The 15 Best Sailing Trips in Portugal

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

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

Join a small group of up to 10 people for a two-hour sail from Belém. Your crew, often including guides such as Benny, Miguel, Telma, or João, shares Lisbon history while you pass Belém Tower, Cristo-Rei, Commerce Square, and MAAT. Choose daytime, sunset, or night sailing, with one drink and water included.

“We actually sailed some. The skipper/guide was knowledgeable and fun, and the crew member was good. The views were good. I recommend the trip”

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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 small group of up to 12 at Lisbon’s Alcântara marina for a two-hour sunset sail. Your skipper handles the boat while you enjoy Portuguese wine, views of Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and commentary from hosts such as Joe, Henry, JP, or Marta.

“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

Join a small sailboat or catamaran at Belém’s Doca do Bom Sucesso for a relaxed Tagus cruise. You can help steer with the crew or stretch out on deck. Expect a safety briefing, city views, one drink, water, a light snack, and about 105 minutes on the river. Sunset departures add Lisbon’s skyline in warm evening light.

“I really enjoyed the sailboat tour—the guides were very friendly, and it was a great value for the money.”

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4.Funchal: Sunset Sailing Tour

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

Join Bruno, Joe, Victor, or another friendly guide for a three-hour sunset sail from Funchal. The small yacht carries up to 20 people, with swimming and snorkeling at Cabo Girão, an open bar, coastal views, and a chance to spot dolphins or whales. Wildlife is never promised, but the relaxed setting and sunset are.

“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

Spend two hours with Douro Captain Lda on a small-group sailboat from Douro Marina past Porto, Gaia, Ribeira, and Foz do Douro. Expect port wine, a welcome drink, music, city stories, bridge views, and a possible Atlantic stretch. Crew members such as Miguel, Henrique, Eric, Francesco, and Claudio are praised for warm service, though the boat may use its motor when sailing conditions are poor.

“Friendly and capable crew. Excellent sunset cruise. Highly recommend.”

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6.Champagne Sailing Tours

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

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. Small groups keep the mood personal.

“On top of amazing views and fun guide, food was my absolute highlight!”

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7.Funchal: Dolphin and Whale Watching Sailing Trip

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

From Funchal Marina, sail up to three miles offshore with a captain and guide in search of dolphins, whales, and sea turtles. Bruno and Joseph are among the crew members praised for their warm, informative hosting. You will stop near Cabo Girão to swim or snorkel, then return with a drink and wide ocean views.

“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

Join Eduardo, Carlotta, Angelo, or another Furanai host for a two-hour vintage sail from Santo Amaro Dock. You’ll pass Belém Tower, Jerónimos Monastery, Praça do Comércio, São Jorge Castle, Christ the King, and the 25 de Abril Bridge while enjoying Portuguese snacks and white or rosé wine. Sunset departures add the best light, but daytime sails offer clearer monument views.

“Glad we chose this tour! Not too crowded, plenty of space to lounge and enjoy the views. Loved our tour guide, he was very accommodating with drinks, a mini charcuterie spread, and even blankets when it started to get cooler. He explained monuments and history of Lisbon to us, too. Relaxing music all the way through the ride. We thoroughly enjoyed this experience and would recommend to anyone!”

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9.Tagus River Sailboat City Cruise

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

Sail from Belém past Lisbon’s great riverfront sights, including Belém Tower, the Discoveries Monument, Praça do Comércio, the 25 de Abril Bridge, and Christ the King. Your crew provides live commentary in English, Portuguese, or Spanish, plus music and one drink. Choose a shared or private cruise, with sunset departures especially appealing.

“We took the sailboat cruise on the last day of our trip to Lisbon and it was the perfect end to our vacation. Our tour guides were Mr Miguel and Mr Tiago, both of them were extremely jovial, humorous and kept us all engaged during the cruise. It was a great experience all thanks to our guides. We loved every bit of it and would absolutely recommend everyone to take the cruise- it is one of a kind experience.”

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10.Sunset Sailing Cruise with Wine

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

Spend two hours sailing the Tagus at sunset, with a welcome glass of Portuguese wine and wide views of Lisbon’s waterfront. The crew explains sights such as Belém Tower, the Ponte bridge, and the Cristo Rei statue without filling every quiet moment. Boats may be private or shared, and meeting points vary by booking option.

“Amazing service! The crew were very nice, explained the turistics places we were passing through and kept our wine glass always full! The sunset was fabulous and we were able to see even the full moon rising! It was perfect! Thank you for this experience!”

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

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

Spend two hours on a 33-foot sailboat with up to eight people, local guides such as Andre, Mariana, Francisco, and Felipe, and an open bar of Portuguese Vinho Verde. You’ll pass Belém Tower, the Discoveries Monument, Almada, Alfama, and Commerce Square. Sunset departures offer the best light, but bring warm layers.

“the setting was very chill and intimate. my cup was never empty, it was always filled with wine. Our Guide, Andrei and Marina were so accomodating. 10/10 experience. highly recommend this tour.”

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12.City Skyline Sailboat Cruise with Drink and Snacks

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

Spend two hours on a small sailboat from Santo Amaro Dock, cruising past Praça do Comércio, Cacilhas, Cristo Rei, Belém Tower, and the MAAT museum. Your welcome drink may be wine, beer, or water, with simple snacks. Guides such as Teresa and Manuel offer commentary in several languages, and sunset departures add warm evening light.

“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

From Vilamoura Marina, you sail west aboard the schooner Condor past Falésia, Olhos d’Agua, Albufeira, São Rafael, and Galé. Expect coastal narration, a possible sea swim, and a small-boat trip into caves when conditions allow. The onboard bar sells drinks and snacks, and the crew speaks English, French, Portuguese, and Spanish.

“Fabulous crew. Absolutely beautiful sail boat. So nice being out in the ocean with the sails up. Then hopped into a dinghy to see the caves. Alcohol was pleasantly very good priced too.”

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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 small craft for a close look at arches, grottoes, and rock towers. Local guides such as Luis, Mariana, and Mauricio have been praised for safety and commentary. Portuguese tapas, swimming time, and deck space round out the 2.5-hour trip.

“We loved it. The crew put up the sails on the way to Ponta da Piedade which we enjoyed. The speed boat trip thought the caves was beautiful. We did 2 hour trip but would have liked longer.”

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15.Best Charming Sailboat Cruise Sunset

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

Join a small crew at Douro Marina for a two-hour sunset sail along the Douro. You’ll pass Porto’s bridges, Ribeira, Gaia, Foz, and the Felgueiras Lighthouse while tasting Douro wine and regional snacks. Guides such as Juan, Tomas, Pedro, and Jorge are known for friendly local stories. Blankets and jackets may be available when the breeze turns cool.

“Loved the people who ran it and their local knowledge was excellent!”

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