Sailing trips · PORTUGAL SAILING TRIPS

Sailing Trips in Portugal: The 15 Best Days Under Sail

76 trips  ·  from $11 a head

Two hours on the Tagus with Lisbon going past, Algarve catamarans into the Benagil caves, and Madeira boats that find dolphins most mornings. These 15 are priced per person and honest about the swell.

From Funchal: Ecological Catamaran Dolphin Whale Watching - Choosing your best place on the catamaran
Catamaran Cruises, Catamaran Cruises in Portugal, Madeira Sailing Trips, Portugal Sailing Trips, Tour Reviews, Whale & Dolphin Watching Sails

From Funchal: Ecological Catamaran Dolphin Whale Watching

1.Ecological Catamaran Dolphin Whale Watching

★★★★★★★★★★4.5 · 8,204 reviews · 3 hours · from $41Our pick

Join Magic Dolphin Atividades Maritimas in Funchal for a three-hour wildlife cruise aboard a 2022 hybrid-electric catamaran. Land-based spotters help locate dolphins, whales, turtles, and seabirds, while certified guides explain the animals and coastal sights. Bring warm, waterproof layers for the open sea.

“Great tour, saw some whales and the crew was great. Just like described.”

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Funchal: Dolphin and Whale Watching Catamaran Cruise - Leaving Seaborn Catamaran from Funchal Marina
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Funchal: Dolphin and Whale Watching Catamaran Cruise

2.Dolphin and Whale Watching Catamaran Cruise

★★★★★★★★★★4.5 · 5,697 reviews · 3 hours · from $41

Set out from Funchal Marina on Catamaran Seaborn for a three-hour search for dolphins, whales, and turtles. The English and Portuguese crew explain the species you see, then stop beneath Cabo Girão for a summer swim. Expect an open, stable boat, onboard drinks for purchase, and no guaranteed sightings.

“We enjoyed a cruise along the coast in an Easterly direction. We were very lucky to spot a pod of Pilot Whales including a mother and baby swimming along together. This put the icing on the cruise cake! We celebrated with a small glass of beer and wine from the onboard bar on the way back! I can recommend this 3 hour activity to anyone looking for a shortish trip out on the ocean. I should also say that we had very calm weather which helped make the trip comfortable.”

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Albufeira: Coastline and Benagil Caves Tour by Catamaran - São Rafael and Praia da Coelha
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Albufeira: Coastline and Benagil Caves Tour by Catamaran

3.Coastline and Benagil Caves Tour by Catamaran

★★★★★★★★★★4.7 · 4,077 reviews · 2.5 hours · from $35

Sail from Albufeira Marina toward Benagil on a spacious catamaran with multilingual guides such as Filipe and Tomas. Expect dramatic cliffs, beaches, cave views, music, onboard drinks, and a roughly 10-minute Atlantic swim stop when conditions allow.

“Was a great day out seeing the coastlines of Portugal. The tour guides were brilliant, very friendly and informative. If you are still deciding on whether to book or not, do it. And book with this company.”

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Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink - From the Monument to the Discoveries to Belém Tower
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Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

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

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

Join PalmaYachts for a two-hour Tagus River sail from Belém, limited to 10 people. Guides such as Benny, Miguel, João, and Telma share Lisbon’s stories while you pass Belém Tower, Commerce Square, Christ the King, and the 25 de Abril Bridge with a drink in hand.

“We had a wonderful experience on the sunset sailboat tour - Telma was so friendly and informative as this was our first time on a sailboat like this and she had interesting facts about the sites we passed. We were also given the chance to have our own time and take in our beautiful surroundings so we appreciated this too. Would definitely recommend! ✨”

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Lisbon: Sunset Catamaran Boat Tour with Music and Drinks - The 25th of April Bridge and Christ the King
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Lisbon: Sunset Catamaran Boat Tour with Music and Drinks

5.Sunset Catamaran Boat Tour with Music and Drinks

★★★★★★★★★★4.7 · 2,834 reviews · 1h 30m · from $26

Meet Sardinha do Tejo at Doca de Santo Amaro for a 90-minute sunset sail past Christ the King, the 25th of April Bridge, Belém Tower, and more. Choose the open nets or covered deck, enjoy one welcome drink, and buy cocktails aboard. This is a scenic, music-led cruise, not a guided sightseeing tour.

“Beautiful evening for a boat ride. All the hosts were very nice and helpful. They frequently came around for drink refills. I was super lucky and the boat only had 6 other guests that night so had plenty of room. Blankets were provided when it got chilly.”

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Funchal Bay: Dolphin & Whale Watch Luxury Catamaran Cruise - Searching for dolphins and whales
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Funchal Bay: Dolphin & Whale Watch Luxury Catamaran Cruise

6.Dolphin & Whale Watch Luxury Catamaran Cruise

★★★★★★★★★★4.2 · 2,684 reviews · 3 hours · from $47

Join Atlantic Pearl Catamaran in Funchal for a three-hour cruise with Portuguese- and English-speaking guides. Search for dolphins and whales, learn about marine life, then stop near Cabo Girão for swimming and snorkeling. The boat carries up to about 20 people, with shaded seating, hammocks, bathrooms, and drinks for sale.

“Terrific , good access to the boat, good seating. Great staff and we were lucky and saw both sperm whales and dolphins.”

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2 Hour Lisbon Sunset and Wine Sailing Tour - Setting out past Belém’s waterfront
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2 Hour Lisbon Sunset and Wine Sailing Tour

7.2 Hour Lisbon Sunset and Wine Sailing Tour

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

Meet Joe, Henry, JP, Marta, or another skipper at the Alcântara marina for a two-hour shared sail past Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and more. Portuguese wine, blankets, and skipper commentary are included, but this is a relaxed cruise, not a formal wine tasting.

“Very easy going. The boat was extremely clean and well kept. Our two guides were excellent- very knowledgeable, very friendly and nothing was too much trouble. We had great chats with the other guests and overall it was wonderful. You get fantastic views of the Lisbon ‘coastline’ as well as the 25th April bridge and Sanctuary of Christ the King. I should have tipped them more on departure as it was such a lovely experience”

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Lisbon: Sailing Tour on the Tagus River - Choosing Between a Sailing Boat and Catamaran
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Lisbon: Sailing Tour on the Tagus River

8.Sailing Tour on the Tagus River

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

Cruise from Belém past the Discoveries Monument, 25 de Abril Bridge, Christ the King, and Belém Tower. You can help sail or relax with a drink and snack. The crew may share local river knowledge, and sunset trips add glowing views over Lisbon.

“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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Funchal: Sunset Sailing Tour - Watching Madeira from the Atlantic
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Funchal: Sunset Sailing Tour

9.Sunset Sailing Tour

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

Join Bruno, Joe, Victor, or another friendly crew member on a small sailing yacht from Funchal. Cruise toward Cabo Girão, watch for dolphins and whales, swim or snorkel below the 580-meter cliff, then return with an open bar and sunset views.

“We really enjoyed the time on the sailboat. We saw some dolphins several times and the sunset was beautiful. We enjoyed swimming as well!! The hosts were awesome and added to the overall experience”

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From Lagos: Ponta da Piedade Caves Kayak Tour from Catamaran - Why the kayak view beats a standard coastal cruise
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From Lagos: Ponta da Piedade Caves Kayak Tour from Catamaran

10.Ponta da Piedade Caves Kayak Tour from Catamaran

★★★★★★★★★★4.9 · 2,015 reviews · 2 hours · from $37

From Lagos Marina, a skipper takes you by catamaran to Ponta da Piedade, where you slide into a double kayak for a guided cave tour. Guides such as Bruno, Ricardo, and Alfonso keep beginners on track, then return you to the boat for swimming and the onboard slide.

“Our guide Bruno was very helpful and guided everyone throughout the tour. He took us to the caves, which were breathtaking. The boat who took us to the kayaking spot was always nearby, all the crew was kind and helpful. Amazing experience! Absolutely recommended.”

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Porto: Charming Sailboat Cruise with Port Wine,Sunset Option - Under the Arrábida Bridge and past Gaia
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Porto: Charming Sailboat Cruise with Port Wine,Sunset Option

11.Charming Sailboat Cruise with Port Wine,Sunset Option

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

Set out from Douro Marina with a certified crew such as Miguel, Henrique, or Claudio for a two-hour cruise past Porto, Gaia, Ribeira, and Foz do Douro. Expect port wine, city stories, Spotify music, comfortable seating, and blankets when the boat reaches the cooler Atlantic air.

“Although the weather wasn’t perfect, we really enjoyed this boat trip!”

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Madeira Dolphin and Whale Watching on a Ecological Catamaran - What you learn from the crew
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Madeira Dolphin and Whale Watching on a Ecological Catamaran

12.Madeira Dolphin and Whale Watching on a Ecological Catamaran

★★★★★★★★★★4.5 · 1,957 reviews · 3 hours (approx.) · from $42

Cruise Madeira’s southern coast for 2.5 to 3 hours aboard Magic Dolphin’s 2022 hybrid-electric catamaran. Shore spotters guide the captain toward dolphins and whales, while certified guides explain the animals and ocean ecology. Expect Cabo Girão, Câmara de Lobos, and possible sea spray on the return.

“Close to the cruise port or 10e in a taxi. Whilst the sea journey was very choppy, to see Bottle nose Dolphins and Pilot whales was an amazing experience. I highly recommend this company, great communication and a fabulous tour. Highly recommended.”

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Funchal: Dolphin and Whale Watching by Luxury Catamaran - Searching for dolphins and whales off Madeira
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Funchal: Dolphin and Whale Watching by Luxury Catamaran

13.Dolphin and Whale Watching by Luxury Catamaran

★★★★★★★★★★4.5 · 1,709 reviews · 3 hours · from $47

Join Magic Dolphin Atividades Maritimas for a three-hour cruise from Funchal. An English or Portuguese-speaking crew looks for dolphins, whales, turtles, and seabirds before sailing to Cabo Girão. You get indoor seating, sun beds, trampoline nets, a welcome drink, and a seasonal swim stop.

“The crew was very knowledgeable and fantastic. thank you crew”

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Lagos: Piedade Caves & Coastline - Catamaran - Leaving Lagos Marina for Ponta da Piedade
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Lagos: Piedade Caves & Coastline – Catamaran

14.Piedade Caves & Coastline – Catamaran

★★★★★★★★★★4.7 · 1,694 reviews · 2h 30m · from $34

Sail from Lagos Marina along the Algarve coast to Praia da Luz and back, passing Ponta da Piedade, Dona Ana, Camilo, and Porto de Mós. You get a swim stop, paddleboards, a sun deck, Wi-Fi, and a bar, with English or Portuguese commentary. The catamaran carries up to 80 people.

“So much fun!!! The views are beautiful and the crew gave us enough time to be in the water.”

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Lagos: Dolphins & Caves - Catamaran - Searching for dolphins offshore
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Lagos: Dolphins & Caves – Catamaran

15.Dolphins & Caves – Catamaran

★★★★★★★★★★4.9 · 1,512 reviews · 2.5 hours · from $58

From Marina de Lagos, you’ll cruise offshore with marine biologists such as Nadja or Diogo, looking for dolphins and other cetaceans. Afterward, the catamaran anchors near the cliffs for swimming, jumping, and its inflatable slide. Fruit and a cookie are included, but sightings are never guaranteed.

“This trip was enjoyable, firstly looking for dolphins which we luckily saw, they swam around the boat for about 20 minutes, and we had plenty of time to observe and take pictures. Afterwards were given the opportunity to dive off the boat and use the inflatable slide which my husband and son thoroughly enjoyed in a quiet bay. Guides were friendly with everyone and accommodating to everyone's needs. We were all given cookies and delicious fresh fruit skewers as a snack which were very welcome. Overall an enjoyable experience.”

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