Neighborhooding: Cruz Bay, St. John USVI

Back in the olden days of 2004, I spent a short afternoon on St. John, the smallest of the three US Virgin Islands. I was on a college graduation trip with my high school friends (despite the fact that I didn’t graduate until 2005 – victory lap!) to St. Thomas and we did a boat trip to the British Virgin Islands to see the Baths. Either on the way there or on the way back (this is 20 years ago; I can’t remember the details!), we stopped on St. John for a hot minute. Truth be told, I can’t remember a single thing about my first time on St. John, except a fuzzy fact that the island is mostly national park.

Fast forward nearly 20 years, the island is still more than 50% national park and I’m on track to visit twice in the last two years, thanks to friends who’ve dubbed it The Destination for Milestone Birthdays. Before we head back later this year, I wanted to recap my last trip in November 2022 and highlight a few new things I’m looking forward to for December 2024.


Check in

Katie, the bday girl at Villa L’Agave

In 2022, we stayed about a 20-minute drive from Cruz Bay at this VRBO house with a pool in Chocolate Hole (ha) overlooking the bays of the south coast. There is a Westin on St. John but I’d recommend finding a house with a view on VRBO or Airbnb. This year, we’ll be staying on the East End near Coral Bay, which is an area I’ve never been to. On the upside, no matter where you stay, you’ll be able to get anywhere on the island quickly as it’s only a 40-minute drive across the whole island.


Where to Beach

Trunk Bay

Trunk Bay: One of the closest beaches to Cruz Bay, you can be off the ferry from St. Thomas and be in the water in less than 15 minutes. I can confidently say this is the best beach I’ve ever been to in the entire world. The water is bathwater warm and calm and the color of blue Gatorade. Perfection!

The bday crew in Cinnamon Bay

Cinnamon Bay: Just a little further east from Trunk Bay, this is another one of the island’s best beaches. There’s a cafe and facilities.

Maho Bay: East of Cinnamon is Maho, which is a skinny strip of beach right next to the road with beach food & drink shacks and surf shops lining the other side of the road but not in an overly developed way; in a charmingly rundown kind of way.


Where to Eat

The ceiling decor at Skinny Legs

Skinny Legs: Burgers and rum drinks on outdoor picnic tables in Coral Bay.

We had a few drinks at Shambles

Shambles: Super colorful spot for good food and drinks.

The Windmill Bar: An open-air bar & restaurant on the site of a former sugar plantation from the 1700s. Great views overlooking all the beaches of St. John.


Where to Drink

The view from High Tide; literally on the water

High Tide: The closest bar to where the ferry docks, it’s turning into a tradition to have our first & last drink on the island here.

Woody’s

Woody’s: Kenny Chesney is probably St. John’s most famous resident and this is his local drinking spot, apparently. Walkable from the ferry dock, this is a very low-key bar with some outdoor seating. But don’t come for the views (there are none); come for the vibes.


Where to Shop

Groceries are kind of expensive here, which does make sense given the remote location. For our last trip, we shopped at both Love City Market and Dolphin Gourmet Market, the former being larger with more of a selection and easier parking.


Worth a Detour

Keep an eye out for some roadside donkeys while driving around St. John

While you can get around the island via taxis, renting a Jeep is (IMO) a must. But be warned of these St. John-isms while driving:

  • Cars drive on the ‘wrong’ side of the road (left side) but in US-configured vehicles with the steering wheel on the left. This tradition of ‘keeping left’ is thanks to its colonial history as being Danish-ruled from the 17th century until purchased by the US in 1917.
  • The island is basically 80% crazy elevation changes and as you climb into the middle of the island, you will hardly believe the steep roads and driveways you’ll be expected to maneuver. Just go slow and you’ll be fine!
  • Watch out for the donkeys and the goats; they freely wander the roads throughout the island.
Captain Stephen and his trusty first mate Pirate Nemo the rescue rat terrier
Boat Day on the Salty Dog Day Sails catamaran
Lounging on the catamaran hammocks

Salty Dog Day Sails: We booked a private day charter on this luxury catamaran helmed by a husband and wife team (and their adorable rescue dog Pirate Nemo). We went snorkeling in Christmas Cove, jumped off the platform deck, lazed about the hammocks and cruised around Little Saint James (infamous private island owned by Jeffrey Epstein), while being fed endless rum punches. Depending on the time of year and the day of the week, they can incorporate a visit to PizzaPi or LimeOut (both are floating restaurants) but neither worked out for us so we ended up bringing aboard lunch that we ordered from Northshore Deli.

The Baths in the British Virgin Islands
The Baths, Virgin Gorda, photo courtesy of gooddaycharters.com

The Baths, Virgin Gorda, British Virgin Islands: Massive granite boulders (similar to the Seychelles), secret tide pools and white sand beaches make up The Baths. You can either take a ferry from Cruz Bay to Virgin Gorda, or better yet, book a day charter that takes you to a few of the BVIs, making sure to stop at The Baths along the way. Just keep in mind: though you won’t need a passport if American going to St. John, you will need one if going to the BVIs.


On the List for Our Next Trip

I can’t wait to try a few of these places later this year.

LIME OUT
LimeOut

LimeOut: A floating taco restaurant off the east end of St. John in Hansen Bay, LimeOut is known for its inflatable floats where you can drink & dine while floating in the ocean. You have to take a boat (you can’t swim or kayak), so check out their website for suggestions.

Floating Restaurants Offer Pizza & Tacos | US Virgin Islands
PizzaPi

PizzaPi: Another floating restaurant, located in Christmas Cove in between St. Thomas and St. John, PizzaPi has floats like LimeOut, but also the ability to “drive-through” on a boat for takeout.

Soggy Dollar bar - Jost Van Dyke
Soggy Dollar in Jost Van Dyke, BVI

Jost Van Dyke: There’s a legendary beach bar, the Soggy Dollar, on this tiny island in the BVIs that I really want to try. For some unknown reason, my fav sushi spot in Cohasset MA has a live-feed of the beach in front of the Soggy Dollar and I need to see it IRL.

Photo of vibe
The Longboard

The Longboard: From the pics, this looks like an upscale island vibe kind of a restaurant right in Cruz Bay. Harbour Island meets Miami type vibe.

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