Gallipoli
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Sailboat hire in Gallipoli, Italy with skipper

10 boats available in Gallipoli
Here are all the boats in the vicinity

These boats available around Gallipoli, may also be of interest to you!

X-Yachts X-45
5.0 (2 reviews)
Porto Cesareo
Embark on a sailing adventure of a lifetime aboard this stunning yacht! Perfect for a day out with friends and family, this charismatic vessel offers spacious deck areas, sun-kissed lounging spots, and a cozy cockpit to unwind. Discover the hidden gems of Porto Cesareo and Gallipoli, snorkel in crystal-clear waters, and enjoy a refreshing aperitif in a secluded cove. Let us take care of the sailing, so you can focus on making unforgettable memories. Book your charter today and get ready for an u...
Sailboat
Skipper mandatory
8 pers.
3 cabins
2020
43 ft
Flexible Cancellation
from $231,02
Jeanneau 60
Santa Maria di Leuca
Embark on board the Elyvian Breeze, an amazing Jeanneau 60 to discover the region of Santa Maria di Leuca. This sailboat was built in 2025 to ensure complete comfort and performance at sea. The boat has 4 fully-equipped cabins and a capacity of 9 people. With an overall length of 18 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Santa Maria di Leuca For your comfort, Elyvian Breeze has 4 toilet(s) with a shower It has the following e...
Sailboat
Skipper mandatory
9 pers.
4 cabins
2025
60 ft
from $2 252,45
Jeanneau Sun Odyssey 519
Santa Maria di Leuca
Sailing boat for rent from . This Sun Odyssey 519 built in 2018 offers excellent quality/price for a cruise of a few days or a few weeks. The boat has 6 comfortable cabins and a boat capacity of 11 people. With a total length of 16 meters, it will be your best ally to spend an extraordinary holiday on the water around This Sun Odyssey 519 has 3 bathrooms with shower. This boat is equipped with a Furling mainsail and a Furling genoa. It has the following equipment: Autopilot, Outboard engin...
Sailboat
Skipper mandatory
11 pers.
6 cabins
2018
52 ft
from $659,56
Bénéteau Oceanis Clipper 423
5.0 (2 reviews)
Santa Maria di Leuca
We present our Beneteau Oceanis Clipper 423, a beautiful 13-meter sailboat from 2005, based in Santa Maria di Leuca. Thanks to its spacious and comfortable areas, it can accommodate up to 10 people during day trips and up to 6 during weekly/3-day charters. Onboard there are 4 cabins, 3 double cabins, and one with bunk beds. During the cruises, only 3 cabins will be available for customers. Onboard there are also 3 bathrooms and a dinette with a fully equipped kitchen. Outside, you will find a...
Sailboat
Skipper mandatory
10 pers.
4 cabins
2005
43 ft
Top owner
from $924,08
Jeanneau Sun Odyssey 37.1
Santa Maria di Leuca
Boarding this Jeanneau Sun Odyssey 37.1 means experiencing the sea authentically, worry-free, and with all the comfort you need. It's the ideal boat for those who want to relax, sunbathe, take a dip in crystal clear waters, and let the wind guide them, even without any sailing experience. The spaces are large and welcoming: outside, you can enjoy the scenery in total relaxation, while inside you will find comfortable and well-kept environments, perfect for a day at sea or a multi-day vacation....
Sailboat
Skipper mandatory
8 pers.
3 cabins
2004
37 ft
from $519,80
Jeanneau Sun Odyssey 37.1
5.0 (1 reviews)
Santa Maria di Leuca
WHAT WE OFFER Do you want to spend a day in the sun, by the sea, with the wind in your hair? We offer the opportunity to experience nature, away from the chaos of everyday life and in a relaxing environment. We organize daily outings on occasional rental basis from the Tourist Port of Santa Maria di Leuca to visit the coastal areas and caves of the Heel of Italy (Marina di Novaglie, Ponte Ciolo, Punta Ristola, Marina di San Gregorio, Felloniche Beach). We will sail and chase the winds to make...
Sailboat
Skipper mandatory
7 pers.
3 cabins
1995
37 ft
from $577,55
Dufour 385 Grand Large
Santa Maria di Leuca
EQUIPMENT: WATER TANK 600 Lt, DIESEL TANK 80 Lt, TV, STEREO, VHF, AIS, COCKPIT FRIDGE, GALLEY, OVEN, ICE MAKER. MAINSAIL, GENOA, GENNAKER, CODE ZERO, A 0. TEAK DECK and COCKPIT
Sailboat
Skipper mandatory
6 pers.
3 cabins
2008
38 ft
from $577,55
Aynakic mod 78 t
Santa Maria di Leuca
Leave with us on board a twin-masted “Gulet” of Turkish origin, equipped with large spaces and comfort perfect for everyone's holidays, singles, friends, couples and families, completely in mahogany and teak of about 24 meters. The price indicated on the page is for 12 people in half board and drinks with meals. Price per person: - low season €150 per day - high season €210 per day - mid season €180 per day The free cabins can be completed, the rental to the person does not privatize the boat
Sailboat
Skipper mandatory
12 pers.
6 cabins
2000
79 ft
from $1 648,33
Jeanneau 60
Otranto
Meet Elyvian Breeze, an incredible sailboat dedicated for charters. Made in 2025, the Jeanneau 60 will take you to the most beautiful anchorages in Otranto. The boat has 4 fully-equipped cabins and a capacity of 9 people. With an overall length of 18 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Otranto This Jeanneau 60 is equipped with 4 heads with shower. It has the following equipment: Auto-pilot, Electric winch. If you have an...
Sailboat
Skipper mandatory
9 pers.
4 cabins
2025
60 ft
from $2 252,45
Jeanneau 60
San Foca
Meet Elyvian Breeze, an incredible sailboat dedicated for charters. Made in 2025, the Jeanneau 60 will take you to the most beautiful anchorages in . The boat has 4 fully-equipped cabins and a capacity of 9 people. With an overall length of 18 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of For your comfort, Elyvian Breeze has 4 toilet(s) with a shower It has the following equipment: Auto-pilot, Electric winch. If you have any ques...
Sailboat
Skipper mandatory
9 pers.
4 cabins
2025
60 ft
from $2 252,45
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Is a Sailboat with a skipper the right choice for Gallipoli, Italy?

Exploring Gallipoli, Italy from the water is an unforgettable experience. The combination of beautiful scenery and open spaces creates the perfect setting for any journey. Whether you are looking for a peaceful cruise or a more thrilling ride, the right Sailboat with a skipper will add to the adventure. Comfortable seating, easy handling, and reliable performance make the journey even better. Every trip on the water brings discoveries and special moments.

Hiring a Sailboat with a skipper in Gallipoli, Italy, how does it work?

Whether you're looking for a Sailboat with a skipper for a family day out or for some activity on the water, you can book online in just a few minutes.

What is the starting price to hire a Sailboat with a skipper?

The price of hiring a Sailboat in Gallipoli, Italy is influenced by several aspects, such as the Sailboat’s capacity, features and the time of year. Peak-season hires tend to be more expensive than off-season bookings.

In Gallipoli, Italy, listings start at $231,02, while the average hire price is $1 189,75.

Sailboat capacity for hires in Gallipoli, Italy

Hire Sailboats have different capacities depending on their size, type and safety equipment. In Gallipoli, Italy, the maximum number of passengers varies between 6 and 12, depending on the listing.

What is the best time of year to hire a Sailboat with a skipper in Gallipoli, Italy?

The best time for a Sailboat hire in Gallipoli, Italy is during the peak season between June - August when the weather is warm and the conditions are ideal for sailing. The average water temperature is around 22–27°C, making it ideal for swimming and water sports. If you prefer a more relaxed atmosphere, the shoulder seasons in May and September offer pleasant temperatures and fewer crowds. This period still offers excellent boating conditions for a quiet and enjoyable experience. No matter when you choose to hire, Gallipoli, Italy promises stunning landscapes and unforgettable moments on the water.

Best boating destinations in Gallipoli, Italy

Sailing in Gallipoli, Italy offers many great destinations to explore. Popular spots include Salento Coast. Whether you prefer a short trip or a longer one, there are plenty of options to enjoy. Whatever your itinerary, Gallipoli, Italy guarantees a great boating experience.

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The sea gives us unique moments. Enjoying it also means respecting it: protecting marine ecosystems, reducing our impact, and preserving the places we explore. Discover how SamBoat is working alongside Fondation de la Mer to protect marine biodiversity, preserve coastal ecosystems, and fight plastic pollution.

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