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0 - 15+ m
0 - 400+ hp
2005 - 2025
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22 sailboats available
Rental Sailboat BENETEAU FIRST 40.7 Road Town

Road Town

1.3(1)

BENETEAU - FIRST 40.7 | 10 people (2008)

  • Skipper mandatory
  • Super owner
10 people · 3 cabins · 8 berths · 12 m

From 
$354 / day

Rental Sailboat  Oceanis 461/3/3 Road Town

Road Town

New

- Oceanis 461/3/3 | 8 people (2023)

  • Without captain
  • Super owner
8 people · 3 cabins · 8 berths · 14 m

From 
$516 / day

Rental Sailboat  Sunsail 42 Road Town

Road Town

New

- Sunsail 42 | 6 people (2023)

  • Without captain
  • Super owner
6 people · 3 cabins · 6 berths · 12 m

From 
$420 / day

Rental Sailboat Jeanneau Sun Loft 47 Tortola

Tortola

Jeanneau - Sun Loft 47 | 12 people (2020)

  • Skipper optional
12 people · 7 cabins · 12 berths · 14.4 m
Rental Sailboat Sunsail 46 Mon Road Town

Road Town

Sunsail - 46 Mon | 6 people (2019)

  • Without captain
  • Super owner
6 people · 3 cabins · 6 berths · 14.6 m

From 
$873 / day

Rental Sailboat  Sunsail 410 Road Town

Road Town

- Sunsail 410 | 8 people (2019)

  • Without captain
  • Super owner
8 people · 3 cabins · 8 berths · 12.4 m

From 
$756 / day

Rental Sailboat BENETEAU OCEANIS 48 Tortola

Tortola

BENETEAU - OCEANIS 48 | 10 people (2018)

  • Without captain
10 people · 4 cabins · 8 berths · 14.6 m
Rental Sailboat  Moorings 464PC/10 Road Town

Road Town

5.0(1)

- Moorings 464PC/10 | 10 people (2022)

  • Without captain
  • Super owner
10 people · 5 cabins · 10 berths · 14 m

From 
$1,266 / day

Rental Sailboat Bénéteau Oceanis 51.1 - 5 + 1 cab. Tortola

Tortola

Bénéteau - Oceanis 51.1 - 5 + 1 cab. | 12 people (2020)

  • Without captain
12 people · 6 cabins · 13 berths · 15.9 m
Rental Sailboat Dufour Yachts Dufour 390 Tortola

Tortola

New

Dufour Yachts - Dufour 390 | 8 people (2023)

  • Skipper optional
8 people · 3 cabins · 8 berths · 11 m

From 
$369 / day

Rental Sailboat Jeanneau Sun Odyssey 440 - 3 cab. Tortola

Tortola

Jeanneau - Sun Odyssey 440 - 3 cab. | 6 people (2022)

  • Without captain
6 people · 3 cabins · 6 berths · 13 m
Rental Sailboat Dufour Yachts 350 Adventure Tortola

Tortola

Dufour Yachts - 350 Adventure | 5 people (2018)

  • Without captain
5 people · 2 cabins · 4 berths · 10.3 m
Rental Sailboat Dufour Yachts 520 GL Tortola

Tortola

0.0(1)

Dufour Yachts - 520 GL | 12 people (2018)

  • Without captain
12 people · 5 cabins · 10 berths · 15.2 m
Rental Sailboat Bénéteau Oceanis 41.1 Tortola

Tortola

Bénéteau - Oceanis 41.1 | 8 people (2018)

  • Skipper optional
8 people · 3 cabins · 8 berths · 12.4 m
Rental Sailboat Bénéteau Oceanis 41.1 Tortola

Tortola

Bénéteau - Oceanis 41.1 | 8 people (2018)

  • Skipper optional
8 people · 3 cabins · 8 berths · 12.4 m
Rental Sailboat JEANNEAU Sun Odyssey 519  with watermaker & A/C - PLUS Tortola

Tortola

JEANNEAU - Sun Odyssey 519 with watermaker & A/C - PLUS | 13 people (2018)

  • Without captain
13 people · 6 cabins · 11 berths · 15.8 m
Rental Sailboat Dufour Dufour 520 Gl British Virgin Islands

British Virgin Islands

Dufour - Dufour 520 Gl | 12 people (2018)

  • Without captain
12 people · 5 cabins · 10 berths · 12 m
Rental Sailboat Bénéteau Oceanis 54 - 3 + 1 cab. British Virgin Islands

British Virgin Islands

Bénéteau - Oceanis 54 - 3 + 1 cab. | 9 people (2024)

  • Skipper optional
9 people · 4 cabins · 9 berths · 17.1 m

From 
$641 / day

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Sailing boat rentals in Tortola

Tortola is the largest of the British Virgin Islands located in the Caribbean. Its name comes from the Spanish tórtola which directly translates to ‘turtle dove.’ 

It is located about 60 miles (100km) east of Puerto Rico, making it the ultimate place to rent a sailing boat. Tortola is composed of a long chain of steep hills uninterrupted by any transverse valley. Sailing boat rentals in Tortola are popular amongst locals as a way to experience the amazing British Virgin Islands.

What to do with your sailing boat rental in Tortola

Sailing boat rentals in Tortola allow sailors to experience the island from a different perspective. Explore secret coves and bays that the average tourist will never see, sink your toes into white sand and absorb the charm of the island from the sea.
Step back on land and check out the cultural side of Tortola. The Wall Mural of Fahie Hill is a local work of art that depicts a variety of cultural scenes. It was painted by a local artist who successfully turned a 10-feet-high, 60-feet-wide wall into a masterpiece showing how the people of the island really live. 
We also recommend that you see the city from above by visiting the Sky world, which shows a spectacular panoramic view from one of Tortola's tallest towers. 
Lastly, follow the famous trail between Spring Bay and Devil’s Bay. In fact, some may say its more like an obstacle course than a walking trail. Use ropes, ladders, and your own wits as you reach your destination.

Tortola Spots to Eat, Drink, and Hang Out

Drink delicious rum at Callwood’s distillery, yummy food at Myett’s Restaurant, or a more casual experience at Bomba’s Surf Shack for drinks and a bbq. The shack is a popular hot spot for sailors to meet, enjoy a drink and catch up on adventures of the sea.