Cascais is a sailor’s paradise—crystal-clear waters, scenic coastlines, and a lively mariner atmosphere make it a top spot for maritime adventures. Whether you’re after a romantic sunset sail, a private day on the water, or a lively cruise with drinks in hand, Cascais offers something for all. We’re particularly fond of the Cascais Private Sailing 2h Cruise with a drink, which combines intimacy, flexibility, and delightful views of Cascais Marina, old forts, and beaches—all while sipping local wines.
What really sets Cascais apart is how accessible and varied these sailing tours are. You can choose a quick, two-hour private cruise or go for a full-day adventure that takes in landmarks like the Santa Marta Lighthouse or even the chance to see dolphins. Plus, the option to tailor your experience—whether it’s a sunset, a private half-day, or a relaxed bay mooring—means there’s a perfect fit no matter your interests or schedule.
1. Cascais Private Sailing 2h Cruise with a drink
This private 2-hour cruise is a fantastic way to enjoy the Cascais coastline without committing to a whole day on the water. Perfect for families or small groups, it offers a relaxed, personalized experience aboard a private sailboat. The tour includes free drinks, with local wines and beers flowing as you take in sights like Cascais Marina, the Santa Marta Lighthouse, beaches, and old forts. You can choose a morning or afternoon sail, making it flexible for your schedule.
What makes this experience stand out is the intimate setting. The crew is attentive, and the reviews highlight how friendly and hospitable they are—”Great crew and hospitality,” says one happy traveler. Families love the peaceful scenery, while others talk about seeing dolphins, which makes it even more memorable. Because it’s a private tour, you can customize your route slightly and focus on the sights that matter most.
Bottom line: For a quick, laid-back taste of Cascais by boat, this private 2-hour cruise hits the spot. It’s perfect if you want a personalized experience with plenty of time to enjoy the scenery and a drink.
2. Cascais Private Sailing Cruise with a drink – Half day/full day
Looking for a more extended escape? This half-day or full-day private sailing tour offers a comprehensive exploration of Cascais from the water. Starting from Cascais Marina, you’ll cruise past landmarks like the Santa Marta Lighthouse, and the cultural site of Cidadela de Cascais, all while enjoying complimentary drinks. The longer duration allows you to relax at your pace, perhaps anchoring near beaches or watching the sunset over the horizon.
This tour’s strength is its bespoke nature. Guests rave about the crew’s attentiveness and the flexibility to tailor the experience. One reviewer mentions dolphins joining the cruise, which adds a magical touch. The tour covers major sights and offers a chance to see the scenic coast in detail, from charming fishing boats to the towering Cascais Citadel walls.
Bottom line: For travelers who want a personalized, flexible adventure with plenty of time on the water, this private cruise is an excellent choice—especially if you’re keen to see Cascais’s coastline from the sea at your own pace.
3. Cascais: Sailing Tour with Drink
This 2-4 hour sailing tour offers a more relaxed, flexible experience along Cascais’s stunning coast. During this cruise, you’ll enjoy views of white sandy beaches and coastlines, with the option to drop anchor wherever you like, making it perfect for a leisurely day on the water. An exciting highlight is sailing to Cabo da Roca, the westernmost point of mainland Europe.
What makes this tour appealing is how it balances adventure with comfort. The guides are friendly, and the review quotes describe the crew as “informative” and “considerate.” Guests particularly appreciated the opportunity to connect their own music systems onboard and chill out while taking in the scenery. The customizable nature means you can focus on relaxing or exploring specific sights, all while enjoying drinks on deck.
Bottom line: This tour is suitable for those wanting a flexible, intimate sailing experience with the chance to explore the coast and see iconic landmarks like Cabo da Roca in a laid-back atmosphere.
4. 2 hours Private sunset experience by sailboat in Cascais
Sunset in Cascais is breathtaking, and this private 2-hour sunset sail makes the most of that magic. Departing from Cascais Marina, you’ll glide past landmarks like the Cidadela Fortress and the Boca do Inferno viewpoint, both iconic sites of the region. The tour is crafted for romance, with the sunset creating a stunning backdrop to the experience.
What makes this tour stand out is its romantic appeal. Passengers rave about the “perfect conditions” and “picture-perfect sunset,” and reviews mention how the crew’s attentive service enhances the mood. The boat’s cozy setting and the chance to share a special moment with loved ones make it a top pick for couples or anyone celebrating a special occasion.
This experience is ideal if you’re after a romantic escape that combines scenic beauty with intimate moments, and it’s well-reviewed for its peaceful, enchanting atmosphere.
Bottom line: For a romantic, sunset-filled adventure, this private sail offers stunning views and a memorable experience perfect for couples or celebrating special milestones.
5. 2 hours Private Sailing Experience in Cascais
This private 2-hour sailing experience is described as “the perfect reset,” making it ideal for those wanting to unwind and reconnect with nature. Starting in Cascais, you’ll enjoy panoramic views of the coast, including the Boca do Inferno and Farol da Guia, a lighthouse dating back to 1610.
What makes this tour special is its focus on leaving the past behind. Guests comment on how the experience helps them de-stress and focus on the present, with some describing the scenery as “divine” and the atmosphere as “peaceful.” The itinerary includes beautiful spots like Boca do Inferno, with its dramatic caldera, and the historic Lighthouse, giving a sense of history and natural beauty.
It’s best suited for travelers seeking a meditative escape or a quick but meaningful break from sightseeing. The reviews highlight how the crew makes it memorable, with “amazing” hosts and personalized touches.
Bottom line: This short but meaningful trip is perfect for those looking for tranquility and scenic beauty in a private setting.
6. Cascais: Lisbon Morning Breeze Sailing Tour, Thursday
This morning cruise takes you from Lisbon’s Tagus River into the quiet, early hours of the day. Over four hours, you’ll learn the basics of sailing or simply relax while enjoying views of Lisbon’s most iconic landmarks bathed in morning light. The tour begins with a pickup from several locations, and you’ll cruise past Commerce Square, Alfama, and Belem, capturing photos and soaking in the city’s skyline.
What makes this stand out is its combination of learning and relaxation. The crew is praised for their friendliness and the opportunity to connect with fellow travelers. You’ll also enjoy a complimentary drink, making the experience both educational and leisurely.
While it’s more suited for morning people and those interested in sailing basics, it’s a great way to combine a city tour with a boat ride. The reviews are positive, emphasizing the peaceful start to the day.
Bottom line: Ideal for travelers wanting a scenic, educational morning cruise in Lisbon with a relaxed, social vibe.
$71 per person
7. 2 Hours Romantic experience for two by sailboat in Cascais
This romantic two-hour tour is tailor-made for couples celebrating special moments. Departing from Cascais, it features iconic sights like Boca do Inferno and the Farol da Guia, all wrapped in a serene, intimate setting. The experience is designed for renewing love or proposing marriage, with a focus on creating unforgettable memories.
Guests call it “perfect for rekindling the spark,” praising the beautiful scenery and quiet, tranquil atmosphere. The crew’s attention to detail and the ability to customize the experience—perhaps with champagne or special music—make it stand out. It’s especially suited for those who value intimacy and a peaceful environment.
If you’re after a special occasion or a meaningful gift, this tour provides a private, unforgettable moment on the water.
Bottom line: A superb choice for couples seeking a personalized, romantic sailing experience that emphasizes intimacy and scenic beauty.
$428
8. Private Sailing Tour at Cascais: Lazy Mooring in the Bay
This lazy mooring tour is all about relaxing. Anchored in Cascais Bay, you’ll enjoy onboard lunch, paddleboarding, snorkeling, and even swinging in a hammock while listening to the sound of the sea. You can also opt to sail to Oeiras, exploring more of the Linha Coast and ending at Marina de Oeiras.
What makes this experience unique is its focus on leisure. The reviews mention how perfect it is for just chilling out—“lovely relaxing hours on the boat,” says one reviewer. The combination of water activities and relaxation makes it great for families or anyone wanting to wind down away from busy sightseeing.
It’s a flexible, all-inclusive experience that’s ideal if your priority is unwinding in a beautiful setting.
Bottom line: For a laid-back, activity-filled day with plenty of opportunities to relax and enjoy the sea, this tour offers great value and a memorable experience.
$428.19 per group (up to 8)
How to Choose Your Perfect Cascais Sailing Experience
When selecting the best sailing trip, consider your budget, schedule, and what you most want to get out of the experience. If you’re after a quick, romantic escape, the sunset cruise is hard to beat. For those wanting a full day on the water, the half or full-day private cruise offers flexibility and a chance to explore in depth. Budget-conscious travelers might opt for the Lisbon morning cruise, especially if combining it with sightseeing in the city.
If you prefer a more relaxed, activity-oriented day, the Lazy Mooring tour with paddleboarding and snorkeling is perfect. Meanwhile, couples or celebrating milestones should look into the romantic tours, designed for intimacy and special moments.
Booking early is advisable, particularly in peak season (spring and summer), and always confirm availability for sunset or full-day trips. Many tours offer customizable options, so don’t hesitate to ask for special touches like champagne or specific routes.
In summary, Cascais provides a diverse array of sailing experiences designed to suit every taste and budget. From private sunset cruises that make for memorable romantic evenings to relaxed bay moorings perfect for unwinding, the options are plentiful. For a quick taste, the private 2-hour cruise offers great value, while those seeking a full day can enjoy tailored adventures along the coast. If you’re traveling as a couple, the romantic sail is a wonderful choice, and families will appreciate the leisurely, activity-packed lazy mooring trips.
Don’t forget to book early — these trips fill up fast during high season. No matter which experience you choose, a day on Cascais’s waters promises beautiful views, relaxation, and a genuine taste of Portugal’s maritime spirit.