The 6 Sailing Trips in the Azores That Earn Their Price

1.Private Sailing Sunset Tour PDL

★★★★★★★★★★5.0 · 41 reviews · 3 hours · from $212Our pick

Private sunset sail from Ponta Delgada on São Miguel. 3 hours with wine, snorkeling gear, SUP, and calm time for swimming.

“I gifted this activity to my boyfriend on his birthday. What we enjoyed the most was swimming on the open sea and watching the sunset. We didn’t have the best weather as it was cloudy and we wished we could have seen some more marine life like dolphins. However, despite this, we had a great time and we learned a lot about sailling with the crew and took great photos during our trip”

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2.Private Sailboat Cruise with Drinks & Snacks

★★★★★★★★★★4.9 · 35 reviews · 4 hours · from $506

Private 4-hour sail from Ponta Delgada to Caloura on a 12-meter sailboat, with snorkeling, snacks, and helm time (up to 6).

“Thank you so much for accepting the booking! It was a pleasure to meet you and be on board of your watercraft. You are great hosts and would love to recommend you to others - don't look any further! Super clean boat, comfortable boat, and very friendly hosts!”

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3.Sailboat trip from Ponta Delgada

★★★★★★★★★★5.0 · 20 reviews · 4 to 8 hours (approx.) · from $468

Private sail from Ponta Delgada past Ilheu de Vila Franca do Campo, snacks and swimming breaks, friendly hosts. Up to 6.

“Owners were knowledgeable and helpful. Got some decent wind, so had some fun sailing for this old salt. Then managed to track a school of porpoises. So all in all, a great day.”

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4.Ponta Delgada Full Day Sailing Tour with Drinks and Snacks

★★★★★★★★★★5.0 · 10 reviews · 8 hours · from $1,155

Sail the south coast of São Miguel from Ponta Delgada, take the helm, snorkel at a bay, and snack with Azorean bites.

“Huéspedes y velero increíbles. Hicimos varias paradas en distintos puntos de la costa, siempre adaptándose a nuestras preferencias y haciendo recomendaciones de lugares. Comida snack mejor de lo esperado y bebidas durante el día completo. Muy recomendable.”

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5.Full Day: Sailing tour with lunch & snorkeling included.

★★★★★★★★★★4.5 · 7 reviews · 8 hours · from $141Best value

Full-day sailing from Ponta Delgada with lunch and snorkeling at Vila Franca do Campo islet, guided tour, and ferry return.

“Excellent guide, tailored made trip, great snorkeling experience (despite the cold water), enjoy at fullest the entire sailing journey!”

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6.Azores Sailing Yacht Charter and Liveaboard Expeditions

★★★★★★★★★★5.0 · 1 reviews · 6 days (approx.) · from $786

Sail between Faial, Pico, and São Jorge on a classic 41ft yacht, with onboard meals, snorkeling, and Azores stops in Horta and beyond.

“Amazing! The best charter ever. João, the captain is not just the greatest skipper but also a worderfull Azores guide that gives you an experience of a lifetime. I highly recomend Salty Planet!”

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