Sailing Trips in Portugal: 15 to Book

1.Daytime/Sunset/Night City Sailboat Tour with Drink

★★★★★★★★★★4.9 · 3,114 reviews · 2 hours · from $41Our pick

Sail Lisbon’s Tagus River under the 25 de Abril Bridge with a drink, live commentary, and daytime, sunset, or night departures.

“Luis (apologies if I spelt that incorrectly!) was brilliant, he is so passionate about boats & what he does it's infectious. His appreciation for Lisbon & Portugal it's so respectful & proud he makes the history sound natural & interesting without being too much information you don't be able to retain when you leave! Thanks so much we had a brilliant time, it's a very romantic trip even though we went with friends!”

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2.2 Hour Lisbon Sunset and Wine Sailing Tour

★★★★★★★★★★5.0 · 2,680 reviews · 2 hours (approx.) · from $66Top rated

Review of Lisbon’s two-hour sunset sailing tour, with wine, Belém landmarks, practical tips, pricing, boat details, and who should book.

“We really enjoyed our time sailing with these guys on a cool night. They were attentive to our wine glasses as well as blankets for those who needed them. The meeting point is a little hard to find in the huge marina even with the detailed instructions they provided. Give yourself some time to find them, its worth it.”

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3.Sailing Tour on the Tagus River

★★★★★★★★★★4.8 · 2,632 reviews · 1 - 2 hours · from $23Best value

Sail Lisbon’s Tagus for $23, passing Belém Tower, the 25 de Abril Bridge, and Christ the King with a drink and sunset option.

“It was a lovely one hour sailing trip across the Tagus to the bridge and back It was slightly windy so on a hot day I’m sure it would be even better. Free beer water and the young skipper and his mate were very good Worth the money and definitely recommend”

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4.Sunset Sailing Tour

★★★★★★★★★★4.7 · 2,144 reviews · 3 hours · from $58

Review of Funchal’s sunset sailing tour, with Cabo Girão swimming, open drinks, small groups, coastal views, and possible dolphin sightings.

“Fantastic boat! Wonderful crew: entertaining but very responsible. They encouraged everyone to jump into the water, it was brilliant! Sunset was perfect, drinks were welcomed, no whales have been seen but it didn’t matter. Experience was FANTASTIC!”

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5.Charming Sailboat Cruise with Port Wine,Sunset Option

★★★★★★★★★★5.0 · 1,978 reviews · 2 hours · from $41

Review of Porto’s 2-hour sailboat cruise, with port wine, city views, sunset scenery, friendly crew, practical tips, and honest value advice.

“Loved everything about this activity- the hosts were warm and informative, the boat was spacious for our small group and we got port to add to the whole experience! Highly recommend!”

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6.Champagne Sailing Tours

★★★★★★★★★★4.9 · 1,366 reviews · 2 hours · from $58

Review of Lisbon’s 2-hour Champagne Sailing Tour, with Tagus views, small groups, snacks, drinks, itinerary details, value, and practical tips.

“This was an amazing tour, enjoyed every minute. Nigel and his assistant were brilliant and so attentive, and made sure our glasses were always topped up. Food/snack were very nice too. We would definitely do this again. Thanks for an amazing time! Liam and Lewis.”

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7.Dolphin and Whale Watching Sailing Trip

★★★★★★★★★★4.6 · 1,325 reviews · 3 hours · from $47

Sail from Funchal to Cabo Girão for dolphin and whale watching, swimming, snorkeling, coastal views, and a relaxed small-group cruise.

“My husband and I had a fantastic 3 hour trip on this lovely sailboat. We weren’t lucky enough to spot any sea life, but nevertheless, the crew took good care of us, and were very skilled and knowledgeable. Seeing the island from the ocean gave a whole new perspective, and snorkeling in the warm waters was a special touch! Definitely recommend 🫶🏼”

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8.Daylight or Sunset on a Vintage Sailboat

★★★★★★★★★★4.9 · 1,265 reviews · 2 hours · from $64

Sail Lisbon’s Tagus River on a vintage boat with wine, petiscos, sunset views, Belém monuments, and a small relaxed group.

“See Lisbon from the river was a great perspective. Captain Angelo was a great host and very informative.”

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9.Tagus River Sailboat City Cruise

★★★★★★★★★★4.9 · 1,212 reviews · 2 hours · from $41

See Lisbon’s monuments from the Tagus on a relaxed two-hour sailboat cruise with a drink, music, guides, and sunset views.

“Miguel was very knowledgeable and friendly. He made for a great evening, even with the overcast weather.”

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10.Sunset Sailing Cruise with Wine

★★★★★★★★★★4.9 · 800 reviews · 2 hours · from $64

Review of Lisbon’s 2-hour sunset sail on the Tagus River, with wine, skyline views, practical tips, value advice, and booking details.

“Super casual cruise on the water. Great way to see the city from a different perspective and rest your legs from a long day of walking. Staff was super friendly.”

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11.Sailboat Tour w/ Local Guide and Open Bar Green Wine

★★★★★★★★★★4.9 · 625 reviews · 2 hours · from $35

Sail Lisbon’s Tagus River on a small-group sunset cruise with local guides, Vinho Verde, music, and views of Belém Tower and Alfama.

“Super friendly and professional guides Mariana and Andre!! Great people . They made us feel super comfortable and safe at every turn . We would highly recommend this tour . Good people .”

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12.City Skyline Sailboat Cruise with Drink and Snacks

★★★★★★★★★★4.9 · 503 reviews · 2 hours · from $45

Sail Lisbon’s Tagus River for two hours with wine, snacks, bridge and Belém views, friendly guides, and a memorable sunset option.

“Me and my family loved it!! Thank you so so much to the team!”

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13.Vilamoura: Algarve Coast 3-Hour Sailing Cruise With Open Bar

★★★★★★★★★★4.7 · 362 reviews · 3 hours · from $33

Review of Vilamoura’s 3-hour schooner cruise, with Algarve cliffs, caves, swimming, onboard bar, practical tips, and honest value advice.

“Lovely trip staff very friendly make sure to bring a hat as cit gets very hot”

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14.Ponta Piedade Sail & Caves Cruise w/Portuguese Tapas

★★★★★★★★★★4.8 · 360 reviews · 2.5 hours · from $38

Sail from Lagos to Ponta da Piedade for cave views, Portuguese tapas, swimming, and a small-boat grotto tour.

“Riding in the smaller boat around the rock formations was very fun!”

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15.Best Charming Sailboat Cruise Sunset

★★★★★★★★★★4.9 · 334 reviews · 2 hours · from $70

Cruise Porto’s Douro River at sunset on a small sailboat with local wine, charcuterie, city views, and friendly guides.

“We had an amazing boat tour with Pedro and Juan. Both were extremely friendly, helpful, skilled sailors, and full of knowledge about the local area. Because of the weather, we weren’t able to see the sunset we had hoped for, but nevertheless, Pedro and Juan made it a trip we will never forget. 5+ stars”

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