity to be on a private yacht. This was amazing experience of a lifetime. We had a pick up and drop off from our hotel. Everything was planned top notch from getting on a boat, having towels , cabins to changed and freshly cooked meal . We had excellent time”

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9.S’Arenal: Sunset Catamaran Cruise with BBQ

★★★★★★★★★★4.5 · 338 reviews · 3 hours · from $88

Set sail from Playa de S’Arenal on a modern catamaran for a relaxed three-hour trip through Palma Bay. Swim and snorkel near Cala Vella, enjoy a BBQ with pasta salad and bread, and watch the sunset near Cap Enderrocat with water, beer, or sangria included.

“My experience on the **S'Arenal: Sunset Catamaran Cruise with BBQ** was nothing short of exceptional! From start to finish, the entire evening was a perfect blend of relaxation, stunning views, and delightful culinary experiences.”

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10.Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

★★★★★★★★★★4.5 · 328 reviews · 5 hours (approx.) · from $114

Sail Santorini’s caldera for about five hours, stopping near Red and White beaches and the volcano’s thermal springs. Enjoy a Greek barbecue, Santorinian wine, beer, and soft drinks, then watch sunset near Oia. Hotel transfers, towels, Wi-Fi, and a small-group setting are included.

“This was an excursion not to be missed. The boat and staff were exceptional and the meal served on the boat was delicious. The opportunity to just jump off the boat and swim in the caldera and also get a chance to do some snorkeling was just awesome. The boat was in the best position possible for a fantastic sunset over the Aegean. Worth the money and time for sure.”

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11.Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

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

Spend five hours sailing from Vlychada Marina past Red and White beaches, the lighthouse, and volcanic islands. Swim near the caldera, visit warm springs, and eat a seafood and steak BBQ with unlimited beer, wine, and soft drinks. Hotel pickup is included, with day and sunset departures.

“Amazing tour, staff really sweet, food delicious and a lot of plates we didnt eat everything. Views are incredible, really worth it. We had an amazing time i would do it again !”

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