The 10 Key West Must-Dos

The Conch Train

Number One by a landslide. Take the Conch Train tour. Do it first thing. Sure, it’s a “touristy” thing, but we locals do it all the time (we get to ride free on the first Sunday of the month). The Conch Train tour gives you a terrific ride through all the Key West neighborhoods and a real feel for the island and its history. Worth every penny. Do both legs and get your bearings for what you’d like to come back to.

Fort Zachary Taylor State Park

Spend the day on this beautiful beach; tour the historic fort; have a cookout; watch the sunset. Located just a few blocks from historic downtown and Duval Street, Fort Zach is a locals’ favorite. You can walk in, bike in or (if you must) take your car. Taxis, Uber, Lyft all go there, too. Park closes exactly at sunset, so plan to high-tail it out the instant the sun drops below the horizon. There’s a concession stand with food, umbrella and chair rentals and bathrooms.

A Key West sunset

Everyone has sunsets back home, but if you catch one of our best, you’ll be, as they say, “gob smacked.” We celebrate sunset every single night. There are four great ways to do sunset in Key West.

1. The USS Coast Guard Ingham: One of Key West’s best kept secrets and almost like having your private sunset celebration aboard this historic ship. Five bucks to get in; five bucks for wine – and all the view you can hope for – and no crowds. Sunset celebrations are Friday and Saturday.
2. Mallory Square: This is the biggie and the one that gets all the publicity. Worth doing once just to see what all the buzz is about. Free.
   The Knight Pier (AKA to locals as the White Street Pier): Extending about a quarter mile into the Atlantic, the White Street Pier is my go-to sunset. The pier is located at the end of White Street, which is about a mile walk from downtown. No crowds and spectacular views from all sides. Free.
3. A sunset sail: They’re all good. Get reservations in advance. Spend a couple hours loving the water, sipping a beverage, watching a sunset and dreaming about the days when sailing ships ruled the world. Cost varies.

Duval Crawl

(Not for kids) If you’re visiting, you have to do this. Walk from the Atlantic to the Gulf, up one side of Duval and down the other. About a mile each way. There are bars and restaurants too many to count. Stop in them all. Enjoy the live music. Upper Duval (that’s the Atlantic end) is filled with art galleries and nicer retail shops and not as crowded. Lower Duval (the Gulf end) is what we call “tourist town.” Get your T-shirts here. Do not; repeat, do not, stop in or buy anything in the Lower Duval cosmetic shops. Too easy to get swindled. I’ll admit that Duval Street can be a bit overwhelming; it’s not as quaint and inviting as it was even five years ago, much less 20 or 30. Locals don’t go there often – except for the restaurants, theaters and music. But, it’s still worth making the Duval Crawl. And, if you’ve got time, wander sideways to Whitehead and Simonton streets. Do the cross streets to find delightful shops and great restaurants.

The historic seaport

A tad commercial these days, but what a great place to wander the waterfront, explore delightful shops, grab a bite to eat and an adult beverage and listen to live music at Schooner Wharf. One of my personal favorites is sitting outdoors at Schooner Wharf and whiling away an afternoon.

The Key West Cemetery

Yes. Really. It’s beautiful, historic, still active and smack in the middle of town. Bike, walk. No cars. Wander up and down the “streets,” explore the historic markers and read the names of the men and women who made – and make – Key West home.

Snorkeling, kayaking, dolphin watch, day sails

If the weather is good, go for it. Can’t go wrong with any of the charter services, though I’m kinda partial to the Lazy Dog and Honest Eco folks just because they’ve been doing these things forever and have it down to a science. The trip to a sandbar is wonderful

Fort Jefferson and the Dry Tortugas

Take the Key West Dry Tortugas Ferry and make a day of it. Explore historic Fort Jefferson, get in some great snorkeling and enjoy the 2.5 hour, open water ride each way. You’re almost guaranteed to see the massive sea turtles. Note: This is a full day trip. Leaves at 7 a.m. and returns about 5:30 p.m. Reservations a must. (And, you can camp overnight if so inclined. One of my favorites! Definitely not for kids under mid-teens. And teenagers are likely to be bored silly.)

Do a walking tour of Key West neighborhoods

You can take a group tour or do it on your own. The island is only about five square miles and you’re not going to get lost (you’ll end up at water no matter which street you take.) Not many tourists get off Duval and the handful of streets right around it. Take the time to walk along Fleming and Southard. Walk Olivia from one end to the other. A walking tour means you’ll actually see the real Key West, the one we live, work and play in. The one we love.

And the other stuff

These are my 10 (now 11) favorite things to do when we have guests and if you want more “structured” destinations and venues:
a. The Hemingway Home: Lines can be long if there are cruise ships in town. Get there when it opens.
b. The Key West Lighthouse: Across the street from Hemingway. Climb to the top and be blown away by the 360-degree island and ocean views.
c. The Butterfly and Nature Conservatory: Butterflies and flamingos.
d. The Shipwreck Museum
e. The Key West Aquarium
f. The Key West Tropical Forest & Botanical Garden (on Stock Island, so grab a cab.)
g. The Key West Garden Club at West Martello Tower (near White Street Pier and Higgs Beach)
h. Ghosts and Gravestones tour: Hop on the trolley for an evening tour of our haunted places.
i. Truman Little White House
j. The Custom House
k. The Truman Waterfront Park: You can combine it with your Fort Zach day or your Ingham sunset. Got kids? The interactive water park is a must-do!