A Guide to (Mostly) Key West

Hemingway House - Even if you’re not much of a reader or much of an Ernest Hemingway Fan, don’t miss the opportunity to tour the home and grounds of Hemingway’s residence. Be on the lookout for the famed six toed cats, of which there are about 60!

Go during a festival - Key West is home to tons of amazing festivals every year: Hemingway Days, Lobster Fest, Seven Mile Bridge Run, Florida Keys Island Fest, Key West Fantasy Fest, Mile 0 Fest and Key Western Fest to name a few. Expect to pay a premium for lodging and for crowds to be higher but to have an epic trip in return.

Southernmost Point - Admittedly, this land-anchored concrete buoy denoting the southernmost point in the continental US is more of a 5 minute stop than something to do; however, it is quintessential Key West and worth standing in line with the other tourists for a quick photo-op.

The Turtle Hospital - Spend an hour or two at this active turtle hospital and rehabilitation center where you’ll get to feed residents at the end. Great for kids and families. Be sure to book ahead online.

Visit John Pennekamp Coral Reef State Park - Make the trip back up north to John Pennekamp Coral Reef State Park for snorkeling or diving in the undersea park. Glass bottom boat tours, kayaking, paddle boarding and other activities are also available.

Seven Mile Bridge / Drive The Florida Keys Overseas Highway - You can totally fly in and out of Key West’s airport, but the drive from the south of Florida to Key West is about 125 miles and is really quite beautiful. Stop at smaller keys to enjoy a far less crowded and some would say more authentic Florida Keys experience.

Hire a fishing charter - But Ashtin… I don’t fish! Same, friend! I’ll tell you though, one of my favorite memories in The Keys is spending the day on the water fishing, which is something I never thought I would actually enjoy. Bring lots of sunscreen, plenty of beverages and a good attitude and you might find yourself returning to shore with a freshly-caught dinner and a lot of fun memories. And don’t worry, boat staff will put the worm on your hook if you ask nicely. :)

Visit Dry Tortugas National Park: Seventy miles west of Key West by boat or seaplane lies Dry Tortugas National Park, one of the least-visited and therefore least-crowded national parks in the US. But listen, She. Is. Stunning. Snorkel, scuba dive, do some bird watching, enjoy the beaches, visit Fort Jefferson and if you’re feeling ultra adventurous, camp out overnight on Garden Key.

Kermit’s Key West - My favorite to-go key lime pie in Key West. Have a classic slice or a slice dipped in chocolate. Have key lime pie every day. This is a judgment-free zone!

The Lobster Shack - This Key West staple serves up some of the best lobster dishes. Lobster rolls, lobster grilled cheese, lobster BLTs… are you hungry yet? Open Tuesday-Saturday from 11am-4pm only.

Little Pearl - This cute little neighborhood restaurant and wine bar focuses on local seafood. Try the chef’s tasting menu for an extra special treat.

Florida Keys Brewing Co - On your way back from John Pennekamp state park, stop at Florida Keys Brewing Co on Islamorada for some local brews in the beer garden.

The Bull + Whistle Bar - Prime for people watching with its location at the corner of Duvall and Caroline. They don’t have a food menu but they typically are very cool with BYOF.

Calusa at Baker’s Cay Resort Key Largo - Creole/Caribbean food is served seaside at Baker’s Cay Resort on Key Largo. Make a reservation on OpenTable and linger with a cocktail while the sun goes down.

Shipwreck's Bar and Grill - My favorite dive bar in the Keys, located in Key Largo. Just trust me on this one.

Sunset Pier - As the name suggests, the perfect place to enjoy a tropical cocktail and watch the sunset. Look for the pier with the lime green umbrellas.

First Flight Island Restaurant + Brewery: Cold beer, good food and a fabulous outdoor dining space. Happy Hour is from 4-6pm daily at the Crash Bar.