7 Charters with a Private Skipper Worth Flying For

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

★★★★★★★★★★5.0 · 1,170 reviews · 5 hours (approx.) · from $133Our pick

Spend about five hours aboard a spacious catamaran with hotel pickup, swimming stops at Red and White beaches, volcanic hot springs, snorkeling, a freshly cooked Greek barbecue, and unlimited drinks. Choose the sunset sailing for sea views of Oia, with room for no more than 20 people.

“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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2.Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 422 reviews · 5 hours (approx.) · from $133

Cruise Santorini’s caldera aboard a catamaran for about five hours, stopping near the hot springs, White Beach, and Red Beach. Your crew serves a Greek barbecue with wine, beer, and soft drinks, while towels, snorkeling gear, and hotel transfers simplify the day. Routes can change with weather.

“We had a great day with sunset Oia! Pick up and drop off from the hotel was made so easy and straightforward. The bbq on the boat was nice and authentic. The staff were great and explained the history of every stop on the boat. Great day overall! Highly recommended.”

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3.Symi Yacht Tour with Unlimited Drinks and Transfer

★★★★★★★★★★4.8 · 380 reviews · 8 hours · from $141

Spend eight hours sailing from Rhodes to Symi with a crew of up to 25. You’ll have about two hours in Symi Town, Greek lunch and unlimited drinks aboard, plus swims at St. George Bay and Seskli Island. Crew members including Anna, Antonio, and Emily have been praised for warm, attentive service.

“memorable experience. The three different locations were all unique and offered something special. Symi Island was absolutely stunning, and the snorkelling in the bay afterwards was a real highlight. The staff made the day even more enjoyable — they were genuinely warm, friendly, and full of positive energy. You could tell they love what they do. A quick tip: if you’re prone to seasickness, definitely bring tablets with you. The journey out can be quite rocky and takes a bit of time — but it’s 100% worth it once you arrive.”

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4.Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer

★★★★★★★★★★5.0 · 310 reviews · 5 hours (approx.) · from $157

Spend about five hours aboard the Ipanema 58, Santorini’s only catamaran of its kind. Swim near the hot springs, snorkel by Red and White Beaches, eat a homemade Greek barbecue, and watch the sunset with drinks included. Pickup, towels, gear, and an English-speaking crew are provided.

“The yacht was fancy and there was enough space for everyone. The crew was very friendly and responsive to our needs. The food was good. The drinks were okay but we wish there was more variety in the drinks like champagne. No sunset which was unfortunate but still a great experience in Santorini.”

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5.Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer

★★★★★★★★★★5.0 · 201 reviews · 5 hours (approx.) · from $157

You’ll sail from Ammoudi Port beside the volcano, Palea Kameni, Red Beach, and White Beach on a five-hour catamaran cruise. Hotel pickup, Greek BBQ, drinks, towels, snorkeling gear, and flotation devices are included. The English-speaking crew keeps the day relaxed and social.

“This tour was amazing!! The sites were beautiful, food was delicious and the boat crew were top notch! I would highly recommend this tour/cruise to anyone! Best experience in Santorini!”

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6.Halong Bay Day Tour With Sunlight Luxury Cruise With Transfer

★★★★★★★★★★5.0 · 136 reviews · from $62Cheapest seat

Spend about six hours on Halong Bay aboard the Sunlight luxury cruise, with hotel pickup, seafood buffet lunch, Sung Sot Cave, kayaking or a bamboo boat at Luon Cave, Titop Island, and a sunset snack service. Expect a long day with roughly five to six hours on the road.

“I booked this tour after carefully researching a premium 1-day experience for my family, but what we received was a nightmare. Despite my wife informing the staff three times before boarding that we were booked for the 1-day tour, we Read more”

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7.Luxury Catamaran to Balos: Sunset, Snacks, Drinks & Transfer

★★★★★★★★★★4.9 · 99 reviews · 4 - 5.5 hours · from $127

From Kissamos, you sail to Balos Lagoon aboard a spacious catamaran with sunbeds, shaded lounges, snacks, drinks, SUP boards, snorkeling gear, and a waterslide. An English-speaking crew and onboard animator keep the trip lively, while the return voyage brings sunset views over Crete.

“The boat trip was amazing! The crew did everything to make sure we had a great time, and the trip itself was super fun. We enjoyed delicious food and got to see some beautiful places. We’d definitely do it again!”

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