9 Easy, Breezy Island Trips to Take from Philadelphia

Let the last two years of frustration and complications drift away at these beachy island getaways.

Island getaways: The beachfront infinity pool at the Ocean Club in the Bahamas. / Photograph by Rupert Peace / Four Seasons Resort

March marks two years since COVID crashed into our lives — two years of Zoom meetings and remote school and, for many of us, outright languishing. You deserve a break — and what better place to take one than on an island, surrounded by sun-soaked beaches and umbrella-topped cocktails? Whether you’re after romance, adventure, or simple seaside tranquility, these nine island trips are guaranteed to get you flourishing again. —Edited by Regan Fletcher Stephens

Island getaways: A tanning pier at Southernmost Beach Resort. / Photograph by Dylan Cross / Southernmost Beach Resort

Find Calm in the Florida Keys

My wife is a teacher who was desperately in need of a vacation, so when I mentioned the possibility of a long weekend on some island destination, her reply was, “I don’t care where we go. Just get me on an airplane.” So on a frozen Philadelphia morning, I did just that, with the island of Key West as our destination: no passports required, no fussy COVID hoops to jump through. Keep reading here.

Island getaways: An ocean view in Aguadilla. / Photograph by Carlos Rivera / Getty Images

Go West in Puerto Rico

Puerto Rico’s capital, San Juan, offers so much history and excitement that you may never leave it during your stay. But you should. In particular, traverse the island to its more relaxed west coast, where beautiful scenery, charming cities and fantastic food await. Keep reading here.

Have a Feast in Curaçao

Island getaways: A view of Willemstad from Queen Emma Bridge. / Photograph by Westend 61 / Getty Images

You know the moment. The one when you’re somewhere far away from home and you start casually looking up property prices. When you finally learn to order coffee in a language that isn’t your own. It’s that moment when you start planning your permanent move to a place where you only imagined yourself vacationing. That moment comes hard and fast when you’re in Curaçao. It hits you like a coconut from a palm, and it hits you hardest when you’re eating or drinking. Which you’ll be doing incessantly. Keep reading here.

Get Outdoorsy in Bonaire

Island getaways: Free-diving with friends. / Photograph by Tourism Corporation Bonaire

If your idea of a good time on an island vacation involves a lot of lounging in the sand and a drink in your hand, Bonaire probably isn’t the destination for you. For one thing, there’s very little sand. This isn’t by accident; sand can smother a coral reef, and this tiny Dutch Caribbean island fringed by coral and home to the oldest marine reserve in the world is all about protecting its environment. Keep reading here.

Go All-Inclusive in Grenada

Island getaways: Pink Gin Beach at Sandals. / Photograph courtesy of Sandals Resorts.

I arrived at the resort feeling like a wilted flower. The five-minute ride from the airport was a breeze, but the thick humidity, combined with a long morning of traveling, left me weary. My mood lifted in a flash, though, the moment I approached the open-air front desk at Sandals, where a crisply dressed woman welcomed me with a confident smile and a declaration: “You deserve to be here.” Keep reading here.

Fall in Love in St. Lucia

Island getaways: St. Lucia’s Jalousie Beach in Soufrière. / Photograph by Afton Almaraz / Getty Images

If you’re jetting to St. Lucia, you’re likely a honeymooner or a couple on holiday. Otherwise, you’re surrounded by them, as I was on my visit sans husband. But that’s no problem: St. Lucia is worth a trip whether you’re traveling solo or basking in newlywed bliss. Keep reading here.

Be Still in Turks and Caicos

Island getaways: A villa at the Shore Club. / Photograph courtesy of the Shore Club.

There are islands you can visit if you love adventure. And islands you can visit if you love nightlife. But what if you adore sitting? Sitting in a hanging wicker chair over a cool tiled pool, a few steps away from an elegant outdoor bar. Sitting in a chaise lounge, staring out at the ocean, watching kitesurfers dip and spin as the breeze changes. Sitting on the top deck of a party boat as it bounces along the clearest turquoise seas you’ve ever seen. Keep reading here.

Make Family Memories in the Dominican Republic

Island getaways: Beachside restaurant La Palapita at Eden Roc Cap Cana. / Photograph courtesy of Eden Roc Cap Cana

It was our first night at Eden Roc Cap Cana, the beachfront resort in the Dominican Republic, and before I could pull out my phone to capture a ridiculous foaming bathtub surprise arranged by the housekeeper while we were eating dinner, my three daughters were frantically peeling off socks and sweaters to dive into the warm cloud. Keep reading here.

Rekindle the Spark in the Bahamas

Island getaways: The Versailles pool at the Ocean Club, with a view of the terraced gardens. / Photograph by Christian Horan / Four Seasons Resort

“Do you like this liquid sunshine?”

It was raining when we landed in Nassau, the capital of the Bahamas. The flight was short and seamless, a new direct route on Frontier from Philly to the West Indies archipelago, and in a flash, my husband and I went from chaotic PHL to the black car whisking us to the Ocean Club, a Four Seasons Resort, situated on the aptly named Paradise Island. Keep reading here.

Published as “Island Time” in the March 2022 issue of Philadelphia magazine.