Key West Getaway: A 3-Day Adventure in Paradise

Start your Key West adventure with a Cuban coffee—you have to! Our favorite spot is Cuban Coffee Queen, where they serve iced coffee with coffee cubes (yep, coffee that gets better as it melts). Plus, they’ve got a quick service breakfast, so you’re fueling up and getting your caffeine fix all in one shot.

Then, dive into the island’s history and quirky museums! Here’s a quick rundown of our faves:

• The Hemingway Home: Psst… look out for the famous six-toed cats.

• The Lighthouse Museum: Climb to the top for a killer view of the island.

• Truman’s Little White House: There is a free museum that’s small but totally worth it—the kids loved it. You can also pay for a tour.

• The Butterfly Garden: Prepare for some serious photo ops with beautiful butterflies!

These places are all close to each other, so you’ll easily hit them all before lunchtime.

Once you’re done soaking in the history, head over to Seaside Café at the Mansion for lunch. You’ve gotta try the lobster pizza and the honey butter lobster biscuits—trust me, they’re as good as they sound. And don’t skip the frozen key lime pie drink! While you're there, ask the staff about “the bullet hole” and grab a flyer to read up on the mansion’s history.

Next, it’s time for that iconic Southernmost Point Buoy photo. Yes, there’s usually a line, but it moves fast! And if you’re feeling thirsty while you wait, there's a frozen drink stand nearby.

After your photo op, you can either head back to your hotel for a dip in the pool or freshen up for the evening. For dinner, make your way to Conch Republic Seafood and order the conch fritters (trust me, it’s a must).

Then, grab a slice of key lime pie from Kermit’s or Key West Key Lime Pie Co. (or both, no judgment) and head to Fat Tuesday’s for a frozen drink. Finally, finish your night at Mallory Square—the spot for the best sunset view and some seriously talented street performers. Our kids’ favorite part of Key West was the performers, so we were at Mallory Square every night!

You can’t come to Key West and not get out on that gorgeous, blue water—it’s basically a rule. Whether you’re into jet skis, snorkeling, wildlife tours, or just floating along on a breezy afternoon booze cruise, there’s an excursion for everyone. Our crew loved the shark and wildlife viewing tour—we learned all about sharks (spoiler: they’re cooler than you think) and even spotted an eagle ray gliding by!

Start the day with breakfast at Harpoon Harry’s or Blue Heaven—both are delicious and kid-approved—then head out for some sun-soaked adventure.

After your day on the water, kick back and relax at your hotel for a bit. In the evening, if you’re traveling kid-free, it’s time to hit up Duval Street for a lively night out—think Sloppy Joe’s, Fat Tuesday, Rick’s, and plenty of music and good vibes. If you’ve got the kiddos in tow, grab a drink to-go and wander back to Mallory Square for another round of sunset magic and street performer fun. It’s a perfect way to wrap up a classic Key West day.

What’s a vacation without a little souvenir hunting? Today’s the day to explore the charming shops of downtown Key West—hit up the market at Mallory Square and take a stroll down Duval Street for everything from quirky gifts to tropical tees.

Grab a cookie or a slice of creamy key lime pie from Mattheessen’s (no judgment if you get both), then pop into the Key West Aquarium for a quick break from the heat—bonus: your ticket is good for two days! Right next door is the Shipwreck Museum, which is a total hit with kids and curious grownups alike.

For lunch, swing by Little Whitehouse Subs (so good!) and fuel up with an iced coffee from Cuban Coffee Queen. Everything’s walkable, so take your time wandering and keep an eye out for the famous Key West chickens and roosters strutting around town like they own the place. Once you've shopped and snacked your way through, head over to Fort Zachary Taylor for some ocean breezes, iguana spotting, and—if you’ve got little ones—a splash pad perfect for cooling off and burning off energy.

End your day with a sunset dinner cruise or choose from one of the island’s amazing seafood spots—try Thirsty Mermaid or Kaya Island Eats—or head back to Blue Heaven for round two (this time, don’t skip the pie). With so many great options, you really can’t go wrong.