Hosted BVI Sailing Adventure
5 Nights Aboard a Moorings 4500L
with Captain Bill Wiggins
Imagine this…
You wake up in the British Virgin Islands aboard a comfortable sailing catamaran. Coffee is brewing, the water is ridiculous shades of blue, and the only real question is whether you want to swim before breakfast or after.
This hosted sailing adventure is being designed for a small group of travelers who want to experience the BVI from the water without needing to captain the boat themselves.
We will be sailing aboard a Moorings 4500L with four guest cabins available for up to eight guests. Bill Wiggins, Travel Advisor and USCG Licensed Captain, will serve as captain and host for the trip.
This is not a giant group tour. This is not a rushed checklist vacation.
This is five nights of sailing, snorkeling, beach bars, island restaurants, sunsets, laughs, and probably at least one person saying, “Why haven’t we done this before?”
The Plan
Day 1: Cooper Island
We ease into the trip with a short sail to Cooper Island.
This is the perfect first stop. Calm water, snorkeling, great views, and the Cooper Island Beach Club.
Possible highlights:
Cooper Island Beach Club
Rum Bar
Beachfront restaurant
Snorkeling at Cistern Point
Sunset drinks
This is where everyone officially shifts into island mode.
Day 2: Virgin Gorda
Next up is Virgin Gorda, home of The Baths.
This is one of the most famous stops in the BVI for a reason. Giant granite boulders, hidden pools, caves, and Caribbean water that looks fake even when you are standing in it.
Possible highlights:
The Baths
Devil’s Bay
Top of the Baths Restaurant
Snapper’s Bar & Grill
CocoMaya
Good shoes recommended. Complaining about how beautiful it is will not be accepted.
Day 3: Jost Van Dyke
Jost Van Dyke is one of those places that tends to create stories.
We will plan to enjoy the beach, the bars, and the laid-back island atmosphere that makes this stop so popular.
Possible highlights:
Foxy’s
White Bay
Soggy Dollar Bar
Hendo’s Hideout
Gertrude’s
Seddy’s One Love
Painkillers, obviously
Hydration is important. So is common sense. We will encourage both.
Day 4: Cane Garden Bay
Cane Garden Bay gives us a beautiful stretch of beach, great local restaurants, and one of the best sunset settings in the BVI.
Possible highlights:
Cane Garden Bay Beach
Callwood Rum Distillery
Quito’s Gazebo
Myett’s Garden & Grille
Paradise Club
Indigo Beach House
Swimming, paddleboarding, kayaking, or doing absolutely nothing
Doing absolutely nothing is underrated and fully supported.
Day 5: Norman Island
Norman Island is one of the classic BVI stops.
We will plan to snorkel the caves, enjoy the anchorage, and wrap up the final night with dinner and drinks ashore.
Possible highlights:
The Caves at Treasure Point
The Indians
Pirate’s Bight
Willy T
This is the kind of final night that can turn into a story. We will try to keep it a story you can actually tell your family.
Day 6: Return to Road Town
We make our way back to Wickhams Cay II in Road Town.
One last breakfast aboard, one last look at the water, and one final reminder that real life is waiting back home.
Rude, but true.
The Boat
We are planning this aboard a Moorings 4500L sailing catamaran.
The trip will be sold by the cabin, with four guest cabins available.
Ideal for:
Couples
Friends traveling together
First-time yacht charter guests
People who like the idea of sailing but do not want to be responsible for figuring out where the anchor goes
No sailing experience is required.
Meals and Provisioning
We will have a few options for provisioning.
We can have the boat pre-provisioned before departure, shop ourselves before we leave, or do a mix of both.
Some meals will be ashore at restaurants and beach bars. Some meals will be onboard.
Important note:
Bill will be captaining the boat.
Bill will not be your chef.
Yes, he can cook.
No, he will not be doing it on this trip.
For onboard meals, we will keep things simple and share galley duties as a group. Think easy breakfasts, casual lunches, snacks, drinks, and simple meals that do not require anyone to miss sunset because they are trapped below making a twelve-step recipe.
This is a sailing adventure, not a cooking competition.
Who This Trip Is For
This trip may be a great fit if you:
Have always wanted to try a yacht charter
Like small-group travel
Enjoy boating, islands, snorkeling, and beach bars
Want a hosted experience instead of figuring everything out yourself
Are comfortable sharing space aboard a catamaran
Understand that boats, weather, and island time all require flexibility
This may not be the right trip if you need a butler, a casino, an elevator, or twenty-seven restaurant choices within four minutes of your cabin.
About Your Captain
Bill Wiggins is a Travel Advisor with Wiggins Travel Group and holds a USCG 100-Ton Master’s License with Sailing Endorsement.
He has spent much of his life around boats, sailing, racing, deliveries, navigation, and marine operations.
On this trip, Bill’s role is simple:
Get the boat safely from place to place, help the group enjoy the BVI, and make sure everyone has a great time.
He may also tell a few boat stories.
Some of them may even be true.
Interested?
We are still putting together the final details, including dates, cabin pricing, provisioning options, and travel logistics.
There will only be four guest cabins available.
If this sounds like something you would like to be part of, send us an email and let us know.
Ask questions. Tell us who might be coming with you. Tell us whether you are more excited about snorkeling, sailing, beach bars, or just sitting on the boat wondering why you ever agreed to go back home.
Email:
billwiggins@dreamvacations.com
Subject line:
BVI Sailing Adventure
We would love to hear from you.
Copper Island
Virgin Gorda
Jost Van Dyke
Cane Garden Bay
Norman Island
Wickhams Cay II
