Hi Reader,

The countdown has begun — the end of hurricane season is near, and the Caribbean is calling. Crews are back aboard and the first early guests of the season are already popping Champagne on the aft deck.

Whether this is your first time chartering or it's your annual island escape, here are five ways to make this season’s trip one for the books.

But first — a quick note you might have seen making the rounds: a charter yacht recently drifted onto the rocks at the Seal Dogs after what appears to have been a mooring failure near Long Bay, Virgin Gorda area.

I don’t have all the details yet, but for skippers out there, it’s a reminder of three key things:

1. Know which mooring balls are suitable for overnight use. To my knowledge, the ones at nearby Mountain Point and the Kodiak Queen are day-use only.
2. Keep an eye on weather conditions. I’m not sure if this played a role here, but during north swells, the west side of Virgin Gorda is not the place to be.
3. Mooring failures do happen, even to well-maintained overnight balls. Always set an anchor alarm. It seems no one noticed the boat had broken free until it grounded nearly a mile away — an alarm could’ve made all the difference.

1. Pick the Right Week to Charter

Timing is everything. The BVI and USVI change character with the months — from the lively buzz of New Year’s to the mellow warmth of late spring. If you’re looking for calm seas, fewer crowds, and better value, April and May are what I call the “sweet spot.” You’ll get longer days, warm water, and quieter anchorages.

Prefer energy and excitement? January to March brings steady tradewinds and the full Caribbean vibe. Want seclusion and special rates? Try mid-November before the holidays or June–July for early-summer family fun.

👉 Read our full BVI season guide here

2. Theme Nights Never Get Old

Every yacht has its unique rhythm — but the real memories often come from the nights you make your own. We once pulled off an 80s night at Saba Rock: neon headbands, loud prints, and a surprise twist when the guys showed up in 1880s gear.

Need inspiration? Try Pirate Night, White Linen Dinner, or a Disco Glow Party with light-up glasses for the whole bay. Crews love getting involved — and it’s amazing how a theme night can turn strangers into friends at any beach bar.

3. Go Fishing — It’s Addictive

You haven’t lived until you’ve heard the reel scream mid-sail. Whether trolling off the stern or dropping a line at anchor, fishing adds an element of surprise to every passage. We’ve landed mahi, tuna, and wahoo in the North Sound — and there’s nothing better than your chef grilling the day’s catch as the sun sets behind the hills of Virgin Gorda.

If you’re into it, mention it to your captain ahead of time so they can help work it into your itinerary. It's also a good idea to check with your charter broker - some crews are more into fishing than others.

4. Get aligned with your group ahead of time

This is the secret to a flawless trip. Every Yacht Warriors crewed charter includes a pre-departure call with your crew — usually about a week before you set sail.

Use that time to share what really matters:

• How adventurous (or relaxed) you want your itinerary to be
• Any “must-see” islands, snorkeling stops, or beach bars
• Your dining and drink preferences — and what to skip

Before the call, talk things over with your group so you’re all aligned. Then, fill out your preference sheet in as much detail as possible. Your crew reviews it ahead of time and uses it to plan provisioning, meals, and even anchorages that match your style. The more detail you give, the more magic they can create once you’re aboard.

5. Fly Your Flag

Make your yacht yours for the week. Our guests receive a Yacht Warriors flag for every trip, and we’ve seen guests raise everything from alma mater banners to inside-joke flags. It’s a small touch that makes your charter feel personal — and it always starts a few friendly dockside conversations.

That's it for today!

- Matt Weidert