The historic fishing town of Cascais offers some of Europe’s finest sailing waters, with reliable winds and stunning Atlantic coastline views. The most worthwhile excursions combine expert local skippers with well-maintained vessels equipped with modern amenities. Private yacht tours, starting at €84, provide intimate experiences for small groups while larger boats can handle up to 10 passengers.
I’m particularly fond of the sunset cruises, which showcase the dramatic golden-hour views of Cascais’ rocky shores and historic fortresses. The half-day private sailing trips earn my recommendation for their perfect mix of relaxation and sightseeing – you’ll get close-up views of landmarks while enjoying the freedom to customize your route.
Let’s explore the standout sailing tours that make the most of these Portuguese waters.
Good To Know
- Cascais offers diverse sailing options, including private yacht cruises, coastal tours, and specialized experiences like sunset and romantic sailing adventures.
- Private sailing tours range from 2 to 6 hours, with customizable itineraries to suit various interests, starting around $84 per person.
- “Go With the Flow” private sailing tour provides a unique eco-friendly option with a 4-hour duration and twice the distance of standard tours.
- Onboard amenities include toilets, Wi-Fi, and a welcome drink, with tours designed for adventurers and not suitable for young children.
- Flexible booking and free cancellation policies are available, with advance reservations recommended due to the popularity of the sailing experiences.
Cascais Private Sailing 2h Cruise With a Drink
For a memorable two-hour sailing experience along Cascais’ picturesque coastline, travelers can embark on a private cruise.
This highly-rated tour boasts a 5.0 rating from 41 reviews, with all travelers recommending the experience.
Sailing along the rugged shoreline, guests will enjoy views of the Cascais Marina, lighthouse, beaches, and old forts.
Sipping on local wines and beers, they’ll delight in the personalized attention from the onboard crew.
With morning and afternoon sailing options, this private sailing adventure offers flexibility.
Inclusive of a welcome drink and gratuities, the cruise is easily accessible by public transportation, though not wheelchair-friendly.
Read our full review: Cascais Private Sailing 2h Cruise With a Drink Review
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Cascais Private Sailing Cruise With a Drink – Half Day/Full Day
Departing from the Marina de Cascais, travelers can embark on a private sailing cruise along the picturesque coastline, with options for either a half-day or full-day experience.
The cruise offers stunning views of Cascais Bay, fishing boats, the Cascais Citadel, and the Santa Marta Lighthouse. Guests can enjoy a complimentary welcome drink and an open bar upon request.
The tour, operated by PALMAYACHTS, is highly recommended, with a 100% rating from 11 reviews praising the knowledgeable crew and personalized service.
Pricing starts at $619.61 for up to 12 guests, with free cancellation available up to 24 hours prior. The cruise is accessible via public transportation but not wheelchair-friendly.
Read our full review: Cascais Private Sailing Cruise With a Drink – Half Day/Full Day Review
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2 Hours Private Sunset Experience by Sailboat in Cascais
Those looking to cap off their day in Cascais with a tranquil sunset experience can embark on a 2-hour private sailboat tour.
Accommodating up to 6 participants, the cruise is led by a skilled skipper and sailor team who’ll ensure a smooth and enjoyable outing. Guests will savor bottled water, beer, and wine as they sail along the picturesque coastline, taking in the stunning sunset views.
With a 5.0 rating from 4 reviews, this experience is a customer favorite, praised for its relaxing atmosphere and knowledgeable crew.
The tour departs and returns to the Marina de Cascais, making it a convenient option for those staying in the area.
Read our full review: 2 Hours Private Sunset Experience by Sailboat in Cascais Review
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2 Hours Private Sailing Experience in Cascais
Visitors to Cascais can indulge in a 2-hour private sailing experience, offering a tranquil respite to cap off their day. Priced from $290.58 for up to 6 people, the tour includes a skipper, sailor team, soda, water, and alcoholic beverages.
Participants meet at the Bavaria Yachts – Motor & Sail marina, 15 minutes before departure, and the activity ends back at the same location. Though not wheelchair accessible, the tour welcomes service animals and infants sitting on laps.
With a perfect 5-star rating from 2 reviews, the experience highlights the crew’s ability to personalize the trip to guests’ preferences.
Read our full review: 2 Hours Private Sailing Experience in Cascais Review
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Cascais: Sailing Tour With Drink
For those seeking a captivating maritime adventure in Cascais, the Sailing Tour with Drink offers an excellent opportunity to explore the coastline and beyond.
Priced at €420.00 per group, the 2-4 hour tour accommodates up to 12 participants and provides an unforgettable experience.
Sail to the westernmost point of Europe, Cabo da Roca, and relax on the white sandy beaches. The tailored cruise allows you to drop anchor at preferred locations, and you may even sail to Lisbon to see its famous monuments from the water.
The tour includes a professional crew, a welcome drink, and hotel pickup and drop-off.
With an impressive 4.8/5 overall rating, this sailing experience is a must-do for visitors to Cascais.
Read our full review: Cascais: Sailing Tour With Drink Review
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Cascais: Romantic Experience for Two by Sailboat
Couples seeking a romantic maritime adventure can embark on a sailboat tour in Cascais. The “Cascais: Romantic Experience for Two by Sailboat” lasts 2 hours and costs from $83.91.
During the private tour, participants can enjoy stunning coastal views, a glass of wine, and quality time together on the water. The activity is highly rated, with 4.9 out of 5 stars from 618 reviews.
Cascais offers a variety of water activities, including dolphin watching and private surf lessons. Visitors can also explore the town’s cultural sites and natural wonders on day trips from Lisbon.
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Cascais: Private Sunset Experience by Sailboat
A private sunset sailboat tour in Cascais offers a romantic maritime experience for couples.
Lasting 2 hours, the tour allows guests to witness the sun dip below the horizon from the comfort of a private sailboat.
At a price starting from $83.91 per person, the experience can accommodate up to 4 people, making it an intimate affair.
Customers have awarded it a high rating of 4.9 out of 5 stars from 618 reviews, praising the stunning views and professional skipper.
Whether seeking a special date night or simply a chance to enjoy Cascais’ coastal beauty, this private sunset sail provides an unforgettable way to experience the region.
Read our full review: Cascais: Private Sunset Experience by Sailboat Review
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Cascais: Private Sailing Experience
Embarking on a private sailing adventure in Cascais allows visitors to fully enjoy the region’s coastal beauty.
Private sailing tours offer a personalized way to explore the charming seaside town and its scenic surroundings. Guests can choose from various duration options, ranging from 2 to 6 hours, and customize their experience based on their interests.
Whether it’s admiring the dramatic cliffs of Boca do Inferno, spotting dolphins along the coast, or simply relaxing on the open water, these private sailing excursions provide an intimate and unforgettable way to experience Cascais.
Prices start from around $84 per person, making it an accessible and memorable activity.
Read our full review: Cascais: Private Sailing Experience Review
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Cascais: Sailing Experiences & Tours
For those seeking to enjoy Cascais’ coastal splendor, the sailing experiences and tours on offer provide an exceptional opportunity.
The OceanVibes, a Dufour 45 Classic, offers a 2-hour sailing adventure for up to 12 participants, starting at $390.20 per group. The experience caters to both Portuguese and English speakers, with flexible reservations and a generous cancellation policy.
Beyond the standard sail, guests can personalize their journey with romantic moments and onboard massages. However, certain restrictions apply, such as no children under 6 and a ban on smoking and high-heeled shoes.
The skilled skippers and professionals ensure a safe and memorable experience.
Read our full review: Cascais: Sailing Experiences & Tours Review
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Boat’n Breakfast Private Sailing Tour
Aboard the Boat’n Breakfast, a private sailing experience in Cascais, guests embark on a leisurely morning excursion along the picturesque coastline.
This 2-hour tour provides a tranquil escape with stunning views of the dramatic Boca do Inferno cliffs and the charming town of Cascais. Rated 4.2 out of 5 stars from 100 reviews, the Boat’n Breakfast offers a customizable experience, with the option to extend the tour or enjoy a gourmet breakfast on board.
Priced at $36.71 per person, the tour offers an intimate and exclusive way to experience the natural beauty of Cascais from the water.
This new activity is an ideal choice for those seeking a relaxing and personalized sailing adventure.
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Cascais: Private Yacht Cruise in the Bay & Sightseeing
Departing from the picturesque Marina de Cascais, guests aboard a luxury yacht embark on an exclusive sightseeing cruise through the bay.
Priced from $1,363.60 per group of up to 10 participants, this 2-4 hour experience offers amazing views of the coast and historical landmarks.
Crew members fluent in multiple languages provide quality snacks and local drinks as the yacht sails past the Hotel where 007 movies were filmed and explores the wild coast, including the famous fortress and Roman cliffs.
With a 5/5 rating and positive reviews on customer service, this private yacht cruise is a must for those seeking a unique way to experience Cascais.
Read our full review: Cascais: Private Yacht Cruise in the Bay & Sightseeing Review
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Cascais: Go With the Flow Private Sailing Tour
Stepping away from the private yacht cruise, the “Cascais: Go with the Flow Private Sailing Tour” offers a distinct experience.
Priced at Kč 14,356 for up to 8 participants, this 4-hour tour sails from Marina de Cascais to Doca de Santo Amaro in Lisbon.
Utilizing wind and currents, the eco-friendly tour covers twice the distance of typical sails, revealing iconic landmarks like Belém Tower and the 25th of April Bridge.
Multilingual crew provide insights into maritime history, and onboard amenities include toilets, Wi-Fi, and a welcome drink.
While unsuitable for children under 6 and wheelchair users, the tour’s flexible booking and free cancellation policy make it an appealing option for adventurous travelers.
Read our full review: Cascais: Go With the Flow Private Sailing Tour Review
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The Sum Up
Cascais offers a range of sailing experiences that cater to diverse preferences. From private cruises and sunset sails to full-day excursions, visitors can enjoy the coastal beauty and enjoy a drink on board. These sailing tours provide an opportunity to explore the bay and surrounding sights in a personalized and relaxed manner, making Cascais a premier destination for sailing enthusiasts.