9 Madeira Sailing Tours for the Logbook

1.Sunset Sailing Tour

★★★★★★★★★★4.7 · 2,144 reviews · 3 hours · from $58Our pick

Sail from Funchal with up to 20 people on a relaxed three-hour sunset trip led in English or Portuguese by guides such as Bruno, Joe, Victor, or Alberto. Look for dolphins and whales, stop to swim or snorkel below Cabo Girão, enjoy unlimited drinks, and watch the sun set over the Atlantic. Wildlife sightings depend on nature.

“Amazing Trip fabulous Guide and Captain, Joe was amazing such a lovely man. Only thing to make it perfect would be dolphins 🐬 but that's nature. Sunset Fabulous”

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2.Dolphin and Whale Watching Sailing Trip

★★★★★★★★★★4.6 · 1,325 reviews · 3 hours · from $47Best value

Sail from Funchal Marina toward Cabo Girão on a small yacht with a captain, crew, and live guide in English or Portuguese. Look for dolphins, whales, and sea turtles up to three miles offshore, then swim or snorkel near Madeira’s highest sea cliff. Guides such as Bruno and Joseph add local insight, while drinks are included.

“Wonderful tour with great guides! The tour was amazing, it was a beautiful sailing boat with enough space for everyone, a small group of roughly 15 people, the guides were very attentive, gave good instructions, shared information about the animals and took a lot of time and patience to find wildlife. We were lucky enough to see both dolphins and whales. We enjoyed the swimming stop and a free glass of wine on the way back. Overall an amazing experience!”

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3.West Bays Sailing Tour with Lunch

★★★★★★★★★★4.7 · 75 reviews · 5 hours · from $82

Sail from Funchal along Madeira’s west coast with a live guide in Portuguese or English. Look for dolphins, whales, and sea turtles, then stop near the cliffs for swimming, snorkeling, lunch, and drinks. Guide Bruno is praised for his warm, attentive style. Expect about 18 to 20 people and mostly motor-powered cruising.

“Sortie en mer absolument géniale ! L’équipage était très accueillant, jovial, le repas était très bon et de bonne quantité On a pu naviguer au large de l’île puis revenir en longeant la côte ouest de plus prêt, la baignade dans les eaux claires au pied de la falaise a bouclé le tout ! Je recommande à 100%, le prix est vraiment plus que bien pour la qualité de l’évènement”

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4.Funchal Half and Full Day Private Sailboat Tour

★★★★★★★★★★5.0 · 19 reviews · 4 hours (approx.) Top rated

Set out from Funchal with Happy Hour Madeira for a private half or full-day sail along Madeira’s south coast. João and Luís may guide you toward sea-only beaches, whale and dolphin sightings, Atlantic swims, and lunch at Fajã dos Padres or on board. The tour returns to the marina.

“Our guides João and Luís were the best! Very kind, knowledgeable and provided great local recommendations. I would highly recommend to anyone traveling to Madeira!”

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5.Luxury Yacht & Sailing Sunset Tour

★★★★★★★★★★4.6 · 10 reviews · from $74

Join Sea La Vie for a three-hour sunset cruise from Funchal’s Cais 8. You’ll sail past Ribeira Brava, Fajã dos Padres, Cabo Girão, and Câmara de Lobos, stop for swimming and snorkeling, and enjoy sparkling wine and Madeiran snacks aboard a small yacht limited to 12 people.

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6.Half and Full Day Private Sailboat Tour

★★★★★★★★★★5.0 · 8 reviews · from $739 whole boat, up to 6

Set out from Funchal Marina on a private 4 to 6-hour sail along Madeira’s south coast. Your English- or Portuguese-speaking crew takes you east or west to sea-access beaches, with chances to spot dolphins and whales, swim, snorkel, or use the paddle board. Drinks, light food, towels, blankets, Wi-Fi, and hot showers are included.

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7.Private Sailing Sunrise, Sunset & Moonlight Cruises

★★★★★★★★★★5.0 · 8 reviews · 2.5 hours · from $530 whole boat, up to 10

Join Manolo and his family for a private 2.5-hour sailing trip from Funchal. Choose sunrise, sunset, or moonlight, then relax under sail toward Cabo Girão, with time for swimming when conditions allow. Coffee, hot chocolate, cakes, wine, and cheese are included, while breakfast, tapas, or a light dinner can be arranged.

“Ich habe diesen Ausflug als Geburtstagsgeschenk für meinen Mann gebucht. Und nur Dank dem Manolo ist es zu einem unvergesslichen Erlebnis geworden. Wie hilfsbereit, herzlichen und besorgt um seine Gäste dieser Mensch ist.... so einen trifft man selten!!!!! Es war ein traumhafter Ausflug gewesen: von dem ersten Kontakt und bis zu unserer Abreise von Madeira! Die Yacht war ansprechend ausgestattet und hat uns vieren viel Platz geboten. Der Ablauf wurde flexibel und ganz nach unseren Wünsche abgestimmt. Uns wurden mehrere Aktivitätsmöglichkeiten angeboten (z.B. snorkeling, standing paddling). Auch Getränke und leckere Snacks dürften nicht fehlen! Erfolgreiches Schnorcheln mit Rochenbeobachtung,...”

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8.Sunset Sailing Private Tour

★★★★★★★★★★4.8 · 6 reviews · from $523 whole boat, up to 6

Join Happy Hour Madeira for a private two-hour sunset sail from Funchal, with space for up to six people. Guides such as Alex, Alfonso, and Louis speak several languages, and you can enjoy a welcome drink, light snacks, swimming, snorkeling gear, blankets, pillows, Wi-Fi, and Spotify music. The boat is blue with a large white company flag.

“Very fun and informative on the island! Alex and Alfonso were great tour guides, and answered any questions we had. Definitely a fun activity to do with your group!”

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9.Sunset on a sailing boat

★★★★★★★★★★5.0 · 2 reviews · 2.5 hours · from $530 whole boat, up to 6

Set sail from Marina Funchal on a private boat for up to six people. Your skipper and live guide take you along Madeira’s coast, with time to look for marine life, swim below Cabo Girão, and watch the sun go down. English, Portuguese, and Spanish are available, and one drink is included.

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