The 15 Best Sailing Trips in Portugal

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

Funchal eco catamaran dolphin and whale watching with hybrid-electric quiet sailing, land spotters, and 360° views along Madeira’s south coast.

“Lovely crew on boat. Delighted to see pod of pilot whales …a real treat. Thank you team. Be warned, it’s gets ve dry chilly out there, on way out to observation area. Bring layers!”

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Boat Tours in Madeira, Cruises & Boat Tours, Dolphin Watching, Sailing, Things to Do in Madeira, Tour Reviews, Whale Watching

Funchal: Dolphin and Whale Watching Catamaran Cruise

2.Dolphin and Whale Watching Catamaran Cruise

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

3 hours off Madeira from Funchal in a stable catamaran, searching for dolphins, whales, turtles, plus Cabo Girão swim time.

“We were lucky to see both dolphins and whales. Staff were great! ,they interacted with everyone, pleasant, friendly and very informative about the sea life.”

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Benagil Sea Cave Tours, Boat Tours in Algarve, Cruises & Boat Tours, Sailing, Things to Do in the Algarve, Tour Reviews, Tours

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

Cruise from Albufeira to Benagil on a modern catamaran, see sea caves and rock arches, then cool off with a short Atlantic swim.

“Lovely day one the sea, the crew were great. I got to have a jump in the water and it was very refreshing.”

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Boat Tours in Lisbon, City Tours, Cruises & Boat Tours, Evening Experiences, Sailing, Sunset Cruises in Lisbon, Things to Do in Lisbon, Tour Reviews, Tours

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

A 2-hour sailboat cruise on the Tagus with live guide commentary, a welcome drink, and standout Lisbon waterfront views at day, sunset, or night.

“Guides Vasco and Luiz were fantastic. Really informative and welcoming. They made the activity feel really special and we thoroughly enjoyed the morning. Would highly recommend!”

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Boat Tours in Lisbon, Cruises & Boat Tours, Evening Experiences, Sailing, Sunset Cruises in Lisbon, Things to Do in Lisbon, Tour Reviews, Tours

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

Lisbon sunset catamaran on the Tagus with music, blankets, and a welcome drink. See 25 de Abril Bridge and Belém from water.

“Really nice chill sunset ride. Music was lovely and the welcome drink includes cocktails as well as wine! Would 100% recommend, if you do go bring a jumper as it gets chilly once the sun sets”

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Boat Tours in Madeira, Cruises & Boat Tours, Dolphin Watching, Sailing, Things to Do in Madeira, Tour Reviews, VIP, Whale Watching

Funchal Bay: Dolphin & Whale Watch Luxury Catamaran Cruise

6.Funchal Bay: Dolphin & Whale Watch Luxury Catamaran Cruise

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

3-hour luxury catamaran cruise from Funchal with dolphin and whale spotting, plus a swim and snorkel stop at Cabo Girão.

“Here is the revised version without the part about needing anything: ⸻ My mother and I had an absolutely amazing catamaran trip in Madeira! The skipper was incredibly friendly and made the whole experience unforgettable. He even sang along to the music, which created such a fun and relaxed atmosphere on board. His positive energy really set the tone for the entire trip. The combination of beautiful views, great music, and his fantastic mood made this one of the highlights of our stay in Madeira. It was such a special experience for both of us, and we truly enjoyed every minute. Highly recommended – we would definitely do it again!”

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2-Hour Experiences, Boat Tours in Lisbon, Cruises & Boat Tours, Evening Experiences, Sailing, Sunset Cruises in Lisbon, Things to Do in Lisbon, Tour Reviews, Tours, Wine Tours, Wine Tours in Lisbon

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 $66.51Top rated

Two hour sunset sailing from Belém with Portuguese wine and easy skipper commentary on Lisbon’s landmarks, in a small group.

“Very nice cruise...met some very nice people. The clouds didn't accommodate the sunset but still worthwhile seeing the shore from the water. The crew was wonderful.”

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Boat Tours in Lisbon, Cruises & Boat Tours, Sailing, Things to Do in Lisbon, Tour Reviews, Tours

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

Sail Lisbon on the Tagus in a small group with a free drink, snacks, and a chance to help steer, plus optional sunset views.

“We had an amazing time! The crew was really nice, we felt welcomed & would 100% recommend!”

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Boat Tours in Madeira, Cruises & Boat Tours, Evening Experiences, Sailing, Sunset Cruises in Madeira, Things to Do in Madeira, Tour Reviews, Tours

Funchal: Sunset Sailing Tour

9.Sunset Sailing Tour

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

Funchal sunset sailing in Madeira with unlimited drinks, a swim at Cabo Girão, and real chances to spot dolphins and whales.

“Everything was great! The guide was super nice and chatty, the experience was amazing.”

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Boat Tours in Algarve, Canoes & Kayaks, Cruises & Boat Tours, Ponta da Piedade Boat Trips, Sailing, Things to Do in the Algarve, Tour Reviews, Tours

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

Kayak the Ponta da Piedade caves from a comfortable Lagos catamaran, with a boat slide and a quick swim in clear water.

“The kayaking was amazing. The guides brought great energy which elevated the whole experience. We thoroughly enjoyed it and would recommend”

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Boat Tours in Porto, Cruises & Boat Tours, Evening Experiences, Port Wine Lodges & Tastings, Sailing, Sunset Cruises in Porto, Things to Do in Porto, Tour Reviews, Wine Tours, Wine Tours in Porto

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

Porto sunset sailboat on the Douro with Port wine, city views, and stories from the crew. 2 hours from about $41.

“That was a once in a lifetime experience. Sipping a drink while on a sailboat watching the sunrise names better thing”

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Boat Tours in Madeira, Cruises & Boat Tours, Dolphin Watching, Sailing, Things to Do in Madeira, Tour Reviews, Whale Watching

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 $42.33

Eco-friendly catamaran whale watching from Funchal with land spotters, hybrid-electric quiet cruising, and scenic passes like Cabo Girão.

“The guide was very knowledgeable and shared information about both pilot whales and dolphins. We were fortunate enough to see a family of whales as well as several dolphins.”

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Boat Tours in Madeira, Cruises & Boat Tours, Dolphin Watching, Sailing, Things to Do in Madeira, Tour Reviews, VIP, Whale Watching

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

Funchal dolphins and whales on a luxury catamaran to Cabo Girão, with onboard guide, comfort, and a summer swim option.

“Absolutely loved this trip, the chap speaking to us about the wildlife found off the coast was incredibly knowledgeable. Really good value for money. And we saw a group of dolphins up close! You also get a free drink included which was a nice touch. Would definitely go back to this company again!”

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Boat Tours in Algarve, Cruises & Boat Tours, Ponta da Piedade Boat Trips, Sailing, Things to Do in the Algarve, Tour Reviews

Lagos: Piedade Caves & Coastline – Catamaran

14.Piedade Caves & Coastline – Catamaran

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

Stable catamaran cruise from Lagos to Ponta da Piedade and Praia da Luz. Swim, paddle boards, WiFi, scenic Algarve cliffs. From $34.

“This was so much fun. Th crew was so nice and professional. Amazing tour for the price we paid. It’s so much more worth. Would recommend this to everyone.”

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