Cheese Sailing Trips Worldwide: The 6 Best Days Out

1.JFarwell Sunset Wine and Cheese Yacht Sailing

★★★★★★★★★★5.0 · 149 reviews · 2 hours 30 minutes (approx.) · from $150Our pick

Set out from Halifax’s waterfront for a 2.5-hour sunset sail with J Farwell Sailing Tours. You’ll taste four Nova Scotia wines, including Tidal Bay, with local charcuterie while the crew shares sailing tips, wine notes, and Halifax history. The route passes George’s Island, McNabs Island, and the Northwest Arm. Crews may include Ryan, Finn, Andrew, Ali, or other JFarwell staff.

“This was a wonderful sail through Halifax Harbor. Our captain, Ryan and first mate, Emerson, provided a fun, informative, and relaxing tour. The snacks and wine was great too! Overall, 5 stars out of 5 stars.”

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2.Wine and cheese tasting on a sailboat on the Douro River

★★★★★★★★★★5.0 · 37 reviews · 2 hours (approx.)

Set sail from Marina da Afurada toward Ribeira, Gaia, and the Luís I Bridge while tasting Douro wines, Port, cheese, charcuterie, fruit, and tapas. Your crew may include Ricardo, Tatiana, Claudio, Pedro, or Paulo. The private two-hour cruise returns to the marina and can switch to a yacht if weather turns poor.

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3.JFarwell Private Yacht Wine & Cheese Sunset Sail

★★★★★★★★★★5.0 · 18 reviews · 2 hours 30 minutes (approx.) · from $149

Spend about two and a half hours aboard a private yacht with Nova Scotia wine, cheese, and charcuterie as Halifax’s skyline fades into sunset. The route follows the waterfront and reaches the Northwest Arm. Crews may include Finn, Paul, Ryan, or Caleigh, with sailing stories and local facts along the way.

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4.Douro River Cruise with Cheese & Tonic Porto in a Sailboat

★★★★★★★★★★5.0 · 7 reviews · 2 hours · from $59Best value

Join a small group of up to 10 for a two-hour sail from R. da Praia 430. You’ll pass Porto, Gaia, Arrábida Bridge, Ribeira and Dom Luís I Bridge while guides speak in English, Portuguese or Spanish. Port Tonic, snacks and cheese are included, with sunset trips reaching the Atlantic when weather allows.

“très belle expérience, et la dégustation de vin et les explications historiques”

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5.Halifax: Sunset Wine and Cheese Sailboat Cruise

★★★★★★★★★★5.0 · 5 reviews · 2h 30m · from $118

Spend 2.5 hours sailing from Halifax with a hosted tasting of four Nova Scotia wines and a local cheese board. You can help hoist the sails, assist with tacks, or take the helm while guides such as Finn, Emerson, Ali, and Derek share stories about the wines, waterfront, and Northwest Arm.

“This event was truly excellent. The boat was spotless and comfortable, our skipper Finn and host Emerson were very knowledgeable and fun. I wouldn’t hesitate to recommend this event to others. Well worth the money!”

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6.Potrerillos Lake Sailing Tour with Wine and Cheese

★★★★★★★★★★4.4 · 2 reviews · 4 hours · from $213

You’ll sail for 1.5 hours aboard the award-winning VAIU, a luxury sailboat limited to eight passengers. Your crew handles safety while you enjoy sparkling wine, wine, cheeses, and dried fruit against the Andes. Hotel pickup and drop-off are included, with service available in six languages.

“El paseo por el lago es excelente , simplemente el paisaje es hermoso y muy relajante , en cuanto a la selección de Vino y Quesos aun les falta variedad a la hora de degustar”

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