We Rank Madeira’s 15 Top Sailing Experiences

Discover the top 15 sailing experiences in Madeira, from dolphin watching to sunset cruises, with practical insights to help you choose.

Madeira, Portugal, is a captivating island where the sea and sky come together in perfect harmony. Its rugged coastline, rich marine life, and warm waters make it a prime destination for sailing adventures. Whether you’re after a peaceful sunset, a wildlife encounter, or a luxury cruise, Madeira offers a wide range of options. We’re particularly fond of the Eco-friendly Catamaran Dolphin Whale Watching for its silent, emissions-free approach and the chance to see dolphins and whales in their natural habitat, as well as the Sunset Sailing Tour for its romantic views and tranquil atmosphere. For those looking for a more luxurious experience, the Funchal Bay Dolphin & Whale Watch Luxury Catamaran Cruise combines comfort with wildlife viewing effortlessly.

This list features a variety of tours, including eco-conscious trips, family-friendly excursions, private sailboat adventures, and special occasion cruises, each offering a unique way to experience Madeira’s stunning maritime environment. To get the best sense of what suits your style and needs, read on as we explore each experience in detail.

1. From Funchal: Ecological Catamaran Dolphin Whale Watching

From Funchal: Ecological Catamaran Dolphin Whale Watching

At number 1, this ecological dolphin and whale watching tour stands out for its commitment to sustainability. The custom-built Eco-catamaran runs on hybrid engines, making it the only one of its kind in Madeira. It glides silently through the water, minimizing disturbance to marine life, which greatly increases your chances to see dolphins and whales behaving naturally. The boat features large observation nets and a spacious interior, ensuring everyone gets a good view. The trip lasts about 2.5 to 3 hours, perfect for a quick yet meaningful wildlife encounter.

Guests consistently praise the friendly, knowledgeable guides and the chance to swim at Cabo Girão at the trip’s end. One reviewer calls it “an unforgettable experience,” highlighting the silent approach that feels more respectful to the animals. The focus on eco-friendly technology also means you can enjoy the adventure guilt-free. Bottom line: If you want a sustainable, quiet, and immersive wildlife experience, this tour is a top choice.

2. Funchal: Dolphin and Whale Watching Catamaran Cruise

Funchal: Dolphin and Whale Watching Catamaran Cruise

A close runner-up, this 3-hour boat trip offers a comfortable ride along Madeira’s coast, with plenty of chances to spot dolphins, whales, and even turtles. The tour departs from two convenient locations and includes a stop at Cabo Girão with the option to swim in crystal-clear waters. The guides are praised for their enthusiasm and expertise, making the wildlife sightings both educational and exciting. For around $40, you get a relaxed sail with gorgeous panoramic views and plenty of time to observe marine life.

Guests note the boat’s cleanliness and the guides’ ability to explain the different species seen, enhancing the experience. Some mention the thrill of seeing pilot whales and monk seals, which makes this trip especially rewarding for wildlife lovers. Bottom line: Great for families or anyone seeking a comfortable, wildlife-focused tour with good value.

3. Funchal: Sunset Sailing Tour

Funchal: Sunset Sailing Tour

At number 3, the Sunset Sailing Tour provides a beautifully peaceful way to experience Madeira. The trip lasts three hours, with the chance to spot dolphins and whales in the early part of the cruise. As the sun dips below the horizon, you can swim or snorkel at Cabo Girão, or simply sip a drink and soak in the changing colors of the sky. It’s a romantic, less adrenaline-driven experience ideal for couples or anyone wanting a serene evening on the water.

Rated 4.7 out of 5, travelers love the scenic views and the chance to enjoy Madeira’s natural beauty in both daylight and sunset. The boat’s relaxed vibe and the crew’s friendly service make it a trip to remember. Bottom line: Perfect for a romantic, laid-back experience with a good shot at spotting marine life and enjoying a stunning sunset.

4. Funchal: Dolphin and Whale Watching Sailing Trip

Funchal: Dolphin and Whale Watching Sailing Trip

Number 4 on our list is the Dolphin and Whale Watching Sailing Trip, which combines the thrill of wildlife spotting with the charm of a traditional sailing vessel. This 3-hour cruise offers opportunities to see dolphins, whales, and sea turtles. The relaxed atmosphere and the opportunity to swim or snorkel in the summer make it especially appealing. The crew is described as professional, attentive, and knowledgeable, with many reviews mentioning sightings of pilot whales and bottlenose dolphins.

Guests appreciate the boat’s stability and the scenic views of Madeira’s coast. The experience is ideal for those who want a mix of wildlife, scenic sailing, and a touch of adventure. Bottom line: A solid choice for wildlife enthusiasts who appreciate the romance of sailing.

5. Funchal Bay: Dolphin & Whale Watch Luxury Catamaran Cruise

Funchal Bay: Dolphin & Whale Watch Luxury Catamaran Cruise

Number 5 offers a luxurious take on the classic whale watching trip. This 3-hour cruise focuses on comfort and style, with a spacious, well-appointed catamaran. It’s perfect for travelers who want to combine wildlife viewing with a touch of elegance. The boat offers a swim stop in Cabo Girão and chances to see whales and dolphins in their natural environment, with reviews mentioning sightings of pilot whales and seals.

The crew’s attentive service and the chance to relax in a sophisticated setting make it stand out. Prices are reasonable given the upscale experience, and guests frequently praise the friendly staff and the quality of wildlife sightings. Bottom line: Ideal for couples or small groups seeking a more refined experience.

6. Funchal: Dolphin and Whale Watching by Luxury Catamaran

Funchal: Dolphin and Whale Watching by Luxury Catamaran

Number 6 is a more intimate luxury cruise that emphasizes a relaxed atmosphere with fewer passengers—perfect for those who crave a more personal experience. It includes opportunities to spot dolphins, whales, turtles, and endemic birds, with optional swimming in summer. The boat departs from two convenient spots and offers indoor and outdoor seating.

Guests note the knowledgeable crew’s explanations of Madeira’s ocean ecology and the chance to see dolphins and whales up close. The limited passenger count adds to the feeling of exclusivity and comfort. Bottom line: Best suited for travelers who want a private, personalized adventure with a focus on natural encounters.

7. Madeira: Funchal Sunset Tour by Catamaran

Madeira: Funchal Sunset Tour by Catamaran

This sunset cruise combines beautiful scenery with the chance to see dolphins and whales, and the unique opportunity to swim at Cabo Girão while watching the sun go down. The 3-hour trip from Praça do Povo is perfect for those wanting a romantic, scenic experience. The reviews highlight the peaceful journey, with many mentioning the magnificent sunset and the surprise of seeing whales.

The crew’s professionalism and the boat’s comfortable setup make it a favorite for couples. Bottom line: A highly recommended option for a romantic evening with wildlife and spectacular views.

8. Dolphin and Whale Watching Catamaran Cruise from Funchal

Dolphin and Whale Watching Catamaran Cruise from Funchal

Number 8 features a stylish 3-hour wildlife cruise that emphasizes both dolphin and whale sightings and the chance to swim or try basic sailing techniques if conditions are right. The crew’s expertise ensures you’re in good hands, and the reviews mention sightings of pilot whales, dolphins, sharks, and turtles, plus the opportunity to relax and enjoy Madeira’s scenery.

Guests appreciate the comfort of the boat and the friendly staff’s knowledge. It’s great for those who want a bit of everything—wildlife, relaxation, and scenic views. Bottom line: Well-rounded tour combining wildlife with casual sailing.

9. Eco-Friendly Catamaran Dolphin and Whale Watching

Eco-Friendly Catamaran Dolphin and Whale Watching

This eco-conscious half-day adventure offers a silent, emission-free ride to observe dolphins, whales, monk seals, and seabirds. Departing from Funchal, it prioritizes sustainability while providing a close encounter with marine life. The boat features trampoline nets at the bow for relaxing and a bar for drinks.

Guests love the minimal disturbance to wildlife and the detailed onboard commentary. With a focus on conservation and comfort, this tour is perfect for eco-minded travelers. Bottom line: If your priority is an environmentally friendly, respectful wildlife experience, this tour hits the mark.

10. Madeira: New Year’s Eve Fireworks Catamaran Cruise

Madeira: New Years Eve Fireworks Catamaran Cruise

Number 10 is a special occasion option, offering a front-row seat for Madeira’s famous New Year fireworks. The 1.5-hour cruise includes champagne and Madeira wine as you enjoy the spectacle from the water, making it ideal for celebrating a special night. The reviews highlight the fantastic pyrotechnic show and the memorable atmosphere onboard.

This cruise is perfect for travelers celebrating New Year’s or those wanting a unique way to ring in the year. Bottom line: A once-in-a-lifetime experience in Madeira’s vibrant New Year scene.

11. Half Day Tour on a Luxury Catamaran on Madeira Island

Half Day Tour on a Luxury Catamaran on Madeira Island

This luxury half-day cruise offers a relaxed environment with ample space and comfort. It includes the chance to see dolphins, whales, or turtles, with a swim stop at Cabo Girão. The boat’s elegant design and small group size make it popular among travelers seeking a more upscale experience.

Many reviews mention the friendly crew, the quality of the boat, and sightings of dolphins. It’s a good choice if you want a balance of wildlife, comfort, and shorter duration. Bottom line: For those valuing luxury and personalized service, this cruise is a top pick.

12. From Funchal: West Bays Sailing Tour with Lunch

From Funchal: West Bays Sailing Tour with Lunch

Number 12 takes you along Madeira’s dramatic west coast on a 5-hour sailing trip with lunch included. You visit Ponta do Sol Bay and Ribeira Brava Bay, with opportunities to spot dolphins and whales. The trip also features snorkeling among colorful marine life, making it ideal for active travelers.

Guests praise the enthusiastic crew and the scenic, varied coastline. The longer duration and included lunch provide excellent value for those wanting a full day on the water. Bottom line: A great option for travelers who want to combine sailing, wildlife, and a substantial meal.

13. Funchal Half and Full Day Private Sailboat Tour

Funchal Half and Full Day Private Sailboat Tour

Number 13 offers a personalized private experience for up to six people, with the flexibility to explore both east and west coasts. The trip includes visits to private beaches only accessible by sea, with the chance to swim in warm Atlantic waters and enjoy lunch at Fajã dos Padres. It’s suitable for travelers who want exclusivity and tailored itineraries.

Guests describe the guides as very knowledgeable and attentive. This tour is ideal for special occasions or travelers who prefer privacy and custom schedules. Bottom line: Perfect for small groups seeking a bespoke, memorable experience.

14. Desertas Islands Full-Day Catamaran Trip from Funchal

Desertas Islands Full-Day Catamaran Trip from Funchal

This full-day excursion takes you to Madeira’s natural reserve, the Desertas Islands. The trip includes a guided tour, a swim in pristine waters, and the chance to learn about monk seal conservation efforts. It’s a longer, more comprehensive experience that appeals to nature lovers and curious travelers.

Guests mention the stunning volcanic landscapes, wildlife sightings—sometimes killer whales—and the well-organized tour. The 9-hour schedule is ideal for those wanting an immersive day on the water. Bottom line: Best for travelers who want a full, educational, and scenic day exploring Madeira’s wild side.

15. Catamaran Sunset Cruise from Funchal

Catamaran Sunset Cruise from Funchal

Closing out our list, this sunset cruise combines relaxed sailing with spectacular views. Departing Funchal, it’s a 3-hour journey with the chance to spot dolphins and whales if luck is on your side. The highlight is the glow of dusk over Madeira, perfect for a romantic evening. Reviews mention the peaceful atmosphere and the beautiful cliffs and ocean scenery.

Ideal for couples or anyone wanting a calm, scenic wind-down, this cruise offers a memorable way to end a day. Bottom line: A peaceful, romantic option that emphasizes sunset views and marine life sightings.

How to Choose Your Perfect Madeira Sailing Experience

When selecting a tour, consider your priorities: Do you want a sustainable, eco-friendly trip? The Eco-friendly Catamaran Dolphin Whale Watching is perfect. If a luxury, comfortable cruise appeals, then the Funchal Bay Dolphin & Whale Watch Luxury Catamaran fits the bill. For a romantic sunset, the Sunset Sailing Tour or Sunset Cruise from Funchal are top contenders. Budget-conscious travelers may prefer the $40 dolphin cruise, while those seeking a private, tailored adventure should look at the Private Sailboat Tour.

Booking early is wise, especially during peak seasons or special occasions like New Year’s. Check available times and weather forecasts, as marine wildlife sightings depend a lot on ocean conditions.

To sum it up, Madeira’s sailing options are as diverse as its landscapes. For wildlife lovers, the ecological and luxury cruises provide unique dolphin and whale encounters. For those seeking a peaceful, scenic evening, the sunset cruises won’t disappoint. And if privacy and tailored experiences matter, the private sailboat tours offer true exclusivity. No matter your style, Madeira’s waters promise unforgettable moments—so don’t delay, book early, and prepare for an ocean adventure that will stay with you long after you leave the island.