A great value and very fun holiday for people not completely comfortable being in command of a sailing yacht, and for those who might like some expert coaching!

Road Town, British Virgin Islands • Captain Included

50 feet • 4 guests • Bavaria • 50 • 1999

$3,000 per 8 hours

This 55' Cat is the Ultimate Virgin Islands Daysail!

St. Thomas, U.S. Virgin Islands • Captain Included

55 feet • 49 guests • Morrelli & Melvin • Morrelli & Melvin • 2001

$2,300 per 8 hours

The best way to experience US- Virgin Islands, VI is by sailing

4.0 (1)

Us Virgin Island, U.S. Virgin Islands • Bareboat

40 feet • 12 guests • Lagoon-Bénéteau • Lagoon 40 • 2019

$679 per 8 hours

32' Contender — Private BVI & USVI Charters to Explore the Virgin Islands!

5.0 (1)

US- Virgin Islands, U.S. Virgin Islands • Captain Included

32 feet • 10 guests • Contender • 32' Cuddy • 2004

$850 per 4 hours

Luxury Sailing Experience Aboard the Bali 4.2 Catamaran

Charlotte Amalie, U.S. Virgin Islands • Bareboat

42 feet • 9 guests • Catana • Bali • 2022

$7,353 per week

Experience sailing at its best on this sailboat charter

US- Virgin Islands, U.S. Virgin Islands • Captain Available

44 feet • 6 guests • Fountaine Pajot • Fountaine Pajot FP 44 Maestro - 3 cab. • 2026

$8,600 per week

Enjoy luxury and comfort on this Fountaine Pajot Fountaine Pajot FP 44 Maestro - 3 cab. in US- Virgin Islands

US- Virgin Islands, U.S. Virgin Islands • Captain Available

44 feet • 6 guests • Fountaine Pajot • Fountaine Pajot FP 44 Maestro - 3 cab. • 2026

$8,600 per week

Relax and have fun on this gorgeous sailboat charter

US- Virgin Islands, U.S. Virgin Islands • Captain Available

46 feet • 10 guests • Fountaine Pajot • Fountaine Pajot Tanna 47 - 5 + 1 cab. • 2021

$10,000 per week

Your premier destination for unforgettable Caribbean experiences

St Thomas, U.S. Virgin Islands • Captain Included

26 feet • 6 guests • MacGregor • 26X • 2002

$290 per 2 hours

Climb aboard this sailboat for a great sailing experience!

US- Virgin Islands, U.S. Virgin Islands • Captain Available

44 feet • 8 guests • Fountaine Pajot • Fountaine Pajot FP 44 Quatuor - 4 cab. • 2026

$10,900 per week

Take this Fountaine Pajot Fountaine Pajot FP 48 Quintet 5 for a spin!

US- Virgin Islands, U.S. Virgin Islands • Captain Available

47 feet • 10 guests • Fountaine Pajot • Fountaine Pajot FP 48 Quintet 5 • 2026

$12,000 per week

Fun in the sun is all you will experience in US- Virgin Islands, VI

US- Virgin Islands, U.S. Virgin Islands • Captain Available

43 feet • 6 guests • Dufour Yachts • Dufour 430 • 2024

$4,700 per week

Sail with this Yacht Charter and explore USVI

Charlotte Amalie, U.S. Virgin Islands • Bareboat

43 feet • 8 guests • Leopard • 43 • 2020

$14,000 per week

Relax and have fun on this gorgeous sailboat charter

US- Virgin Islands, U.S. Virgin Islands • Captain Available

42 feet • 6 guests • Dufour Yachts • Dufour 41 - 3 cab. • 2023

$4,500 per week

Sail Away in Style: Bali 4.2 Charters Await in the US Virgin Islands!

4.0 (1)

Charlotte Amalie, U.S. Virgin Islands • Bareboat

42 feet • 8 guests • Bali • 4.2 • 2022

$3,417 per week

Let the wind whip through your hair aboard Lucia 40 in St. Thomas

Charlotte Amalie, U.S. Virgin Islands • Captain Available

38 feet • 8 guests • Lucia • 40 • 2017

$5,495 per week

Create memories in this USVI aboard this lovely catamaran

Charlotte Amalie, U.S. Virgin Islands • Bareboat

52 feet • 14 guests • Lagoon • 52 F • 2017

$14,000 per week

Relax onboard this Beautiful Sail Boat in Virgin Island

Charlotte Amalie, U.S. Virgin Islands • Bareboat

45 feet • 10 guests • Sun Odyssey • 449 • 2018

$8,650 per week

789 boat rentals in Spanish Town, British Virgin Islands

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