Believe it or not, it’s already a good time to start thinking about your next season yacht charter — especially if you have specific yachts or dates in mind. While holiday weeks tend to fill up early, most of the season still has good availability. So if sailing turquoise waters with your favorite crew is on the horizon, consider this your gentle nudge to start dreaming (and maybe penciling something in).
Below, we break down when to charter in the British Virgin Islands — from peak season perfection to underrated shoulder gems — to help you choose the best fit for your next sailing adventure.
Epic sunsets await anytime of year
January–March: Peak Season BVI Paradise
This is the classic time to charter in the BVI. Steady tradewinds, warm days, and a lower chance of rain make for near-perfect sailing conditions. It's also peak season, so expect anchorages to be more crowded — but there's a reason the islands are buzzing this time of year.
Pro tip: The week after New Year’s, once those holiday charters disembark, often sees a brief lull before mid-January crowds return. If your schedule allows for flexibility, it’s a magical time to sail with a little more elbow room.
Swimming at Long Bay Virgin Gorda
April–May: The Underrated Sweet Spot
This is what we call one of the shoulder seasons, and honestly? It’s one of our favorite times to sail. The days stretch longer, the seas stay settled, and the crowds thin out a bit. If you want warmth without the chaos, this is your window.
We often recommend April or May charters to flexible travelers — availability is better, rates are lower, and the water warms up for those longer swims off the stern.
Cooper Island
June–July: BVI Family Time and Summer Specials
Yes, hurricane season officially starts June 1st, but serious disturbances are rare this early. The trade winds do slacken, and it can feel warmer with less breeze — but the plus side is availability. Most of the BVI fleet stays put until the end of July, and some yachts drop to their summer rates: 10–15% lower than peak pricing.
We just wrapped up some amazing family crewed charters on Iara, Infinity, and Ohana, with new families heading out in the next few days aboard Awatea and Aquanimity. If your kids are out of school and you want to introduce them to island time, this is your moment.
Seclusion at Muskmelon Bay
August–October: Seclusion... with a Side of Flexibility
This is the off-season in the BVI. Most yachts head south to Grenada to escape the heart of the hurricane belt, but a few stick around — and if you're willing to be flexible, it could be your best shot at finding true solitude in these increasingly busy islands.
Heavy rain is possible, and winds are light. But if you're the type who values empty anchorages over cocktail-packed beach bars, and you're willing to plan around the weather (with travel insurance, please!), this could be your time.
Hiking on Norman Island
Mid-November to Mid-December: Calm Before the Holiday Storm
The fleet returns, the temps are still warm, and crowds haven’t yet taken over. While hurricane season technically lasts through November, risk decreases by the week. You’ll still want trip insurance, but this shoulder season offers solid sailing, great fishing, and more open calendars.
If you’re looking for good value and fewer crowds, this is another underrated gem.
Soggy Dollar Bar decked out in December
The Holidays: Bucket List Season
There’s nothing like the holidays in the BVI. Crews go all out for Christmas and New Year’s — we’re talking twinkling lights, themed menus, tropical Santa hats, and unforgettable vibes. If you haven’t experienced it, put it on your list.
But take note:
Christmas charters typically end by Dec 27–28 to allow turnaround for New Year’s guests.
Pricing is 15–20% higher for these two weeks.
The best yachts book fast.
If you're even thinking about ringing in the holidays aboard a yacht, let’s talk soon. We still have some holiday availability, too — but the window is closing fast.
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