Top Cascais Holidays

18 results

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Cascais to Lisbon Sunset Cruise With Open Bar

End your day in unforgettable style with a stunning sunset cruise, departing from Cascais Marina and heading towards Lisbon. For two hours, embark on a panoramic journey along the Atlantic coast and the majestic Tagus estuary — the most beautiful way to return to the capital. Enjoy the beauty of the landscape while savouring unlimited drinks — we offer white wine, sangria and draught beer. As the sun begins to set on the horizon, the sky is painted with warm, golden tones — the perfect backdrop for memorable photos and moments of pure tranquillity at sea. The arrival in the capital is a magical moment, a stunning entrance into the Tagus estuary, Lisbon's monumental gateway — once the departure point for great explorers. Contemplate the historic neighbourhood of Belém, with all its imposing monuments by the river, pass under the 25th of April Bridge and marvel at the brightness of the lights of the Commerce Square. The tour ends at Doca da Marinha right in the heart of the city!

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Cascais to Lisbon Sunset Cruise With Open Bar

2 hoursFree Cancellation

5.0

(23)

from $45

Enjoy an unforgettable afternoon with a boat trip along the stunning coastline of Cascais. For 90 minutes, embark on a panoramic journey along the picturesque shores of Cascais and Estoril, while toasting the moment with unlimited drinks — cold beer, sangria or white wine on tap, all included. Let yourself be carried away by the waves and the stories that have shaped this coastline — tales of kings and navigators, of faith and battles and secrets kept by the sea. Admire, from a privileged viewpoint that only the sea can offer, the majestic Fortresses of Nossa Senhora da Luz and of St. António da Barra, the summer palaces, the picturesque St. Marta and Guia Lighthouses and the impressive cliff that protects the mysterious Boca do Inferno. Perfect for couples, families or groups of friends, this tour is a unique and authentic experience that combines relaxation, culture and breathtaking scenery. A different — and absolutely memorable — way to discover the magic of the Cascais coast.

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Cascais Coastal Secrets 90 Minute Cruise with Free Wine and Beer

1 hour 30 minutesFree Cancellation

5.0

(29)

from $45

Half-Day Tour in Cascais / Sintra with Brunch and Wine Tasting

I have chosen to get off the beaten tracks and the mainstream routes. Instead, I prefer to explore hidden places, out of the ordinary, try new flavours and be bold. Each discovery gives me an excuse to gather my friends, depart into new adventures, and share my latest findings. Now, it is time to share with you what, as a local, I consider to be unmissable while visiting my hometown. Bring a positive attitude, good vibes and plenty of space for new memories!

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Half-Day Tour in Cascais / Sintra with Brunch and Wine Tasting

5 hoursFree Cancellation

4.9

(33)

from $83

Cascais: Glamour and Decay by The Lisbon Coastline - Private Tour

3 to 4 hoursFree Cancellation

4.9

(60)

from $35

Price varies by group size

E-Bike & Wine Tasting Experience from Ericeira

With this guided bike ride, you can access incredible scenery and also learn about local wines too. Starting in Ericeira, a guide leads the way and takes you on an adventure through vineyards and agricultural fields, so you don’t have to worry about getting lost. When you reach the beautiful town of Cheleiros, have the chance to try six wines, with delicious local bread and olive oil included too.

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E-Bike & Wine Tasting Experience from Ericeira

4 hours

5.0

(27)

from $130

Porto Heritage & Wine: Exclusive Private Day Trip from Lisbon

10 to 12 hoursFree Cancellation

5.0

(32)

from $460

Price varies by group size

SINTRA Day Trip - Tickets & Lunch Included

See Sintra’s top highlights without worrying about tickets, transportation, or planning your route. This private tour combines guided visits to the historic Centro Histórico, Quinta da Regaleira, and Monserrate Palace with scenic stops at Azenhas do Mar and Cabo da Roca. Hotel pickup, palace admission, and a traditional Portuguese lunch make for a relaxed day exploring the region’s history, coastline, and culture.

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SINTRA Day Trip - Tickets & Lunch Included

8 hoursFree Cancellation

5.0

(45)

from $472

Price varies by group size

Cascais Private Sailing 2h Cruise with a drink

Sail along the rugged coastline of Cascais and take in the sights on this private cruise. Climb aboard your private sailboat with your group and sip on included drinks while you sail. Enjoy private transportation, restroom facilities on board, and the option to anchor for swimming if weather allows. Take in the Cascais Marina, the lighthouse, several beaches, and old forts over a couple of hours.

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Cascais Private Sailing 2h Cruise with a drink

2 hoursFree Cancellation

5.0

(52)

from $531

Per group

There’s no better time to learn to surf than during your vacation in Portugal. Visit one of the city’s two best beaches for surfing—Guincho or Carcavelos—and get the basics down or improve your skills. If you’re new, learn to paddle out to sea, how to get up on your board, and how to balance, before catching some waves. For more experienced surfers, your instructor provides feedback on how to improve.

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Surf Experience in Cascais

2 hoursFree Cancellation

5.0

(461)

from $50

Surf Lesson

2 hoursFree Cancellation

4.9

(99)

from $41

Price varies by group size

Likely to Sell Out

Cascais Romantic Luxury Private 2h Cruise with sparkling wine

2 hoursFree Cancellation

5.0

(9)

from $442

Per group

Private Tour from Lisbon to Evora and Monsaraz with Wine Tasting

This tour departs from the Greater Lisbon area (including Lisbon, Oeiras, Cascais, Sintra, Amadora, Loures, Odivelas, Almada) and takes you deep into the heart of Portugal’s countryside, known for its world-renowned wines and as the world’s largest cork-producing region. You’ll enjoy an Évora tour as part of your journey to Évora from Lisbon, the “museum city,” where every corner reveals a historical monument, from Roman ruins to medieval architecture. With a certified guide by your side, you’ll explore this UNESCO World Heritage Site in depth. Visit a traditional cork factory to learn how cork is harvested and processed, and enjoy a wine tasting at a local winery. The journey continues to the medieval village of Monsaraz, offering panoramic views over the Alentejo landscape and Alqueva Lake. Travel in a comfortable, air-conditioned vehicle, always accompanied by your guide, ensuring a smooth, educational, and memorable experience from start to finish.

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Private Tour from Lisbon to Evora and Monsaraz with Wine Tasting

9 hours 30 minutesFree Cancellation

5.0

(4)

from $324

Price varies by group size

Embark on a Breathtaking Journey Through Nature and Flavour Discover the charm of Cheleiros on a scenic 7 km walk designed to be accessible and enjoyable for most. Surrounded by rolling hills and stunning landscapes, this immersive experience invites you to slow down and connect with nature at its finest. But the adventure doesn’t end there—after soaking in the beauty of the outdoors, step into the warm, welcoming home of a local wine producer. Here, you'll uncover the fascinating story of Cheleiros' wine culture and its deep-rooted connection to the region’s unique terroir. Let your senses come alive with a guided tasting of six exceptional wines, perfectly paired with authentic regional tapas. This is more than just a walk—it's a celebration of nature, tradition, and taste. Join us for an unforgettable blend of scenery, storytelling, and sensational flavours.

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Hike & Wine Ericeira

4 hoursFree Cancellation

5.0

(6)

from $118

See Cascais, its landmarks, and its beaches from the water on this private sailing tour. Cruise out onto Cascais Bay and sail along the coastline to enjoy the scenery of this seaside town. Spot charming fishing boats, the towering walls of the Cascais Citadel, and the Santa Marta Lighthouse before watching the sunset over the horizon. This private tour includes private transportation and insurance for a seamless experience.

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Cascais Private Sailing Cruise with a drink - Half day/full day

4 to 8 hoursFree Cancellation

5.0

(26)

from $731

Per group

Private Sunset Sailing and Wine Tasting Experience in Cascais

Sail the stunning Cascais coastline on a private boat, perfect for couples and families seeking memorable moments. Enjoy a serene sunset cruise, indulge in fine Portuguese wines during a wine tasting at sea, or savor dinner under a starlit sky. With options for half-day and full-day excursions, each journey invites relaxation and connection with the ocean. Tailor your experience to fit your preferences and enjoy the comfort of a private sailing adventure.

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Private Sunset Sailing and Wine Tasting Experience in Cascais

3 hoursFree Cancellation

from $708

Per group

From Lisbon: Hidden Alentejo Wine & Royal Lusitano Horses

Hidden Alentejo: PremiumWine & Lusitano Horses from Lisbon Escape the crowds and discover some of Portugal's best-kept secrets. Journey into the heart of the Alentejo, where award-winning wines, breathtaking landscapes and the world-famous Lusitano horses create an unforgettable luxury experience away from the usual tourist routes. Enjoy a premium wine tasting at Torre de Palma Winery. Visit the famous Coudelaria de Alter, the oldest stud farm in the world that remains in the place where it began in 1748. See the prestigious Lusitano Purebred and a large herd of mares and foals Explore Alter do Chão, including its medieval castle and ancient Roman ruins. End the day with breathtaking views from Alter Pedroso, one of the region’s hidden gems. Perfect for wine lovers, culture enthusiasts, and travellers seeking authentic experiences beyond the usual tourist routes, this small-group tour offers a genuine taste of Portugal’s traditions, flavours, and stunning landscapes.

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From Lisbon: Hidden Alentejo Wine & Royal Lusitano Horses

10 to 11 hoursFree Cancellation

from $230

Arrábida & Setúbal, coastal getaway - Private Tour

8 hoursFree Cancellation

5.0

(9)

from $212

Price varies by group size

Cascais DJ and Bar Experience

4 hoursFree Cancellation

from $83

Price varies by group size

Top Attractions in Cascais

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Medieval architecture of the Castelo de Sao Jorge in Lisbon.

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Top Cascais Holidays

18 results

Top Attractions in Cascais

Estoril

Boca do Inferno

Marina de Cascais

Casa da Guia

Castelo de São Jorge

Cabo da Roca

Estoril

Boca do Inferno

Marina de Cascais

Casa da Guia

Castelo de São Jorge

Cabo da Roca

Estoril

Boca do Inferno

Marina de Cascais

Casa da Guia