The Perfect Game Plan for 3 Islands on the Florida Keys

By Jennifer Ceaser

Whichever side of the spring break spectrum you fall on — from party animal to kid-pleaser — Florida is best enjoyed this season off the mainland.

The Florida Keys are a large collection of islands off the far southern coast of the state.

While there are dozens upon dozens of them to choose from, here’s a guide to three of our favorites — Islamorada, Marathon, and Key West — along with the best places to stay and soak up all that sun and sand.

Islamorada

Girls drinking smoothies poolside at Islamorada’s Cheeca Lodge. (Photo: Cheeca Lodge & Spa)

The biggest challenge when visiting Islamorada — located halfway between Miami and Key West — is mastering the correct pronunciation: EYE-la-more-AH-dah.

Related: How to Catch a Lobster in the Florida Keys

Once you’ve got it down pat, you’re ready to tackle everything else on offer on the six small islands that make up this 20-mile-long key. First and foremost is the world-class sportfishing, but non-anglers have plenty of options, too: Snorkel or dive out on the U.S.’s only living coral reef, or head bayside to paddleboard through the tidal channels and mangroves looking for manatees and the occasional nurse shark.

Dusk falls on Cheeca Lodge’s pier. (Photo: Cheeca Lodge & Spa)

Cheeca Lodge & Spa (from $379) will arrange for all the above; the 212-room oceanfront resort’s lengthy roster of activities also includes tennis and golf (nine holes) on a 27-acre property that’s been a celeb destination since 1946. (Baseball great Ted Williams, George H.W. Bush, Jack Nicklaus and Paul Newman all stayed here.)

For kids, there’s Camp Cheeca; a new game room, complete with Xboxes, will be introduced this spring. Dining options include the family-friendly Atlantic’s Edge (for seafood) and Limoncello (for Italian); couples might prefer the more mature ambiance of the Nakai Sushi Bar, the al fresco Tiki Bar, or the upper-level Chart Room, with a sprawling deck overlooking the Atlantic.

It’s hard to tear yourself away from this amenity-filled resort, but it’s worth heading bayside to catch a spectacular keys sunset. Arrive early to Morada Bay Beach Café to snag an Adirondack chair under the palm trees, then grab a cocktail, stick your toes in the sand and take in the show.

Marathon

Feel the breeze on a beachfront porch at Tranquility Bay Beach House Resort. (Photo: Tranquility Bay Beach House Resort)

Half as long as Islamorada but thick with restaurants, shops, and strip malls (there’s even an airport, mainly for private planes), Marathon’s busyness fades away once you turn off Route 1 and into Tranquility Bay Beach House Resort (from $449).

The aptly named property is situated on 12 lush acres, with a private bayside beach, three swimming pools, and a putting green.

Geared toward families and larger groups, the 87 two- and three-bedroom duplex beach houses have porches, full kitchens, and laundry facilities; there are also 16 new Tropical Garden Guestrooms, perfect for couples.

Grab a cocktail at TJ’s Tiki Bar. (Photo: Tranquility Bay Beach House Resort)

The resort’s flip-flop-friendly TJ’s Tiki Bar is for casual lunches; dinner calls for the upscale Butterfly Cafe, considered one of Marathon’s best restaurants.

Occupy yourself with watersports galore — kayaks, paddleboards, Hobie Cats are available for rent — but you’ll want to head off-site to see the nearby Seven Mile Bridge, the crumbling original thoroughfare connecting the middle and lower keys.

(You might recognize it as the bridge that’s blown up in the Arnold Schwarzenegger film True Lies.)

Key West

Famous for its six-toed cats and roaming roosters, this southernmost key boasts a beautiful Old Town district lined with highly ornamental 19th-century wooden houses that wouldn’t look out of place in chi-chi Charleston.

Beyond the party hearty atmosphere — centered along Old Town’s Duval Street — there is some fine food and drink to be had: Try swanky cocktails at The Other Side, tucked inside an 1838 mansion, and for steaks in very old-school surroundings, there’s Pepe’s Cafe Key West, which dates back over a century.

Related: Provincetown vs. Key West: Which City Has the Best Small-Town Charm?

They’re both within walking distance of The Marker (from $449), a brand-new, 96-room boutique property that breathes some much-needed chic into the tired, B&B-dominated Old Town.

The Marker is Old Town’s first hotel in 20 years. (Photo: Carmel Brantley)

Rooms are big and bright, decked out in bright coastal blues with clever touches like a bedside copy of Ernest Hemingway’s “To Have and Have Not.”

In a Miami-like fashion, guests can be found lounging around the tranquil main pools, sipping cocktails and snacking on Cal-Mex fare from the open-air Cero Bodega restaurant (which also serves a stellar breakfast).

Steps away is the historic seaport where dozens of boats depart each evening for a sunset sail. Opt for a highly civilized adventure aboard the Hindu Schooner ($85), a family-owned and -operated vessel dating back to 1925; the crew serves complimentary fine wines, craft beer and gourmet cheeses (no lame Cracker Barrel here) as you skim across the water and take in one of Key West’s famed sunsets.

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