15 Wine Sailing Trips Around the World to Build an Afternoon Around

1.2 Hour Lisbon Sunset and Wine Sailing Tour

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

Set sail from Alcântara with a skipper such as Joe, Henry, JP, or Marta, depending on the departure. Over two hours, you’ll see Belém Tower, Jerónimos Monastery, the 25 April Bridge, and Lisbon’s waterfront while drinking Portuguese wine in a group of no more than 12.

“Beautiful! Great way to see lisbon from a different view. Guides were very knowledgeable and kept the wine flowing. It was chilly but the had blankets that kept us toasty! Small group. Highly recommend them.”

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2.Charming Sailboat Cruise with Port Wine,Sunset Option

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

Join a small-group or private two-hour cruise from Douro Marina with an English, Spanish, or Portuguese-speaking crew. Expect port wine, music, city stories, and views of Ribeira, Gaia, the Luis I Bridge, Foz do Douro, and the Atlantic when conditions allow. Boats and crew may vary.

“Delightful way to start the day. I'd recommend getting the first tour of the day. The guides were excellent, and the price was really good.”

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3.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 no more than 12 people aboard, you’ll see Belém Tower, Christ the King, Alfama, and the 25 de Abril Bridge while enjoying Portuguese champagne, wine, beer, soft drinks, and homemade snacks.

“Our host Nigel was great Very friendly and engaging with everyone. Great evening on the water . Would definitely recommend it and do it again 🤩”

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

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

Set out from Doca de Santo Amaro at 3:30 pm for a two-hour Tagus sailing with up to 10 people. Your certified crew shares Lisbon stories as you pass Cristo Rei, Belém Tower, MAAT, and the Discoveries Monument, with wine, cheese, and chouriço served on board.

“This was a great experience for our last night in Lisbon. The crew was great and we got to meet great people on the boat.”

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5.Miami: 2 Hour Private Yacht Cruise

★★★★★★★★★★5.0 · 899 reviews · 2 hours (approx.) · from $98

You’ll spend two hours on a private Miami yacht with your own group, captain, restroom, cooler with ice, and Bluetooth audio. The route passes Bayside Marketplace, Star Island, and celebrity homes. Captain Jorge, Alex, Eduardo, Juan, and others have earned especially strong praise, but captain and fuel fees are paid separately.

“Don’t book with this app! You get charged more than they tell you. My trip total was $361 including the captain fee and fuel. They tricked me and had me pay the fuel and captain fee separate (to the actual company) and still charged my card $361. I ended up paying a total of $501. I would not have booked had I known it was going to be that much! Then when I called the rep hung up on me. NEVER EVER AGAIN. DONT BOOK WITH THEM.”

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6.Sunset Sailing Cruise with Wine

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

Spend two hours sailing the Tagus at sunset, with a welcome glass of wine and views of Lisbon’s waterfront monuments. English and Portuguese-speaking hosts, including guides such as Henri, João, Joe, and José on different sailings, share local details while the boat drifts past Belém Tower and the Ponte 25 de Abril area.

“It has been proven that watching the sunrise or sunset gives you a better sense of gratitude for the earth. This sunset sailboat ride is a must in Lisbon! The crew were very friendly and even waited for us as we arrived a few minutes late. They poured wine many times into my glass ^^. Apart from the amazing views and the sunset, we got to see dolphins swimming next to the sailboat in the Tagus river!”

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7.Barcelona Small Group Sailing with Snacks and Cava

★★★★★★★★★★5.0 · 758 reviews · 2 hours (approx.) · from $66

Set sail from Port Olímpic for two relaxed hours along Barcelona’s coast. Your English-speaking captain may point out the Sagrada Família, Tibidabo, W Hotel, and Barceloneta Beach while you enjoy cava, snacks, bottled water, and, weather permitting, a swim. Captains include David, Fiona, Marcos, and Alessio.

“My daughter and I had an amazing time. The captain of Maggie worked so hard to make the time enjoyable. We had some swells, which made sailing great but no swimming. Not a problem. She was very personal and just a wonderful start to our morning in Barcelona. Highly recommended”

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8.Luxury 6 Bridges Yacht Cruise with Wine & Snacks

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

Spend two relaxed hours aboard a shared luxury yacht from Freixo Marina to Foz do Douro and back. Your Portuguese or English-speaking crew points out Porto’s bridges, Ribeira, Gaia, and the Atlantic entrance while serving vinho verde or rosé, regional meats, cheeses, bread, and fruit.

“Staff on board were excellent. Some poor comms prior ref pick up. Ended up getting an Uber. Food and drink on board were very good. More expensive than other offerings and would have been worth it with the transport.”

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9.Lisbon Sunset Sailing with Portuguese Wine and History

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

Join Pedro, David, or another two-person crew for a two-hour shared sail from Doca de Santo Amaro. You’ll pass Lisbon’s major riverfront sights, hear local history, and enjoy Vinho Verde, iced tea, water, and blankets aboard a boat limited to 14 people.

“The tour was a lot of fun and our guides were incredibly friendly and knowledgeable. They were experts that genuinely enjoy informing travelers of Lisbon’s history, while also creating a lively and exciting experience being on a sail boat. The harbor was lovely at sunset and the boat was very clean, organized, and comfortable. Highly recommend!”

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

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

Join local guides such as Andre, Mariana, Felipe, or Francisco for a two-hour sail from beneath the 25 de Abril Bridge. You’ll see Belém Tower, the Discoveries Monument, Alfama, and Commerce Square from the Tagus, with music, sofas, blankets, and an open bar of Portuguese Vinho Verde.

“Diana and Francisco were fantastic guides who are highly knowledgeable and passionate about their city and its history. The boat was immaculate and the tour was incredible, as was the green wine! Thanks so much for a fantastic tour.”

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11.Key West Champagne Sunset Catamaran Cruise

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

Sail from Key West Historic Harbor on a 60 to 69 foot catamaran for about 90 minutes. Sip included champagne, wine, beer, sangria, or soft drinks while the crew points out sunset views, island sights, fish, birds, and marine life. Bring a light jacket, hat, sunglasses, and photo ID.

“We booked this champagne catamaran cruise for a bachelorette trip, and it exceeded all of our expectations! The crew was incredibly welcoming, providing a great selection of drinks and even letting us blast some *Mamma Mia!*, which made the whole experience so much fun. The sunset was absolutely stunning—a perfect backdrop for our celebration. I was a bit nervous beforehand because some previous reviews mentioned it was hard to find the boat, but it was actually super accessible and easy to locate. If you're planning a special event or just want a relaxing and scenic way to experience the Keys, I highly recommend this cruise!”

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12.Catamaran Cruise with Fresh Lunch and Wine

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

Spend five hours aboard a spacious sailing catamaran from Alimos Marina, with stops near Hydroussa, Vouliagmeni, and Voula. The two-person crew, often Bill with Julia or Claudia, serves fresh Greek food, fruit, wine, and soft drinks, with snorkeling gear and a paddleboard provided.

“We loved it. The food was great. Everything was just as incredible as we imagined.”

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13.Private Yacht Tour with Wine, Snacks & 6 Bridges

★★★★★★★★★★5.0 · 515 reviews

Sail from Freixo Marina to the Atlantic Ocean on a private yacht for up to eight people. Your Portuguese, English, or Spanish-speaking crew serves green or rosé wine, regional snacks, blankets, and local stories as you pass Porto’s six bridges, Ribeira, Gaia, Afurada, and Foz.

“The guides were incredible and this was such an amazing experience !! 10/10 would recommend. Food and wine were amazing, amazing views, guides were extremely personable and made the experience very memorable.”

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14.Catamaran Tour, Swimming, Snorkeling, & Prosecco

★★★★★★★★★★4.9 · 487 reviews · 3 hours · from $72

Join Alma Sailing Charter for a three-hour catamaran trip from central Cagliari. With Alma, Patrick, Paolo, or Laura guiding, you’ll visit Cala Mosca, Cala Fighera, and the Devil’s Saddle for swimming and snorkeling, then toast with prosecco.

“Dear Alma, We could give you and your captain husband one thousand stars. In spite of the weather being not so good as we wish, you made our boat tour an amazing experiece. Thank you both for the sailing, good music and all information provided. All the best!”

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15.Sunset Sailing Cruise with Dinner and Wine

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

Meet the Goélette Alliance beside Ferry Boat pier 2 at Marseille’s Old Port. Sail to a cove in the Frioul archipelago for swimming, a fresh vegetarian buffet, music, and sunset. Fabio and a multilingual crew may help raise the sails. Return beneath Marseille’s evening lights.

“Excellent activity - it was very well organised and the tour was lovely. Thanks to the guide Fabio who was kind and informative. I'd definitely recommend.”

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