If your cruise itinerary includes Key West, Florida, get ready for one of the most colorful, quirky, and unforgettable ports in the Caribbean! From legendary bars and delicious eats to scenic photo ops and unique local culture, this tiny island packs in a ton of charm. Whether you’re a first-time visitor or returning for another round of paradise, here are our top 10 things to do in Key West when visiting on your cruise – plus a few bonus tips to make the most of your day ashore.
1. Sloppy Joe’s – Home of the Original Sloppy Joe
No visit to Key West is complete without a stop at Sloppy Joe’s, the iconic bar that’s been a staple since 1933. A favorite hangout of Ernest Hemingway, this lively spot serves up the original Sloppy Joe sandwich, great drinks, and live music all day long. Grab a seat, sip something tropical, and soak in the atmosphere of Duval Street.
Cruise Tip: Key West is full of amazing spots to enjoy a bit of food. We recommend splitting the Sloppy Joe so that you have room for some of the other spots on our list!
Address: 201 Duval St, Key West, FL 33040
Website: sloppyjoes.com
2. Shopping and Art Galleries Along Duval Street
Duval Street is the heart and soul of Key West. Stroll past colorful galleries, boutique shops, and souvenir stands filled with shirts, hats, and other souviners. You’ll find everything from handmade art to Key West-themed apparel. Even if you don’t buy anything, window shopping and people-watching along Duval is an activity in itself.
Cruise Tip: If you’re looking for some inexpensive gifts to bring back home, look for the stores that are “going out of business” for the best prices. Ironically, they’ve been going out of business the past five years we’ve been sailing to Key West. While their faux closing seems to violate marketing laws, their prices can’t be beat!
Address: Duval Street
Website: Trip Advisor’s 15 Best Key West Art Galleries
3. Mary Ellen’s – Lunch and a Frozen Irish Coffee
Remember how we told you to save room for more food? For a laid-back local lunch, stop at Mary Ellen’s, a fun spot known for great comfort food and their famous Frozen Irish Coffee. Fun fact: the owners are friends with the team behind Erin Rose in New Orleans – another spot known for incredible frozen Irish coffees! Between the atmosphere, delicious food, and friendly service, it’s a can’t-miss Key West gem.
Cruise Tip: You can add Oreos and a Jamison Whiskey float to your Frozen Irish Coffee. I mean… why not?!
Address: 420 Applerouth Lane, Key West, FL 33040
Website: maryellensbar.com
4. 801 Bourbon Bar (21+)
If you’re over 21 and want to experience authentic Key West nightlife (albeit, during the day), head to 801 Bourbon Bar. Known for its strong pours, lively drag shows, and fun-loving bartenders, it’s a guaranteed good time. During the week, things are a bit quieter which is perfect for great service and conversation.
Cruise Tip: If Alvin is working, be sure to say hi and tell him Mark and Rocky sent you. He might just surprise you with a custom cocktail!
Address: 801 Duval St, Key West, FL 33040
Website: 801.bar
5. Margaritaville – The Original
Before it became a global brand, Margaritaville started right here in Key West. Stop by the original location to enjoy a Cheeseburger in Paradise, sip a margarita, and take in the tropical soundtrack that inspired Jimmy Buffett himself. It’s a slice of Key West history and the perfect spot to unwind. And if you’re sailing to Key West on Margaritaville at Sea, it would be a crime not to stop!
Cruise Tip: Even if you don’t order food or drinks, you MUST at least get a selfie in front of the Original Jimmy Buffett’s Margaritaville sign.
Address: 500 Duval St, Key West, FL 33040
Website: margaritavillekeywest.com
6. Southernmost Point
Snap a photo at one of the most famous landmarks in Florida: the Southernmost Point Buoy! As of the time of this writing, the Southernmost Point buoy is undergoing repairs to its plaza and seawall. While the original site is being restored, the city has placed a temporary replica/photo spot at the Duval Street Pocket Park so visitors can still grab the classic shot during your cruise stop.
This colorful concrete marker sits just 90 miles from Cuba and makes for an iconic souvenir photo.
Cruise Tip: Arrive early to beat the crowds (and the heat), or visit mid-afternoon when the light is perfect for pictures. Or, just snap a selfie from a distance while everyone else waits in the long line!
Location: 1400 Whitehead St, Key West, FL 33040
Temporary location: Duval Street Pocket Park / 1499 Duval St, Key West, FL
Website: cityofkeywest-fl.gov
7. Kermit’s Key Lime Pie Shoppe
You can’t leave Key West without a slice (or two) of Kermit’s Key Lime Pie. Their pies are legendary. They’re tangy, sweet, and perfectly creamy. Whether you go classic or opt for a chocolate-dipped slice on a stick, this stop is a must for dessert lovers. It truly is the perfect end to your amazing day in Key West!
Cruise Tip: You can grab a whole pie to take back on the ship and share with friends!
Address: 200A Elizabeth St, Key West, FL 33040
Website: kermitskeylime.com
8. Hog’s Breath Saloon
They say that “Hog’s Breath is better than no breath at all” here at this iconic saloon. Hog’s Breath has been serving up good times since 1976 and is celebrating its 50th anniversary in 2026! Stop in for live music, friendly locals, and a refreshing Key Lime Cocktail that ties in perfectly with the island’s signature flavor.
Cruise Tip: This spot is right near the port so you could cross it off the list at the start of your day instead. It’s a tourist spot and the drinks are kind of pricey, but you’ve at least got to stop once. Plus, you get a white Hog’s Breath Saloon Souvenir Cup!
Address: 400 Front St, Key West, FL 33040
Website: hogsbreath.com
9. Key West Museum of Art & History at the Custom House
As you head back to the pier after your amazing day in Key West, you reach the Custom House. It’s one of the island’s most recognizable landmarks, showcasing red-brick architecture and fascinating history. Even if you don’t have time to tour inside, it’s worth a visit just to see the building and snap a photo with the museum’s sign. History buffs will love diving deeper into the stories of old Key West inside.
Cruise Tip: You can get an iconic photo of the Custom House as your ship approaches Key West on your visit. Find a spot up on deck to grab an awesome photo!
Address: 281 Front St, Key West, FL 33040.
Website: kwahs.org
10. Photo Spot on the Pier with Your Cruise Ship
Looking for that perfect Instagram shot? Head to the pier near Mallory Square for a gorgeous view of your cruise ship docked against the turquoise waters. It’s one of the best vantage points on the island for capturing both your ship and the laid-back Key West vibe.
Cruise Tip: If it’s busy when your ship first ports, wait until the end of your day to grab a photo. But check the weather first to make sure it’ll still be nice outside. Key West Selfies look best with the beautiful sunshine.
Wrapping It Up
Whether you’re visiting for just a few hours or spending the night, Key West is one of the most walkable, vibrant, and personality-packed ports in the Caribbean. From its rich history and delicious food to its legendary bars and sunsets, every corner has something to discover.
So, next time your cruise docks here, grab your camera, your sense of adventure, and maybe a slice of Key Lime Pie and get ready to fall in love with Key West, one quirky stop at a time.
What did we miss in our Top 10 Things to Do in Key West When Visiting on Your Cruise? Let us know what you love to do in Key West, Florida in the comments below!