THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail on a private journey to Porto Santo Island with Happy Hour Madeira, where pristine waters and sandy beaches create a perfect backdrop for unforgettable adventures. Discover the region’s natural beauty from the deck of a private yacht, complete with cozy cabins for overnight stays.
Set sail on a private journey to Porto Santo Island with Happy Hour Madeira, where pristine waters and sandy beaches create a perfect backdrop for unforgettable adventures. Discover the region’s natural beauty from the deck of a private yacht, complete with cozy cabins for overnight stays.
Book with Happy Hour Madeira
Verified experiences and guided adventures in the surrounding area.
Operated by Happy Hour Madeira · Funchal, Madeira
Located off the coast of Portugal, the Triangle of Islands offers an inviting escape from the mainland—a place where azure waters and golden beaches set the scene for a truly memorable sailing adventure. Based in the Madeira archipelago, this area is renowned for its unspoiled beauty, rugged coastlines, and crystal-clear waters, making it a prime spot for those craving an authentic maritime experience. The centerpiece is Porto Santo Island, a stretch of paradise accessible only by boat, where gentle waves lap against a shoreline of soft, golden sand and sweeping vistas unfold at every turn. The schooners and private yachts operated by Happy Hour Madeira deliver a personalized voyage across sparkling Atlantic waters. Onboard, travelers indulge in light, locally sourced meals while basking in the sun, feeling the sea breeze on their skin, and marveling at the dramatic coastlines and scenic cliffs that characterize the island's landscape. For those wanting more than just a daytime trip, cozy cabins are available, allowing guests to spend a night under a blanket of stars, waking up to the peaceful rhythm of the Atlantic. This sailing route isn't just about relaxation—it's about connecting with nature and discovering the rugged beauty that defines Madeira’s maritime heritage. The region’s clear waters also make it an excellent spot for snorkeling and swimming, revealing vibrant marine life within reach of the boat. With year-round warm weather and spectacular sunsets casting fiery hues across the ocean, the Triangle of Islands promises an adventure that balances comfort, discovery, and natural wonder. Whether you're celebrating a special occasion or seeking a heartfelt escape, Happy Hour Madeira’s private sailing trips elevate your Madeira experience, creating memories that last long after the sails are furled.
Moderate.
6–8 hours.
Moderate fitness required; participants should be comfortable with outdoor activity.
Yes, the private sailing trips are family-friendly and suitable for children of all ages.
Trips usually range from half-day excursions to overnight adventures, depending on your preference.
No prior experience is necessary; the crew will assist and ensure your safety.
Light, locally prepared meals and snacks are provided on board.
Yes, guests are welcome to bring their own beverages to enjoy during the trip.
Bring personal essentials, a change of clothes, and a sense of adventure.
Porto Santo has been a key maritime stop for explorers since the Age of Discovery, with a rich seafaring history.
The company emphasizes eco-friendly practices, such as waste reduction and respecting marine habitats to preserve the region’s natural beauty.
Happy Hour Madeira is a Funchal-based sailing operator offering a focused collection of sea experiences around Madeira and Porto Santo. Departures originate from Funchal on the island's south coast, and the operator provides a variety of trip lengths and formats, including half-day and full-day cruises, sunrise and sunset outings, day trips to Ponta de São Lourenço, and longer passages to Porto Santo and the Triangle of Islands. Several itineraries include onboard dining: optional gourmet or light lunch menus are available on many day trips, and the Chef's Experience features a private chef preparing a five-course canapé menu using local ingredients, with vegetarian options. The Sunrise Tour typically includes a crew-prepared breakfast served near Belmond Reid's Hotel bay. Overnight options are available on specific island passages, with cabins offered for guests who wish to stay on board. Many tours highlight snorkeling, swimming, and wildlife viewing opportunities such as whale and dolphin watching along Madeira's south coast. Trip descriptions make clear which experiences include meals, cabin options, or private crew services so visitors can choose the right sailing experience. Booking details, departure logistics and specific itineraries are centered on Funchal, Madeira. Reservations and specific itineraries should be confirmed directly with Happy Hour Madeira prior to travel for availability.
Book with Happy Hour Madeira