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15 Best Tall Ships & Sailing Boats Tours Worldwide

The best days on the water.

The 15 most popular tall ships & sailing boats tours. What each sail costs, how long you are on the water, and which crews run it well.

15 Best Tall Ships & Sailing Boats Tours Worldwide

Oslo: Oslo Fjord Sightseeing Cruise by Sailing Ship - The Oslo Fjord route: islands, Opera House, and the Munch spotlight
Cruises & Boat Tours, Fjord Cruises, Oslo, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Oslo: Oslo Fjord Sightseeing Cruise by Sailing Ship

Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink - Where to Meet: Doca de Belém, Gate 1 by Padrão dos Descobrimentos
City Tours, Cruises & Boat Tours, Evening Experiences, Lisbon, Lisbon Sailing Trips, Sailing, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews, Tours

Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

2.Lisbon: Daytime/Sunset/Night City Sailboat Tour with Drink

Sail Lisbon’s Tagus on a small-group cruise with live commentary, a welcome drink, and big views under the 25 de Abril Bridge.

4.9

“This was the highlight of our trip to Lisbon. It was fantastic to see the sights from the water on this extremely relaxing and peaceful trip. André and Vasco were extremely attentive and lovely and told us many facts and information throughout. They couldn’t have done more to ensure we had the best time. The…”

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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Small-Group Sailing with a hard cap of 14
Cruises & Boat Tours, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Sailing, Swim-Stop Cruises, Tall Ships & Sailing Boats, Tour Reviews

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Porto: Charming Sailboat Cruise with Port Wine,Sunset Option - Boarding at Douro Marina: picking the start point that fits your day
Cruises & Boat Tours, Evening Experiences, Sailing, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews, Vila Nova De Gaia, Wine Tours

Porto: Charming Sailboat Cruise with Port Wine,Sunset Option

4.Porto: Charming Sailboat Cruise with Port Wine,Sunset Option

Porto sunset sail on the Douro with port wine, great Luís I Bridge photo spots, and friendly crew commentary. 2 hours, small groups.

5.0

“We had a great time! The weather was drizzly, so it ended up just being the two of us with the two guides. They were both excellent and we had a great conversation while seeing so much of Porto and Gaia.”

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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch - Polyaigos: The “Only by Boat” Swim Break
Adamantas, Adamantas Sailing Trips, Cruises & Boat Tours, Full-Day, Lunch Experiences, Sailing, Tall Ships & Sailing Boats, Tour Reviews, Tours

Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

5.Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

Full-day Milos sail to Polyaigos for snorkel and cave swims, with lunch and drinks. Stops include Sarakiniko, Kleftiko, and more.

4.9

“Best trip we have ever been on! The boat was amazing, the food was amazing (we were fed fresh yummy food multiple times and there was unlimited drinks). Our tour guide Dora was amazing, very friendly and knowledgeable about the tour stops. She made the tour great! Couldn’t recommend enough, she even taught us traditional…”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Picking the right option: shared half-day, private, or 1-hour coastal
Crete, Crete Sailing Trips, Cruises & Boat Tours, Island-Hopping Sails, Lunch Experiences, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Barcelona Helicopter, Sailboat & Old Town Private Walking Tour - Plaza de Catalunya Stops: Fast Orientation, Easy Photo Breaks
Barcelona, Barcelona Sailing Trips, Cruises & Boat Tours, Helicopter Tours, Private, Private Sailing Charters, Sailing, Tall Ships & Sailing Boats, Tour Reviews, Tours, Walking Tours

Barcelona Helicopter, Sailboat & Old Town Private Walking Tour

7.Barcelona Helicopter, Sailboat & Old Town Private Walking Tour

Private Old Town walk plus Port Vell boat transfer and a short helicopter flight over Barcelona, with free video and small-group guiding.

5.0

“Great walking tour with awesome guide. Tour is mis sold there is no sailing as promised you get a water bus to the helicopter pad. Helicopter flight mediocre at best and only about 6 minutes long”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Picking the right option: shared half-day, private, or 1-hour coastal
Crete, Crete Sailing Trips, Cruises & Boat Tours, Island-Hopping Sails, Lunch Experiences, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

8.Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Sail from Heraklion to Dia Island for snorkeling, unlimited drinks, and lunch on a yacht, with easy pickup options available.

4.9

“Amazing! From the start to the end, the crew were wonderful and the meal was very tasteful! Dimitry was the co captain but I don’t remember the captain’s name! But thanks for that mid day cruise! I definitely recommend it 😁”

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Lisbon: Daylight or Sunset on a Vintage Sailboat - Where you meet near the 25 de Abril Bridge (and how to avoid stress)
Cruises & Boat Tours, Evening Experiences, Lisbon, Lisbon Sailing Trips, Sailing, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews

Lisbon: Daylight or Sunset on a Vintage Sailboat

Lisbon: Tagus River Sailboat City Cruise - The Belém stretch: Torre de Belém to LX Factory from the river
City Tours, Cruises & Boat Tours, Lisbon, Lisbon Sailing Trips, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Lisbon: Tagus River Sailboat City Cruise

Lisbon: Daylight or Sunset on a Vintage Sailboat - Where you meet near the 25 de Abril Bridge (and how to avoid stress)
Cruises & Boat Tours, Evening Experiences, Lisbon, Lisbon Sailing Trips, Sailing, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews

Lisbon: Daylight or Sunset on a Vintage Sailboat

11.Lisbon: Daylight or Sunset on a Vintage Sailboat

Vintage Tagus sunset sail with petiscos and wine, plus views of Belém, Praça do Comércio, São Jorge Castle, and Christ the King.

4.9

“It was wonderful being on the boat and the crew were so helpful and friendly. The refreshments and tapas were very welcome. A brilliant way to spend an afternoon. Thanks to all the crew.”

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Lisbon: Sailboat Sunset Tour with a Drink - Porta 2, Doca de Alcântara: where to meet and how to avoid stress
Cruises & Boat Tours, Evening Experiences, Lisbon, Lisbon Sailing Trips, Sailing, Sunset Sails, Tall Ships & Sailing Boats, Tour Reviews, Tours

Lisbon: Sailboat Sunset Tour with a Drink

Lake Taupo: Sailboat Trip to the Maori Rock Carvings - Meeting point, shoes, and what to wear in Taupō weather
Cruises & Boat Tours, Sailing, Tall Ships & Sailing Boats, Taupo, Taupo Sailing Trips, Tour Reviews

Lake Taupo: Sailboat Trip to the Maori Rock Carvings

Sailboat tour from PALAU to the Maddalena Archipelago. - Meet-up at Piazza del Molo: show up early and be chill
Cruises & Boat Tours, Sailing, Sardinia, Sardinia Sailing Trips, Tall Ships & Sailing Boats, Tour Reviews, Tours

Sailboat tour from PALAU to the Maddalena Archipelago.

14.Sailboat tour from PALAU to the Maddalena Archipelago.

Small-group sailing from Palau to La Maddalena with wine, Sardinian lunch, snorkel stops, and plenty of swim time near the pink beach.

5.0

“This site is a SCAM and will review it on any site possible. Payed a reservation with viator on the phone to be cancelled a few min later although available on the site, payed for a 2nd one by phone again , to start receiving messages through email and whatsapp from who turned out to…”

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From Palau or La Maddalena: Archipelago Sailing Ship Tour - Palau vs La Maddalena: Which Port Gives You the Better Day?
Cruises & Boat Tours, Palau, Palau Sailing Trips, Sailing, Tall Ships & Sailing Boats, Tour Reviews, Tours

From Palau or La Maddalena: Archipelago Sailing Ship Tour

More Tall Ships & Sailing Boats Tours Worldwide

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The sailing ports worth the trip, grouped by the sea they sit on.