The timing of our Virgin Islands hopping adventure made the islands seem a bit more virgin than anticipated. We landed upon those beautiful shores in the off season and also after a major hurricane. The region was scrambling to recover from the destruction of Irma and this report reflects a point in time where the islands were quiet and in rebuilding mode.


St. Thomas USVI
To acclimate to island time, we arrived in St Thomas a couple days early and it was easy to tell the area was not in its best form. That was expected and understandable. Fortunately, Frenchman’s Cove resort was fully operational and quite nice . My only gripe was the locals’ attitude towards tourists and their dollars needed to bring the islands back. Not as many smiles and good vibes as advertised.
Cabs from the airport are an exercise in packing a van full of as many passengers as can reasonably fit and then adding a few more. If you happen to be at the last resort on the route, you will be in for a sweaty hour long van ride. Luckily, we were first. More stressful than seating on Southwest!
Oh and bags cost extra in the shuttle. Normally I would say that’s silly because bags in the back of a van don’t take up any space from paying passengers. However in their case, I truly believe the taxi mafia would stack some children and elderly in the cargo area.
Private cab? How about $65 to go 2 miles. Come on St Thomas, this ain’t Monaco. Lets get it together on the transportation.
On the bright side, we were quickly introduced to the joys of the island specialty – the painkiller. Such a smooth concoction. The only debate is whether its better with or without the traditional nutmeg.


Day 1 Virgin Islands Hopping
Monday Oct 1 and it happened to be the international holiday known as Mr Wanderfool’s birthday. We were up early to cab to the ferry that runs to Tortola, BVI. Ferry service in those parts is a challenge, especially post hurricane. While island time is acceptable for a bar tender making a painkiller, a ferry that needs to get you to your boat on another island in another country is quite a different thing. Island time isn’t cute then.



USVI boating
Luckily the ferry was on schedule and did not break down or sink, though both seemed to be legitimate possibilities. Once at the Moorings marina in Tortola BVI, we commenced the cumbersome and disorganized process of boat briefings. Island time and work ethic in full effect on the first day of bareboat season for Virgin Islands hopping.
Half our crew shopped for supplies, mostly of the liquid variety. Meanwhile first mate and I sat through a chart briefing with a dude who seemed to have smoked too much weed that morning. Or maybe too little.

Virgin Islands hopping trip
We were instructed helpful hints like give way to sailboats. I thought well I don’t at home so why should I in the Caribbean sea. Just kidding my sailboat friends. Fortunately that was never an issue as nary a charter sailboat ever unfurled its sails from what I saw all week. Curious- does that still make it a sailing trip? And you sir at the helm in the captains hat and Sperrys, are you a sailor or a power boater?
The rest of the crew went to stock up on food. I awaited my boat orientation from a salty old fella in a Hawaiian shirt who complained that he was already three sheets to the wind at a bar that morning when they called him in to work. Fair enough. Can we just get this done and cut us loose? We got islands to hop! Any longer a wait and we might have just untied and figured it out on the fly.
Virgin Islands catamaran


Our vessel was a 43 foot power catamaran named Last Call. 22 foot beam. Twin diesels. 3 cabins. 2 showers plus an outdoor shower. Full galley plus an outdoor grill. It was love at first sight. Handles like a dream. Super comfy and roomy for four. A RIB dingy and electric hoist is included for shore excursions and exploring. A perfect rig for hopping the islands.

So we finally got Last Call away from the slip in the afternoon before her namesake became a factor. We set a course straight for the Willy T, the famous floating bar accessible only by boat. I saw it one time on the travel channel and said some day…

The original Willy T was off Norman Island and sadly became a victim of Irma. It was still washed ashore. The owner, a Scottish expat, found a new vessel and ran it over from Louisiana. The folks that run Norman Island would not renew his anchorage there so its now moored at nearby Peter Island.
BVI boating
Willy T is known for its patrons jumping off the top deck. Traditionally a naked jump earns a free T-shirt. That is no longer policy in these enlightened times. Staff consists of one: a manager/ bartender/ cook/ bouncer/ T-shirt administrator. He stays and sleeps on board for 4 nights and then the next guy comes in for 4 nights. Yes I put my application in.

As for T-shirts, its possible- though by no means confirmed here -that some in our crew earned a free one. Seems the original T-shirt policy was never formally revoked and can be administered subject to the discretion and professional opinion of staff. Despite my best efforts, I did not earn a free T-shirt. In fact I recall something about charging me double.


The Willy T was slow that night due to the off season but we had a blast. Traveler’s tip: do not allow yourself to be pushed off the Willy T and land on your back. Thanks Buddy! Now I realize why they call that coconutty rummy goodness a painkiller. Quite effective for that specific set of injuries.
We stayed the night at our mooring ball by the Willy T. Additional island hopping was not an option. Such a fun and unique spot for our first night. I heard I had a great birthday celebration.
Day 2 Virgin Islands Hopping
Sun was up and so were we. Our nights tended to end early and our days started early. Please, no jokes about too many birthdays. It’s a boat thing ok!
The Last Call was unhooked and we headed to Virgin Gorda with a first stop at the Baths. These are awesome rock formations where you can climb and wade through clear waters. Very cool spot. We did some hiking and then a long snorkeling session.




Eventually we made our way to Leverick Bay, the only marina area still standing in northern Virgin Gorda post Irma. It was quiet there. A few drinks at a tiki bar that oddly had Elvis playing nonstop. Before they got to the one Elvis song I like, it was four sleepy heads and time to head back to the boat.

Day 3 Virgin Islands Hopping
Off to the Dogs for snorkeling and exploring an uninhabited island. Then to Scrub Island, a high end resort where we day tripped. Nice facility but very low key there. Bottom line their $12 painkillers were no better than the ones we could make on the boat and certainly a lower dosage. So we dinghied back to the Last Call with a quick stop at little Marina Cay island which unfortunately was still out of commission.


Next we headed to Guana which didn’t offer much clear water so we continued to Cane Garden Bay, Tortola to set up for the evening. The rollers and big waves are on that north side of Tortola. We took the dinghy to shore and beached it.
Travelers tip: beaching a dinghy in the surf is easy. Relaunching it is not. Darkness and painkillers provide bravery but decrease seamanship. Visions of blasting back through the waves like Seal Team 6 ended more like an overloaded refugee boat caught in a hurricane… dinghy full of water, gear floating, passengers sinking, and hurtful words from the typically ladylike members of our crew. Fortunately, there were no casualties and not even a single flip flop was unaccounted for.
Safe and sound back at the boat, it was just us and those rollers- a sharp contrast to the previous calm nights. This makes for a peaceful sleep only for those who have earned their sea legs. It’s rumored someone in our crew donated their dinner back to the ocean in the wee hours, though surely the many tarpon around the boat appreciated it.

Day 4 Virgin Islands Hopping
We escape the north coast Tortola swells for the calmness of Jost Van Dyke island. First stop was Diamond Cay to do a little swim and hike to see monster waves crash the rocks on the north side. Then it was over to Great Harbour to check out a couple of famous beach bars.

Soggy Dollar Bar in White Bay Jost Van Dyke is the most famous. Did they invent the painkiller? Not sure but they make good ones. White Bay was also the scene of our second and last attempt at beaching a dinghy. Many thanks to the construction worker who loaned us a bucket to bail her out this time.


Foxys: Great Harbour. Our much anticipated visit to the famous Foxys bar was a dud. We pulled the dinghy in (to a dock thank goodness) just after sunset and the place was empty. A shirtless, dreaded dude behind the bar was hanging around with a couple of his homies. We asked if we could get a drink. He replied that he had been doing roof repairs but could make us one. Decent drink, though I am not sure he was even an employee there. Perhaps that had something to do with his cash only policy. I do want another try at Foxys when things are ramped up and the roofer isn’t mixing painkillers.


Day 5 Virgin Islands Hopping
The Last Call set a course to Sopers Hole on the West side of Tortola. On the way we passed Little thatch Key owned by the Otterbox founder. That’s a lot of phone cases to buy that big island. Pulled into Sopers Hole Marina and docked to fill the water tanks. Checked out the little village and the Pussers Rum bar but things were very much a work in progress.

We paid our water tab and set a course for Norman Island, back where we started. Our hardy crew encountered its first real rainstorm but it cleared about the time we got to the Indians off Norman Island, a superb snorkel spot. Deep rock formations and massive amounts of fish. The bright areas felt like you were swimming in an aquarium.
Virgin Islands Hopping snorkeling


Next we headed for the Caves, another fantastic snorkeling area with rock formations and caves you can swim into.
Virgin Islands Hopping trip


Most were small caves. One was deeper. And dark. A tad eerie to swim in towards the blackness. Primal fear that something will get you. Well primal man knew what was up because as soon as I entered the dark zone I was face to face with a sizable barracuda. A bold one who yielded not an inch.
I backed out and scolded myself for being spooked by a fish. Afterall who is the apex predator here. So back in I went assuring myself of what they say about every wild animal: he was the one afraid and had no doubt swam away. He had not. Face to face again. Not only did this toothy bastard not flinch, the wave action gave the impression that he was lunging toward me. I decided that he wins and the cave was his. For my part, I am pretty sure I warmed the water for him.

BVI bareboat
For our last night of island hopping, we ended where we started at Willy T. More boats started showing up and a good time was had by all. No attempt was made for a free T-shirt this go around as I had lost faith in the impartiality of staff. Instead, the credit card worked just fine and yes I require a large sir, despite your comments to the contrary last time.


The next morning we got the Last Call turned in and it was time for the Virgin Islands hopping adventure to end. One more spot to check out though. Our final night was spent at Gallows Point on St John, an island with great vibes that I would like to revisit.



Island hopping on your own bareboat is a truly amazing experience. I frequently mix up a Painkiller and revisit the memories. My concoction is never as good but then again, everything is better in the islands. As far as bucket list trips, Virgin Islands hopping certainly qualifies and I recommend it to anyone who enjoys boats and boatlife adventures. And if you need a captain….


Wisdom of the ‘Fool
Travelers Tips for Virgin Islands Hopping
- Arrive in the islands at least a day before your island hopping trip
- Everything is on island time including the ferries. Leave an extra buffer of time
- Be prepared to definitively answer whether you want nutmeg in your painkiller. This is important
- Contemplate how much you intend to cook on the boat and buy that food in Tortola as the captain in your crew daydreams through the orientation. Booze can be restocked at various stops along the way
- Plan your route. Leave room for flexibility but at least have a rough game plan of what you want to see. Debating itinerary along the way can lead to mutinies
- October thru December is slow season for Virgin Islands hopping. Things get much more crowded after the first of the year. There are pros and cons to both. Decide what vibe you want. Best deals are in Oct and Nov.
- If you don’t earn a free T-shirt at the Willy T, that’s ok. Especially if you are a male. If they present you a kids T-shirt, that’s not ok