Hi Reader,

The countdown has begun! The end of hurricane season is approaching, and the new charter season is upon us. As the weather moderates, excitement is in the air, and the anticipation for upcoming charters is building. It’s that time of year when you can almost hear the gentle lapping of waves against the hull and feel the warm breeze as you set sail.

Now, you might be able to outrace me close-hauled up the Sir Francis Drake Channel, but after 12 years of chartering, we've certainly learned how to have a great time out there on the water. Whether it’s your first charter or you’re a seasoned veteran, these are my top five tips to help enhance your next sailing adventure.

In case you missed it last week, we've already had a great response to our owner listings on the Yacht Warriors site. You can check out our first listing, a Lagooon 46 from Horizon in BVI.

1. Theme night shenanigans

Why not mix it up with a theme night ashore? A well-chosen theme can transform an ordinary evening into one of the highlights of the trip. Recently, we pulled off an 80s night at Saba Rock—neon colors, big hair, and all the classic 80s vibes. But the real twist? While the girls went full 80s glam, the guys surprised everyone by dressing in 1880s gear! It was a huge hit, and we ended up with some of our favorite trip photos.

To add to the fun, we got everyone involved at Saba Rock by handing out over 50 pairs of light-up glasses we brought along. It’s the little things like this that make memories stick, and it really brought everyone together for a fantastic night.

Other theme night ideas? How about a Pirate Night, an elegant White Linen evening, a swanky Gala, or even a Hawaiian Luau? Get creative and make it your own!

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2. Skip the BoatyBall rat race

Yes, the mooring ball network has spread across many beloved BVI spots, and BoatyBall can add convenience for sure. But there’s something special about dropping the hook for the night instead of playing the 7 a.m. reservation scramble. Consider finding those spots where you can still anchor and enjoy a bit of elbow room. Even after more than a decade of chartering in the BVI, we still manage to discover new anchorages that offer a fresh perspective and a bit of seclusion.

Chartering from the USVI? Why not go for a downwind run to the Spanish Virgin Islands—Culebra and the surrounding cays are often quieter, letting you slip into a rhythm that’s all your own. You’ll gain the kind of tranquility you can only find when you’re swinging at anchor. Plus, it's easy to clear through customs. Nothing is required on your return to St. Thomas.

3. High-quality or prepared meals are game-changers

Look, I love cooking, but let’s be real—when I’m on the boat, I’d rather spend my evenings soaking in the sunset with a drink in hand than being stuck in the galley.

That’s why we’ve bring some prepared or high-quality frozen meals. On a recent trip, we packed everything from taquitos and grilled chicken thighs to some excellent Costco filets for that all-important first night’s dinner. Prepping meals ahead means more time for stargazing, swimming, or just relaxing.

4. Drag some fishing lines

On our early charters, we didn’t think much about fishing, but it’s now one of the activities we look forward to the most. Trolling while under sail adds a layer of excitement—you never know when the reel might start screaming, announcing dinner. We’ve caught everything from barracuda to wahoo, mahi, snapper, and even tuna.

If you don’t have your own gear, rent a rod or two, but I'd recommend bringing your own tackle - check out some of my tips here. There’s nothing quite like grilling your catch of the day while watching the sun dip below the horizon.

5. Fly Your Favorite Flags

Flying a flag is the perfect way to let everyone know who you are and what you stand for. Whether it’s your alma mater, your favorite sports team, or a custom crew flag, it’s all about making your boat feel like home. I even recently had a 6-foot Yacht Warriors flag made—it now flies proudly from the topping lift every trip.

Bigger flags can go up the topping lift, while smaller burgees can fly from the spreaders. It’s your boat, your adventure—so fly whatever floats your boat!

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These tips are just a few ways to elevate your next charter and make it unforgettable. At the end of the day, it’s all about relaxing, having fun, and making memories that will last a lifetime.

So, anchors up—adventure awaits. That's it for today!

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Have a great week! - Matt Weidert