72 sailboats available
How we rank results
Sint Maarten
Hanse - 418 | 9 people (2020)
9 people · 3 cabins · 9 berths · 12 m
From €857 / day
Marigot
4.9(12)
Kirie - Feeling - 446 | 4 people (1989)
4 people · 3 cabins · 4 berths · 14 m
From €400 / day
Sint Maarten
4.8(4)
Jeanneau - 53 | 10 people (2011)
10 people · 3 cabins · 6 berths · 16 m
Road Town
- Sunsail 42 | 6 people (2023)
6 people · 3 cabins · 6 berths · 12 m
From €450 / day
Gustavia
Hanse - 445 | 8 people (2013)
8 people · 3 cabins · 8 berths · 13.4 m
From €1,000 / day
Road Town
- Sunsail 41.3 | 6 people (2024)
6 people · 3 cabins · 6 berths · 11 m
From €430 / day
Saint Martin
- Sunsail 44.3 | 6 people (2025)
6 people · 3 cabins · 6 berths · 13 m
From €485 / day
Road Town
- Sunsail 44.3 | 6 people (2025)
6 people · 3 cabins · 6 berths · 13 m
From €540 / day
Road Town
- Sunsail 47 | 10 people (2025)
10 people · 4 cabins · 10 berths · 14 m
From €705 / day
Road Town
- Sunsail 41.3 | 6 people (2025)
6 people · 3 cabins · 6 berths · 11 m
From €470 / day
Road Town
- Oceanis 461/3/3 | 8 people (2024)
8 people · 3 cabins · 8 berths · 14 m
From €495 / day
Road Town
- Sunsail 41.3 | 6 people (2025)
6 people · 3 cabins · 6 berths · 11 m
From €470 / day
Marigot
Beneteau - Océanis 38 | 8 people (2014)
8 people · 3 cabins · 7 berths · 11 m
From €286 / day
Road Town
- Oceanis 461/3/3 | 8 people (2023)
8 people · 3 cabins · 8 berths · 14 m
From €495 / day
Saint Martin
Hanse - 470e | 4 people (2008)
4 people · 2 cabins · 4 berths · 14.2 m
From €571 / day
Saint Martin
0.0(1)
BENETEAU - OCEANIS 48 | 4 people (2011)
4 people · 4 cabins · 8 berths · 15 m
From €714 / day
Road Town
1.3(1)
BENETEAU - FIRST 40.7 | 10 people (2008)
10 people · 3 cabins · 8 berths · 12 m
From €857 / day
San Juan
Pearson - 35 sloop | 7 people (1977)
7 people · 2 cabins · 6 berths · 10.7 m
From €600 / day
Our client reviews
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.