THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Sail Madeira’s vibrant islands on a 5-day journey with Pimpas Sailing Charter. Swim in pristine bays, visit Calheta and Funchal, and enjoy restful nights aboard a luxury sailboat.
Sail Madeira’s vibrant islands on a 5-day journey with Pimpas Sailing Charter. Swim in pristine bays, visit Calheta and Funchal, and enjoy restful nights aboard a luxury sailboat.
Book with Pimpas Sailing Charter
Verified experiences and guided adventures in the surrounding area.
Operated by Pimpas Sailing Charter · Funchal, Madeira
Set sail on an immersive five-day voyage with Pimpas Sailing Charter, cruising through Madeira’s striking island coastline. Operating out of Funchal, this trip invites adventurers to experience the Atlantic’s deep blues aboard a well-appointed sailboat designed for comfort and maritime discovery. Madeira, a Portuguese archipelago off the northwest African coast, is famed for its rugged volcanic landscape, dramatic cliffs, and unique laurel forests—a UNESCO World Heritage site. The waters linking its islands teem with marine life, crystal clear and perfect for snorkeling.
Pimpas Sailing Charter’s 5 Days Charter is not just a cruise but an intimate encounter with the natural diversity of Madeira, Calheta, and neighboring isles such as Porto Santo and the Desertas. Each destination showcases distinct coastal features: Calheta’s golden sandy beaches contrast with the rocky, wild bays of Ponta de São Lourenço. Along the way, guests can dive into remote bays where underwater visibility reveals colorful fish and curious rays. Snorkeling gear and paddleboards come standard, allowing travelers to move freely between sea and ship.
Nights onboard bring a luxurious calm with ample space to relax and absorb the starlit skies, accompanied by soft ocean sounds. The company’s commitment to small group sizes ensures attentive service and a personalized experience. This charter stands out by combining active marine adventures with restful evenings, making it a top choice for those wanting to connect deeply with Madeira’s maritime culture and environment.
Ideal for travelers keen on mastering some sailing basics alongside seasoned captains, Pimpas Sailing Charter enhances the local outdoor scene by offering a unique way to traverse the islands sustainably. For anyone seeking both exhilaration and tranquility beneath Madeira’s skies, this multi-day sailing charter is a compelling option to consider.
moderate.
5 days.
Good general fitness recommended; ability to move comfortably on a boat and swim is helpful.
The trip includes welcome drinks, finger foods, snorkeling equipment, paddleboard use, accommodation aboard the boat, and towels.
No, lunch and dinner are not included, so guests should bring their own food or arrange meals separately.
The boat is not wheelchair accessible and requires some mobility to board and move around; please contact the company if you have specific needs.
Yes, but all children and infants must be accompanied by an adult at all times on board.
Tours may be rescheduled or canceled for safety reasons, with full refunds or alternative dates offered.
The charter operates from Marina do Funchal in Madeira, Portugal.
Madeira has a rich maritime heritage from 15th-century Portuguese explorers, with Funchal historically serving as a key Atlantic port.
The charter promotes sustainable sailing practices and respects protected marine areas to preserve local biodiversity.
Pimpas Sailing Charter is a privately operated sailing company based in Funchal, Madeira. The company offers a range of day and multi-day sailing experiences along Madeira's coastline and to nearby islands. Trips include Full Day Tour, Half Day Tour, Sunset and Sunrise cruises, private charters to Porto Santo, an excursion to the Desertas Islands, and a five-day sailing charter. Each experience is conducted from Funchal and focuses on coastal exploration, swimming, snorkeling, wildlife watching and relaxed sailing. Guests can expect opportunities to swim and snorkel in clear waters, visit secluded coves and view dramatic cliffs along the coast. Several trips include snacks and drinks; multi-day charters provide nights aboard the vessel and extended island itineraries. Pimpas Sailing Charter highlights Madeira’s marine environment and nearby islands while operating private and small-group sailings. The company follows local regulations for protected areas such as the Desertas Islands and plans routes that showcase sites like Cabo Girão and Garajau. On transfers to Porto Santo, guests explore beaches and turquoise waters. Booking information, safety briefings and equipment such as snorkel gear are provided on each trip as appropriate. Crews offer instruction on sailing during private or learning-oriented charters. The business maintains a schedule of half-day, full-day and specialty cruises leaving from Funchal, making it accessible for visitors staying on the island. Pimpas Sailing Charter presents a range of tailored sailing options from short coastal cruises to extended multi-day voyages, all delivered from Funchal, Madeira. Reservations can be made from Funchal year-round, subject to availability online.
Book with Pimpas Sailing Charter