Sailing in Cascais

49 boats available

The best out of 49 deals in Cascais - enter dates to check availability

Top Sailing in Cascais

  • 34 ft
    •
    up to 6
    2 Hour – Sunset Wedding proposal
    We prepare everything in advance so you can make an unforgettable wedding proposal. You choose the music to be played when it's time, and we take care of the flowers, the champagne, and the most romantic time and place. A professional photographer will make photos and register the moment.
    Instant Confirmation
    Price for up to 6 people
    US $549
  • 45 ft
    •
    up to 12
    2 Hour – Sailing Yacht Ride
    Cascais Luxury Private Boat Tour: An experience to remember! How about spending a couple of hours aboard a private sailing boat? A fabulous idea! Starting from Cascais, we can adapt our route to your preferences and to the duration of the cruise. You can leave Cascais behind and enjoy the stunning coast, aboard a beautiful sailing yacht.
    Price for up to 12 people
    US $504
  • 41 ft
    •
    up to 12
    2 Hour – Private Sunset Boat Tour
    Finish your day in a unique and relaxing way and start a completely relaxing evening. Enjoy the unique views of Lisbon, like the Cais das Colunas, Praça do Comércio, and the colors that the sunset provides. Private 2-hour sunset cruise with a complimentary welcome drink and a tour guide/host. Catering and extra drinks can be provided by quote. Do not bring food or extra drinks. Fall in love with Lisbon aboard this cruise! Welcome aboard!
    Instant Confirmation
    Price for up to 2 people
    US $330
  • 32 ft
    •
    up to 6
    3 Hour – Sunset Wine Tasting at Sea
    Indulge in a private sailing experience paired with a curated tasting of 3 exceptional Portuguese IGP white wines, and a complimentary bottle of your favorite.
    Instant Confirmation
    Price for up to 6 people
    US $672
  • 27 ft
    •
    up to 5
    3 Hour – Sustainable Sailing Tour
    Enjoy the energy of the wind in the sails, the tides, and the energy of the waves in this Silent and Sustainable Navigation. On this calm trip in Lisbon, you will fall in love with relaxing and unique moments along the Tagus River. Enjoy the wonderful landscape of the river Tagus and see and hear brief stories of the main riverside monuments. We will sail on the Tagus River, where we will have the opportunity to relax and feel the breeze.
    Instant Confirmation
    Price for up to 5 people
    US $336
  • 33 ft
    •
    up to 8
    2 Hour – Sunset with Green Wine
    Enjoy a relaxed 2-hour sail along the beautiful riverfront of Lisbon, passing iconic landmarks like Belém Tower and Praça do Comércio. This modest yet charming sailboat offers a cozy and authentic experience on the Tagus River. Feel the breeze, take in the city views, and unwind with endless servings of refreshing Portuguese Vinho Verde as you cruise in comfort. A perfect escape on the water.
    Instant Confirmation
    Price for up to 8 people
    US $358
  • 38 ft
    •
    up to 6
    4 Hr – Cascais Sailing Experience
    We offer a relaxed sailing experience along the bay of Cascais, with the option to enjoy swimming and sunbathing in a beautiful, sheltered spot. On board, we provide a welcome drink (water, Coca-Cola, and beer). The boat is a fully equipped cruising sailboat, designed for comfort, with all the facilities you may need. This is a fully custom experience, so the itinerary is flexible. If the weather changes or we spot dolphins along the way, we can always adjust the plan to make the most of the moment.
    Price for up to 6 people
    US $487
  • 40 ft
    •
    up to 11
    4 Hour – Yacht Cruise
    Enjoy a complete half-day escape along the beautiful coastline of Cascais. This 4-hour sailing experience gives you the perfect balance of relaxation, exploration, and time on the water. Start times are flexible.
    Price for up to 4 people
    US $504
  • 41 ft
    •
    up to 8
    2 Hour – Sunset Tour (up to 8 Pax)
    Private Sunset Tour offering exclusive, unforgettable moments with a touch of elegance and charm aboard our iconic boat. Come and experience truly special moments on the water! Up to 8 persons.
    Instant Confirmation
    Price for up to 8 people
    US $381
  • 30 ft
    •
    up to 4
    2 Hour – Sailing Experience
    Embark on a private sailing adventure along the Cascais coast. Whether you prefer to learn the basics of sailing or anchor in the bay for a refreshing swim or some snorkeling, the choice is yours.
    Instant Confirmation
    Price for up to 4 people
    US $336

What boaters said about Sailing

  • 5.0
    /5
    (2 Hour – Golden Hour Sailing Escape)

    It was a treat!!!

    We enjoyed a wonderfut Sundowner sailing - even with a glas of portuguese champagne for my Birthday. The experienced and very kind crew have us interesting informatons about history. We had a Great time!
    Paul R.
    Paul R.
    Reviewed on Aug 30, 2026
  • 5.0
    /5
    (2 Hour – Golden Hour Sailing Escape)

    Golden Hour Gold!

    Our group had the best experience with Luis and crew. Originally booked a longer time but owner was flexible and communication on point. Pure gold!
    Tim S.
    Tim S.
    Reviewed on Sep 7, 2026
  • 5.0
    /5
    (Cascais Riviera Escape - 2 hr - 1:00 PM)

    September boating trip

    We had a wonderful experience! We recently took our family of five on the boat. Saw all of the coast of Cascais and my teenage daughters loved swimming in the sea and using the paddle board. Crew were amazing. Highly recommend this experience!
    Una M.
    Una M.
    Reviewed on Sep 4, 2026
  • 5.0
    /5
    (Cascais Riviera Escape - 2 hr - 3:30 PM)

    Such a fun birthday day out in the water

    I hired the boat for 2 hours for my birthday and we had so much fun!! From cruising along the coast, to docking by the shore and swimming. Great day on the Cascais water and the crew were so friendly and helpful. Even had some wine and grapes when we stopped for a swim. Would definitely recommend
    Susanna K.
    Susanna K.
    Reviewed on Aug 30, 2026
  • 5.0
    /5
    (3 Hour – Sunset Wine Tasting at Sea)

    Great Experience

    We had a an amazing sunset cruise with wine tasting. The crew was incredible
    Steve D.
    Steve D.
    Reviewed on Sep 8, 2026

Other great boat types in Cascais