Set aboard the elegant AESTUS, a 2007 Azimut Atlantis motor yacht based in Calheta, this premium charter offers the perfect blend of speed, comfort, and luxury for up to 10 guests.
trips from
US $1,793
Flipper II
Calheta4.9/5(153 external reviews)Flipper II is a 2010 Beneteau Antares Sportfishing vessel, offering an exceptional experience based out of Calheta. Accommodating up to six guests, this luxurious boat is powered by two 220 HP Volvo diesel engines, reaching a cruising speed of 18 knots.
trips fromUS $280Boca Raton
CalhetaStep aboard the Boca Raton, a sleek 2005 Black Watch 310 Deep Vee Sportfishing, and experience the ultimate blend of adventure and relaxation.
trips fromUS $532Sea Wolf
Calheta+1Sea Wolf is a beautifully restored 2003 Monterey 265 Cruiser, offering unforgettable private charters from Calheta.
"We’ve had a wonderful trip on the Seawolf. Captain Thomas and his crew are very friendly." — Erwin,trips fromUS $336On Tales – Gringo Yacht
Calheta+1Step aboard Gringo, our elegant yacht, and treat yourself to an unforgettable journey along Madeira’s beautiful coastline.
"We had such a great time with this company! The communication from booking all the way to the boat ride itself made it stress free and very enjoyable." — Nikki,trips fromUS $997Pesca Grossa Hard and Play
CalhetaPesca Grossa Hard and Play is a 2007 Rodman 10.40 Cruiser based out of Calheta, designed to host up to six guests in comfort and style. Powered by twin 280 HP Volvo diesel engines, she offers a smooth ride with a cruising speed of up to 30 knots.
trips fromUS $616On Tales – Miranda Yacht
Calheta+1Step aboard for a unique experience where comfort and adventure meet in the middle of the Atlantic Ocean.
"We booked the afternoon trip departing at 16:30 and had a great time from start to finish." — Vukan,trips fromUS $587SeaYou - Premium Cruises from Funchal/Calheta
Funchal: 17.0 miles from Calheta5+ external reviews+5Step aboard SeaYou Madeira, a sleek Cheetah Marine Custom Catamaran based in Funchal, designed to deliver unforgettable moments on the water.
"we had a great day boating and exploring the Desertas island." — Evelina,trips fromUS $773Easy Sailing Madeira
Funchal: 17.0 miles from CalhetaSet sail from Funchal aboard Easy Sailing Madeira, a classic 1977 Contention 33 sailing yacht offering a relaxed and comfortable way to explore Madeira from the water.
trips fromUS $504
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Boating in Calheta
Discover Calheta, Madeira, where rugged volcanic cliffs meet calm Atlantic waters—an inviting base for Calheta boating charters. With a modern marina and reliable sunshine, this southwestern coastline sets the stage for relaxed cruising, active adventures, and memorable days at sea.
Choose from skippered excursions or bareboat rentals to explore sheltered bays, dramatic sea caves, and striking rock formations. The region's clear water and typically gentle swells make it ideal for snorkeling, paddleboarding from the stern, or simply dropping anchor to swim in a tranquil cove.
Wildlife encounters are a highlight of Calheta boating charters. Local operators frequently navigate routes known for sightings of dolphins and seabirds, offering respectful, conservation-minded viewing from stable, comfortable vessels. Between encounters, you'll enjoy open-ocean vistas framed by terraced hillsides and coastal villages.
Active travelers can tailor itineraries for trolling or light-tackle fun, while sunset cruisers can drift along the coast as golden light reflects off the cliffs. Families will appreciate the easy marina access, protected launch conditions, and flexible trip lengths that keep every age engaged and at ease on the water.
Whether you're planning a leisurely half day along the shoreline or a full-day voyage to discover new coves, Calheta boating charters deliver an effortless blend of scenery, serenity, and soft adventure—making this corner of Madeira a standout destination for boat tours and rentals.