Caneel Bay

St. John, US Virgin Islands

The Proposition: It’s clear from the moment your private ferry taxis you into Caneel Bay that this resort is different than most. Founded by conservationist Laurance Rockefeller, the property sprawls across 170 acres jutting into the Caribbean Sea. Though there are 166 rooms (starting at $549) spread across its seven private beaches, even at full capacity you’ll feel like the only soul enjoying this paradise. 

When God created heaven, he used Caneel Bay Resort as the model. And I swear that’s not just the bottle of Cruzan rum (gifted to each guest at check-in) talking. I’m sitting in a lounge chair, a few footprints in the sand leading back to my ocean-facing room, the clear water and blue horizon off Turtle Bay beach ahead. It’s like I fell asleep and woke up in a postcard (or a swimsuit spread in Sports Illustrated, which used this very beach as a backdrop a few years back). 

- Advertisement -

This afternoon of relaxation comes on the heels of a morning spent exploring. I hiked Mary’s Trail, the property’s half-mile loop that offers Instagram-worthy lookouts off the island’s north shore. Then it was a short stroll off-property to Honeymoon Beach for a group watersports excursion. We kayaked a few miles as our guide pointed out the celebrity mansions barely gripping the island’s massive hills. Hopping into the water, we spent the next hour or so snorkeling with turtles and sea creatures popping up to say hello.

 Now it’s time for what the resort offers in spades: pure relaxation. And that, of course, includes a sunset catamaran sail around the island. As we embark on the sail, with steel-pan music filling the air and the bartender filling my rum punch, I realize there’s only one place I want to be: right here. (

Do: Tennis

Grab a racquet and head to one of Caneel Bay’s nine tennis courts (the resort is among the top spots for tennis in the Caribbean). Down a partner? Join one of the club’s clinics or social round-robins, sign up for one-on-one instruction, or let the pro shop match you with another guest. 

Dine: Zozo’s at the Sugar Mill

- Partner Content -

If I had one last meal on earth, I’d choose Zozo’s—and not just for the food. The open-air restaurant, built atop sugar mill ruins on the resort’s grounds, offers one of the most beautiful atmospheres you’ll ever find.

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.