Welcome to Paradise: 4 Days in the Virgin Islands

I’ve been visiting the Virgin Islands in the Caribbean for over twenty years and have a family-owned villa on St. Thomas that I frequent at least once per year. On each visit I discover somewhere new to explore in addition to my tried and true favorite spots.

After being inflicted with two Category 5 hurricanes in September 2017, you may be wondering if the Virgin Islands are worth a visit. I can assure you, they are! Six months after the hurricanes I took a trip to St. Thomas and was amazed at how quickly nature rejuvenates. The beauty of the turquoise water never fades, but the flora of the island had taken a beating. Just six months later the island was lush and green again, palm trees were being replanted across the beaches, and normalcy was being restored. The power is ON and the islands have just as much to offer as ever!  While many hotels have not yet reopened (as of this posting in August 2018), there are still many options for renting villas, homes or condos. I’m here to tell you how you can get the most out of your 4-day trip to the Virgin Islands and bring much needed tourism to the people who live there.

Where to Stay

Stay on the East End. There are plenty of villa rental options and you will be close to the nightlife of Red Hook, as well as the ferry that goes to St. John and other islands.

View from Cowpet Bay East villas on the East End of St. Thomas

How to Get Around

Rent a Jeep. What better way to explore the curvy, scenic roads of St. Thomas than in a soft top jeep! Just remember to drive on the left side of the road! Taxis are also available, but don’t expect a ride from Uber or Lyft, as they do not currently operate on the island.

Helpful tip: Grab a copy of the St. Thomas/St. John THIS WEEK magazine. You can find them at the airport and also outside the pharmacy in Red Hook. This will give you helpful tips for your stay, including restaurants, current events, ferry schedules, shopping and the number of cruise ships in town per day. Knowing the number of cruise ships in town will help determine how busy certain areas will be, such as downtown shopping and Magens Bay.


Day 1

Magens Bay

Why not visit a beach that was voted one of the top 10 most beautiful beaches in the world? Known for its 1 mile long, heart-shaped beach, Magens Bay has some of the most beautiful, clear water you will ever see, plus all the amenities you need to make a day of it. There are several restrooms and changing areas, a beach bar and concession stand, a well-stocked gift shop with bathing suits, sunscreen and souvenirs, as well as beach chair rentals. There is also a beach hut renting stand up paddle boards and kayaks.

Must have: The rum punch! 

View from Magens Bay Beach Bar with their famous rum punches. This picture was taken 6 months post hurricanes Irma and Maria – still as beautiful as ever!

Helpful tip: Late afternoon is beautiful and quiet at Magens Bay. Cruise ship visitors are usually gone by 2:00 p.m. Hang out until sunset for a peaceful afternoon.

What to Eat

  • Breakfast: Grab a quick bite and an iced coffee from Latte’s in Paradise in Red Hook
  • Lunch: Magen’s Bay has a concession stand with burgers, fries, pizza, sandwiches and salads
  • Happy Hour: Grab a drink and a light bite at the Cruzan Beach Club @ Sunset Grille, Secret Harbour
  • Dinner: Caribbean Fish Market, located at the Elysian Hotel. Enjoy fresh seafood and views of Cowpet Bay. They often have a piano player in the lounge area.


You must check out Duffy’s Love Shack, an open-air parking lot tiki bar. Yes, it’s a tourist trap with its tropical drinks that come in souvenir glasses with over-the-top drink flair, but you can skip all that and just order a rum and coke in a plastic cup if you wish. Wednesday night is ladies night and women drink for free! Enjoy the music, the people watching, and dance the night away at this quirky, crazy bar.

Across the street you can also check out Island Time Pub (ITP) known for their pizza and outdoor bar overlooking the marina. Next to ITP is Caribbean Saloon, which is a lively restaurant/bar with slot machines, music and karaoke on Friday nights.


St. John

Just a quick, 15 minute ferry ride away is the beautiful, unspoiled island of St. John. If you rented a jeep, take it over on the car ferry so you can explore the island and its many hidden beaches. Otherwise, you can rent a jeep on St. John or take a taxi.

Use this guide to get a little more info on the beaches before you go: St. John Beach Guide Driving along North Shore Rd will lead you to many of the most beautiful and most popular beaches, such as Trunk Bay and Cinnamon Bay. But be sure to explore the little, hidden gems, as well.

View of Trunk Bay from North Shore Rd

Helpful tip: Looking to snorkel and see sea turtles? Find a beach that has sea grass in the water. Maho Bay is a great spot. Don’t chase or touch the sea turtles! It is against the law in the U.S. and you could be fined up to $10,000.

Did you know? 60% of the island of St. John is considered a National Park. If you enjoy hiking there are plenty of options. Just check out this web site: National Park Service

Where to Shop

St. John is great for shopping too! Walk around Mongoose Junction, the beautiful stone and mahogany shopping center, and Cruz Bay near the main passenger ferry terminal. For beautiful, island-inspired handmade jewelry, check out Bamboo Studio, a favorite of mine.

What to Eat

  • Breakfast/Lunch: Eat at High Tide Bar & Grill located in Cruz Bay near the ferry terminal
  • Happy Hour: Stop at Longboard for happy hour from 3-6 and grab a bite and a drink. They are always coming up with new, original food and craft cocktails.
  • Dinner: When you arrive back in St. Thomas, have a casual dinner in Red Hook after your long day on St. John. Try Fish Tails for some casual seafood or The Tap & Still for a burger and a brew.


The Baths & Soggy Dollar

Get out of the U.S for the day and head to the British Virgin Islands to see pristine beaches, unique rock formations, and enjoy one of Soggy’s Dollar’s famous Painkillers. Meet your New Horizon charter at the Sapphire Marina in St. Thomas at 7:00 a.m. for a full day exploring the British Virgin Islands.

You WILL need your passport for this excursion so don’t leave home without it!

First Stop: The Baths at Virgin Gorda

Tour the baths, climb through hidden caves and pools and splash around in the crystal clear water. Then have lunch overlooking the Baths before returning to the boat.

The Baths at Virgin Gorda
The famous “Cathedral Room” at the Baths

Second stop: Jost Van Dyke

Swim to shore and enjoy the afternoon on the beach at White Bay. Here you will find the famous Soggy Dollar bar, aptly named due to the need to swim to shore with your money.


White Bay, Jost Van Dyke

What to Eat

  • Breakfast: A light continental breakfast will be available on the boat
  • Lunch: Enjoy lunch with a view at the Top of the Baths. There is also food available at Jost Van Dyke.
  • Dinner: Head back to Red Hook for dinner at XO Bistro. It is an upscale wine bar with great martinis and a nice dinner menu. Seating is limited so make a reservation or try to grab a seat at the bar.


Choose Your Own Adventure

It was so difficult to decide where to send you on your last day! A relaxing half-day sail or a beach day on a quiet island off the coast of St. Thomas? I’ll give you the rundown of both and you can choose your adventure!

Adventure 1: Sail, Snorkel & Shop

Head downtown to Yacht Haven Grande where you will meet Captain Mike of Fury Charters. The morning sail is from 8:30 a.m. – noon and will take you to Buck Island on a 46′ sailboat, where you will swim with sea turtles, enjoy rum punch and other beverages as well as light snacks. Bring your underwater camera or GoPro to capture the magnificent sea life!

You will not be crowded onto this boat with tons of people like some other excursions. There are plenty of comfortable sitting and sunning areas throughout the boat. 

When the boat returns, enjoy lunch and duty-free shopping in the capital of St. Thomas, Charlotte Amalie. You will encounter historic buildings, stone passageways and shop after shop, including everything from fine jewelry and art to souvenirs and clothes.

What to Eat

  • Breakfast:  Grab something on the go or enjoy the granola bars and lights snacks on your sail.
  • Lunch: Dine at the Greenhouse in Charlotte Amalie. Sit by the window for a nice view of the harbor and you may see a few cruise ships docked. Must have: Bang Bang Shrimp
99 Steps of Charlotte Amalie

Adventure 2: Water Island & Charlotte Amalie

From Crown Bay Marina in Charlotte Amalie, you can catch a 10 minute ferry over to Water Island, a quiet island with no stores, hotels, or taxis and less than 200 residents. When you arrive on the island you have the option of renting a golf cart to get around or taking a shuttle bus to Honeymoon Beach (not to be confused with the beach of the same name on St. John). A short ride on the bus brings you to Honeymoon where you will often see sail boats anchored past the swim area and great snorkeling spots (including grassy areas where the sea turtles feed).

View from the beach on Water Island

There are only two restaurant options, both of which are casual beach bars. I enjoy Heidi’s Honeymoon Grill because you can watch them cook on open flamed grills. Pull up some lounge chairs, grab a beer and enjoy the serenity of the island. Bring some snorkel gear so you can snorkel along the rocks or search for sea turtles in the long grass.

When you’re done at the beach, head back to Charlotte Amalie and go shopping!

What to Eat

  • Breakfast:  Tickles Dockside Pub is right where you will be meeting your ferry to Water Island and they’re always serving up delicious, casual dishes.
  • Lunch: Have a cheeseburger in paradise at Heidi’s Honeymoon Grill on Water Island (or anything else they might be throwing on the grill).

The Last Supper

Save the best for last. Head to Yacht Haven Grande for a delicious meal at Grande Cru Restaurant & Wine Bar, an upscale dining experience with fresh seafood and creative dishes. Get a table on the outdoor deck overlooking the marina and million dollar yachts. End the night with one of Grande Cru’s signature cocktails or martini’s and make a toast to a great trip!


How can you help the islands?

Although things are getting back to normal, many residents are still struggling to rebuild. Many still live with blue tarps in place of roofs and have lost jobs due to the closing of hotels and businesses that have yet to reopen. Just visiting the islands will bring much needed tourism income, but if you’d like to do more to help the people of the Virgin Islands, below are a few reputable charities that are directly helping the residents:

  • Adopt a Family USVI – Connect with a family, school or business and send them the supplies they need most in both the USVI and Puerto Rico.
  • Virgin Islands Relief Fund – Dedicated to the rescue, relief and rebuild of the islands
  • Love for Love City – Relief fund started by country music superstar, Kenny Chesney, a regular staple in the Virgin Islands. He is working with local charities to channel the relief directly to the people who need it most.

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