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Sailboat rental with captain

8165 boats available in World
-25%
Bénéteau Oceanis 51.1
4.3 (13 reviews)
Lávrio
Embark on board the Orion, an amazing Oceanis 51.1 to discover the region of Lávrio. This sailboat was built in 2021 to ensure complete comfort and performance at sea. The boat has 5 cabins with total comfort and a capacity of 12 passengers. With a total length of 16 meters and 110 horsepower, it will be your best friend when spending extraordinary holidays on the waters of Lávrio For your comfort, Orion has 3 toilets with a shower This boat is equipped with a Furling mainsail and a Furling ge...
Sailboat
Captain optional
12 pers.
5 cabins
2021
52 ft
from $610,20
-10%
Bavaria C46
4.8 (4 reviews)
Alimos
We offer for rent a Cruiser 46 of 2025 departing from Álimos. Smaragda is a sailboat perfectly adapted for all rentals. This sailboat is very pleasant to handle for a week cruise or more. The boat has 4 cabins with total comfort and a capacity of 9 passengers. With a total length of 14 meters and 57 horsepower, it will be your best friend when spending extraordinary holidays on the waters of Álimos This Cruiser 46 is equipped with 4 heads with a shower. This boat is equipped with a Furlin...
Sailboat
Captain optional
9 pers.
4 cabins
2025
48 ft
from $411,80
-33%
Bénéteau Oceanis 51.1
4.3 (13 reviews)
Alimos
We offer for rent a Oceanis 51.1 of 2022 departing from Alimos Marina. Annezia Star is a sailboat perfectly adapted for all rentals. This sailboat is very pleasant to handle for a week cruise or more. The sailboat is 16 meters in length with 110 horsepower. The 5 cabins can accommodate 13 passengers when cruising. For your comfort, Annezia Star has 3 toilets with a shower This boat is equipped with a Furling mainsail and a Furling genoa. It has the following equipment: Auto-pilot, Outboard eng...
Sailboat
Captain optional
12 pers.
5 cabins
2022
52 ft
from $626,35
-10%
Jeanneau Sun Odyssey 350
5.0 (5 reviews)
Cádiz
Spectacular sailboat Jeanneau Sun Odyssey 350 arrived from the shipyard in 2025. The price includes professional skipper, fuel, insurance, drinks, double paddle surf boards, giant mats, snorkeling equipment, action cameras, etc. The boat is for 9 passengers in addition to the skipper. Contact us if you have any questions, we will be happy to accommodate your needs.
Sailboat
Captain mandatory
9 pers.
2 cabins
2025
36 ft
from $288,38
-15%
Bénéteau Oceanis 40.1
4.3 (13 reviews)
Paros (Island)
Incredible sailboat for rent in Paros (Ile). This Oceanis 40.1 from 2025 is an ideal boat for a vacation with family or friends. You are going to have an exceptional cruise on this sailboat of 13 meters. You will be able to accommodate up to 10 passengers when cruising and take advantage of its 4 cabins with total comfort. This Oceanis 40.1 is equipped with 2 heads with a shower. This boat is equipped with a Furling mainsail and a Furling geno...
Sailboat
Captain optional
10 pers.
4 cabins
2025
42 ft
from $411,80
-5%
Jeanneau Sun Odyssey 33i
5.0 (3 reviews)
Saint-Quay-Portrieux
Welcome aboard EliTHEO. Maximum number of people 5. You will embark with JEAN-FRANCOIS, your qualified captain who will be your coach for a discovery cruise. Set sail for a unique and unforgettable day at sea, your adventure in the bay of Saint Brieuc! Come and learn sailing and discover the bay of Saint Brieuc. Excursion: Starting from 140 euros Discovery circuit to learn sailing. Pleasure ride with the possibility of eating on the boat Possible swimming Trolling fishing Port maneuvers Sail...
Sailboat
Captain mandatory
4 pers.
2 cabins
2013
33 ft
Flexible Cancellation
Top owner
from $92,28
-10%
Bénéteau Oceanis 51.1
4.5 (2 reviews)
Alimos
Welcome to onboard, Antonios! Discover this magnificent sailboat available for rent at Alimos Marina. This Oceanis 51.1, built in 2019, offers an unparalleled experience for a family or friends' vacation. You are going to have an exceptional cruise on this sailboat of 16 meters in length. You will be able to accommodate up to 12 passengers when cruising and take advantage of its 5 cabins with total comfort. This Oceanis 51.1 is equipped with a Furling mainsail and a Furling genoa. It has the f...
Sailboat
Captain optional
12 pers.
5 cabins
2019
52 ft
from $370,27
-10%
Bavaria Cruiser 46
4.8 (4 reviews)
Alimos
Welcome to onboard, Efi! Discover this magnificent sailboat available for rent at Alimos Marina. The Cruiser 46, built in 2017, offers an unparalleled experience for a family or friends' vacation. You are going to have an exceptional cruise on this sailboat of 14 meters. You will be able to accommodate up to 9 passengers when cruising and take advantage of its 4 cabins with total comfort. This Cruiser 46 is equipped with a Furling mainsail and a Furling genoa. It has the following equipment: Au...
Sailboat
Captain optional
9 pers.
4 cabins
2017
47 ft
from $246,85
-45%
Bénéteau Oceanis 40.1 (3 double and 1 bunk beds)
4.0 (9 reviews)
Lefkáda
Meet ARIA, an incredible sailboat dedicated for charters. Made in 2021, the Oceanis 40.1 (3 double and 1 bunk beds) will take you to the most beautiful anchorages in Lefkáda. The boat has 4 fully-equipped cabins and a capacity of 10 people. With an overall length of 12 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Lefkáda This Oceanis 40.1 (3 double and 1 bunk beds) is equipped with 2 heads with a shower. This boat is equipped with...
Sailboat
Captain optional
10 pers.
4 cabins
2021
39 ft
from $312,60
-24%
Bénéteau Oceanis 46.1
4.3 (13 reviews)
Lefkáda
Sailboat for rent in Lefkáda. This Oceanis 46.1 built in 2025 offers an excellent quality for its price for a cruise of a few days or even a few weeks. You are going to have an exceptional cruise on this sailboat of 15 meters. You will be able to accommodate up to 10 passengers when cruising and take advantage of its 5 cabins with total comfort. This Oceanis 46.1 is equipped with 3 heads with a shower. This boat is equipped with a Furling main...
Sailboat
Captain optional
10 pers.
5 cabins
2025
48 ft
from $560,60
-15%
Jeanneau Sun Odyssey 469
4.1 (24 reviews)
Alimos
Sailboat for rent in Álimos. This Sun Odyssey 469 built in 2016 offers an excellent quality for its price for a cruise of a few days or even a few weeks. The boat has 4 fully-equipped cabins and a capacity of 10 people. With an overall length of 14 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Álimos This Sun Odyssey 469 is equipped with 4 heads with a shower. This boat is equipped with a Full batten mainsail and a Furling genoa. It...
Sailboat
Captain optional
10 pers.
4 cabins
2016
45 ft
from $427,95
-15%
Jeanneau Sun Odyssey 490
4.1 (24 reviews)
Alimos
Meet Konstantinos, an incredible sailboat dedicated for charters. Made in 2020, the Sun Odyssey 490 will take you to the most beautiful anchorages in Álimos. The boat has 6 fully-equipped cabins and a capacity of 12 people. With an overall length of 14 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Álimos This Sun Odyssey 490 is equipped with 3 heads with a shower. This boat is equipped w...
Sailboat
Captain optional
12 pers.
6 cabins
2020
47 ft
from $649,42
-10%
Bavaria Cruiser 46
4.8 (4 reviews)
Alimos
Welcome to onboard, Lina! Discover this magnificent sailboat available for rent at Alimos Marina. The Cruiser 46, built in 2015, offers an unparalleled experience for a family or friends' vacation. You are going to have an exceptional cruise on this sailboat of 14 meters. You will be able to accommodate up to 9 passengers when cruising and take advantage of its 4 cabins with total comfort. This Cruiser 46 is equipped with a Furling mainsail and a Furling genoa. It has the following equipment: A...
Sailboat
Captain optional
9 pers.
4 cabins
2015
47 ft
from $214,55
-20%
Jeanneau Sun Odyssey 490
4.4 (39 reviews)
Neo Klima
Embark on board the Etheria, an amazing Sun Odyssey 490 to discover the region of . This sailboat was built in 2023 to ensure complete comfort and performance at sea. The sailboat is 14 meters in length with 80 horsepower. The 5 cabins can accommodate 12 passengers when cruising. For your comfort, Etheria has 3 toilets with a shower This boat is equipped with a Half-batten mainsail and a Furling genoa. It has the following equipment: Auto-pilo...
Sailboat
Captain optional
12 pers.
5 cabins
2023
47 ft
from $535,22
-20%
Jeanneau Sun Odyssey 440
4.4 (39 reviews)
Neo Klima
We offer for rent a Sun Odyssey 440 of 2020 departing from . Endeavour is a sailboat perfectly adapted for all rentals. This sailboat is very pleasant to handle for a week cruise or more. The boat has 4 cabins with total comfort and a capacity of 10 passengers. With a total length of 13 meters and 57 horsepower, it will be your best friend when spending extraordinary holidays on the waters of This Sun Odyssey 440 is equipped with 2 heads with a shower....
Sailboat
Captain optional
10 pers.
4 cabins
2020
43 ft
from $427,95
-20%
X-Yachts X 3/4 Ton
5.0 (11 reviews)
Lisbon
Step aboard for a sail in experience in our charming 30-foot sailing boat, where comfort meets tradition. Fully renovated yet rich in history, this vessel offers a cozy and inviting space, complete with a bathroom, refrigerator, and all the essentials for a relaxing trip. Our friendly local crew is ready to welcome you and ensure an unforgettable experience on the water. Prices Start at 270 euros for 2 hours! OUR 2026 PUBLIC TOURS: - Morning Tour - Lunch Tour - Sunset Tour - Night Tour OUR 2...
Sailboat
Captain mandatory
8 pers.
2 cabins
1988
30 ft
Flexible Cancellation
Top owner
from $249,16
-5%
Jeanneau Sun Odyssey 49
5.0 (4 reviews)
Vlychada
Our yacht Sun Odyssey 49 successfully combines contemporary style and harmony, all while respecting the heritage of designing company. This sailboat from 49 feet has revolutionized cruising: she is the only sailboat in their category to feature movement about the deck without obstacle. Life on board has never been so simple and comfortable. We do 2 half-day cruises per day, visiting all the highlights of Santorini: Red & White beach, lighthouse, Volcano and Caldera. Seafood BBQ meal is served o...
Sailboat
Captain mandatory
8 pers.
4 cabins
2004
48 ft
Flexible Cancellation
Top owner
from $1 095,83
-30%
Bénéteau Oceanis 51.1
5.0 (1 reviews)
Alimos
Embark on board the Nireas, an amazing Oceanis 51.1 to discover the region of Alimos Marina. This sailboat was built in 2020 to ensure complete comfort and performance at sea. You are going to have an exceptional cruise on this sailboat of 16 meters. You will be able to accommodate up to 10 passengers when cruising and take advantage of its 4 cabins with total comfort. This Oceanis 51.1 is equipped with 4 heads with a shower. This boat is equipped with a Furling mainsail and a Furling genoa. I...
Sailboat
Captain optional
10 pers.
4 cabins
2020
52 ft
from $610,20
-45%
Bénéteau Oceanis 41.1
4.0 (9 reviews)
Alimos
Incredible sailboat for rent in Alimos Marina. This Oceanis 41.1 from 2020 is an ideal boat for a vacation with family or friends. The boat has 3 fully-equipped cabin(s) and a capacity of 8 people. With an overall length of 12 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Alimos Marina For your comfort, IRIS has 2 toilets with a shower This boat is equipped with a Full batten mainsail and a Furling genoa. It has the following equipment:...
Sailboat
Captain optional
8 pers.
3 cabins
2020
39 ft
from $264,15
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An expert will find you the best offers

Can I rent a Sailboat with a captain?

We offer Sailboats with a captain. Captain fees differ depending on the region and the Sailboat supplier. The average price per day for a captain is $379,50.

You’ll find a variety of Sailboats that are available for rent with a captain, depending on the kind of adventure you’re seeking.

How to book a Sailboat with a captain?

Choose your sailing date, search through the 554 available listings. Once your booking is confirmed, you must pay the deposit, sign the rental contract, and you're good to go. At the end of your rental, you can leave a review about your experience.

What is the starting price to rent a Sailboat with a captain?

Sailboat rental rates fluctuate depending on the size, the time of year, and the length of the rental. Additional equipment and optional services may also affect the final price.

The starting price to rent a Sailboat is $72,67. However, most rentals cost around $785,53 per day.

What is the maximum number of people allowed on board?

Rental Sailboats have different capacities depending on their size, type, and safety equipment. The maximum number of passengers varies between 2 and 38, depending on the listing.

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