SAILING WORLDWIDE
The best days on the water.
The 15 most popular wine tours. What each sail costs, how long you are on the water, and which crews run it well.
Small-group 2-hour Lisbon sunset sail from Belém with Portuguese wine, Belem Tower and 25 de Abril Bridge views, and skipper stories.
Most Popular“0n time, plenty of food and drink, good musicquestions answered, informative, right length, friendly”
Aruba morning catamaran with 3 snorkeling stops, open-bar mimosas, and a champagne brunch-style breakfast and lunch on the water.
“Very well informed tour guide. Cliff was very helpful to people whose first time snorkeling. Great time. Only suggestion would be to play better music.”
Porto sunset sail on the Douro with port wine, great Luís I Bridge photo spots, and friendly crew commentary. 2 hours, small groups.
“Lovely cruise, great host, delicious wine and great weather. Couldn’t ask for more!”
Key West small-group sunset sail with wine and hors d’oeuvres: up to eight wines, five beers, and a calm, romantic 2-hour cruise.
“What a great time. Enjoyed all the wines and hors d oeuvres. They kept on coming. Tony and the crew told great stories they were friendly and on it! Great job you all! Thanks for beautiful sunset pics and a great sailing!”
A small-group 2-hour Lisbon sailing cruise with Portuguese champagne and snacks, sailing under the 25 de Abril Bridge and past Belém.
“Amazing boat trip, Nigel was amazing and he let us steer the boat!”
Lisbon sunset sailing on the Tagus with wine and snacks, small group views of key sights, and guided stories from a certified crew.
“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.”
2-hour sunset sail on Lisbon’s Tagus with complimentary green wine, big skyline views, and possible dolphins. Relaxed way to start your evening.
“This was a great tour. Our hosts were wonderful and fun. Very enjoyable and would definitely recommend!”
Sail the Douro from Porto or Gaia with a glass of port. See wine caves, bridges, and wildlife on a relaxed 2-hour cruise.
“Fabulous trip on a luxury yacht, very friendly tour guide and skipper. We were well impressed with the whole experience”
Luxury yacht on the Douro past Porto’s 6 bridges with green or rosé wine and regional snacks, departing Freixo Marina.
“We had a fantastic time on the boat. The Portuguese snacks and wine were excellent and the whole experience felt relaxed and special. Gill and Ines were superb hosts, offering a great mix of history, local culture and genuinely engaging conversation. Both were incredibly warm, welcoming and personable, which made the trip feel more like…”
Small-group Key West sunset sail with dolphin watching, premium wine, and chef-selected tapas on a luxury catamaran.
“This is a great opportunity to see Key West's beautiful dolphins. Luckily, we saw several dolphins and enjoyed every moment while being entertained by the knowledgable crew.”
Sip champagne on a new catamaran sail in St. Thomas. Open bar, heavy bites, sunset and moonrise views in about 2 hours.
“Very nice and relaxing and great crew - beautiful views. Wish the tour went out a little further instead of going in same circle”
2-hour Lisbon sunset sail with free-flow Vinho Verde, history from the Tagus, and skyline views from 25 de Abril Bridge to Belém.
“This tour was amazing. The guides were friendly and knowledgeable, and they were very generous with their wine pours. We never had an empty glass. The tour was beautiful and I would highly recommend this experience for anyone.”
A small-group Lisbon sailboat on the Tagus with local guides and an open bar of Portuguese Vinho Verde, best at sunset.
“This is by far the best boat trip to take. Sailed and owned by LOCAL PEOPLE, incredibly friendly, experienced, knowledgeable. Andre and Dian (apologies for any bad spelling) were the perfect hosts - you should definitely use them for a great trip!! Check their Instagram too 😍😍”
Sail Key West’s Historic Harbor on a champagne sunset catamaran with included drinks, captain-led viewing spots, and ocean views.
“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres.…”
Sail Athens Riviera on a modern catamaran with wine, fresh Greek meze, two swim stops, and snorkeling gear for a relaxing half-day escape.
“Claudia and Bill are amzing guides. I would stay there the whole day with them teaching all the greek words to us. I will certainly do it again soon.”
The sailing ports worth the trip, grouped by the sea they sit on.
