Secret Escapes: Puerto Rico & U.S. Virgin Islands


Where do you go when you get a six week (mostly) all expense paid vacation? That was the question facing my friends Jake and Em as they considered how to spend their honeymoon. Instead of wedding gifts, the smart adventure-savvy duo asked well-wishers to toss their dead presidents into a travel fund. The only question was…where to go? This was an especially interesting question for Jake—possibly the most well traveled globetrotter I know.

So when he chose Puerto Rico and the US Virgin Islands I wanted to know why. I also handed him a GoPro and said…take notes. It was the right call.

Why Puerto Rico and The USVI?
Because it’s relatively cheap, fast, and easy to get there (for an American). As a US territory, there are no customs forms or currency exchange to hassle with. It’s also super laid back. The USVI defines the idea of “Island Time.” So finding your own little slice of paradise isn’t hard. Also, Puerto Rico’s Old San Juan district has a vibrant arts and culture scene with a diverse array of bars, cafés, and restaurants packed into the blue cobblestone streets and open courtyards of an an epic 400-year-old colonial Spanish garrison. If you’re looking for a cheap, fun, romantic adventure that takes little more than a driver’s license, credit card, and carry-on bag…it’s pretty hard to beat.


Getting There
Flights into either San Juan Puerto Rico (SJU) or St Thomas (STT) are relatively inexpensive, with SJU trending about $100 cheaper. Puddle-jumpers between the islands run around $80-$100. Jake and Em kicked their honeymoon off by flying from Portland, Oregon to Charlotte Amalie, St. Thomas, renting a jeep and touring the island for a few days, and then branching out to the other islands via ferry and plane—returning home from Puerto Rico (for about $1000 in flights). Bonus Jake tip: If you fly from St. Thomas to San Juan, bundle in a rental car for extra savings.

Staying There
The Galleon House in Charlotte Amalie (the largest town on the island of St. Thomas—described fondly by Jake as a “Jamaican-flavored Monaco”) is a good starting point. In addition to being centrally-located near Blackbeard’s castle and the diamond district, it has a small pool, a complimentary breakfast, and a cool owner. Also, Airbnb is your friend—making it easy to find/pay for lodging as you go on one simple tab.

Being There
A jeep is essential if you want to enjoy St. Thomas by land—but the best rental deals are found away from the airport (head to “yacht haven” or ask your hotel for a local recommendation). The island roads are steep, narrow and windy—but deliver an awesome payoff in the way of secluded beaches, lush jungle canopy, and delicious roadside food stands. One of those food stands located on nearby St. Johns (accessible by ferry) is Vie’s Snack Shack, where you can pay a small fee to access Hansen Bay for a killer day of swimming/snorkeling and walking back up the trail to get another piece of Vie’s delicious fried chicken. Hull Bay on St. Thomas is an excellent spot for snorkeling and surfing. In Puerto Rico, there’s much to do and see in Old San Juan—which has a thriving tourist economy coupled with a culturally vibrant local scene and a dash of fringe-wandering expats. If you have the skills, you can hit up Rincon the island’s legendary surf spot. Or you can do a short hike to the “local’s swimming hole” at Gozalandia Waterfall in San Sebastian and get your cliff jumping on.

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