FAQ: Planning a 2026 Sailing Vacation in the Virgin Islands
Make the year 2026 extraordinary by taking the sailing trip of your dreams in the Virgin Islands! We’ve addressed some of your most important questions below to help you start planning your perfect 2026 sailing vacation:
What do the Virgin Islands have to offer?
The Virgin Islands are a level 1 sailing destination, meaning sailing here is a breeze. Sailors love the VI because we have some of the best sailing conditions in the world, such as steady trade winds, calm waters, and numerous protected anchorages. The Virgin Islands also captivate vacationers with world-class snorkeling, pristine beaches, and a laid-back island atmosphere.
Is it easy to visit both the USVI and the BVI?
With the flexibility of sailing a bareboat charter, you can hop from island to island without waiting for ferries. Go Sail VI has exceptional fleets of sailboats ready to charter in both the USVI and BVI.
Please note that the USVI and BVI are distinct territories, requiring a valid passport for travel between them. Therefore, it is more efficient to complete a voyage around one territory before starting the other.
When is the best time of the year to sail in the Virgin Islands?
Peak sailing season in the Virgin Islands is December through May. Outside of these months, weather conditions might not be as consistent, but you will encounter fewer crowds. Likewise, the period from August through October is peak hurricane season, so we do not operate trips during this time.
What qualifications are needed to sail in the VI?
For Go Sail’s bareboat charters, we prefer completion of ASA 104 and its prerequisites, as well as previous sailing experience.
I don’t meet those qualifications to sail. Can I still go on a 2026 sailing vacation?
Absolutely! If you’re not ready to charter a sailboat, our exciting liveaboard sailing courses are the perfect mix of sailing instruction and island vacation. By completing the course, you will earn ASA certification, which will prove your competence for future charter opportunities, while exploring the Virgin Islands’ stunning turquoise waters and white sand beaches.
What provisions should I bring on a Virgin Islands sailing vacation?
Because space is limited on sailboats, try not to overpack. Bring only essential toiletries and light, casual clothing. For bareboat charters, you will need to purchase groceries and sanitation items like sponges, plastic bags, and air fresheners. Small flashlights and a microfiber towel for the galley are recommended. View our provision shopping list here.
How do I start planning my 2026 sailing vacation?
The best place to start is by contacting Go Sail VI! We will be happy to assist you in selecting the right yacht or course for your needs and answer your questions about a 2026 sailing vacation in the Virgin Islands.