5 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.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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