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“Very nice cruise...met some very nice people. The clouds didn't accommodate the sunset but still worthwhile seeing the shore from the water. The crew was wonderful.”
Aruba morning catamaran with 3 snorkeling stops, open-bar mimosas, and a champagne brunch-style breakfast and lunch on the water.
“It was great even for inexperienced swimmers or snorkelers. Food was ok as well as the open bar, but plentiful. Staff was wonderful! Had a great time and would definitely recommend and will do this again on our next visit.”
Porto sunset sail on the Douro with port wine, great Luís I Bridge photo spots, and friendly crew commentary. 2 hours, small groups.
“We had a great time! The weather was drizzly, so it ended up just being the two of us with the two guides. They were both excellent and we had a great conversation while seeing so much of Porto and Gaia.”
A small-group 2-hour Lisbon sailing cruise with Portuguese champagne and snacks, sailing under the 25 de Abril Bridge and past Belém.
“Our host Nigel was great Very friendly and engaging with everyone. Great evening on the water . Would definitely recommend it and do it again 🤩”
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.
“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!!”
Lisbon sunset sailing on the Tagus with wine and snacks, small group views of key sights, and guided stories from a certified crew.
“There isn't much of a proper "tour" aspect -- just sailing around and having a good time with music and wine. Still a very fun time, but I would have liked to learn more about what we saw! Ultimately my friends and I had a wonderful time relaxing after days full of walking all over…”
2-hour sunset sail on Lisbon’s Tagus with complimentary green wine, big skyline views, and possible dolphins. Relaxed way to start your evening.
“What a fun excursion on our first night in Lisbon! Fabolous guide with a generous pour and great atmosphere on the boat. Highly recommend at either the beginning of the end of your visit to the city!”
Sail the Douro from Porto or Gaia with a glass of port. See wine caves, bridges, and wildlife on a relaxed 2-hour cruise.
“Our captains were incredibly hospitable and friendly. We made the best of the not so optimal weather and would definitely go on this experience again.”
Luxury yacht on the Douro past Porto’s 6 bridges with green or rosé wine and regional snacks, departing Freixo Marina.
“I had the nicest view with unlimited green wine. what else can i ask for?”
Small-group Key West sunset sail with dolphin watching, premium wine, and chef-selected tapas on a luxury catamaran.
“Great seeing the dolphins in their natural habitat. The boat crew were great and no point we didn't feel unsafe.”
Sip champagne on a new catamaran sail in St. Thomas. Open bar, heavy bites, sunset and moonrise views in about 2 hours.
“This was the most amazing experience for our girls trip! Everything was clean, the food was amazing, and the service was excellent, we loved Noelle and the crew! ✨ thank you!”
2-hour Lisbon sunset sail with free-flow Vinho Verde, history from the Tagus, and skyline views from 25 de Abril Bridge to Belém.
“It. Was. Wonderful. Our first big activity after we arrived in Lisbon. My wife and I were so tired from the flight so we thought this would be a perfect way to wind down and relax. And it was. We also met some very nice people. Do this boat ride.”
A small-group Lisbon sailboat on the Tagus with local guides and an open bar of Portuguese Vinho Verde, best at sunset.
“amazing tour! staff was super helpful and had a lot of knowledge about the city. boat had giant bean bags which were super super comfortable and good wine. Also gave us a great dinner rec!”
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.
“Such a nice time, absolutely recommend! Bill and Julia (our guides) were lovely, the food was amazing, service was outstanding, the boat was very clean, the music not too loud and the swimming stops perfect. Loved every minute of it.”
The sailing ports worth the trip, grouped by the sea they sit on.
