Like so many people, we never moved to the Keys—we just ended up here. Since the early days of vineyard vines, we’ve been a steady fixture on the water, in the watering holes and up and down A1A. It’s where we took the crew for our first-ever company outing, where we’ve had nights we’ll never forget and a few we don’t remember. We’ve brought our friends, families and customers. We’ve shared with all of them what we love about the Keys, and now it’s our time to share our stories and friends with all of you.

LIGHTWEIGHT AND READY TO FLY

Button-Downs

Pants

Quarter-Zips

Lightweight Layers

PLACES TO "SEA"

TOP SPOTS FOR BEST VIEWS & VIBES

ALLIGATOR REEF LIGHTHOUSE

Located about 3 miles offshore, this iconic lighthouse sits atop a stretch of water that bridges the shallow reefs of the Upper Keys with the deeper reefs of the Middle Keys, making it a prime spot for snorkeling and fishing.

ROBBIE'S OF ISLAMORADA

Hand-feed massive tarpon, stock up on local wares or feast on fresh seafood—you can do it all at this one-stop-spot for all the best of what Islamorada has to offer.

ISLAMORADA SANDBAR

Less than a mile offshore, this popular hangout spot features crystal clear water, soft sand and picture-perfect views, making it the ideal place for swimming, snorkeling and soaking up island

party vibes.

SHOP ISLAND-HOPPING ESSENTIALS

WHERE TO GET A BITE

WITHOUT HAVING TO STICK YOUR HAND IN FRONT OF A GATOR

LORELEI RESTAURANT

We loved the Lorelei when we first visited in 1999 for Shep’s bachelor party. And there’s a reason we keep coming back whenever we’re in Islamorada. Well, actually a bunch of reasons: the food is great, the drinks are strong, the live music’s rocking and the view is unbeatable.

THE GREEN TURTLE INN

An Islamorada icon since 1947, the Green Turtle Inn still offers diners the most authentic Florida Keys cooking around. We’re big fans of the laid-back vibes, the breakfast menu and the not-to-be-missed specials, featuring just-caught seafood.

GARDENIA’S BISTRO

A mother-and-daughter run local gem serving up organic, sustainably-sourced nourishment. You won’t find better wraps and smoothies in the Keys. Pro move: stop in for a quick coffee before heading out on your island adventure.

GEAR UP FOR A DAY ON THE WATER

HOW TO PREP FOR A FISHING TRIP

FROM TROLLING THE FLATS TO OFF-SHORE ANGLING

READ UP

Tarpon are the ultimate Keys trophy—powerful, unpredictable, and not exactly easy to land. Do a little homework so you know what you’re up against (and can enjoy every jump, run, and near-miss along the way).

GEAR UP

For the best selection of saltwater flies in all the Keys, stop by Florida Keys Outfitters before your trip. (And if you happen to bump into our good friend and local fly-fishing legend, Sandy Moret, tell him we said hi.)

EASE UP

In the Keys, the best fishing often starts once you leave the crowds behind. Go fast to get away, then slow down to fish. Keep an eye on the flats, trust the water, and enjoy the kind of fishing that rewards patience over pressure.

SHOP FOR YOUR FAMILY GETAWAY

(THEY CAN'T ALL BE GUYS' TRIPS, AFTER ALL)

Boys'

Girls'

PLACES TO GET AWAY

WHEN YOU NEED A VACATION FROM YOUR VACATION

THE MOORINGS

We send friends here when they want the “before-it-was-a-thing” Keys. Family-owned and shaded by palms, it feels more like a private beach hideaway than a resort—unhurried, uncrowded and quietly charming.

CHEECA LODGE

Dive into resort mode with a luxe spa, a round of golf and plenty of on-site dining when you feel like staying put. Private balconies and oceanfront views invite you to slow down and settle into island time.

ISLANDER RESORT

An Islamorada favorite that stretches from oceanfront to bayside. Choose a bungalow, suite or villa, then do the Keys your way. Water sports and daily activities, a night of local fine dining—or a beach chair and zero agenda.