Sailing trips · DRINKING TOURS

15 Sailing Trips with Drinks in the World Worth Booking

63 trips  ·  from $33 a head

This is the shortlist you would send a friend: 15 sailing trips with drinks worth the money, each with its price, its traveller verdict and the one thing to know before the lines come off.

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer - Mesa Pigadia, the first proper swim stop
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Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

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

★★★★★★★★★★5.0 · 4,209 reviews · 5 hours (approx.) · from $151Our pick

Spend about five hours aboard a small catamaran with a crew such as Captain John, George, or Elena. Swim at Mesa Pigadia and a quiet cove, visit the hot springs, view the caldera from sea level, and enjoy a BBQ buffet with Greek wine. Daytime and sunset departures are available.

“Absolutely incredible. The captain and crew on the Evanna could not have been better. Was a wonderful experience from start to finish”

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Santorini: Luxury Catamaran Day Trip with Meal and Open Bar - Red Beach and the first swim stop
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Santorini: Luxury Catamaran Day Trip with Meal and Open Bar

2.Luxury Catamaran Day Trip with Meal and Open Bar

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

Spend 5 to 6 hours aboard a luxury catamaran with a maximum of 20 people. Swim near Red Beach, White Beach, and the volcanic hot springs, then enjoy a Greek meal, open bar, music, and caldera views. Sunset trips include a cocktail and Oia sunset, with crews such as Evi, Giannis, and Angela helping set the mood.

“Nikos our captain, and our crew members Ilias, Giannis and Rafaela were amazing! This was an unforgettable experience for us on our honeymoon and the whole day was so great. The swim spots were awesome and our Greek feed was 10/10. Such an incredible day ☺️”

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Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - The Key West sights from the water
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Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

3.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79

Sail from Key West for about two hours aboard a spacious catamaran with sunset views, live local music, an open bar, shrimp, antipasti, mini tarts, and soft drinks. Arrive 30 minutes early, claim a good bow seat, and bring a sweater for breezy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

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Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar - The lighthouse and the volcanic caldera
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Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar

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

★★★★★★★★★★5.0 · 2,975 reviews · 5 hours (approx.) · from $133

You’ll sail from Vlychada Marina with a crew that may include Giannis, Alex, Natalie, Mika, Kostas, or Bill, depending on the boat. Expect Red Beach, the volcano, hot springs, Thirassia, snorkeling, a fresh onboard meal, open wine and beer, and hotel pickup.

“It was social and informative, and a wonderful way to see the landscape. The crew was beyond fantastic!! They made the entire experience genuinely fun and were beyond accommodating.”

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Isla Mujeres: Catamaran with Open Bar, Snorkeling and Lunch - Getting to Marina Las Perlas
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Isla Mujeres: Catamaran with Open Bar, Snorkeling and Lunch

5.Catamaran with Open Bar, Snorkeling and Lunch

★★★★★★★★★★4.1 · 2,848 reviews · 8 - 10 hours · from $59

Sail from Cancun to Isla Mujeres with a lively crew, national open bar, a short reef snorkel, Playa Norte time, and optional buffet lunch. Guides such as Juam, Ivet, Luis, and Romando have earned praise for keeping the day friendly and well organized, though the dock fee and crowded snorkel stop deserve attention.

“A really fun day out. The staff are very friendly and welcoming. Really fun vibe. Would highly recommend.”

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Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar - Red Beach and the first swim
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Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar

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

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

Sail from Vlychada Marina with an English-speaking guide and a small group, stopping at Red Beach, the White Beach area, the volcano hot springs, and Mesa Pigadia. You’ll get snorkeling gear, towels, a Greek BBQ, meze, soft drinks, and open white wine. Crews have included Hris, Filipos, Vivi, and Alice.

“The experience was 10/10. This was one of the excursions we did for our honeymoon. The views were beautiful and food was great. Some things I would love to share for the next group: - One of the stops to swim is near the volcano, they don’t suggest you wear light color swimwear because of sulfur in the water. - Bring a light jacket/sweater for the ride back if you are doing sunset. - They provide everything, water,’sodas, beer, wine, a light app, and dinner. - They have a room downstairs to change too. Ammos, and the crew were amazing. So friendly and genuine.”

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Dolphin Catamaran Snorkel and Sail with Open Bar - First stop: the Antilla shipwreck
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Dolphin Catamaran Snorkel and Sail with Open Bar

7.Dolphin Catamaran Snorkel and Sail with Open Bar

★★★★★★★★★★4.5 · 2,291 reviews · from $69

Sail aboard The Dolphin from Noord for a three-hour Aruba cruise with two snorkel stops at the Antilla shipwreck and Boca Catalina Bay. You get fresh gear, wraps, fruit, an open bar, a spinning slide, and rope swing. Crew members including Frederick, Oscar, Rio, Jay, and Brandon have earned warm praise.

“Whole Lotta fun! Catamaran beautiful. Snorkeling, swing and slide were great!! Drinks were good! Had a ball!”

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Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar - The route to El Arco and Lover’s Beach
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Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

8.Los Cabos Luxury Sunset Sail with Light Appetizers and Open Bar

★★★★★★★★★★5.0 · 2,267 reviews · 2 hours 30 minutes (approx.) · from $109

Sail Cabo San Lucas Bay for 2.5 hours on a 50-foot boat with up to 16 people. Expect the Arch, Lover’s Beach, sea lions, open-bar drinks, light appetizers, and a relaxed sunset setting. Pickup is available for $10 per person, with a $2 dock fee.

“Very well organized, the comisny was very responsive and accommodating. The pick up was right on time and everything about the logistics went smoothly. The sailboat was beautiful and the crew really great. The food and drink was also delicious! We even got to see whales. I’d highly recommend this sunset sail. It was a really, really great trip! I’d choice this company again and will remember them for the next time we come to Cabo”

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Barcelona: Midday or Sunset Sailing with Open Bar and Snacks - What the two-hour route feels like
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Barcelona: Midday or Sunset Sailing with Open Bar and Snacks

9.Midday or Sunset Sailing with Open Bar and Snacks

★★★★★★★★★★4.9 · 2,044 reviews · 2 hours · from $33Best value

Set sail from Marina Port Vell on a two-hour shared or private cruise with a skipper and crew. Enjoy cava, wine, beer, soft drinks, snacks, music, skyline views, and a swim when conditions allow. Sunset departures are especially appealing for couples, families, and small celebrations.

“Faith was an amazing captain. Sorry I don't remember the mattress name but she was equally amazing. They served some really great snacks, variety of wine, very and cava. The boat was clean and the weather was cooperative as well.”

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Aruba Sunset Sail with Appetizers and Open Bar - The open bar and included food
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Aruba Sunset Sail with Appetizers and Open Bar

10.Aruba Sunset Sail with Appetizers and Open Bar

★★★★★★★★★★4.5 · 2,024 reviews · from $92

Sail Aruba’s coast aboard a luxury catamaran from Piet’s Pier Bar at 5:30 pm. Enjoy Palm Beach views, unlimited drinks, finger foods, local music, dancing, and crew storytelling. Crew members such as Junior, Brandon, Lizzie, and Captain D are often praised for keeping the evening relaxed and fun.

“We have heard great things about this activity and had to test it out for ourselves! This experience was a blast and the crew was to thank for that! Drinks were flowing, vibes were high, and the views were something from a dream. If you are wondering if this is worth it…. My answer it is worth ever dollar and some!! Book it and you won’t regret it!”

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Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Sailing Across Santorini’s Caldera
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Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

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

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

Spend about five hours on a shared Santorini catamaran with hotel pickup, volcanic hot springs, Red Beach, swimming stops, a Greek meal, wine, beer, and soft drinks. Choose a morning or sunset sailing, with luxury options adding Oia and Ammoudi Bay views.

“Such an amazing experience with a friendly and knowledgeable crew. We would definitely recommend this sunset cruise to any of our friends who may come to Santorini in the future.”

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Barbados Catamaran Turtle Snorkel with Lunch and Open Bar - Carlisle Bay and the turtle search
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Barbados Catamaran Turtle Snorkel with Lunch and Open Bar

12.Barbados Catamaran Turtle Snorkel with Lunch and Open Bar

★★★★★★★★★★5.0 · 1,396 reviews · from $110

Spend about five hours aboard a small-group catamaran off Barbados. Snorkel near turtles, fish, stingrays, and shipwrecks, then enjoy a Bajan buffet, snacks, and an open bar. The crew, including captains such as Colin and Graham, provides gear and help in the water.

“Amazing, relaxing tour. We saw 2 different ship wrecks, plenty of fish and turtles. The crew was very attentive. There was not a moment that we did not have a beer in our hands from the time we got on the boat until we got off. Highly recommend this trip.”

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Isla Mujeres Catamaran Tour with Snorkel, Open bar and Transport - Sailing south toward El Meco reef
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Isla Mujeres Catamaran Tour with Snorkel, Open bar and Transport

13.Isla Mujeres Catamaran Tour with Snorkel, Open bar and Transport

★★★★★★★★★★4.5 · 1,275 reviews · 6 to 8 hours (approx.) · from $85

Sail from Playa Tortugas to Isla Mujeres on a shared catamaran with a guided El Meco reef snorkel, national open bar, buffet meal, music, and downtown free time. Crew members such as Javier, Sergio, and Joel have earned praise for friendly service, though weather, crowded water, and inconsistent transport can affect the day.

“The boating, snorkel, and island experience was good. The boat crew was amazing and friendly. But my largest complain is for the “SAT company”. Their communication and shuttle team is horrible. The pick up time initially gave a large window of 7am-9am. I spent a week messaging them every day asking for the time with no respond. In the middle of the night before, they decided to message me that pick up time is 9:05am with such a little notice. For the shuttle back, they were initially 30 minutes late. After the driver arrived, he had us sit in the shuttle for another 30 mins. We kept telling him that…”

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Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer - Thirasia and the caldera from sea level
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Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer

14.Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer

★★★★★★★★★★5.0 · 1,047 reviews · 5 hours (approx.) · from $169

Sail from Ammoudi Bay or Vlychada with Captain Leo, Heleni, or another Spiridakos crew member. Swim near Palea Kameni, Mesa Pigadia, and White Beach, enjoy a Greek BBQ buffet with wine and cocktails, and watch Santorini from the water with up to 20 passengers.

“Captain and crew were amazing! Great trip with beautiful scenery and swimming locations. Highly recommend making this part of your visit to Santorini.”

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Barcelona: Unique Sunset Sailing Tour with Tapas & Open Bar - The two-hour route along Barcelona’s coast
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Barcelona: Unique Sunset Sailing Tour with Tapas & Open Bar

15.Unique Sunset Sailing Tour with Tapas & Open Bar

★★★★★★★★★★4.7 · 959 reviews · 2 hours · from $66

Meet at Port Olimpic for a two-hour sunset sail along Barcelona’s coast. You’ll see the Sagrada Família, W Hotel, Montjuïc, Torre Glòries, and Barceloneta while enjoying three tapas per person, snacks, and drinks. Skippers such as Louigi and Cristobal may invite you to help steer.

“Wow!!! What a fab trip we had. Stunning weather, great company & our captain was so lovely & friendly. Food & drink was such a lovely touch too. Would highly recommend & definitely do again & again 😀”

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Luxury Yacht & Snorkel with All inclusive Open bar and lunch - Meeting the boat at Puerto Mágico
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Luxury Yacht & Snorkel with All inclusive Open bar and lunch

20★ 4.5Luxury Yacht & Snorkel with All inclusive Open bar and lunchFrom $119754 reviews
Mallorca: Midday or Sunset Sailing with Snacks and Open Bar - Four Hours Around Palma Bay
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Mallorca: Midday or Sunset Sailing with Snacks and Open Bar

21★ 4.7Midday or Sunset Sailing with Snacks and Open BarFrom $82733 reviews

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