We first came to Key West in 2010. Since then, we have made dozens trips to this tropical Southernmost Town. Sometimes a quick weekend jaunt, and other times choosing to laze away for weeks on end. We definitely agree with Key West’s motto: “Close to perfect; far from normal.” This quirky city has stolen a piece of our hearts, and we will always venture back to this beautiful place!!
With its laid-back island vibe, Key West is a magical town, where the Caribbean can be experienced while still in the continental US! Key West is just a short flight from anywhere in the southeast, making it perfect long weekend tropical escape!
Want to see it all and do it all? Check out this packed itinerary for a sampling of the best of Key West!
Day 1: Around Town Day
Key West is not large, and there are a few great ways to explore! We prefer to rent bikes and take a leisurely ride around the island! Be sure to make your first stop one of the many great breakfast spots on the island! If you like lobster, try the lobster benedict or lobster omelet at Blue Heaven
. Save room for dessert, their Key Lime Pie is consistently rated as one of the best!
There are a few directions your day can take from breakfast — if you like History, you could spend some time exploring The Hemmingway Home & Museum and the Lighthouse (OMG, the views!!!), or the Key West Museum of Art & History at the Custom House. You could also opt for the Conch Train Tour, which takes you around town and does a mobile history lesson of sorts. These all offer some really cool glimpses into Old Key West!
Once you’ve worked up an appetite, check out Moondog Café & Bakery – this is a great place to take a break mid-day. We usually opt for pizzas and dessert here! After lunch, either continue your history hopping or head to the southernmost point for your obligatory Key West Buoy Picture! From there, you could sneak back along Duval Street, checking out the artists shops along the way and people watching.
Alternately, you can do the time-honored tradition of “The Duval Crawl”, starting at one end of Duval Street and making your way down the street, stopping at [most of] the bars between one end and the other, if you can make it! Upside of this option, bragging rights! Downside, you may not remember your day! Don’t forget to grab some lunch — Smokin’ Tuna Saloon has a good menu and live music!
The Sunset Festival in Mallory Square is a festival in the truest sense of the word! There are street performers, artisans, vendors of food and wares, tourists, chickens, and cats! The excitement in the air is palpable. As the sun dips towards the horizon, everything stops — the music, the performers — and a hush falls over the crowd. The sunset is the main attraction every night. Take it in, breathe deeply, it’s a magical time of day. After the sunset, the performers all do one more show, then you can start the next part of your evening (Key West doesn’t sleep!)
For dinner, head to Eaton Street Seafood Market for amazing Stone Crab Claws (if they’re in season) or a lobster roll if they’re not! Order inside the Seafood Market, right at the coolers, and sit outside under an awning, enjoying your bounty of the sea! After dinner, if you have room (save room!), head to Kermit’s Key West Key Lime Shoppe and get your fill of Key Lime Desserts! Walk along the waterfront and check out all of the boats!
Day 2: Get on the Water!
They say that breakfast is the most important meal of the day — Fisherman’s Café, at the Historic Seaport, is worth getting out of bed early for! Order at the counter and be prepared to wait a bit for your grub. Don’t worry, it’s worth it! We recommend the El Cubano breakfast sandwich (it’s big enough that you will want to share it with a friend or stranger!)
Choose a full-day water-based adventure with one of the many outfitters on the island. We recommend Danger Charters Full Day Sail, Snorkel, Kayak trip or the Fury’s Ultimate Adventure H2.0. Guests have a bit more room to spread out on Danger’s trips. Lunch and drinks are included with both.
After a day on the water, you might not be up for too exciting of a night. Grab some tacos at Garbo’s Grill and a drink from inside at Hanks Hair of the Dog Saloon. Garbo’s is a food truck in the back yard of Hanks! Trust us, it’s worth it; these aren’t your average tacos!!! Relax and decide if it’s time to call it a night. If not, check out some music — maybe Green Parrot, Sloppy Joe’s Bar, or Irish Kevin’s. Walk around Key West after dark and the music will find you!
Day 3: Beach Day!
You’re on an island, relax mon! It’s true that the Keys are not known for their beaches, but there are still some fun spots to spend some time on the island! Start your day at La Creperie French Café with, you guessed it, crepes!!! Their whole menu is fantastic and varied. It’s tucked away on a side street, but it’s worth the effort to get there. Grab some paninis from here to throw in the cooler for lunch later!
After breakfast, head towards Fort Zachary Taylor State Park. On the way there, be sure to stop in the Florida Keys Eco-Discovery Center. Informational, educational, and fun – this is a great quick stop (and it’s free!). Once inside Ft Zach State Park, choose to either head straight for the beach, or do a self-guided tour of the fort. Either way, check out the fort at some point during the day! We always choose the first beach entrance at the beach, where we have a little more space to spread out, set up hammocks, and chill. The shoreline is rocky, so bring appropriate footwear. If you didn’t pack sandwiches, you can get some grub at the grill that’s just down the beach. There’s also chair and umbrella rentals there as well as an informational display from Mote Marine — they constructed a snorkel trail located just offshore if you’re feeling adventurous!
For an early dinner, check out Santiago’s Bodega for some sangria and tapas on happy hour! We always opt for a pitcher of red sangria and the cheeseboard, as well as whatever treats they happen to have on their happy hour menu at the time!
For your last evening in Key West, you need to experience the Sunset from a different vantage point — from a sailboat! We heartily recommend the Schooner America 2.0 for a beautiful, premium sailing experience! This historic ship is stunning and the perfect place to spend a few hours watching the sun dip below the horizon. Your sailing experience includes beer, wine, and champagne to enjoy, as well as a nice selection of munchies including a cheese tray, veggies, and shrimp. If you’re lucky, the captain may even let you steer the boat!!!
That wraps up the perfect three days in Key West, Florida! Please head over to our Facebook page, like it, and follow along on our adventures, which will help you to plan your adventures!!!!
Making the drive from South Florida to Key West and want to know where you need to stop? Click here!
Wondering where to find the best Key Lime Pie in Key West? Click here!
Want to spend a few days in Marathon (even a day trip is worth it!)? Click here for our favorite stuff to do and places to eat in Marathon!
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