Sailing trips · WINE TOURS

The 15 Best Wine Sailing Trips in the World

31 trips  ·  from $35 a head

Good wine sailing trips fill up weeks ahead and the small-group boats go first. Below: the 15 to book early, what each includes on board and how they differ.

2 Hour Lisbon Sunset and Wine Sailing Tour - Setting out past Belém’s waterfront
2-Hour Experiences, Evening Experiences, Lisbon Sailing Trips, Portugal Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Lisbon, Sunset Sailing Cruises in Portugal, Tour Reviews, Tours, Wine Tours

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

Meet Joe, Henry, JP, Marta, or another skipper at the Alcântara marina for a two-hour shared sail past Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and more. Portuguese wine, blankets, and skipper commentary are included, but this is a relaxed cruise, not a formal wine tasting.

“Very easy going. The boat was extremely clean and well kept. Our two guides were excellent- very knowledgeable, very friendly and nothing was too much trouble. We had great chats with the other guests and overall it was wonderful. You get fantastic views of the Lisbon ‘coastline’ as well as the 25th April bridge and Sanctuary of Christ the King. I should have tipped them more on departure as it was such a lovely experience”

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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

Start at Pelican Pier for a four-hour catamaran sail with three snorkel stops, breakfast, paella lunch, mimosas, and an open bar. The crew helps first-timers, and the morning schedule leaves your afternoon free. You may also try the third-lung air system at selected stops.

“So much fun! Great way to spend time on the water while having an adventure. Got to see multiple sea turtles and a shipwreck. Lunch was great too! 10/10 recommend! Beginner friendly for snorkeling as well.”

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Porto: Charming Sailboat Cruise with Port Wine,Sunset Option - Under the Arrábida Bridge and past Gaia
Evening Experiences, Portugal Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Portugal, Tour Reviews, Wine Tours

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

Set out from Douro Marina with a certified crew such as Miguel, Henrique, or Claudio for a two-hour cruise past Porto, Gaia, Ribeira, and Foz do Douro. Expect port wine, city stories, Spotify music, comfortable seating, and blankets when the boat reaches the cooler Atlantic air.

“Although the weather wasn’t perfect, we really enjoyed this boat trip!”

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Lisbon: Champagne Sailing Tours - Leaving Doca de Santo Amaro beneath Lisbon’s bridge
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Lisbon: Champagne Sailing Tours

4.Champagne Sailing Tours

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

Join Nigel and his crew aboard the 15-meter yacht Mara for a relaxed two-hour sail from Doca de Santo Amaro. With up to 12 people aboard, you’ll pass Belém Tower, Christ the King, Alfama, and the 25 de Abril Bridge while enjoying Portuguese champagne, wine, beer, soft drinks, and homemade snacks.

“It was such an amazing experience and the highlight of our trip to Lisbon. Would highly recommend doing this tour with Nigel. He knows so much about the city and gave us great recommendations. The food and drinks he served were excellent. Thank you very much!”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Checking in at 255 Front Street
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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

Board Danger Charters at 255 Front Street for a two-hour sunset sail limited to 26 people. Crew members such as Mary, Connor, Lexi, Tony, and Molly have served wines, beer, small bites, stories, and blankets while the boat heads offshore for sunset.

“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”

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Lisbon Sunset Sailing Tour with White or Rosé Wine and Snacks - Looking across the river at Cristo Rei
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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 a crew of up to 10 at Doca de Santo Amaro for a two-hour sunset sail past Lisbon’s bridge, Cristo Rei, Belém Tower, MAAT, and riverside museums. Expect Portuguese wine, cheese, chouriço, music, and stories from guides such as Manuel, Vasco, Fernando, Anna, and Sergio.

“Skipper and crew were awesome! Very nice and knowledgeable about the country’s history. Wine was delicious!”

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Lisbon: Sunset Sailing Cruise with Wine - Setting out from the marina
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Lisbon: Sunset Sailing Cruise with Wine

7.Sunset Sailing Cruise with Wine

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

Set sail on the Tagus for two hours as Lisbon’s waterfront turns gold. English- and Portuguese-speaking hosts, including guides such as Henri, João, and JP on past departures, explain the sights while you enjoy a welcome glass of wine. Bring a jacket, since the river gets breezy after sunset.

“Loved our crew! Enjoyed this cruise very much. Beautiful sunset, boat and company! Highly recommend.”

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Porto Douro River Cruise With Port Wine - Daytime or Sunset - Leaving Douro Marina near Afurada
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Porto Douro River Cruise With Port Wine – Daytime or Sunset

8.Porto Douro River Cruise With Port Wine – Daytime or Sunset

★★★★★★★★★★4.5 · 759 reviews · 2 hours (approx.) · from $54

Join BBDouro at Douro Marina for a two-hour English-language sail along Porto and Vila Nova de Gaia. See the Luís I and Arrábida bridges, Gaia’s port lodges, Afurada, and the Douro Estuary, with one glass of port included. Sunset trips can reach the Atlantic, though sails may remain down.

“Overall we liked the cruise and our tour guides were really fun and informative . We were disappointed, however, that there was a lot of rain during the tour and the protecrive awning was not used. We were given blankets which were helpful. We were actually surprised the tour wasn’t canceled in the first place . Due to the winds , the guide asked if we wanted to continue or head back with an out 1/2 hour left and the group opted to head back however we do feel a discount on this tour is warranted. We would use the company again we just feel that they didn’t handle the…”

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Porto: Luxury 6 Bridges Yacht Cruise with Wine & Snacks - Starting at Freixo Marina
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Porto: Luxury 6 Bridges Yacht Cruise with Wine & Snacks

9.Luxury 6 Bridges Yacht Cruise with Wine & Snacks

★★★★★★★★★★4.9 · 708 reviews · 2 hours · from $64

Spend two hours aboard a shared Azimut yacht with guides such as Gonçalo, Diego, Alex, or Gil. Cruise from Freixo Marina beneath Porto’s famous bridges, enjoy vinho verde or rosé with a generous cheese and meat board, and continue toward Foz do Douro.

“Absolutely amazing! One of the highlights of our trip! Thank you!!!!”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Dolphin watching without false promises
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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

10.Dolphin Watching, Wine, and Tapas

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

Set out from Key West Historic Seaport for a 2.5-hour catamaran cruise with dolphin watching, wine, beer, champagne, and chef-selected tapas. Expect views of Mallory Square, Fort Zachary Taylor, and Sunset Key. Crew members such as Captain Daniel, John, Gracie, Jordan, and Brandon have been praised for friendly service, though dolphin sightings depend on nature.

“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”

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Champagne Sunset Sail from Margaritaville - The view from St. Thomas’s eastern shore
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Champagne Sunset Sail from Margaritaville

11.Champagne Sunset Sail from Margaritaville

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

Sail from Frydendal aboard a new catamaran for roughly two hours, with champagne, rum punch, Painkillers, cocktails, wine, beer, soda, and hors d’oeuvres. The crew may include captains such as Big Tuna, Danny Boy, or Sean, and the trip returns to the same meeting point after sunset and moonrise views.

“Tour was good food wasn’t great. Crew was friendly and willing to help. Was 50 people on the boat wasn’t to crowded anymore then that would have been hard to move around the deck. Heavy hors d’oeuvres was an overstatement. We booked snorkel with this company was far better experience.”

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

12.Lisbon Sunset Sailing with Portuguese Wine and History

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

Set out from Doca de Santo Amaro for a two-hour shared sail on the Tagus. Guides such as Pedro and David point out Lisbon landmarks, while Vinho Verde, iced tea, water, snacks, and blankets keep the ride relaxed. The boat carries no more than 14 people.

“This was a wonderful experience on the last night of our trip. The sailing was very peaceful, the weather perfect, and wine plentiful. Karolina was very helpful. Any other time I’d be disappointed by not learning enough about the building gs we were sailing by but this time I was happy just enjoying the peaceful beauty.”

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Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine - Finding the boat beneath the 25 de Abril Bridge
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Lisbon: Sailboat Tour w/ Local Guide and Open Bar Green Wine

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

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

Spend two hours on a relaxed Tagus River sailboat tour with up to eight people, local guides such as Andre, Mariana, Felipe, and Francisco, and Portuguese Vinho Verde. You’ll see Belém Tower, the Discoveries Monument, Almada, Alfama, and Commerce Square from the water.

“It was our second time in Lisbon and we enjoyed this trip so much the first time we had to do it again. Excellent value and very friendly people. Would highly recommend.”

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Key West Champagne Sunset Catamaran Cruise - Drinks Included, Food Not the Main Event
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Key West Champagne Sunset Catamaran Cruise

14.Key West Champagne Sunset Catamaran Cruise

★★★★★★★★★★4.5 · 586 reviews · 1 hour 30 minutes (approx.) · from $59

Sail from Key West’s Historic Harbor for about 90 minutes aboard a spacious catamaran. Enjoy included champagne, wine, beer, sangria, soft drinks, and water while the captain points out sunset views, marine life, Mallory Square, and Fort Zachary Taylor. Bring a light jacket, camera, and photo ID if you drink.

“activity for a mid-sized bachelorette party: captain and crew were awesome, boat was gorgeous, bottomless cocktails, and the perfect length of time on board. event was a hit for the group and the peak of the trip!”

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Athens: Catamaran Cruise with Fresh Lunch and Wine - Meeting the crew at Alimos Marina
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Athens: Catamaran Cruise with Fresh Lunch and Wine

15.Catamaran Cruise with Fresh Lunch and Wine

★★★★★★★★★★4.9 · 534 reviews · 5 hours · from $147

Join a two-person crew aboard a spacious sailing catamaran from Alimos Marina. Swim near Hydroussa and Vouliagmeni, use the paddleboard and snorkel gear, then enjoy fresh Greek meze, fruit, soft drinks, and wine. Captain Bill, Julia, Claudia, Nikki, or another crew pairing may host your cruise.

“Julia and Bill did a great job! it was really fun.”

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Porto: Private Yacht Tour with Wine, Snacks & 6 Bridges - Starting at Freixo Marina
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Porto: Private Yacht Tour with Wine, Snacks & 6 Bridges

16★ 5.0Private Yacht Tour with Wine, Snacks & 6 Bridges515 reviews
Porto: Private Yacht Cruise with Local Wine, Snacks and 6 Bridges - Luís I Bridge, Porto’s great river landmark
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Porto: Private Yacht Cruise with Local Wine, Snacks and 6 Bridges

17★ 5.0Private Yacht Cruise with Local Wine, Snacks and 6 Bridges489 reviews

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