Hi Reader,

Later this month, I'll be pushing off the dock in Tortola for another British Virgin Islands charter.

But this trip is a little different.

Normally when I head down to the BVI, the "float plan" is more of a suggestion than a plan. If the wind shifts, if someone hears about a great beach bar, or if the anchorage just feels right, we pivot.

This time? It's a bit more structured.

I'm bringing five adult first-timers along with my two kids (5 and 9), who technically have one charter under their belt already after our Exuma Bahamas trip last year. And because we're sailing during spring break — peak season in the BVI — a few reservations and logistics need to happen on specific days.

The moke rentals in Anegada.

Taxi timing to the Baths (this will be my first time going land-based).

Restaurant reservations filling up.

So for once, I actually sat down and mapped out a real itinerary.

If you've never chartered the BVI before, this route basically hits all the highlights while still keeping the relaxed pace that makes sailing here so magical.

And even after countless trips to the islands, I always try to mix in something new. This year's experiment? Spending the final night docked at the recently reopened Peter Island Resort.

Here's how the week is shaping up.

Day 1 — First Sail Through Sir Francis Drake Channel

Once the lines are tossed, we'll head north up the Sir Francis Drake Channel, letting the trade winds give everyone their first taste of sailing as we tack north.

Lunch will be a snorkel stop at either The Dogs or Mountain Point, both great warm-up reefs before the bigger spots later in the week. If the kids aren't in the water seconds after we tie-off, I'll be shocked.

From there we'll round Virgin Gorda and enter the legendary North Sound.

If you've never sailed into North Sound before, it feels like slipping through a hidden entrance into a protected inland sea — calm water surrounded by steep slopes, with some of the most famous sailing hangouts in the Caribbean spread out around you.

We'll grab a mooring or anchor near Saba Rock, and when the sun starts to dip, it's time for one of the great BVI traditions:

The evening tarpon feeding with an evening happy hour drink or two to follow upstairs.

Day 2 — The Baths Before the Cruise Ships Arrive

​The Baths are one of the most famous spots in the Caribbean, but they can also turn into a zoo when cruise ships arrive.

So the plan is to move early.

We'll motor over to Leverick Bay, grab a safari bus, and head south across Virgin Gorda before the crowds show up.

If you've never seen the Baths, imagine giant granite boulders stacked like a playground designed by nature, forming caves and tunnels you scramble through. It's unlike any other place I've visited.

On the way back we'll stop for lunch at Hog Heaven BBQ, which has one of the best panoramic views in the islands — you can see all the way across the Sir Francis Drake Channel and out to Anegada on a clear day.

The afternoon is all about slowing down again — sailing back toward Bitter End Yacht Club for shopping, watersports, and maybe a a visit from the Rum Runner.

Day 3 — The Offshore Run to Anegada

Monday is one of my favorite sailing days of the week.

We'll point the bow north and sail offshore to Anegada, the only coral island in the BVI.

Unlike the volcanic islands around it, Anegada sits low and flat on the horizon, surrounded by miles of barrier reef and impossibly blue water.

Once we pick up a mooring, we'll grab our rental truck and head out to explore the north shore beaches. The kids will ride in the back of the truck with the wind in their hair — one of those moments that would never happen at home.

I usually start on the east end at Loblolly/Flash of Beauty and make way west to finish for some afternoon swimming at Cow Wreck. Tipsy's is our favorite spot to wind down the afternoon.

Each beach feels like its own version of a Caribbean postcard.

We'll pack a picnic from the boat for lunch and then return to Setting Point for what might be the most famous meal in the BVI - Anegada lobster dinner on the beach.

Tables set up in the sand. Lanterns flickering. The crackle of lobster shells over an open fire. It's simple, but it's one of those meals that stays with you.

Day 4 — Back Toward Tortola

After breakfast we'll sail back toward Tortola, stopping for lunch and snorkeling at Muskmelon Bay at Guana Island.

This is one of those quieter anchorages that many doesn't find it's way onto many itineraries. I enjoy it for the seclusion (really only room for one boat) and the rugged setting.

By afternoon we'll settle into Cane Garden Bay, a lively harbor on Tortola's north shore.

There's a good chance we'll wander ashore for a little shopping and possibly a quick provisioning stop at Bobby's Marketplace if anything ran low during the week.

Otherwise?

Swimming, floating, and relaxing aboard.

Day 5 — Sandy Spit and Diamond Cay

Wednesday is about classic BVI scenery.

First stop: Sandy Spit.

It's barely more than a sandbar, but it might be the most photographed anchorage in the islands.

We'll swim, float, and have lunch aboard before making the short hop to Diamond Cay on Jost Van Dyke.

Ashore on Little Jost Van Dyke, you'll find the rustic B-Line Beach Bar, a place that feels refreshingly unchanged from decades ago.

We may also consider a short hike to the Bubbly Pool, where waves surge through a rocky basin creating a natural jacuzzi effect.

Kids absolutely love it.

Day 6 — White Bay and the Soggy Dollar

Thursday morning we'll move early again — this time to White Bay.

If you arrive first thing, you can usually anchor in the front row adjacent to the Soggy Dollar Bar.

The water here is that unreal shade of Caribbean turquoise and it's always fun to make the quick swim ashore from your charter yacht.

After everyone's had their fill of Painkillers, beach time and lunch perhaps at Hendo's Hideout, we'll continue on to Norman Island.

Here you can snorkel the famous Caves, hike above the harbor, or visit the floating pirate bar Willy T's.

Day 7 — One Last Snorkel and a New Stop

The final full day always sneaks up faster than you expect.

We'll start the morning at The Indians, one of the best snorkeling sites in the BVI. Getting there early means beating the charter crowds to the limited number of available moorings.

After lunch we'll head to something new for me.

Peter Island Resort recently reopened after years of rebuilding from Hurricane Irma, and they've introduced a new marina and yacht club experience.

So instead of anchoring somewhere quiet for the final night, we're going to dock at the resort - also something I've never done before while on charter.

For $200, docking includes access to the pool, sport courts, and other amenities ashore — which feels like a pretty good trade after a week of salty sailing. No dinghy runs, no coordinating shore logistics. Just walk off the boat and go.

And if it works out, I might even fuel up there so we can skip the early-morning fuel line back at Nanny Cay.

Dinner will be ashore at the Drunken Pelican for one final celebration.

Saturday — Back to Nanny Cay

We'll motor back early for checkout.

And if the week goes the way most BVI charters do, the crew will step off the boat already talking about when they're coming back.

That's the thing about sailing these islands.

Even when you've done it many times, there's always a new anchorage to try, a new beach bar to stumble into, or a different way to experience the same stretch of water.

If a week like this sounds like your kind of trip — whether it's spring break, summer, or the holidays — reach out. This is exactly the kind of charter we help people plan.

Have a great week! - Matt Weidert