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Top Madeira Sailing Trips

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Madeira Tours

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Madeira Private Sunset Boat Tour from Funchal
5.0 (93)

Madeira Private Sunset Boat Tour from Funchal

Feel the wind in your hair and smell the salty air. Madeira has so much to offer and so do our boat trips. One thing...

2 hours 30 minutes • Free Cancellation
5.0 (93)
from
$367
Time Travel on Columbus Replica Flag Ship in Madeira
4.4 (186)

Time Travel on Columbus Replica Flag Ship in Madeira

The Santa Maria de Colombo is a replica of Christopher Columbus's flag ship. It makes a trip along the souht coast of Madeira Island, usually...

3 hours • Free Cancellation
4.4 (186)
from
$53
Seaborn Catamaran trips
Funchal, Portugal
4.6 (355)

Seaborn Catamaran trips

- Search for dolphins, whales and turtles in their natural habitat - Take in panoramic views of the island from the sea - Explore the...

3 hours • Free Cancellation
4.6 (355)
from
$41
Private Sunset Boat Trip Funchal, Madeira with Snacks & Beverages
5.0 (22)

Private Sunset Boat Trip Funchal, Madeira with Snacks & Beverages

Experience the beauty of a Madeira sunset on a private 2.5-hour boat trip with Luv Sailing for up to 8 people from Funchal. (sunrise trips...

2 hours 30 minutes • Free Cancellation
5.0 (22)
from
$532
Sunrise, Sunset & Moonlight private Sailing Cruises in Madeira
5.0 (11)

Sunrise, Sunset & Moonlight private Sailing Cruises in Madeira

Since 2001, we've been cruising the waters of Madeira and Porto Santo in all sorts of nifty vessels, from dinghies to windsurfing boards and catamarans....

3 hours • Free Cancellation
5.0 (11)
from
$532
Madeira Private Boat Tour from Funchal
5.0 (9)

Madeira Private Boat Tour from Funchal

Feel the wind in your hair and smell the salty air. Madeira has so much to offer and so do our boat trips. One thing...

3 hours • Free Cancellation
5.0 (9)
from
$461
Half Day Sailing Experience in Madeira´s South Coast
5.0 (7)

Half Day Sailing Experience in Madeira´s South Coast

Since 2001, we've been cruising the waters of Madeira and Porto Santo in all sorts of nifty vessels, from dinghies to windsurfing boards and catamarans....

5 hours • Free Cancellation
5.0 (7)
from
$830
Madeira Bays Sailing Tour
4.7 (7)

Madeira Bays Sailing Tour

Discover Madeira’s stunning coastline on a full-day sailing tour aboard the classic Ventura do Mar. Sail towards Ponta de San Lorenzo and explore beautiful bays,...

7 hours 30 minutes • Free Cancellation
4.7 (7)
from
$100
Luxury Yacht 4 hours in Madeira
Funchal, Portugal
5.0 (1)

Luxury Yacht 4 hours in Madeira

This luxury yacht in Madeira gives you the opportunity to enjoy the island your way. If you are looking for a yacht to rent in...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$3,488
Full Day Private Sailing Cruise

Full Day Private Sailing Cruise

Join us for an unforgettable one-day sailing adventure along the stunning coastline of Madeira Island! Our expert crew will guide you through breathtaking waters, allowing...

7 hours • Free Cancellation
from
$1,067
Private Catamaran Trips in Madeira Island

Private Catamaran Trips in Madeira Island

Sailing Sensation - Unique Catamaran Experiences Around Madeira & Porto Santo At Sailing Sensation, we specialize in creating personalized and unforgettable catamaran tours around the...

3 hours • Free Cancellation
from
$1,132

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Great trip for September with Gonsalo and Diego
New York City
Time Travel on Columbus Replica Flag Ship in Madeira
kristinec103, Sep 2026
Great trip for September with Gonsalo and Diego
Amazing experience with Gonsalo and Diego, they made everyone feel welcome, provided comfortable atmosphere with a lot of jokes! Diego is amazing at jumping in the water from the ship from different heights at the swim spot-our trip took place on 15/09 and water was around 24 degrees, Gonsalo had a good knowledge of showing the dolphins and telling stories about seeing whales, also served the wine and honey cake to all-allowed to have some extra slices too! The trip started on time at 15:00, and arrival was on time as well, just before 18:00. Recommend this for everyone, the guys said the best time for trip is from June to September so get your tickets and go for the trip!
Read more
Fun at sea!
New York City
Seaborn Catamaran trips
coly_82, Sep 2026
Fun at sea!
This trip on the catamaran was just spectacular, they have a fabulous netted area at the front of the boat providing great views and the opportunity for sun bathing. We were lucky enough to see whales and got the opportunity for a swim with some amazing views. The crew were very friendly and fun! We would highly recommend this trip!
Read more
Great way of seeing part of the island
New York City
Time Travel on Columbus Replica Flag Ship in Madeira
Judith_P, Sep 2026
Great way of seeing part of the island
It was brilliant...worth every penny ... Great Morning and you get to see part of the island ...we even saw whales...Amazing... The guides were extremely informative. Also the Honey cake and maderia wine was very tasty.
Read more
Nice
New York City
Private Sunset Boat Trip Funchal, Madeira with Snacks & Beverages
marianadW534XW, Sep 2026
Nice
Was amazing. Nice service. Thank you
Read more
We loved it!
New York City
Seaborn Catamaran trips
M9427JOpetrab, Sep 2026
We loved it!
The whole experience was great, we saw two types of whales! The ride was nice and we also swam near the Cabo Girao! We would recommend it!
Read more
It was truly an unforgettable experience!😍
New York City
Private Sunset Boat Trip Funchal, Madeira with Snacks & Beverages
jj1282, Sep 2026
It was truly an unforgettable experience!😍
We received a sunset sailing trip with Luv Sailing as a gift for our honeymoon, and honestly, it was one of the most beautiful experiences of our entire trip!The sunset was absolutely breathtaking, and seeing the island from a completely different perspective made the experience even more special. The crew was also a friendly company, we had great conversations, laughs.We also enjoyed some delicious drinks and snacks along the way.We loved every single minute of it and would wholeheartedly recommend Luv Sailing to anyone visiting Madeira. It was truly an unforgettable experience, thank you! ❤️ J&L
Read more
Awesome experience!
New York City
Madeira Private Boat Tour from Funchal
Rachel_K, Aug 2026
Awesome experience!
We had a great time on this boat trip. The views were gorgeous and the swim was the highlight. Right under the cliffs and the water was a stunning marine blue and very clear. The crew was super nice. Thanks so much for an awesome ride!
Read more
West Maderia Boat Tour
New York City
Madeira Bays Sailing Tour
erikai922, Aug 2026
West Maderia Boat Tour
Our experience was beautiful from beginning to end. Our guide, Cofofo, tended to every need, from providing morning juice and setting out the paddle boards to serving a delicious lunch and afternoon drinks. Ours was a small group of five. It says the boat only goes out on Thursday, but if you have a group of six, message them. Highly recommended,
Read more
It does not get any better than this for a sunset sail and some wine.
New York City
Sunrise, Sunset & Moonlight private Sailing Cruises in Madeira
Harry_K, May 2026
It does not get any better than this for a sunset sail and some wine.
It does not get any better than this. If you like sailboats rather than catamaran or power boat and you want to see the sunset with some wine and small bites, then this is for you.
Read more
Captain, oh Captain...
New York City
Madeira Private Sunset Boat Tour from Funchal
452lucieb, Mar 2026
Captain, oh Captain...
We had the best experience with the captain, slowly sailing into the sunset. His calm demeanour, skill and overall attitude was wonderful and one of the highlights of our stay.
Read more
Unforgettable Evening on the Water
New York City
Madeira Private Sunset Boat Tour from Funchal
Lynn_K, Sep 2025
Unforgettable Evening on the Water
We had such a wonderful experience on our sunset cruise with Captain Paulo! From start to finish, everything was smooth, relaxing, and enjoyable. Paulo was friendly, welcoming, and made sure everyone felt comfortable on board. He provided snacks and drinks, which was such a thoughtful touch while we enjoyed the gorgeous views. The timing of the cruise was perfect—the sunset was absolutely stunning and made for such a memorable evening. Highly recommend booking with Captain Paulo if you’re looking for a relaxing and unforgettable experience on the water!
Read more
Spectacular sail
New York City
Sunrise, Sunset & Moonlight private Sailing Cruises in Madeira
Ewbailey, Sep 2025
Spectacular sail
This sunset cruise was spectacular and a highlight of our honeymoon trip to Madeira! Manolo and his son were so kind, knowledgeable, and professional. Their love for sailing was evident and contagious. We loved being able to stop and swim and really enjoyed our charcuterie board with wine as we watched the sunset. We could not recommend this trip enough, it’s a trip you’ll forever cherish. Thank you so much Manolo!
Read more
New York City
Madeira Bays Sailing Tour
Voyage33506843705, Aug 2025
"Unforgettable experience with Ventura!"
From the moment of booking to the return to the harbor, everything went impeccably. The booking was quick and simple, and the Ventura team was always attentive and professional. The boat ride to the Deserts was simply spectacular! We were lucky to spot dolphins — a real thrill. Between refreshing dives, snorkeling and fun moments at the stand up paddle, visiting the island, there were activities to get the most out of the day. The lunch, already included in the tour, was delicious, with meat or fish options, drinks and dessert included — all very well served and in a relaxed Mood. The good weather helped, but it was the sympathy and dedication of the Ventura team that made this experience memorable. No doubt, an Enterprise I recommend to those who want to know the wonders of the Deserts (and other tour options that the Enterprise has) in a safe, fun and unforgettable way!
Read more
Great day of sailing!!
New York City
Half Day Sailing Experience in Madeira´s South Coast
Seth_P, Jul 2025
Great day of sailing!!
Carlos was an amazing captain and the boat was wonderful. Great day of sailing and we even spotted a bunch of dolphins. The food and wine they served was awesome. Great way to see the coast and even go for a swim. Highly recommend.
Read more
Very special
New York City
Madeira Private Boat Tour from Funchal
Steve T, Jul 2025
Very special
We booked this as part of a big birthday celebration! It made the day feel very special. Paolo and George were great hosts and very professional. We loved sailing down the coast, stopping under the high cliff where they produced great drinks and snacks and loved swimming in the sea.If you want to do something really special while you're in Madeira, this is the thing!
Read more
A Must- Do
New York City
Half Day Sailing Experience in Madeira´s South Coast
F1256ICthomash, May 2025
A Must- Do
As always, the captain did an outstanding job in making time on board unforgettable. Having sailing experience myself its always great to help during the trip, the view onto the coast and the atmosphere on board always wants me to come back. Highly recommendable!!
Read more
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