Sail the British Virgin Islands
A 7-Day Sample Itinerary Adventure
Tortola • Norman Island • Cooper Island • Virgin Gorda • Anegada • Jost Van Dyke
Turquoise water. Steady trade winds. White-sand beaches. Coral reefs. Legendary beach bars.
There may be no better place in the world to spend a week aboard a catamaran than the British Virgin Islands.
Here, the islands are close enough that the next adventure is usually only a short sail away. Spend the morning snorkeling a reef, sail to another island for lunch, drop anchor beside an incredible beach and finish the day barefoot at a beach bar.
With STL Skippers, the boat isn't simply where you sleep.
It's your front-row seat to the Caribbean.
Here's a taste of what seven days sailing the British Virgin Islands could look like.
DAY 1
Tortola → Norman Island
Welcome to the Caribbean
Step aboard, unpack your bags and leave the real world behind.
Once everyone is settled into the catamaran, we'll cast off from Tortola and make our first sail across the Sir Francis Drake Channel toward Norman Island.
Legend has long connected Norman Island with stories of pirates and buried treasure—and it's the perfect place to begin our adventure.
We'll grab a mooring, jump into that impossibly clear Caribbean water and officially start island time.
Later, we'll dinghy ashore for dinner and drinks.
And if the crew is feeling adventurous, there's always the legendary floating Willy T.
Experience: First Sail • Swimming • Snorkeling • Island Dinner • Willy T • Caribbean Sunset
DAY 2
Norman Island → Cooper Island
Reefs, Caves & Rum
Coffee on deck.
Breakfast overlooking the Caribbean.
Then it's time to get wet.
We'll explore The Caves at Norman Island, where you can snorkel directly into sea caves surrounded by tropical fish.
From there we'll raise the sails and head toward Cooper Island.
After grabbing a mooring in Manchioneel Bay, spend the afternoon snorkeling, paddleboarding or simply relaxing aboard.
Later we'll head ashore to the Cooper Island Beach Club.
This is also home to one of our favorite stops in the BVI:
The Rum Bar.
With hundreds of different rums available, you're almost guaranteed to find one worth bringing home.
Experience: Snorkeling • Sea Caves • Sailing • Paddleboarding • Beach Club • Rum Tasting
DAY 3
Cooper Island → Virgin Gorda
The Baths
Today we're headed for one of the most famous places in the entire Caribbean.
The Baths at Virgin Gorda.
Massive granite boulders create natural pools, caves and passageways along the shoreline.
We'll head ashore and follow the trail through the rocks to Devil's Bay, stopping along the way to swim and explore.
Afterward, we'll continue north along Virgin Gorda and settle into our anchorage or mooring for the evening.
Tonight might mean dinner ashore—or steaks on the grill aboard the catamaran underneath a Caribbean sunset.
Hard decision.
Experience: The Baths • Devil's Bay • Hiking • Swimming • Exploring • Dinner Under the Stars
DAY 4
Virgin Gorda → Anegada
Sail Beyond the Horizon
Today is different.
Instead of hopping between mountainous islands, we'll point the bow north and sail across open Caribbean water toward Anegada.
Anegada is unlike anywhere else in the BVI.
The island is almost completely flat, surrounded by coral reefs and miles of white-sand beaches.
After arriving, we'll head ashore and explore.
Rent a jeep.
Find the flamingos.
Spend the afternoon on Loblolly Bay or Cow Wreck Beach.
And tonight?
There's really only one answer.
Anegada lobster.
Fresh Caribbean lobster grilled on the beach while the sun disappears over the water.
This is one of those nights you'll remember.
Experience: Open-Water Sailing • Beaches • Island Exploring • Flamingos • Beach Bars • Anegada Lobster
DAY 5
Anegada → Jost Van Dyke
The Legendary Beach-Bar Day
We'll get an early start because today we're heading toward one of the most famous little islands in the Caribbean.
Jost Van Dyke.
After a great sail back through the islands, we'll eventually work our way toward White Bay.
White sand.
Turquoise water.
Bare feet.
And one very famous beach bar.
Welcome to the Soggy Dollar Bar, birthplace of the Painkiller.
Swim ashore.
Order one.
Maybe order another.
We'll spend the afternoon enjoying White Bay before eventually heading toward our overnight anchorage.
No shoes required.
Experience: Sailing • White Bay • Soggy Dollar • Painkillers • Beach Bars • Swimming
DAY 6
Jost Van Dyke
No Hurry Today
By now everyone has figured out how island time works.
So we're not going to ruin it with a schedule.
Maybe we start with breakfast aboard.
Maybe we dinghy ashore.
Maybe we head over to Foxy's.
Maybe we explore Sandy Cay or find another quiet beach.
Or maybe everyone votes to stay exactly where we are.
That's the beauty of having our own catamaran.
We'll spend our final full day chasing whatever sounds good.
Swim.
Snorkel.
Paddleboard.
Beach hop.
Find another Painkiller.
Repeat as necessary.
Tonight we'll watch our final full Caribbean sunset aboard the boat.
Experience: Beach Hopping • Snorkeling • Sandy Cay • Foxy's • Swimming • Absolutely No Schedule
DAY 7
Jost Van Dyke → Tortola
One Last Sail
Nobody is going to be excited about this part.
But we're not finished yet.
We'll have breakfast aboard and enjoy one last morning in the islands before raising the sails toward Tortola.
If time allows, we'll find somewhere for one final swim.
One final jump off the boat.
One final look around at the Caribbean.
Then we'll make our way back to the marina.
Seven days earlier, everyone arrived with luggage.
Now we're coming back with sunburned noses, wet swimsuits, hundreds of pictures and stories we'll probably be telling for years.
And somewhere along the way, somebody is going to ask:
“When are we doing this again?”
This Isn't a Cruise.
There are no crowds pouring off a giant ship.
No buffet lines.
No excursion buses.
And nobody telling us we have to be back aboard in exactly 90 minutes.
This is your week.
Want more snorkeling? Grab your mask.
Want to sail? Let's raise the sails.
Want to find a quiet beach? We'll find one.
Want to spend the afternoon floating behind the catamaran with a cold drink?
That's a perfectly acceptable itinerary.
Weather and sea conditions ultimately determine where we can safely go, but beyond that, the adventure is built around the people aboard.
Come Sail With Us.
Seven days. Six islands. One catamaran.
And an entirely different way to experience the Caribbean.
STL Skippers
Your Adventure Starts Here
You didn’t come this far to stop