WINE TOURS

15 Wine Sailings Worth Rearranging a Trip For

100 sailings  ·  from $29 a head

The good boats go first and the cheap seats go fastest of all. Below: 15 wine sailings worth booking ahead, what each includes and where they differ once you are aboard.

2 Hour Lisbon Sunset and Wine Sailing Tour - Belém Tower from the river
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2 Hour Lisbon Sunset and Wine Sailing Tour

1.2 Hour Lisbon Sunset and Wine Sailing Tour

★★★★★★★★★★5.0 · 2,680 reviews · 2 hours (approx.) · from $66Our pick

Sail from Alcântara for about two hours with up to 12 people, passing Belém Tower, Jerónimos Monastery, Ajuda National Palace, the 25 de Abril Bridge, and Cristo Rei. Skippers such as Joe, Henry, JP, and Marta offer informal Lisbon commentary while Portuguese wine is served. Bring warm layers, and allow extra time to find the marina office.

“The guide (JP) was very knowledgeable, and the tour was very relaxing. This was such a nice evening getting to know the other riders, and enjoying the atmosphere.”

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Premium Morning Snorkel Sail with Champagne Brunch - Stop one: clear water and an easy introduction
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Premium Morning Snorkel Sail with Champagne Brunch

2.Premium Morning Snorkel Sail with Champagne Brunch

★★★★★★★★★★4.5 · 2,036 reviews · from $85

Meet at Pelican Pier at 9 a.m. for a four-hour catamaran sail with breakfast, lunch, mimosas, an open bar, and three snorkeling stops. Expect tropical fish, possible sea turtles, a shipwreck, and support from a lively crew. The third-lung system offers extra underwater time without a private charter price.

“Good excursion, good staff! We visited 3 spots (the ship, Tres Trapi and Boca Catalina). We enjoyed the 4h hour trip!”

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Porto: Charming Sailboat Cruise with Port Wine,Sunset Option - Gaia, Serra do Pilar, and Porto’s famous bridge
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Porto: Charming Sailboat Cruise with Port Wine,Sunset Option

3.Charming Sailboat Cruise with Port Wine,Sunset Option

★★★★★★★★★★5.0 · 1,978 reviews · 2 hours · from $41

Join Douro Captain for a two-hour small-group or private cruise from Douro Marina. Your English, Spanish, or Portuguese-speaking crew guides you past Ribeira, Gaia, the Dom Luís I Bridge, Foz do Douro, and the estuary. Expect port wine, music, panoramic views, blankets when needed, and a possible Atlantic dolphin sighting.

“That was a once in a lifetime experience. Sipping a drink while on a sailboat watching the sunrise names better thing”

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Lisbon: Champagne Sailing Tours - Under the 25 de Abril Bridge
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Lisbon: Champagne Sailing Tours

4.Champagne Sailing Tours

★★★★★★★★★★4.9 · 1,366 reviews · 2 hours · from $58

Join Nigel, Manuel, or another member of the Sailing with Nigel team aboard the 15-meter yacht Mara for a relaxed two-hour cruise from Doca de Santo Amaro. Sip Portuguese Champagne, wine, beer, or soft drinks, try the wheel under sail, and see Belém Tower, Christ the King, Alfama, and Lisbon’s waterfront from the Tagus.

“THIS WAS AMAZING. A SERIOUS MUST DO. I had the time of my life with my friend doing this sailing activity at sunset. It was BEAUTIFUL and the captain and skipper made it even better. They let us steer the boat, took pictures, didn’t let our glasses go empty, and were extremely funny and kind people. If you’re going to do anything in Lisbon, I would do this :)”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Setting sail with wine and small plates
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Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

5.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125

Spend about two hours sailing from 255 Front Street with a group capped at 26 people. The crew serves up to eight wines, five beers, soft drinks, and easy-to-eat hors d’oeuvres while sharing stories and tending to the boat. Recent sailings have featured crew members including Mary, James, Connor, Lexi, Tony, and Molly.

“Our sunset sail was perfect from start to finish. We absolutely loved the wine tasting and appetizers — you never know what you’re going to get on these types of excursions, and sometimes you brace yourself for cheap wine and sad snacks… but this was the total opposite. The wines were genuinely great bottles, and the cheese apps were delicious and beautifully done. We also adored our all-women crew. They were fun, warm, and made the whole experience feel extra special — the perfect vibe for a girls trip celebrating our 40ths. Would 100% recommend this sail to anyone looking for something elevated, relaxing, and unforgettable.”

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Lisbon Sunset Sailing Tour with White or Rosé Wine and Snacks - Doca de Santo Amaro and the first stretch upriver
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Lisbon Sunset Sailing Tour with White or Rosé Wine and Snacks

6.Lisbon Sunset Sailing Tour with White or Rosé Wine and Snacks

★★★★★★★★★★5.0 · 976 reviews · 2 hours (approx.) · from $50

Join BYX Best Yacht Xperience for a two-hour sunset sail from Doca de Santo Amaro. A certified crew, Portuguese wine, cheese, chouriço, music, and views of Belém, Cristo Rei, and the 25 de Abril Bridge set the tone. Guides such as Manuel, Vasco, Fernando, Anna, and Sergio have added local stories and humor to the ride.

“We had an excellent time. Can't thank enough for the operator who gave such a wonderful time! They are so professional and curious people! Book your next boat trip with them without any hesitation! Keep up the good work guys!”

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Lisbon: Sunset Sailing Cruise with Wine - Lisbon’s waterfront from a different angle
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Lisbon: Sunset Sailing Cruise with Wine

7.Sunset Sailing Cruise with Wine

★★★★★★★★★★4.9 · 800 reviews · 2 hours · from $64

Join an English- or Portuguese-speaking crew for a relaxed two-hour sail on Lisbon’s Tagus River. Sip a welcome glass of wine, watch the city turn gold, and see landmarks such as Belém Tower and the riverside monuments from the water. The crew may share local stories, and private groups are available.

“a fantastic trip - the guided were great fun, we laughed and learnt a lot about the history of Lisbon too. Would highly recommend!”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Passing Mallory Square and Key West’s western shore
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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

8.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Sail from Key West’s Historic Seaport on a catamaran with Captain Daniel, John, Jordan, Gracie, and other rotating crew members. Look for wild dolphins, pass Mallory Square, Fort Zachary Taylor, and Sunset Key, then settle in for sunset with wine, champagne, beer, and tapas including shrimp cocktail. Dolphin sightings and sailing under wind are not guaranteed.

“Best couple hours during our entire vacation. Sunset, dolphin, drinks, snacks, romantic,, picture perfect.”

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Champagne Sunset Sail from Margaritaville - Champagne, PainKillers, and the open bar
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Champagne Sunset Sail from Margaritaville

9.Champagne Sunset Sail from Margaritaville

★★★★★★★★★★4.5 · 691 reviews · from $130

Set sail from Margaritaville at 4:30 p.m. aboard a modern catamaran for a two-hour sunset cruise around St. Thomas. Enjoy champagne, wine, rum punch, PainKillers, mixed drinks, soft drinks, and passed appetizers while the crew keeps the mood lively. Captains and crew members such as Big Tuna, Danny Boy, Carolina, Dawn, and Noel have earned warm praise for their service.

“The staff last night was excellent. Michael made sure we experienced the perfect sunset! The drinks were plenty and the apps tasty! Daniel was charming, Dawn accommodating and “Adam sandler” super sweet . the only thing I would change is the amount of time… leaving at 4:30 on the nose would’ve given more boat time but other than that? perfection”

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Lisbon: Sunset Sailing with Portuguese Wine and History - Starting beneath the 25 de Abril Bridge
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Lisbon Sunset Sailing with Portuguese Wine and History

10.Lisbon Sunset Sailing with Portuguese Wine and History

★★★★★★★★★★5.0 · 668 reviews · 2 hours (approx.) · from $54

Join a small shared sailboat from Doca de Santo Amaro for a two-hour sunset cruise along Lisbon’s Tagus River. Guides such as Pedro and David share stories about the city while you see Belém Tower, the 25th April Bridge, Christ the King, Alfama, and Praça do Comércio. Vinho Verde, iced tea, water, and blankets are included.

“David and Pedro were brilliant hosts. Tjey were friendly, knowledgable, and took the time to get to know everyone on board. The sunset was amazing as was the company, and the wine. We would 100% recommend for anyone who wants to see the sights of Lisbon!”

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Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine - Meeting the crew beneath the 25th of April Bridge
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Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine

11.Sailboat Tour w/ Local Guide and Open Bar Green Wine

★★★★★★★★★★4.9 · 625 reviews · 2 hours · from $35Best value

Cruise the Tagus on a 33-foot sailboat limited to eight passengers. Local guides such as Andre, Mariana, Francisco, and Felipe share Lisbon stories in English, Portuguese, or Spanish while you enjoy Portuguese Vinho Verde, music, sofas, and views of Belém Tower, the Discoveries Monument, Almada, Alfama, and Commerce Square. Sunset departures are the best choice.

“The guides were beautiful people that gave a beautiful experience. Extremely thoughtful, courteous, and very kind. Very skilled sailor and gave the absolute best tour. I am so thankful to have found these people beautiful. It was a very nice highlight to my first trip to Portugal! Highly recommended!”

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Marseille: Sunset Sailing Cruise with Dinner and Wine - Frioul’s sheltered cove is the heart of the evening
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Marseille: Sunset Sailing Cruise with Dinner and Wine

12.Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.7 · 453 reviews · 1 day · from $64

Join the Goélette Alliance at Marseille’s Old Port for an evening sail toward the Frioul archipelago. Swim in a sheltered cove, enjoy a fresh vegetarian buffet with a glass of Provençal rosé, listen to music, and watch the city lights appear on the return. Fabio is one of the guides, and the crew speaks English, French, and Italian.

“A very nice sunset cruise, the buffet dinner was good only they offered pasta and rice with focaccia so Italian food…no fish at all. The atmosphere on the boat was great as well as the crew, they were friendly and professional, they had the sails hoisted by some of the passengers so that they had the impression to be part of the crew. All well organized, I definitely recommend this tour!”

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Marseille: Calanques Sailing Day Trip with Lunch and Wine - Boarding with coffee and Marseille navettes
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Marseille: Calanques Sailing Day Trip with Lunch and Wine

13.Calanques Sailing Day Trip with Lunch and Wine

★★★★★★★★★★4.8 · 411 reviews · 7 hours · from $159

Spend a full day aboard the historic sailing yacht Le Don du Vent, leaving from pier 2 beside Marseille City Hall. Your French and English-speaking crew takes you toward Sormiou, Morgiou, Sugiton, or La Côte bleue, depending on conditions. Swim, snorkel, enjoy a vegetarian buffet prepared onboard, and sip organic white wine and rosé in the sun.

“Everything was wonderful. The entire staff were friendly and accommodating. I would highly recommend taking some sort of anti-nausea medication before setting sail though. Shout out to Sam who was hilarious and very kind!♥️”

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Barcelona Sailing Adventure and Small Group Winery Tasting Tour - Starting at Port Olimpic
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Barcelona Sailing Adventure and Small Group Winery Tasting Tour

14.Barcelona Sailing Adventure and Small Group Winery Tasting Tour

★★★★★★★★★★4.5 · 394 reviews · from $132

You’ll sail from Port Olimpic toward El Masnou, then visit a family-run Alella winery in a 14th-century house. Expect four local wines, Catalan food, vineyard and cellar time, and a return by luxury minibus. The sailing portion may come first or last, depending on weather and tour operations.

“This was so incredible. The wine tour staff was super friendly and knowledgable and we loved our boat captain! I'm so happy we woke up just in time because this experience was by far my favorite of the trip. Not to mention everyone else part of the group was excellent and friendly!”

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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine - Capo Caccia and the Coral Riviera
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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

15.Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

★★★★★★★★★★5.0 · 360 reviews · 7 hours (approx.) · from $169

Spend about seven hours aboard the 86-year-old wooden tall ship Andrea Jensen, sailing from Alghero with Colin and Rachel. See Capo Caccia’s cliffs, stop in a clear bay for swimming and snorkeling, and enjoy a freshly prepared two-course lunch with wine, beer, soft drinks, and water. The group is limited to 12 people.

“A wonderful day trip on a beautiful boat, with some freshly prepared lunch and opportunities to snorkel and enjoy the water - would highly recommend!”

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