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Top Portugal Sailing Trips

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Portugal Tours

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Exclusive Private Sailing Tour Algarve Portimão

This tour is lead by locals with deep knowledge of our coast and with sailing experience. Considering the weather conditions and your own interests they …More

Portimao, Portugal
5.0 (2)

Exclusive Private Sailing Tour Algarve Portimão

This tour is lead by locals with deep knowledge of our coast and with sailing experience. Considering the weather conditions and your own interests they...

3 hours Free Cancellation
5.0 (2)
from
$677
Private Sunset Cruise in Lisboa

Without any doubt an extravagant way to finish your day before dinner... If you really want to watch the unique sunset with your partner or …More

Lisbon, Portugal
5.0 (4)

Private Sunset Cruise in Lisboa

Without any doubt an extravagant way to finish your day before dinner... If you really want to watch the unique sunset with your partner or...

2 hours Free Cancellation
5.0 (4)
from
$669
Private Luxury Sail Yacht Cruise

2h30 - Luxury Sail-Yacht Cruise with 2 options available: a)Benagil; b)Joao d’Arens(Millionaires Bay) /Alvor Included: 2 Qualified & Experienced crew members & 2 Paddle Boards …More

Portimao, Portugal
5.0 (2)

Private Luxury Sail Yacht Cruise

2h30 - Luxury Sail-Yacht Cruise with 2 options available: a)Benagil; b)Joao d’Arens(Millionaires Bay) /Alvor Included: 2 Qualified & Experienced crew members & 2 Paddle Boards...

2 hours 30 minutes Free Cancellation
5.0 (2)
from
$657
Porto: Douro River 2h Private Tour With Port Wine

Welcome to your Porto Boat Private Tour Go on a walk along the banks of Porto and get to know some of the most beautiful …More

Likely to Sell Out
Likely to Sell Out
Porto, Portugal
5.0 (9)

Porto: Douro River 2h Private Tour With Port Wine

Welcome to your Porto Boat Private Tour Go on a walk along the banks of Porto and get to know some of the most beautiful...

2 hours Free Cancellation
5.0 (9)
from
$620
Private Porto Sailing Yacht Sunset Sightseeing Tour

Conclude your day in Porto with a luxury Sail Yacht private ride. A two hour cruise along the river, from Douro Marina until downtown Porto …More

Porto, Portugal
5.0 (16)

Private Porto Sailing Yacht Sunset Sightseeing Tour

Conclude your day in Porto with a luxury Sail Yacht private ride. A two hour cruise along the river, from Douro Marina until downtown Porto...

2 hours Free Cancellation
5.0 (16)
from
$618
Cascais Private Luxury Sunset 2h Cruise with a drink

Enjoy an exclusive 2-hour private sunset cruise along the magnificent coast of Cascais, aboard a fully crewed luxury yacht. Designed for those who appreciate elegance, …More

Likely to Sell Out
Likely to Sell Out
Cascais, Portugal
5.0 (35)

Cascais Private Luxury Sunset 2h Cruise with a drink

Enjoy an exclusive 2-hour private sunset cruise along the magnificent coast of Cascais, aboard a fully crewed luxury yacht. Designed for those who appreciate elegance,...

2 hours Free Cancellation
5.0 (35)
from
$600
4 Hours Private Swimming/Sailing Tour on Sailboat in Lisbon Beach

Our boat takes a maximum of 8 guests per tour, which makes it a very cozy and premium experience. (June-August): 11AM - 3PM Enjoy a …More

Lisbon, Portugal
5.0 (4)

4 Hours Private Swimming/Sailing Tour on Sailboat in Lisbon Beach

Our boat takes a maximum of 8 guests per tour, which makes it a very cozy and premium experience. (June-August): 11AM - 3PM Enjoy a...

4 hours Free Cancellation
5.0 (4)
from
$571
Private Motor Yacht Tour - Ria Formosa

A private motor yacht boat trip at Ria Formosa is a luxurious and exclusive way to explore the breathtaking natural beauty of the Algarve region. …More

Likely to Sell Out
Likely to Sell Out
Faro, Portugal
4.7 (10)

Private Motor Yacht Tour - Ria Formosa

A private motor yacht boat trip at Ria Formosa is a luxurious and exclusive way to explore the breathtaking natural beauty of the Algarve region....

3 to 7 hours Free Cancellation
4.7 (10)
from
$559
Lisbon Wine Tasting with Sommelier on a Private Sailboat

Portuguese wine tasting with a sommelier sets the tone for a private sailboat cruise along Lisbon’s Tagus River. Sample Portuguese wines with Portuguese delicacies while …More

Likely to Sell Out
Likely to Sell Out
Lisbon, Portugal
5.0 (8)

Lisbon Wine Tasting with Sommelier on a Private Sailboat

Portuguese wine tasting with a sommelier sets the tone for a private sailboat cruise along Lisbon’s Tagus River. Sample Portuguese wines with Portuguese delicacies while...

2 hours Free Cancellation
5.0 (8)
from
$536
Fall in love in Lisbon!

• Surprise your beloved with an unforgettable moment. • Toast in an intimate and unique atmosphere, filled with glamour! • Indulge yourself in the warm …More

Lisbon, Portugal
5.0 (1)

Fall in love in Lisbon!

• Surprise your beloved with an unforgettable moment. • Toast in an intimate and unique atmosphere, filled with glamour! • Indulge yourself in the warm...

2 hours 30 minutes
5.0 (1)
from
$520
4h Private Boat Tour - Sailing, Swimming and Sunbathing

Looking for an exclusive experience on the Tagus River? Our private tours on a sailboat offer the perfect opportunity to escape the crowds and soak …More

Lisbon, Portugal
5.0 (42)

4h Private Boat Tour - Sailing, Swimming and Sunbathing

Looking for an exclusive experience on the Tagus River? Our private tours on a sailboat offer the perfect opportunity to escape the crowds and soak...

4 hours Free Cancellation
5.0 (42)
from
$517
Cascais Private Sailing 2h Cruise with a drink

During the 2-Hours Sailing Cruise in Cascais with drinks, you will Start your cruise from Cascais and enjoy the beautiful coastline aboard a new sailboat. …More

Cascais, Portugal
5.0 (52)

Cascais Private Sailing 2h Cruise with a drink

During the 2-Hours Sailing Cruise in Cascais with drinks, you will Start your cruise from Cascais and enjoy the beautiful coastline aboard a new sailboat....

2 hours Free Cancellation
5.0 (52)
from
$515
Sunrise, Sunset & Moonlight private Sailing Cruises in Madeira

Since 2001, we've been cruising the waters of Madeira and Porto Santo in all sorts of nifty vessels, from dinghies to windsurfing boards and catamarans. …More

5.0 (11)

Sunrise, Sunset & Moonlight private Sailing Cruises in Madeira

Since 2001, we've been cruising the waters of Madeira and Porto Santo in all sorts of nifty vessels, from dinghies to windsurfing boards and catamarans....

3 hours Free Cancellation
5.0 (11)
from
$514
Private Sunset Boat Trip Funchal, Madeira with Snacks & Beverages

Experience the beauty of a Madeira sunset on a private 2.5-hour boat trip with Luv Sailing for up to 8 people from Funchal. (sunrise trips …More

5.0 (22)

Private Sunset Boat Trip Funchal, Madeira with Snacks & Beverages

Experience the beauty of a Madeira sunset on a private 2.5-hour boat trip with Luv Sailing for up to 8 people from Funchal. (sunrise trips...

2 hours 30 minutes Free Cancellation
5.0 (22)
from
$511
Private Beach Tour on a Luxury Sailing Boat in Lisbon

In summer there is a lot of traffic to get to the beaches and when we get there they are full of people! This is …More

Lisbon, Portugal
5.0 (4)

Private Beach Tour on a Luxury Sailing Boat in Lisbon

In summer there is a lot of traffic to get to the beaches and when we get there they are full of people! This is...

4 hours Free Cancellation
5.0 (4)
from
$482
Half-Day boat experience - Comporta - Troia - Setubal

This is a unique opportunity to visit one of the Europe secrets. The beautiful and small caves in Serra da Arrabida, the small beaches only …More

Setubal District, Portugal
4.9 (16)

Half-Day boat experience - Comporta - Troia - Setubal

This is a unique opportunity to visit one of the Europe secrets. The beautiful and small caves in Serra da Arrabida, the small beaches only...

3 hours Free Cancellation
4.9 (16)
from
$454
Madeira Private Boat Tour from Funchal

Feel the wind in your hair and smell the salty air. Madeira has so much to offer and so do our boat trips. One thing …More

5.0 (9)

Madeira Private Boat Tour from Funchal

Feel the wind in your hair and smell the salty air. Madeira has so much to offer and so do our boat trips. One thing...

3 hours Free Cancellation
5.0 (9)
from
$448
Cascais Romantic Luxury Private 2h Cruise with sparkling wine

Celebrate Love on a Luxury Yacht Imagine you and your better half sailing into the sunset, under a magnificent blue sky — just the two …More

Cascais, Portugal
5.0 (8)

Cascais Romantic Luxury Private 2h Cruise with sparkling wine

Celebrate Love on a Luxury Yacht Imagine you and your better half sailing into the sunset, under a magnificent blue sky — just the two...

2 hours Free Cancellation
5.0 (8)
from
$426
2.5h Sunset Navigation with Azorean appetizers and Wine

Sail aboard a modern and comfortable sailboat where you can learn sailing concepts and take the helm. Enjoy coastal views at the best time of …More

5.0 (25)

2.5h Sunset Navigation with Azorean appetizers and Wine

Sail aboard a modern and comfortable sailboat where you can learn sailing concepts and take the helm. Enjoy coastal views at the best time of...

2 hours 30 minutes Free Cancellation
5.0 (25)
from
$413
Porto: Private Classic Boat on the River Douro

Exclusive tours of the 6 Bridges on board a Classic Sailboat, passing through the Historic area of Ribeira and ending at the Foz do Rio …More

Porto, Portugal
5.0 (27)

Porto: Private Classic Boat on the River Douro

Exclusive tours of the 6 Bridges on board a Classic Sailboat, passing through the Historic area of Ribeira and ending at the Foz do Rio...

2 hours Free Cancellation
5.0 (27)
from
$402

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

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Discover Portugal

Luxury & Special Occasions

Luxury & Special Occasions

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Tours & Sightseeing

Tours & Sightseeing

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Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

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Cultural & Theme Tours

Cultural & Theme Tours

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Walking & Biking Tours

Walking & Biking Tours

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Food, Wine & Nightlife

Food, Wine & Nightlife

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Outdoor Activities

Outdoor Activities

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Private & Custom Tours

Private & Custom Tours

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Shore Excursions

Shore Excursions

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Day Trips & Excursions

Day Trips & Excursions

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Water Sports

Water Sports

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Holiday & Seasonal Tours

Holiday & Seasonal Tours

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Belém Tower (Torre de Belém)

Belém Tower (Torre de Belém)

Prices from $1
Commerce Square (Praça do Comércio)

Commerce Square (Praça do Comércio)

Prices from $1
Monument to the Discoveries (Padrão dos Descobrimentos)

Monument to the Discoveries (Padrão dos Descobrimentos)

Prices from $1
Alfama

Alfama

Prices from $1
25th of April Bridge (Ponte 25 de Abril)

25th of April Bridge (Ponte 25 de Abril)

Prices from $1
Electricity Museum (Museu da Electricidade)

Electricity Museum (Museu da Electricidade)

Prices from $11
Museum of Art, Architecture and Technology (MAAT)

Museum of Art, Architecture and Technology (MAAT)

Prices from $11
Dom Luis Bridge (Ponte de Dom Luis I)

Dom Luis Bridge (Ponte de Dom Luis I)

Prices from $1
Clérigos Church and Tower (Torre & Igreja dos Clérigos)

Clérigos Church and Tower (Torre & Igreja dos Clérigos)

Prices from $1
Porto Cathedral (Sé Catedral do Porto)

Porto Cathedral (Sé Catedral do Porto)

Prices from $1
Baixa District (Lower Town)

Baixa District (Lower Town)

Prices from $3
Benagil Cave

Benagil Cave

Prices from $3
Rainy day activities in Portugal

Rainy day activities in Portugal
Senior-friendly tours Portugal

Senior-friendly tours Portugal
Portugal Foodie Tours

Portugal Foodie Tours
Family-friendly Portugal Tours

Family-friendly Portugal Tours
The best tours and activities for culture lovers in Portugal

The best tours and activities for culture lovers in Portugal
Top 10 Portugal 2026

Top 10 Portugal 2026
Top Day Trips from Portugal

Top Day Trips from Portugal
Things to do in Portugal this summer

Things to do in Portugal this summer
New Year’s Day long weekend in Portugal

New Year’s Day long weekend in Portugal
Christmas Eve in Portugal

Christmas Eve in Portugal
New Year’s Eve in Portugal

New Year’s Eve in Portugal
Hanukkah in Portugal

Hanukkah in Portugal

Colosseum

Colosseum

Prices from $2
Eiffel Tower

Eiffel Tower

Prices from $1
Stonehenge

Stonehenge

Prices from $7
Acropolis

Acropolis

Prices from $7
Statue of Liberty

Statue of Liberty

Prices from $11
Tower of London

Tower of London

Prices from $8
Antelope Canyon

Antelope Canyon

Prices from $15
Vatican Museums (Musei Vaticani)

Vatican Museums (Musei Vaticani)

Prices from $11
National September 11 Memorial & Museum

National September 11 Memorial & Museum

Prices from $6
Louvre

Louvre

Prices from $1
South Beach

South Beach

Prices from $10