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A Kenny Chesney Guide to the Virgin Islands: All of the Spots from the Songs

If you’re a country music fan, your first introduction to the Virgin Islands (a chain of American and British Islands in the Caribbean) just might have been through a Kenny Chesney music video.

And hey…if you’re planning a trip to the Virgin Islands just because you HAD to get to the place where the “No Shoes, No Shirt, No Problems” music video was shot, you’ll get no judgment here! 

That crystal clear turquoise water, those white sand beaches, and those lush green mountains are the stuff paradise is made of, and if you throw a little Kenny Chesney spotting in, you’ve got the makings of a great vacation!

First, a little disclaimer: Kenny Chesney in no way “discovered” the Virgin Islands but when he bought a house on St. John, started shooting music videos there, and frequently worked the mention of local places into his song lyrics; he did a lot to popularize them. So, if you’re a fan (and if you’re not, I’m not sure we can be friends!) here’s a little tour of the Virgin Islands that includes plenty of places that you’ll find referenced in his songs (and music videos):

St. John

Apart from being Kenny Chesney’s home away from home (his home on Peter Bay was reportedly destroyed during 2017’s Hurricane Irma), St. John is an island with quite a few magical spots. Just a short ferry ride away from St. Thomas, St. John has a super laid back vibe and it’s just plain gorgeous. 

People who really want to see the Virgin Islands make St. John their hub (as opposed to nearby bustling St. Thomas). For this stop on the tour, check out:

Cinnamon Bay: One of St. John’s prettiest beaches is a great place to sit back and watch the boats sail in and out of. At least that’s what Kenny sings in “Old Blue Chair.” And I agree. I could stay here all day.

Quiet Mon Pub: A second story Irish pub overlooking a bustling street in Cruz Bay, this is a local spot (a great place to grab a beer and watch a game).

“Hang with the locals at the Quiet Mon” like Kenny does in “Be As You Are.”

Woody’s Seafood Saloon: Never mentioned in a song, but featured in the “When I See This Bar” music video, Woody’s is a St. John institution. Stop by for happy hour…it’s when this place is really hopping.

St. Thomas

You won’t hear a lot about St. Thomas in any Kenny Chesney songs (probably because it’s too crowded), but if you’re on the island off a cruise ship, check out this spot:

Latitude 18: This is the only St. Thomas reference I found from Chesney, but it’s a

good one! Featured in his “When I See This Bar” music video, this is a good spot to wile the hours away.

St. Croix

Another island that doesn’t get much love is St. Croix, although it’s referenced in “Island Boy.” He sings, “He’s an island boy. Just a stone’s throw from St. Croix,” which is funny because St. Croix is actually one of the most isolated islands in the Virgin Islands and has to be reached by plane, not ferry! Most people traveling to St. Croix don’t island hop much.


Tortola is the hub of the British Virgin Islands and because of its location, it’s usually visible from whatever island you’re on so it makes for great island gazing. 

“Tortola, a full moon, shining down on a blue lagoon” makes me want to do a little island gazing. That one’s from “Key Lime Pie.”

Virgin Gorda

If you’re on Virgin Gorda, you’ll most likely find Kenny “floating around Gorda Sound with a cooler and a bong.” Whatever Kenny. The North Sound (opposite end from the Baths) is THE place to be on Virgin Gorda. Reached only by boat, hang out at either Saba Rock or the Bitter End Yacht Club. Bong optional.

Norman Island

It’s not technically on the island, but Willy T’s is a floating bar just off Norman Island that is famous for general debauchery and pirate like behavior. So of course, it was featured in the “When I See This Bar” music video. There’s also a mention of a “Willy T in Abilene” in “Like Me” but I don’t really think there’s any relation. Being as one is in Abilene and one is in the Caribbean.

Jost Van Dyke

Well folks, I’ve saved the best for last! Not only is it arguably the prettiest (and most fun) island in the BVIs, it’s also home to the most references in song lyrics! “Oh I wish I was there tonight, on Jost Van Dyke. Sipping some of Foxy’s firewater rum.” That one’s from “Somewhere in the Sun” and yes…I have heard it played while sitting at Foxy’s, sipping their firewater rum. Mind blown. Also, when you have to say “Adios to Jost” you just might have a tear in your eye (that’s from “It’s That Time of Day.” Here are some other spots to hit:

Sandy Spit: Not referenced in a song, but you’ll see this perfect little “spit” of sand plenty in the “No Shoes, No Shirt, No Problem” music videos. It’s straight out of heaven.

Ivan’s Stress Free Bar: This place must be Kenny’s FAVORITE spot because he sure talks about it a lot. You’ll find him “kicking back with Ivan” in “Somewhere in the Sun” and you’ll also recognize it from the “No Shoes, No Shirt, No Problem” and “When I See This Bar” music videos.

Foxy’s: Foxy’s is a Jost Van Dyke institution as mentioned above is referenced in “Somewhere in the Sun.” It also makes an appearance in the “When I See This Bar” music video. We’re talking about Foxy’s Tamarind, not to be confused with Foxy’s Taboo, which is great also but to the best of my knowledge not featured in a Kenny Chesney song or music video. Yet.

Soggy Dollar Bar: This place is epic and so of course was featured in the “When I See This Bar” music video. It’s probably the most famous beach bar in the Caribbean so it definitely deserves a stop on your tour.

One Love: And finishing up our tour, you’ve got to make a stop at One Love on White Bay (just down from the Soggy Dollar), which is also featured in the “When I See This Bar” music video.

So there you have it folks! If you’re embarking on a Kenny Chesney inspired tour through the US and British Virgin Islands, you know where you need to go. But here’s a tip: don’t “pass out from too much Cruzan and diet or you’ll wake up to a hundred mosquito bites”. And if you do, Kenny Chesney has a song for you. He probably wrote it while he was sitting in his Old Blue Chair.

P.S. Y’all know while I’m an equal opportunity beach goer, I’m a Hawaii girl at heart and I think Kenny is too. Check out his “Paia, Maui” hat in the “When I See This Bar” music video!!!

More posts about this area:

Virgin Islands Itinerary: How I Spent 2 Weeks Island Hopping the USVI & BVI

The Best Beaches (& Snorkeling Spots) on St. John

14 Things to Do on Jost van Dyke (+ the Best Beach Bars)

Visiting the Virgin Gorda Baths (+ a Few Other Places)

Things to Do on Anegada (the BVIs Least Visited Island) 

Glamping on Anegada, British Virgin Islands

P.S. If you want to follow along on my travel adventures in real time, you can follow me on Instagram (@caitylincoln). My post captions are full of travel tips and I have a ton of story highlights and videos with great info. And share my account with your travel loving friends! Your support really helps me keep this blog running!