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5 Days Exploring the Virgin Islands on an iSUP

5 Days Exploring the Virgin Islands on an iSUP

By: Shane Perrin

The plan was simple: travel the U.S. and British Virgin Islands by living out of 2 bags (one containing an inflatable SUP) and then paddle to Puerto Rico.  Everything needed to have a successful adventure would have to be packed into 2 bags, one checked in the flight and one carry on.


A quick drive to St. Louis's Lambert airport began the day at 4am. Flight check-in and 2 flights later I arrive in St. Thomas' Cyril E. King airport, a small airport where you land on the airfield and walk outside to the terminal. Upon entry, I get some free Rum samples to help with the immediate face sweating from the climate.

I grab my bags, easy to spot coming off the conveyor belt, and make way to find a way out of the airport. This trip is non-luxury and I plan on not spending $40 on a taxi for a 20-minute ride.  So, from local intel I find there are safari rides. Not your typical safari rig in the bush, more-so these are pickup trucks modified to fit people into row seating 3-4 in a row.  If you have a mammoth SUP bag with you then you commandeer most of the seat row yourself.  For $2 the safari will take me across half the island with multiple stops. At the end I can hop a second safari for another $2.  $4 for a ride to the waterfront= saving $38 and adding a little adventure.

The kicker? Safaris are not allowed to roll up to the airport and pick people up. They are more geared for people getting around the island.  Safaris are individually owned and not part of the taxi system. So I have to walk about a mile to get one. No sweat. Or more like loads of sweat! Pulling a 50lb bag on wheels and carrying a 40lb duffel makes me sweat as I trudge down a hot asphalt walkway. I find a convenience store and stop for info and some bottled water.  A 20-minute wait and I hop my first safari.  Interesting group of people on it. People getting off work, going to the market, going who knows where. The fella I'm next to has come off a labor job and is stoned as can be. Island life! He's hilarious and I tell him what I'm up to. He starts to tell me about the dangerous crossing from St. Thomas to St. John. It's entertaining but taken seriously.

I get to the second safari and then finally get to the eastern end of St Thomas at Red hook. I walk about 5 minutes and I'm at the water inflating my SUP. Onlookers are wondering what's going on as they wait for their Ferry boat to come, the last of the night. I even convince a by-stander to pump a while.  Board inflated and loaded up I leave for St. John at the day's end.

The fella from the safari wasn't exaggerating, the water gets rough quickly once in the main channel. It has a washing machine effect. The boats flying by combined with the ferry boats and the channel + wind makes for a hairy paddle.  The worst part is it's now dark and some of these boats are without lights. I have to listen to where they're coming from and make sure my strobe light is positioned so they can see it.  A knuckle biter of a 4.5 hrs. paddling and I make St. John. greeted by "The Beach Bar" I settle in on a beach table and nestle my board and gear on the tree nearby. A mahi sandwich and local St. John brewer’s beer make the crossing worthwhile.  The best part is I put in a call from a friend who lives on the island, Chirag, co-owner of St. John Brewers, he is putting me up for the night at his place.

Day 2 on the island starts slow. Some morning yoga at the Westin Hotel with Chirag's wife and then back to the house to load the board and gear for a paddle.  Loaded up I catch a ride to the Eastern part of the island from Chirag and unload. A quick pump up and I’m prepped for the first big crossing. St John USVI to Jost Van Dyke BVI. A Caribbean Sea crossing of about 10 miles or so.

No easy crossing by any means.  It's a cross wind and swell. winds are blowing at 17mph. On top of that there's a shipping channel I have to navigate with heavy boat traffic. I Leave Leinster Bay and make my way to Tortola BVI. This is the easy leg as it's only 1.5hrs of paddling. In the bay it's calm due to being somewhat protected.

This pic shows Leinster Bay where I launched. It looks peaceful but once I paddled between the 2 small islands the raging Caribbean erupted. 


A quick stop Near Soper's Hole BVI. I don't think I could even call it a beach. It was the best spot I could find though on the western Tortola end to take a break. Everything else was private property.

Unfortunately, I didn't take any pics of the actual crossing from Tortola to Jost Van Dyke. It was a hard 5-hour paddle across the ocean. The winds were closer to 20mph with 2-3' chop.  I lost count how many times I fell off the board. I took all my wits to keep looking in every direction for boats. The shipping channel was busy. Huge ferries, cargo transports, personal catamarans and every other tourist out there renting a boat.  

You can see the distance was no short amount. I left on the far left of St John and paddled to where the blue dot is.

By the time I made it to Jost Van Dyke the sun was just starting to get ready to set. The tourist boats were leaving and I had a beach almost to myself.

After settling in, it was time for a little nighttime exploration of the island by foot...

An empty Soggy Dollar Bar!

After that, it was a good night' sleep in one of Jost Van Dyke's finest cabins (a 12x12 cabin with electric and a ceiling fan).

The morning starts with a sunrise & a coffee... 

From there, it's a swift departure from Jost Van Dyke, and this is the paddle I have not been looking forward to. Crossing back to St John through prime time in the shipping channel. Loads of boats hauling butt across and I'm going right through it. My goal is to make it to Whistling Cay (the circled spot on the map) lying just before St. John.

Leaving the bay is the easy part. Once out in the ocean is where I start falling off the board. 13-18mph winds sometimes gusting to 20+ have their way with me.  It's a constant battle to stay in the direction I want to go. This means I have to paddle only on my right side the entire time.  It ends up being less of a normal front to back stroke and ore so a sweep or C stroke. The wind and the chop continuously pummel the side of the board.  This wouldn't be as big an issue without a fin. The fin "anchors" the board to go straight but there is no straight from the wind and chop. The nose of the board wants to fight to go with the wind. I fight to keep a line across to Whistling Cay.

The paddle across is mostly uneventful.  Mostly me clinging onto the board, falling off, remounting, and paddling like a maniac to stay straight. I do come across a massive sea turtle.  I followed him a ways but he didn't care for my company much and left within a few minutes.

5 hours later and I make it across the main open ocean crossing and am getting ready to enter the shipping lane. I float next to a large rock outcropping of a small uninhabited island watching the boat traffic.  It's about 1 mile from the small island across to Whistling Cay, a small former outpost.
I see a clearing and paddle as fast as I can and get about 1/4 of the way across until I see a large ferry boat coming from the east. I keep a steady eye on it and paddle with a 90% effort cadence.  I get half way across the channel and hear to the west some deep growling engines. A huge Catamaran is motoring full throttle towards me. I'm a blip in the water and he doesn't see me. I am all out in panic mode and at 100% paddling at this point. The boat steadily is closing in on me and It seem like death is now a possibility.   No time to die, I paddle like an idiot and see that I'm going to clear the boat just barely. Get by and have 30 yards to spare. Seems like a lot but it's not.
So, death averted I'm happy to get to Whistling Cay. It was an old outpost way back in the day when the Virgin Islands were colonized. Troops were stationed here to look for invaders coming and they would warn the Government of St. John.    I entered Whistling Cay and beached right where you see here. The far island in the distance is where the shipping channel extends to. Doesn't look far but it is, trust me.

To the left you can see Western St. John. The fort actually faces the north shore of St. John. at Maho Bay:

From Whistling Cay it's a quick paddle to paradise, Maho Bay!

I spend a couple hours here joined by strangers from Wisconsin that conveniently have a cooler of beer.  Later I get a ride from my friend Chirag back to his house to get cleaned up and relax before the night's activities.

At the St. John Brewers Taproom with Chirag that evening.

The following day was supposed to be me paddling to Puerto Rico a distance of about 60 miles of open water. The morning comes and the decision is to abort Puerto Rico. The "Christmas Winds" have arrived and are blowing 20+ mph consistently. On top of which the local paddlers tell me that the area between St. Thomas and Puerto Rico is heavily fished and that attracts lots of sharks. So the easy decision was to play it safe and stay on St. John.  I decide on a North Shore paddle on my last day in paradise.

Leaving Maho Bay
Quick Stop on a Rock Beach
Cool pirate ship on Western St. John
Cruz Bay
Cruz Bay, gear off the board
Back at the beach bar.

The next morning I catch a ferry over to St. Thomas with my gear...

Then, it's a quick check in for Cape Air at St. Thomas Airport for my flight to Puerto Rico, then home to Missouri.

Airport Security
Small Plane
Seems it's a wee bit of a small plane!
Puerto Rico
Landed in Puerto Rico & transferring to my flight back to Missouri.
Heading Home

All in all, traveling and living out of 2 bags was a fun adventure. If you have an inflatable sup, don't mind a little sweat, and have an open adventure mind, you can have quite the adventure. No tour guides. No fancy hotels. No pampering.




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