As told by DIWYY co-founder, Jerri, who previously lived and worked in the Caribbean.

When I went: I lived there while working on a yacht from November 2004 to March 2005 and have been there a few times since on other yachts I was working on. This is the peak season for travelers since hurricane season is mostly over and it’s winter in the Northern Hemisphere so lots of snowbirds are coming down to the Caribbean to get away from the cold weather.

How I Got There: Most of the times I got there by boat. Once we sailed there from Key West and it took about 5 days.  Another time I went I flew to St. Thomas’s Cyril E. King airport (STT) from Miami on American Airlines and then took the ferry from St. Thomas’s, Charlotte Amalie dock to Cruz Bay in St. John.

Where I stayed: Well, I lived on a 110′ Palmer Johnson Ketch moored in Honeymoon Bay, St. John. We had to take the tender into Cruz Bay to get on land.  Since St. John is a small island covered mostly by a national park, lodging options are pretty limited. They range from high end hotels like Caneel Bay and Westin, privately owned villas, to eco-tents on campgrounds like Maho.

Things to do: St. John is famous for the Virgin Islands National Park which takes up about 60% of the island including the coral reefs and ocean offshore. There are a lot of hiking trails with beautiful views of the Caribbean.  Ruins from the old sugar plantations are a must see. Scuba diving and sailing are extremely popular, of course, all around the island.  Mongoose Junction in Cruz Bay has excellent shopping and some consider it to be like the Beverly Hills of the Caribbean. There are plenty of excellent restaurants around the island as well as the the infamous walk-up shacks where you can get a Caribbean favorite, the Roti.  Odd fact: There aren’t any movie theaters in St. John. If you wanna catch the newest flicks you’d have to ferry over to St. Thomas. Don’t worry, you’ll still find plenty of other things to do.

How I got around: It’s pretty easy to catch a taxi in the main areas of St. John like Cruz Bay and your hotel can always call one for you.  If you’re going to be there for a while you can also rent a car but they’re super expensive. If you don’t plan on driving much, your best bet is just taking a taxi.  While romantic and adventurous, scooters aren’t really safe or recommended because of the hilly terrain. You can also walk around in places like Cruz Bay.

Language tips: Since it’s the United States Virgin Islands everyone will speak English but there are different languages spoken on the island from Spanish to French Creole. Be prepared. They speak pretty fast there so you’ll probably be asking them to repeat themselves.

What To Bring: You don’t need any long sleeves or really any long pants (unless maybe you have some light linen pants) so don’t even use up that space in your luggage. You’ll need your swimsuit, shorts, t-shirts, dresses for women, some button down shirts or polo shirts for men, flip flops/sandles and tennis shoes if you plan to go hiking and probably a hat for protection from that tropical sun. If you know you’re going to a nice restaurant try and find out in advance if they have a dress code. Most don’t have formal dress codes anymore but it’s good to know just in case. It’s very unlikely that you’ll ever need heels. And bring plenty of sunblock!

Other advice for someone wanting to go to this location: Just like any other place you travel, remember to stay safe. While the Caribbean is as close to paradise as you can get, it is not crime free. Never walk anywhere alone at night. Make sure you always have a trusted friend with you at all times and let people know where you are going.

Email Jerri at jerri@diwyy.com. Have more questions about the Caribbean? Visit the DIWYY forums and let the discussion begin!