Island Getaways: A Philadelphian’s Guide to Vacationing in the Florida Keys

There’s more to these islands than Margaritaville.

A tanning pier at Southernmost Beach Resort in Key West.

A tanning pier at Southernmost Beach Resort in Key West. / Photograph by Dylan Cross / Southernmost Beach Resort

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.

Nonstop flights to Key West exist, but they’re expensive and not frequent. So we flew into Miami, rented a Mustang convertible, and took a top-down road trip three hours south along Route 1 (point of trivia: the same Route 1 we call Roosevelt Boulevard and City Avenue up our way). The drive is notable for long stretches of highway over crystal-clear waters, especially the part over the self-explanatory Seven-Mile Bridge.

Upon arrival, we realized Key West isn’t your normal island paradise. First, there are the roosters, which roam the streets and outdoor restaurants in great numbers and crow their little heads off in the pre-dawn hours. (Bring a sound machine.) There are the fighter jets, which scream overhead throughout the day thanks to a nearby military training base for future top guns. And then there’s Duval Street, Key West’s nonstop party corridor, where the packed bars don’t close until 4 a.m. We were going to have to find the chill in Key West, because this cacophonous party scene wasn’t what the doctor ordered. And find it we did.

An oceanfront king room at Southernmost Beach Resort.

An oceanfront king room at Southernmost Beach Resort. / Photograph courtesy of Southernmost Beach Resort

Though I advise you to otherwise avoid Duval Street, we happily stayed at the Southernmost Beach Resort  rooms from $499), which sits on a quiet stretch with epic views of the Atlantic Ocean and the famous Key West sunset. Instead of cruising on the insanely popular Commotion On the Ocean tourist boat, with its live cover bands and free margs, our water excursions included the small-group, eco-friendly snorkeling and dolphin-watch services of Honest Eco — and by golly, we saw lots of dolphins. It was magical. We also took some sea kayaks out into the quiet mangroves, led by a guide from Key West Eco Tours.

We dined at Latitudes, a picturesque destination restaurant you can only get to by ferry. And we stared into each other’s eyes (okay, I might be exaggerating the romance) by candlelight at Santiago’s Bodega, a tapas gem in a residential neighborhood. We only found out about it by asking in-the-know locals (read: bartenders).

Key West is an island, but the resort beaches aren’t what those of us who grew up going to the Jersey Shore think of as beaches. They’re private, tiny and overcrowded, more set up for drinking than relaxing. So each day, we drove about 15 minutes to Smathers Beach, one of a handful of public beaches. There’s a stand that rents umbrellas for $20, but who needs an umbrella when you can shade under a palm tree? We spent hours there each day, only pestered by some of the aforementioned roosters. (They’re literally everywhere.)

Sunrise on Smathers Beach on Key West.

Sunrise on Smathers Beach on Key West. / Photograph by Aisha 5 / Getty Images

We planned our exit from Key West to allow enough time for a quick overnight at the luxurious Isla Bella Vista Beach Resort (rooms from $545) on Marathon island. It’s the kind of breezy, picture-perfect oceanfront place you’ll never want to leave, and there’s little reason to, since the resort is very self-contained and the sunset views will have you in awe. Just be sure to leave enough time in planning your return trip to the airport (it’s about two hours from Marathon) to grab a Key lime pie for the family back home. They’re that good.

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Published as “Find Calm in the Florida Keys” in the March 2022 issue of Philadelphia magazine.