By the glass · SAILING
This is the shortlist you would send a friend: 15 sailing trips worth the money, each with its price, its traveller verdict and the one thing to check before you commit.
Cruise from Douro Marina past Gaia, Ribeira, Porto’s bridges, and Foz do Douro on a comfortable small-group sailboat. Your crew shares local stories, serves a welcome drink and port wine, and may head into the Atlantic when conditions allow. Sunset departures add the best light.
“Loved the sunset cruise! Wonderful way to see the city with a very nice crew! Thank you!”
Join Nigel and his crew aboard the 15-meter yacht Mara for a relaxed two-hour sail from Doca de Santo Amaro. You’ll pass Belém Tower, Christ the King, Alfama, and the 25 de Abril Bridge, with Portuguese champagne, wine, beer, soft drinks, and homemade sweet and savory snacks included.
“Nigel and Manuel great hosts. Cruise was lovely. Delicious bites and plenty of drinks.”
Set out from Doca de Santo Amaro about two hours before sunset for a relaxed sail past Lisbon’s bridge, Cristo Rei, Belém Tower, MAAT, and riverside palaces. Expect a small boat, Portuguese wine, cheese or chouriço, music, and guide stories, with hosts such as Manuel, Vasco, Fernando, or Miguel depending on the departure.
“Fun, informative, enjoyable. Wonderful weather, good company. Can't beat that. Miguel & Alfonso we're wonderful.”
Spend two hours on a private Miami yacht for your own group, with a captain, cooler and ice, restroom, Bluetooth audio, and views of Bayside Marketplace and Star Island. Sunset and evening departures are especially appealing, but read the separate captain and fuel fees before booking.
“Had an amazing experience definitely worth it !! Even though the rain was trying to stop our party we still had a great time”
Join Hawaii Nautical for a 90-minute barefoot catamaran cruise from Honolulu toward Diamond Head. Enjoy a snack box, two alcoholic drinks, unlimited nonalcoholic beverages, and a sunset view beside Oahu’s most famous volcanic crater. Shuttle pickup is available with the correct booking option.
“The crew was great, a tentative we saw an amazing sunset, the cocktails were great we enjoyed them. The crew told us about the waters around Waikīkī and the wild life we can see.”
Set out from Port Olímpic for a two-hour small-group sail with a captain such as David, Fiona, or Alessio. Expect cava, drinks, Catalan-style snacks, waterfront views of the Sagrada Família and W Hotel, and a possible Mediterranean swim when conditions allow.
“Great day started with this 2 hour Sail! David our captain was great. Very friendly and took very good care of us. I would definitely recommend this activity. Close to beach to hang out after and Great restaurants right off the dock. Remember to tip your tour guide!”
Sail the Tagus for about two hours with a maximum of 14 people, hearing Lisbon stories from guides such as Pedro and David while sipping Vinho Verde. Expect views of the 25th April Bridge, Christ the King, Belém Tower, and the sunset, with blankets provided for cooler evenings.
“Really great to see Lisbon from the water. Friendly, welcoming, helpful crew. Wine and Bugles snack! We had a wonderful time!”
Sail from Key West Historic Harbor on a spacious catamaran, with champagne, wine, beer, sangria, soft drinks, and water included. You will pass Mallory Square and Fort Zachary Taylor, watch the sunset from the water, and return to 205 Elizabeth Street. Bring a light jacket for the ride home.
“It was above the expectation. Nice crews, open bar and live music were great. Only thing I could’ve done differently is bringing a sweatshirts. It was pretty chilly out in the sea.”
Join Alma Sailing Charter in central Cagliari for a three-hour catamaran trip to Cala Mosca, Cala Fighera, and the Devil’s Saddle. With up to 12 people aboard, you get swimming time, snorkeling gear, floating tubes, coastal stories, and a prosecco toast, with Alma and the crew often leading the way.
“The trip was fantastic , we were sailing in high winds with appropriate music AC/DC. I recommend it to everyone , my 11 year old daughter really enjoyed it”
Spend 3.5 hours aboard DanEri Yachts’ catamaran Karina from Rethymno Marina. Enjoy Prosecco, sushi, Cretan snacks, unlimited beer and wine, SUP, snorkeling, and a sunset near Geropotamos Beach. The English-speaking crew includes Nana, Yannis, Banos, and Sepdos.
“We had a great experience! The waters were a bit rough the day we went out, but the crew was so friendly and constantly made sure everyone was okay and was doing well. The crew obviously can't control the weather, but they were so friendly and attentive, and we still had a great experience seeing Rethymno from the water and watching the sunset. Thank you so much to the entire Dan Eri crew for a great time!”
Sail from Port Olimpic toward El Masnou, then visit a family-run Alella winery in a 14th-century house. You’ll taste four local wines with Catalan food, tour the vineyards and cellar, and return by luxury minibus or sailboat, depending on weather and scheduling.
“The sailing along the coast was value enough. The winery alone was enough. This was the best day of our amazing Barcelona vacation. Yes the meeting point was a challenge but we pre-scouted and once you realize the address number is the boat slip, it was so easy. Just meet at the slip 15 minutes early.”
You’ll ride from Sunny Beach on a red London double-decker bus, board an adult-only catamaran, and sail around Old Nessebar at sunset. Expect a cheese and cold-meat buffet, half a bottle of prosecco per adult, open drinks, sea views, and a return trip after Nessebar lights up.
“From the pickup to drop off this really was a VIP experience, the crew were so attentive. The catamaran was spotless including the toilet. A wide variety of meats and cheeses, crackers, breads, fruit with an endless supply of drinks, finished off with a bottle of prossecco not to mention the breathtaking views and beautiful sunset, my husband and I were blown away, we got so many fantastic photos and made some forever memories, also 2 separate proposals on this wonderfully romantic cruise”
Board the Hanu Lani at Kewalo Basin Harbor for a 90-minute sunset sail past Waikiki and Diamond Head. You get open-air or shaded seating, snacks, restrooms, and a full bar with cocktails, beer, wine, soda, and juice. The crew, including names such as Clay and Captain Mark, keeps the mood relaxed and social.
“Nice casual cruise with drinks and snacks. Fun crew and beautiful views. We really enjoyed this activity.”
Join Go Sailing Lisboa for a two-hour cruise with guides such as Tiago, Valter, Guilherme, and Nuno. Help steer or handle the sails, hear stories about Lisbon, and pass Commerce Square, Christ the King, Belém Tower, and the 25 de Abril Bridge with white wine, beer, snacks, and music.
“Epic sunset sailing trip! Insane views, awesome crew. Do it! Highly recommended!”
Join a small group of up to 10 for a guided e-bike ride from Barcelona to Alella, a sommelier-led wine tasting, and a two-hour coastal sail back. You can replace cycling with a car, and guides speak English, French, German, or Spanish.
“This was one of my favorite tours! We did the ebike to winery to sail, and it was perfect. Wonderful guide and very nice person with good history to share, delicious food and wine tasting with great views. And then a sail with drinks and snacks back to Barcelona. Full stars, would do this tour a million times over.”
Pick a bottle and see where it is poured properly.
