The Calendar is Yours: An Empty Nester's Guide to Key West

Everyone warns you that you’ll miss them, and you will. For twenty years, vacations were planned around tournaments and finals week, in a room with two queens and a pullout, wherever the chicken fingers were good. You’d take every one of those trips again.

Now the trips you’ve been talking about for years are finally yours to take. Here’s why Key West is a good place to start, whether you’re traveling as two or on your own.

Key West Knows a Thing or Two About New Chapters

The empty nest is a new chapter, and Key West has seen a few. Hemingway did his writing here. A young Jimmy Buffett showed up in the early 1970s with a guitar and found his sound.

You don’t need a novel or a hit song to make this chapter count. Just a few days somewhere nobody’s in a hurry. Maybe it starts on a boat headed for the reef, or at a waterfront table that’s been calling your name.

Location, Location, Location: Everything Within Reach

In Key West, the things you’ve been meaning to do aren’t spread across a map. From The Marker, our harbor resort at the Historic Seaport, most are a short stroll or bike ride away. Yes, we have ride shares, but to be honest, you might not need one at all except to get from the airport to the resort. You can be out on the reef in the morning and back in time for a museum before sunset, without once looking for parking. Even a long weekend is enough to cross a few things off.

For more ideas, the Key West bucket list is a good place to start. And if “do absolutely nothing” has been on your list for years, the island makes that easy too. One thing is for sure: you’ll be transported right into that laid-back island vibe the minute you arrive.

Get Out on the Water

For a lot of parents, the reef has been on hold for years. Maybe the snorkel trip got skipped the year somebody was too little, and then it just kept sliding to next year.

Key West sits a boat ride from the only living coral barrier reef in the continental United States, and a day on the water can look however you want it to. Snorkel the reef for the first time, or spend an afternoon standing shin-deep at a backcountry sandbar. Plenty of snorkel, sandbar, and sunset trips leave right from the harbor, a short walk from the resort. Photo courtesy of Fury Water Adventures.

And for the trip you’ve been saving the longest, look about 70 miles west. Dry Tortugas National Park is reachable only by boat or seaplane, and a day there means walking the brick walls of Fort Jefferson and snorkeling along its moat. It takes some planning ahead, which is part of what makes it feel like a someday trip finally happening.

Catch Up on Key West History

You’ve seen plenty of museums at a kid’s pace, which usually meant a quick lap and a long stop at the gift shop. This time you can read every placard.

At the Hemingway Home, descendants of his six-toed cats still have the run of the place, napping wherever they please. Down on Front Street, the Key West Museum of Art & History fills the restored 1891 Custom House. Key West’s museums go well beyond those, from shipwreck salvage to the island’s writers.

And the photos at the Mile 0 sign, the Southernmost Point Buoy, or the Greetings from Key West mural? Send them to the kids with a “Wish you were here.”

Key West Nights: Stay Out Late, or Don’t

After a day of exploring, some pool time, and maybe a quick nap, it’s time to head out. Sunset is how the night starts here. Take an evening stroll along the Seaport and it will find you, or catch it at Mallory Square, where street performers and local vendors gather along the harbor as the sun goes down. You can also watch from the water on a sunset sail that boards a stone’s throw from our harbor resort.

The best waterfront restaurants, live music, and dive bars like Schooner Wharf are right outside your door. Key West nightlife is a little of both: the famous spots everyone should see once, and the small outdoor bar you stumble into and end up loving.

From there, it’s up to you. Stay out late and head a few blocks over to Duval Street, starting with a drink at Sloppy Joe’s, Hemingway’s old haunt. Or don’t, and end the night on your own balcony, overlooking the pool or the harbor, with nowhere else to be.

We’ve Done the Homework for You

After years of checking someone else’s homework, here’s some you don’t have to do. It’s all on our blog. We’ve rounded up 16 museums worth your time, from Hemingway’s house (cats included) to the Truman Little White House. We’ve found the boat trips, whether you want a dolphin watch, a sunset sail with a live band, or a lazy afternoon at a backcountry sandbar. We’ve even done the dive bar research, so all you have to do is pull up a stool. And save room for dessert. Key lime pie every night is completely allowed here.

We’ll Be Back

The empty nest isn’t so empty after all. Somewhere along the way, Key West stops being your someday place and becomes the one where every goodbye ends the same way: “We’ll be back.” #lovethemarker