Sail Highlights
Snorkel the Indians & Paddle the Caribbean's Clearest Waters
Wake up to one of the BVI's best dive sites right off the bow — fins on, worries off.
Hike the Iconic Baths of Virgin Gorda
Wander through massive granite boulders and hidden sea pools before a dip in Devil’s Bay.
Dine on a Tiny Private Island at Saba Rock
Dinghy across to this little slice of paradise for fresh seafood and rum cocktails as the sun goes down.
Snorkel in Turtles’ Playground at Peter Island
Anchor in Little Harbour and glide with sea turtles in one of the BVIs’ most serene bays.
Meet Your People
This trip isn't just about the places, it's about the women you'll share them with. Expect sunrise coffees, sunset cheers, and friendships that long outlast the voyage.
Bars Worth Crossing an Ocean For
Swing by Willy T's, a floating bar anchored in a pirate bay, for sunset drinks on the water, then end the week with the Caribbean's most iconic cocktail at the legendary Soggy Dollar Bar.
Itinerary
See the example itinerary below:
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Day 1: Tortola → Norman Island
Your adventure starts the moment you step on board. Board at Nanny Cay Marina, ease in with a sunset cocktail at Willy T's, then set sail for Norman Island . Anchor in Privateer Bay, enjoy sunset drinks and dinner under the stars.
Day 2: Norman Island → Peter Island
Start the morning with fins on at the Indians, one of the BVI's best snorkel spots, before paddleboarding into the blue. Then sail to the peaceful shores of Peter Island. Swim Deadman's Beach, spot turtles in Little Harbour, and hike to a secret abandoned house as the sun goes down.
Day 3: Peter Island → Virgin Gorda (The Baths)
The most scenic sail of the trip. Snorkel straight off the deck or sip a rare Caribbean rum as you head toward Virgin Gorda. Spend the afternoon lost in The Baths, a granite wonderland of boulders, sea caves, and tidal pools ending at Devil's Bay.
Day 4: Virgin Gorda → North Sound (Leverick Bay / Saba Rock)
A short hop around the tip of Virgin Gorda into the sheltered North Sound. Stock up at Leverick Bay, sip lunchtime cocktails at Bitter End Yacht Club, then dinghy across to Saba Rock for one of the best sunset dinners in the Caribbean: fresh seafood and rum on a tiny private island.
Day 5: North Sound → Little Jost Van Dyke
The longest crossing, and worth every nautical mile. Anchor at Diamond Cay and let Atlantic swells do their thing in the Bubbly Pool, a natural rock jacuzzi like nothing else. End the night at Soggy Dollar with a painkiller cocktail and a goodbye dinner to remember.
Day 6: Little Jost Van Dyke → Tortola (Disembark)
All good things. A gentle final sail back to Tortola sun-kissed, salt-aired, and already planning your return.
About Your Host
Maddie Smith
Maddie is a DC-based travel and lifestyle content creator who is always on the move anywhere and everywhere... She's been hosting girls' group trips since 2025 to create lasting memories while exploring new countries, but perhaps more importantly, to form lasting friendships. She's found so much joy in connecting like-minded female travelers, and hopes to meet you on board soon!
Book With Confidence
We’ve got you covered
• Low deposits - Secure your sail from just £500pp / $675pp • Flexible payment plans - Spread the cost with stress-free monthly instalments • Transferable deposits - Plans change? No problem. Switch your trip, no drama* • 40+ years experience - Our team has over 40 years experience in travel and know how to deliver an 5* rated experience • Real human support - No bots, no endless hold music. Just friendly, know-their-stuff people on the other end
What's included
What's Included
Premium Catamaran
Private En-Suite Cabin
Skipper
Private Chef
Host
Onboard Food & Drink (inc. Alcohol)
Fuel & Mooring Fees
Curated Itinerary
Concierge Service
Frequently Asked Questions
Who can join this trip?
This trip is open to all women aged 21 and over. Whether you're coming solo or with a friend, you're welcome here. The only requirement is that you're ready to have a good time.
Can I book as a solo traveler?
Yes! You can either book a whole cabin to yourself, or book a spot in a double cabin. Double cabins have one double bed shared between two guests, so you'll be paired with and sleeping in the same bed as another solo traveler. You can also request to be paired with a friend.
What are the payment options?
We offer full payment, low deposits (from just £500 / $660 per person) and flexible monthly payment plans - full details are shown on the next step when booking, and we’re always here if you need to discuss options.
Are there any additional costs?
You’ll just need to book your own flights and airport transfers, and arrange personal travel insurance, plus cover the cost of any on-land meals and drinks.
What’s your cancellation and refund policy?
All deposits are non-refundable.
Cancellations made 60 days or more before your sail will receive a refund minus the deposit and any transaction fees. Cancellations made within 60 days of departure are non-refundable.
Refunds will be processed within 10 days of receiving your cancellation request.
If full payment isn’t made by the specified due date, any amount paid to date will be forfeited.
Where do we check in and set sail?
Your Nautica experience begins at Nanny Cay Marina, Tortola. Check-in is from 3pm on the first day of your trip.
You'll need to make your own way to the marina. There are two easy ways to get there:
- Fly into Tortola (EIS) Land at Terrance B. Lettsome International Airport, just 35 minutes from the marina by taxi.
- Fly into St. Thomas (STT) Take a 1-hour ferry from Charlotte Amalie to Road Town, Tortola, then it's just 10 minutes by taxi to Nanny Cay Marina.
Ahead of your sail, we’ll send you a handy travel guide with all you need to know - best flights, transfer tips, and nearby hotels if you want to stay a night pre or post-sail. And we’re always here if you need a little extra advice.
What about dietary restrictions and food allergies?
Our chef can cater to all dietary requirements. We'll be in touch within 4-8 weeks before departure to collect all dietary preferences and requirements so that we can tailor the menu accordingly.
Whether you're vegetarian, vegan, gluten-free, or have specific allergies, just let us know and we'll make sure every meal works for you.
Why Nautica Collective?
Curated Routes - Handpicked journeys blending iconic highlights with hidden gems only accessible by sea. Intimate Groups - Up to 10 guests per yacht, max 5 yachts per sail - come with a friend, leave with a few more. Local Expertise - Sail with crew who know the waters, the culture, and the best-kept secrets. Plates & Pours - Chef-prepared meals, cocktails on deck, and en-suite, air-conditioned cabins with sea views. Flexible Itineraries - Time to explore on land, relax at sea, and treat your yacht as a floating boutique hotel.
Who is the trip for
Your fellow crew
Our customers are mostly millennials, late 20’s, 30’s & 40’s who want more from a travel experience, with the opportunity to meet & connect with people on your wavelength.
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