I first sailed the BVIs with friends in 2013, so it felt full circle to return in 2025 and charter a catamaran for a vacation with my girlfriends and our kids!
We chartered a 58′ crewed catamaran which made the trip so comfortable.
We set off on a bucket list sailing adventure around the British Virgin Islands with The Moorings—four moms, four kiddos, and a crewed catamaran with a gourmet chef, captain, and stewardess to take care of everything.
Our week at sea was full of adventure, turquoise waters, white-sand beaches, and uninterrupted quality time with our little ones—no meal planning, no dishes, just sailing, sun, and a lot of Aperol Spritzes.
Here are my tips and itinerary for sailing the British Virgin Islands!
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Yacht Charter Details
Moorings Crewed 5800 Master – 6 Cabin Catamaran
Booked with: The Moorings
Sailing Dates: February 26-March 5
Type: Crewed Charter with Captain, Chef & Stewardess
Moorings 5800 Master
Crewed 5800 Master Catamaran
If you’re looking for the ultimate sailing experience, a crewed catamaran charter is the way to go, especially when traveling with kiddos.
Catamarans offer extra stability (so there’s way less rocking than a monohull) and have loads of deck space for lounging.
Since this was a crewed charter, we had a captain, gourmet chef, and a stewardess, which meant more time for us moms to actually relax and less time worrying about shopping, cooking, and cleaning.
The catamaran has five guest cabins with ensuite bathrooms. We traveled as four adults and four kids, but there was plenty of space to sleep 10 comfortably. The two Bridgedeck cabins were a dream—you had direct access to the saloon and a front cockpit where we could enjoy the sunrise and our morning coffee.
Check out the full details of the catamaran here!
The All-Inclusive Crewed Catamaran Experience
A crewed charter takes the luxury up a notch. It offers the same effortless sailing but with a serious upgrade in service.
Instead of hiring a skipper and hostess (where you still have to plan meals and cover grocery costs), a crewed catamaran is all-inclusive. That means a gourmet chef whipping up a set menu & endless snacks. A stewardess doing all the tidying around the boat and playing bartender the entire trip. Plus, a captain to sail you from one dreamy destination to the next.
No grocery shopping, meal prepping, cleanup, or stress. Just sit back, sip your cocktail, and enjoy the ride.
Helpful Tip:
The Perfect 7-Day BVIs Sailing Itinerary
Day 1: Tortola
Tortola is the gateway to your British Virgin Islands adventure and the perfect place to kick off your trip! As the largest and busiest island in the BVI, this is where you’ll board your boat and set sail into paradise.
If you arrive early enough, you can opt for an early check-in and set sail the same day (totally worth it!), but we decided to soak up the marina amenities for our first night. The Moorings Yacht Club & Marina has everything—a pool, spa, and a restaurant—so it was the perfect spot to unwind before heading out to sea.
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Overnight in Marina or Sail to Norman Island.
Norman Island Caves
Cooper Island
Day 2: Cooper Island
We kicked off our day with an exciting snorkeling adventure at the caves of Norman Island. These water-level caves carved into the cliffs are steeped in pirate lore and are rumored to have inspired Robert Louis Stevenson’s “Treasure Island”. The three caves are home to colorful fish and vibrant coral.
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Sail to Cooper Island
Cooper Island Beach Club has it ALL. A coffee shop, boutique, brewery, and a beach bar that’s calling your name.
We grabbed cocktails (Pro Tip: skip the Rum Bar unless you’re cool with paying $30 for a Painkiller…ouch!). Instead, hit the restaurant for drinks and Happy Hour specials. With cocktails in hand, we waded out to the ocean-side tables, where you can sip and snack with your feet in the water.
Genius.
As the sun set, we returned to the catamaran, where our chef had a charcuterie board and cocktails waiting for us. The kids cozied up for movie night, while us moms snuck in a moonlit dip in the ocean.
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Overnight anchorage.
Bitter End Yacht Club
Day 3: Bitter End Yacht Club
Sailing into Bitter End Yacht Club is one of those “wow, we’ve made it” moments. Tucked into Virgin Gorda’s North Sound, this legendary sailing stop has been a favorite for decades—and after a full rebuild post-Hurricane Irma, it’s back and better than ever.
This was one of our favorite stops of the trip, especially with kids! The restaurant, boutique, and gorgeous beach made it an easy place to spend the day. For those in the mood for adventure, check out the Watersports Shack which has everything from paddleboarding to sailing lessons, so there’s no shortage of fun.
Our chef even prepped beach snack plates for the kids—crackers, nuts, cheese, apples, and peanut butter—exactly what they needed after hours of playing in the sun.
If you’re planning to dock here, be sure to pre-book a spot in the marina! It’s a popular stop, and for good reason. You won’t want to miss it.
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To wrap up the afternoon, we hopped on the free boat taxi from The Bitter End dock and made our way to the nearby Saba Rock Resort for Happy Hour.
No day in the BVI is complete without a sundowner in hand!
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Overnight in marina.
Cow Wreck Beach
Day 4: Anegada
Anegada is a total change of scenery from the rest of the BVI—flat, quiet, and fringed with some of the most unreal beaches you’ll ever see. It’s also the longest sail of the trip, and the waters can get rough (so if you’re prone to seasickness, be prepared!).
But trust me, it’s so worth it.
When you arrive, the water is SO blue and there are TONS of sea turtles! It’s windier and less populated than the other BVIs, so definitely pack bug spray and expect a little more movement on the mooring line.
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Our captain helped us rent a truck for the day and even played tour guide, which the kids were obsessed with.
The first stop of the day was Flamingo Lookout, where we spotted native flamingos through a telescope and watched them literally run on water—such a cool sight.
Next up was Tipsy by Ann, where we fell in love with the Watermelon Crush cocktail (a solid 10/10), live music, and a dreamy white-sand beach. We loved it so much that we spent the entire afternoon here until sunset.
Anegada is famous for its lobster, and your captain can help you pre-book dinner in the morning. THIS IS A MUST!
There are a few famous lobster dinner spots; Lobster Trap, Potters, and The Wonky Dog.
We opted for The Wonky Dog, where the kids played on the beach while we ate. The half lobster was massive, and we even split one large lobster between two adults and still had leftovers.
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Overnight anchorage.
Scrub Island Resort
Day 5: Scrub Island
This stretch from Anegada to Scrub Island is a pretty long sail and can be rough, so if you’re prone to seasickness, be prepared!
Today, you have two choices: Book a slip in the marina for an overnight stay OR grab a mooring line and pay for day access ($50 for an adult and $25 for a child) to the resort. Pre-book your spot at Scrub Island Resort in advance if you plan to dock in the marina overnight!
We had lunch onboard after tying up to our mooring, and let me tell you—fried shrimp with cocktail sauce hit the spot after a long morning on the water.
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Arrive at Scrub Island Resort
There’s excellent snorkeling right off the resort, so if that’s on your list, plan ahead and bring your gear!
The rest of the afternoon was all about poolside lounging. You can also indulge in a spa treatment or use the gym…but let’s be honest, an afternoon of Aperol Spritzes at the pool was way more appealing.
The kids were absolutely obsessed with the pool slide, and we were happy to sip cocktails and soak in the sun.
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Overnight anchorage or dock in the marina.
Devil's Bay
Pirate's Bight
Day 6: The Baths & Norman Island
There are two ways to get to The Baths: You can either take a dinghy in and swim to the beach or head to the marina and grab a taxi to the walking trail.
Since we had young kiddos, we opted for the walking trail. The taxi ride from the marina was an adventure in itself, in an open-air truck with benches that made for a fun, breezy ride.
If you’re lucky enough to get a ride with Sweet Ice Willie, you’re in for an authentic BVI experience, lol! It’s $5 per person each way, and totally worth it.
The walking trail is a loop and takes about 15–20 minutes to reach The Baths, winding through giant boulders and lots of greenery. If you have time, stop at Devil’s Bay for a swim before continuing on. The earlier you start, the better as this spot gets packed, especially if there’s a cruise ship in town.
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Sail to Pirates Bight
After exploring The Baths, we sailed to Pirate’s Bight on Norman Island for a chill afternoon on the beach. We grabbed a mooring, lounged under an umbrella with beachside service, and even checked out the spa.
If you’re up for something a little wilder, Willy T, the famous floating bar in Bight Bay, is a must. You can sip drinks and even jump from the top deck, though we skipped it this time since we had young kids.
We spent the night anchored in the bay, soaking up one last perfect sunset before heading to our final stop.
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Overnight anchorage.
Day 7: Jost Van Dyke
We set sail early to Jost Van Dyke for a full day at Soggy Dollar on White Bay, one of the most famous beach bars in the BVIs (and for good reason!). We grabbed a mooring in Great Harbour and took a quick taxi from Foxy’s to Soggy Dollar ($5 per person each way).
If you want the best spot, arrive early to snag a table and beach chairs as this place gets busy fast. But once you’re settled in, it’s pure beach bliss.
The kids were all about the ice cream popsicles from the café, while we sipped on Painkillers from the bar. This is where they were invented, after all! The white sand beach and crystal-clear water made it easy to spend the entire day here just soaking it all in.
If you’re here with kids, don’t miss the baby goats! Jost Goats is on White Bay right next to Soggy Dollar.
Helpful Tip:
To wrap up the trip, we grabbed a final drink at Foxy’s to celebrate the last night of this unreal trip.
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Overnight anchorage.
Day 8: Bon Voyage
Just like that, our BVI trip came to an end!
We sailed back to The Moorings marina, soaking up every last bit of salty breeze before disembarking.
Saying goodbye to the boat was bittersweet, but after seven days of swimming in gorgeous waters, sipping drinks at fun beach bars, and creating unforgettable memories, we were already dreaming about the next trip.
Until next time, BVIs!
