The World's 6 Best Cheese Sailing Trips

1.JFarwell Sunset Wine and Cheese Yacht Sailing

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

Spend 2.5 hours sailing from Halifax Harbour toward George’s Island, McNabs Island, and the Northwest Arm. Your crew serves four Nova Scotia wines, local charcuterie, and stories about the area. Captains such as Ryan and Finn may even let you help with the sails.

“Ryan the captain and Mitch his first mate were excellent. The experience from beginning to end was exceptional. If you go to Halifax, I urge you to book this trip.”

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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 for a private two-hour Douro cruise. Your crew serves Douro wine, Ruby, white, and tawny Port with cheese, charcuterie, fruit, chutneys, and tapas while you pass Ribeira, Gaia, the Luis I Bridge, and Porto’s riverfront.

“Very cozy trip, super friendly crew, amazing views, everything you could ask for in a sailboat trip. Would definitely recommend.”

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3.JFarwell Private Yacht Wine & Cheese Sunset Sail

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

Set out from 1599 Lower Water Street for a 2.5-hour private yacht sail through Halifax Harbour and the Northwest Arm. You’ll taste Nova Scotia wines, enjoy charcuterie, hear local stories from the crew, and watch the skyline glow at sunset. Crew members have included Finn, Paul, Ryan, and Caleigh.

“Cullen and Finn - these two lads made the voyage amazing - not just for us - but all 12 passengers. Great stories, great energy, great skill - I mean the sailboat was incredible and so was the wine and cheese - but any brand would be lucky to have two young pros like this representing there brand on Land & Sea.”

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

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

Spend two hours on a comfortable sailboat with up to 10 people, cruising between Porto and Gaia. Enjoy Port tonic, snacks, and guided stories about the bridges, Port wine, and riverside sights. Sunset departures may continue toward the Atlantic when weather allows.

“Il faut dire que nous avons eu le privilège d’avoir la crème de la crème avec notre beau Marlon. Ce guide a fait tout un excellent travail. Sa confiance, son dévouement et sa gentillesse m’ont ravi. Je le recommande fortement, cette excursion est un Wow 5 *. Merci pour ce beau moment.”

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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 four Nova Scotia wines, a local cheese board, and a chance to hoist sails, help with tacks, or take the helm. Your English-speaking crew may include skipper Finn and host Emerson, with views of George’s Island, the Northwest Arm, and Dingle Tower.

“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 spend four hours with private transfers and 1.5 hours sailing Potrerillos Lake aboard the eight-passenger VÃIU. Expect Andes views, sparkling wine, wine, cheeses, dried fruit, and a multilingual crew focused on safety and comfort.

“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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