If you’re looking to see Madeira from a different perspective, a sailing tour along its coast might be just what you need. We haven’t personally been on this exact trip, but based on the glowing reviews and detailed descriptions, it seems like a wonderful way to enjoy the island’s natural beauty without the hustle and bustle of crowded spots. Whether you want to relax with a drink in hand, take in breathtaking scenery, or swim in clear waters, this tour offers a balanced mix of all three.
Two things we really appreciate about this experience are the peaceful setting away from crowds—since you’re on a classic sailboat—and the chance to see Madeira’s rugged coastline up close and personal. The option to choose between three routes, especially the sunset cruise, makes it flexible depending on what kind of view or experience you’re after. The only potential downside? Since the tour is weather-dependent, a less-than-ideal day could impact your plans, so it’s good to check the forecast. This tour seems ideal for travelers who love nature, scenic views, and a bit of tranquility on the water.
This experience suits those who want a relaxed, scenic outing—perfect for couples, friends, or solo travelers looking for a peaceful way to explore Madeira’s coast. It’s less about high-energy adventure and more about soaking in the views and enjoying some leisure time at sea.
Key Points
- Scenic Coastal Views: Experience Madeira’s cliffs, caves, and seaside villages from the water.
- Flexible Routes: Choose between Ponta do Sol, Paul do Mar, or a sunset cruise for tailored experiences.
- Swim and Relax: Swim in crystal-clear waters and unwind on a classic sailboat.
- Small Group Feel: Likely intimate and personal, enhancing the relaxed vibe.
- Weather Dependent: Be prepared for possible schedule changes based on weather.
- Friendly Guides: Tour guides speak multiple languages and are praised for their friendliness.
Why This Tour Stands Out
The idea of drifting along Madeira’s coast on a classic Shipman 28 sailboat already paints a picture of understated elegance and simplicity. It’s not a large, crowded boat tour—more like a shared experience that invites you to relax and take in the scenery at your own pace. The reviews highlight a “very nice tour with friendly staff”, and Sophie from the Netherlands even mentions enjoying wine and food onboard, which adds a special touch of comfort and indulgence.
What truly makes this tour special is the opportunity to see the island from a perspective that’s tough to replicate on land. You’ll love the way the cliffs, volcanic formations, and small caves seem to come alive from the sea. Plus, the chance to swim in Madeira’s crystal-clear waters offers a refreshing break from sightseeing. You’ll find that this is an experience for those who want to disconnect, relax, and take in breathtaking views away from crowded tourist spots.
Enjoy being on the water? Here are other boat experiences we've looked into in Calheta Madeira
The Itinerary Breakdown
While the tour lasts about 3.5 hours, the key is in how you spend that time. Choosing the Ponta do Sol route, for example, begins at Marina da Calheta. From here, you’ll sail along the south coast, passing steep cliffs, volcanic rock formations, small caves, and lively seaside villages. This route offers a good mix of scenery and a peaceful vibe, perfect for photography or just soaking in the views.
The Paul do Mar route is targeted at those interested in the more rugged, wild side of Madeira’s coast. Sailing along the northwest coast, you’ll encounter dramatic vertical cliffs and hidden bays. This part of the coast is less developed and offers a more untouched, natural feel. It’s perfect if you want to really get a sense of Madeira’s rugged beauty away from the more touristy areas.
The sunset route offers a more relaxed, romantic experience. As the name suggests, you’ll sail along the south coast while the sun dips below the horizon. This is a chance to unwind, sip on something, and enjoy the magical colors of the sunset over the Atlantic. Many reviews mention how peaceful and beautiful this time of day is, making it a memorable way to end your day.
What to Expect During the Tour
From the moment you step onto the Shipman 28 sailboat, you’ll notice its classic charm. The boat’s size suggests it’s ideal for smaller groups, which generally means a cozy and friendly atmosphere. The crew is described as friendly and accommodating, making sure everyone feels comfortable whether you’re interested in sailing, swimming, or just relaxing on deck.
The tour is guided in multiple languages—Portuguese, English, and Spanish—which helps make the experience accessible to a wide range of travelers. Guides will share insights about Madeira’s coastline, adding context that deepens your appreciation of the scenery.
Depending on the route chosen, you might stop for a swim in the clear waters. Remember to bring swimwear and a towel if you’re planning on taking a dip. Sunscreen is recommended, especially if you’re on the water during the warmer parts of the day. The boat is open-air, so preparedness for sun exposure and wind is wise.
The entire experience is weather-dependent, which means if the sea is rough or conditions are unfavorable, the tour might be rescheduled or canceled. This adds a bit of unpredictability, but the safety and comfort of guests are paramount.
The Experience from the Passenger’s Perspective
One reviewer, Sophie, shared that the tour was “very nice” and appreciated the friendly staff. She also mentioned enjoying the view and the food and wine, which suggests that there’s a leisurely, enjoyable atmosphere onboard. She recommends the tour, and many others echo her sentiment about the stunning scenery and the relaxing pace.
Travelers can expect to spend about 3.5 hours on the water, which is a good length for a laid-back outing. The route options allow for different experiences—whether you want to explore the wilder northwest coast or watch the sunset. The small group setting typically enhances the sense of intimacy and connection with the crew and fellow travelers.
More Great Tours NearbyValue for Money
The tour’s pricing is not explicitly stated here, but considering it’s a 3.5-hour sailing with the chance to swim, enjoy drinks, and relax on a well-maintained vessel, the value seems fair. It’s a way to enjoy Madeira’s coastline without the crowds, and the small group setting adds to the exclusivity. If you’re someone who appreciates scenic, low-key experiences, this tour offers good bang for your buck.
Practical Tips for Booking and Enjoying
- Book in advance, especially during high season, to secure your preferred route and departure time.
- Arrive a bit early at Marina da Calheta or the designated departure point.
- Bring sun protection—sunscreen, hat, sunglasses—since the boat is open-air.
- Pack swimwear and a towel if you plan to swim.
- Check the weather forecast beforehand since the experience depends heavily on conditions.
- If you’re celebrating a special occasion, the sunset route might be the most romantic choice.
The Sum Up
This sailing tour along Madeira’s coast offers a relaxed, scenic escape that’s perfect for those who want to see the island from the water without the hustle of large tour groups. The chance to enjoy crystal-clear waters, stunning cliffs, and peaceful sunset views makes it a memorable experience. It’s especially suited for travelers who prioritize beautiful scenery and gentle leisure over adrenaline-pumping activities.
While the weather can influence the trip, the friendly guides and the opportunity to choose between different routes make this a flexible, enjoyable option. Whether you’re after the wild beauty of the northwest coast or a romantic sunset sail, this experience provides a quiet, scenic taste of Madeira’s diverse coastline.
If you’re seeking a peaceful day on the water and love capturing striking landscapes, this tour is well worth considering. It’s also a good pick if you prefer a smaller, more intimate setting over crowded boat trips. Just remember to pack sun protection and be ready for a weather-dependent adventure that promises plenty of breathtaking views.
Madeira: Sailing Tour Of The Magical Coast
FAQ
Is this tour suitable for children?
While the description doesn’t specify age restrictions, the nature of the tour—relaxed sailing and swimming—may suit older children and teenagers. Always check with the provider if you’re traveling with young kids or have specific concerns.
What should I bring on the tour?
Bring swimwear, a towel, sunscreen, and perhaps a hat or sunglasses for sun protection. Pack a light jacket if you tend to get cold easily, especially in the evening or on windy days.
Can I swim during the tour?
Yes, swimming in Madeira’s clear waters is one of the highlights. Make sure to bring your swimwear and towel, and follow the crew’s safety instructions.
How long does the tour last?
The tour is approximately 3.5 hours from start to finish, offering a comfortable amount of time to relax, enjoy views, and swim.
What routes are available?
You can choose from three routes: Ponta do Sol, Paul do Mar, or a sunset cruise. Each offers a slightly different perspective of Madeira’s coastline.
Is the tour weather dependent?
Yes, the activity depends on weather conditions. If the weather isn’t suitable, the tour could be canceled or rescheduled. It’s advisable to check the forecast before booking.
What languages are the guides available in?
Guides speak Portuguese, English, and Spanish, making the tour accessible to a range of travelers.
If you’re craving a tranquil but scenic day on the water, this Madeira sailing tour seems like a fantastic way to soak in the island’s beauty while enjoying some peaceful sailing.
You can check availability for your dates here:More Boat Tours & Cruises in Calheta Madeira
More Tours in Calheta Madeira
More Tour Reviews in Calheta Madeira
- Calheta: Private Charter Aestus Luxury Boat
- Madeira West Jeep Tour Fanal, Seixal, Natural Pools & Small Groups
- Madeira : 5 hour West Coast wooden Boat excursion
- Private – 25 Fontes and Risco Waterfall Guided Tour
- From Funchal: Modern Catamaran Coastal Exploration Boat Tour
- Madeira: Calheta Jet Ski Rental



