15 Sailing Trips in Portugal to Build a Day Around

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

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

Spend two hours on a small sailboat with guides such as Benny, Miguel, Telma, or Luiz, hearing Lisbon stories as you pass Belém Tower, MAAT, Alfama, and Christ the King. Choose daytime, sunset, or night sailing. A drink, water, blankets, and a toilet are provided.

“We did the sunset cruise and couldn’t recommend it more! I flew in from the far south with my 79- and 84-year-old family members, and it was the perfect way to start our trip — low activity, high impact, and absolutely stunning. The vessel was comfortable and easy to move around, and the crew were warm, attentive, and genuinely engaging. One guide was a nautical scientist and the other a former banker — both were delightful, sharing interesting insights and keeping our glasses topped up. The music was perfectly curated — relaxed remixes of classic jazz, never too loud — and it truly elevated the atmosphere. We loved every minute…”

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2.2 Hour Lisbon Sunset and Wine Sailing Tour

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

Join a skipper-led evening sail from Alcântara, with Portuguese wine and views of Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and Christ the King. Crew members such as Joe, Henry, JP, and Marta are praised for friendly commentary. Bring a warm layer, since the river air can turn cool.

“The guide (JP) was very knowledgeable, and the tour was very relaxing. This was such a nice evening getting to know the other riders, and enjoying the atmosphere.”

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3.Sailing Tour on the Tagus River

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

Set sail from Belém’s Doca do Bom Sucesso for a relaxed Tagus cruise with a small crew. Pass the Discoveries monument, 25 de Abril Bridge, Belém Tower, and Christ the King. You can help steer, enjoy a drink, or choose a sunset departure. Captain Luis has been praised for his sailing knowledge and lively narration.

“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

Join Gaviao Madeira in Funchal for a three-hour sunset sail with up to 20 people. Guides such as Bruno, Joe, Victor, and Alberto combine wildlife watching, drinks, a swim at Cabo Girão, and coastal views. Dolphins and whales are possible, but never guaranteed.

“The captain and his first mate Bruno were absolutely wonderful host. The day was spectacular and our sailing was just the right speed and wonderful. We saw dolphins and we saw the beautiful coastline and then we got a fantastic sunset.”

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5.Charming Sailboat Cruise with Port Wine,Sunset Option

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

Spend two hours with a small group aboard a comfortable sailboat from Douro Marina. Hear Porto stories from crew such as Miguel, Henrique, or Francesco, sip port wine, photograph the Luis I Bridge, and continue toward Foz when conditions allow.

“The captain and crew were wonderful and informative, always communicated on with qhere to meet, etc. The sunset view was the absolute cherry on top of a cruise filled with a few laughs and historical info on Porto. Highly recommend!!”

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6.Champagne Sailing Tours

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

Spend two hours aboard the 15-meter yacht Mara with Nigel and his crew, sailing from Doca de Santo Amaro past Lisbon’s key waterfront sights. Drinks, warm sweet and savory snacks, city stories, blankets, and a chance to steer are included. Sunset departures add extra atmosphere.

“Do yourself a favour and book this excursion….so good!”

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7.Dolphin and Whale Watching Sailing Trip

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

Join Gaviao Madeira in Funchal for a three-hour yacht trip led in English or Portuguese. Guides such as Bruno and Joseph share facts about local wildlife while you search for dolphins and whales up to three miles offshore, then stop to swim or snorkel near Cabo Girão.

“Bruno was amazing and the rest of the crew. It was such an enjoyable experience and we got to see Dolphins. I would highly recommend.”

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8.Daylight or Sunset on a Vintage Sailboat

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

Spend two hours on Lisbon’s Tagus River aboard a vintage sailboat, usually hosted by skippers such as Eduardo, Carlotta, or Angelo. Cruise past Belém Tower, the Discoveries Monument, Christ the King, Praça do Comércio, and São Jorge Castle with Portuguese snacks, wine, and wide city views.

“We had a great experience on this sail, the host was great and it was a beautiful night!”

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9.Tagus River Sailboat City Cruise

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

Join MagicSail at Belém for a two-hour sail past Lisbon’s best-known sights, from Belém Tower and the Discoveries Monument to Praça do Comércio and Christ the King. Guides such as Miguel, Tiago, Paulo, and Isaac add history, jokes, and local tips. Shared and private options are available.

“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

Spend two hours on a sailboat along Lisbon’s Tagus River, watching the city turn gold while the crew serves a welcome glass of wine. Expect views of Belém Tower, the bridge, riverside monuments, and possibly dolphins. English and Portuguese are spoken, with private groups available.

“Absolutely worth it. Beautiful sunset cruise with wine continually topped up, snacks, blankets provided, knowledgeable and pleasant staff and proper covid safety measures. We got a restaurant recommendation that we followed up on and it was totally great. Thanks again!”

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

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

Join Andre, Mariana, Felipe, Francisco, or another local guide aboard a 33-foot sailboat for two hours on the Tagus. Groups are capped at eight, with Portuguese Vinho Verde, music, sofas, and views of Belém Tower, the 25 de Abril Bridge, Alfama, and Lisbon by sunset or night.

“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 😍😍”

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12.City Skyline Sailboat Cruise with Drink and Snacks

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

Join DiscoverOasis at Santo Amaro Dock for a two-hour sail past Praça do Comércio, Alfama, Cristo Rei, Belém Tower, and MAAT. Teresa, Manuel, or another multilingual crew member provides friendly commentary, wine, beer, water, and simple snacks. Sunset departures add a beautiful final touch.

“It was really a great experience! and Theresa was really a good one!”

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

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

Join the Condor Vilamoura crew for a three-hour schooner cruise west from Vilamoura Marina. You will pass Falésia, Olhos d’Agua, Albufeira, São Rafael, and Galé, with a possible swim and small-boat visit to sea caves. English, French, Portuguese, and Spanish guiding is available.

“Very well organised. Excellent staff. Very nice experience. Well worth it”

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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 Marina toward Ponta da Piedade on a traditional Portuguese boat, then switch to a smaller craft for the caves. English and Portuguese guides, including Luis and Mariana on some departures, explain the rocks and local stories. Tapas, swimming, and sunbathing round out the 2.5-hour trip.

“The guys were really friendly and we got plenty of time to enjoy the boat and even had a mojito !! Loved it !”

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15.Best Charming Sailboat Cruise Sunset

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

Join Oporto Sailing at Pontoon B in Douro Marina for a two-hour sunset cruise with up to eight people. Guides such as Juan, Tomas, Pedro, and Jorge share Porto stories while you enjoy Douro wine, local snacks, blankets, music, and views from Ribeira to Foz do Douro.

“everything was perfect . our guide Juan called us when we were running late due to google directions and we made it on time .”

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