Ponta Delgada: Private Sailboat Cruise with Drinks & Snacks

Exploring the Azores doesn’t get much better than a private sailing trip around São Miguel Island. This 4-hour cruise, offered by Sail4Sailing Azores, promises a relaxed yet immersive way to see the island’s stunning coastlines and hidden bays. With the chance to learn sailing basics, take the helm, and enjoy a handful of local treats, this experience balances adventure with indulgence.

What we really appreciate about this tour is its personalized nature. It’s designed for small groups (up to 6 people), ensuring a more intimate and flexible trip. Plus, the views from the water are truly special—quiet bays, rugged cliffs, and scenic coastlines from a perspective most visitors only dream of.

One thing to keep in mind is that this is a weather-dependent experience. Good wind and sunshine can make or break the sailing vibe, though the crew is accommodating and can adapt the itinerary. If you’re after a peaceful, scenic cruise with a touch of sailing skills and local flavor, this outing is perfect. It’s especially suited for couples, friends, or families wanting a memorable day on the water with plenty of comfort and scenic beauty.

Key Points

• Intimate & Private: Limited to groups of 6 for a personalized experience.
• Multiple Highlights: Sailing, swimming, snorkeling, and enjoying local snacks and drinks.
• Flexible Itinerary: Options for pre-defined routes or free sailing depending on conditions.
• Instructive & Fun: Learn sailing basics and even get a chance to steer the boat.
• Beautiful Scenery: Views of São Miguel’s south coast and Caloura from the water.
• All-Inclusive Comfort: Snacks, drinks, life jackets, and snorkel gear provided.

An In-Depth Look at the Experience

Embarkation at Marina Portas do Mar

Starting from the Marina Portas do Mar in Ponta Delgada, the trip kicks off with a smooth check-in at the access gate next to the reception desk. The boat itself is a luxurious 12-meter sailboat, offering plenty of space and comfort. The crew, including knowledgeable guides, are fluent in English, French, and Portuguese, making communication easy even for non-native speakers.

The Itinerary: What to Expect

The tour features two main stops, each carefully selected for their beauty and tranquility. The first major stop is Caloura, a well-known scenic bay famous for its clear waters and picturesque surroundings. Here, you’ll anchor in a sheltered spot perfect for swimming and snorkeling. Reviewers like Radosaw mention how “swimming alongside playful dolphins” was a highlight, emphasizing how close to nature you can get.

During this time, you can simply relax, enjoy the tasting menu featuring regional Azorean products, or get involved with sailing. The crew is friendly and eager to teach the basics of sailing, allowing guests to come sail at the helm if they wish. This hands-on approach adds a layer of interaction that many travelers find enriching.

The second stop is another scenic stretch along the coast, where you’ll continue sailing, taking in the stunning views and scenic landscapes. This part lasts about an hour and gives everyone a chance to enjoy the ocean breeze and perhaps snap some memorable photos.

The Sailing & Snorkeling Experience

The boat trip is designed for comfort but also for those who want a bit of adventure. As Louis shares, “the kids enjoyed diving in the ocean and swimming around,” highlighting how family-friendly the experience can be. Snorkeling equipment is provided, so you don’t need to worry about bringing your own gear.

Sailing lessons or the chance to take the helm make this trip stand out. It’s not just a passive sightseeing tour but an active, engaging experience. Guides are well-versed and attentive, ensuring you feel safe and informed whether you’re new to sailing or a seasoned sailor.

Snacks & Drinks

A standout feature is the tasting menu with regional products from the Azores. While the tour includes welcome drinks and snacks, the tasting menu isn’t included in the price and can be added for a local culinary experience. Guests have praised the delicious snacks and fine wines, which really elevate the overall value of the trip.

End of the Trip

After about 2.5 hours at the first bay and an hour sailing, you’ll return to Ponta Delgada Marina. The sailboat’s smooth ride and scenic views along the way make the return just as delightful as the start.

Why This Tour Works for Travelers

This cruise is ideal for those who want a personalized, relaxed ocean adventure** with a mix of sailing, swimming, and local flavors. It’s particularly suited for travelers who enjoy small-group experiences and are open to a bit of hands-on fun. The flexible itinerary means you’ll get tailored moments—whether that’s more sailing, swimming, or simply soaking up the scenery.

The price of $443 per group is quite reasonable given the exclusivity, personalized attention, and included amenities. The experience offers good value, especially considering the professional guides, quality equipment, and scenic stops.

What We Love

• The opportunity to learn sailing and even steer the boat, which adds a memorable, engaging element.
• The scenic beauty of São Miguel’s coast seen from the water, offering perspectives that are often missed on land.
• The friendly, knowledgeable crew who make the entire experience relaxed and educational.
• The local snacks and drinks, which give a taste of Azorean flavors while enjoying the sea breeze.

A Few Considerations

• The experience is weather-dependent; wind and sunshine are essential for a great sailing day.
• The price point might be on the higher side for some, but it’s justified by the exclusivity and quality of the experience.
• As it’s a private group experience, it works best for those seeking intimacy rather than a large tour.

Final Thoughts: Is This Experience Worth It?

Absolutely. For adventure lovers, scenic seekers, or those wanting a taste of local life at sea, this private cruise offers a well-balanced blend of comfort, education, and stunning views. It’s a fantastic way to see São Miguel from a different angle, especially if you appreciate personalized service and a more relaxed pace.

It also suits couples and small families who want a memorable, quality experience without feeling crowded or rushed. Plus, the chance to learn sailing and participate actively makes it stand out from more conventional boat tours.

If you’re after a peaceful yet engaging way to explore the Azores’ coast, this sailboat cruise is a superb choice—and one that’s likely to leave you with lasting impressions of the island’s natural beauty.

FAQ

How long is the tour?
The tour lasts approximately 4 hours, including sailing, swimming, and scenic stops.

Where does the tour start and end?
It begins and ends at Marina Portas do Mar in Ponta Delgada.

What’s included in the price?
The price covers the 4-hour boat trip, technical crew, embarkation and disembarkation, welcome drinks and snacks, life jackets, and snorkeling equipment for 2.

Can I learn to sail during the trip?
Yes, the experience includes learning the basics of sailing, and you will have the chance to come sail at the helm if you wish.

Is snorkeling equipment provided?
Yes, snorkeling gear is included, allowing you to explore the underwater scenery during your stop in the bay.

Are meals included?
The tour includes welcome drinks and snacks, but a tasting menu with regional products from the Azores can be added separately for a more culinary experience.

Is this a private experience?
Yes, it’s designed for private groups of up to 6 guests, ensuring a more personal and tailored outing.

What languages are the guides available in?
Guides speak English, French, and Portuguese.

What should I wear?
Bring casual, comfortable clothing suitable for the weather, along with swimwear if you plan to swim or snorkel.

Is this experience suitable for children?
Yes, families with kids who enjoy water activities and a relaxed sailing environment will find it perfect.

In summary, this private sailboat cruise offers an engaging, scenic, and authentic way to experience São Miguel’s coast. From learning basic sailing to swimming in crystal-clear waters and enjoying regional treats, it appeals to travelers seeking a personalized, high-quality adventure on the sea.