It’s no secret that the key to my heart lies in the Florida Keys. This strip of islands on Florida’s most southern point offers travelers a glimpse into Caribbean Island life without needing a passport. The southernmost island, Key West, was a choice destination for countless famous frequenters like acclaimed writer Ernest Hemingway, storied treasure hunter Mel Fisher, and the iconic musician Jimmy Buffett.
From the bustling nightlife to the relaxing resorts to the beautiful beaches, there’s so much to explore in this quintessential Florida destination. The island’s proximity to Miami makes it a perfect weekend road trip destination or extension following a cruise vacation. So come along as I share the keys to maximizing your time in Key West with this two-day itinerary and travel guide.
Travel Guide & Two-Day Itinerary for Key West, Florida
Where to Stay in Key West
The world is your oyster when it comes to Key West accommodations. On our most recent trip, we splurged on credit card points and stayed at The Reach, located on the island's southern side and steps away from the Southernmost Point. I simply cannot recommend this resort enough; there’s a stunning sugar sand beach, a tasty restaurant on site, a gorgeous resort-style pool, and an elevated, beachy theming. I could’ve spent a full day enjoying the resort alone, but that poses a challenge when you’re only a block away from the action of Duval Street. While most of the main bars on Duval are on the northern side of the island, you’re looking at a $8 Uber or a lively 35-minute walk to Mallory Square. The hotel can run around $700 a night, but I snagged a room for 95,000 Hilton points (47,500 AMEX points).
A more family-friendly option is the Hyatt Vacation Club at Windward Point. While technically a timeshare property, the location accepts short-term bookings for non-Hyatt Vacation Club members and offers two-bedroom residential-style villas that sleep up to 6 people. My family stayed here a while back and we especially enjoyed the large resort-style pool and spacious balconies overlooking the ocean. The villas include full kitchens which allow budget-conscious families to cook a meal or two and save money on restaurant bills. This resort is set beside the Key West airport and near the infamous Smathers Beach but is a considerable distance from the hustle and bustle of downtown and Duval Street (which might be a bonus for families). Two-bedroom villas run around $440 a night or 40,000 Hyatt points.
If proximity to the action is your priority, there are countless mom and pop bed and breakfasts in the heart of Key West. My parents raved about their stay at Tropical Inn Key West. Located adjacent to the Hemingway House, this quant property offers a pool tucked away in a luscious garden, select rooms with jacuzzies, and a lovely breakfast basket for all guests. Ranging in price from $440 to $700 per night, this location is ideal for visitors looking to maximize their time experiencing Key West’s major attractions.
Two-Day Key West Itinerary
Day One in Key West
Morning: Enter the Islands
The journey to the destination rarely makes my daily itineraries, but the drive to Key West is an adventure all its own. As you escape the Florida mainland and enter the Keys on US-1, you’ll cross dozens of bridges over tropical water along the way. If the sun is shining, you’ll be ushered into Key West with sparkling shades of bright blues. My favorite moments along the route include the world-famous 7-mile bridge which transports you from Knights Key to Little Duck Key and offers, as the name suggests, seven straight miles of road over water. Enjoy the views and maybe even pull over to soak everything in.
EmmExplorer Extras:
If you’re looking to spend more time in the Keys, there are plenty of fun roadside stops like the Dolphin Research Center or Theater of the Sea for animal experiences, as well as countless divey bars and kitschy gift shops to wander through. For a first-time Florida Keys visitor on a time crunch, I’d power through the drive and prioritize getting to Key West as quickly as possible, but if you’re a frequent Florida visitor or have the luxury of some extra time, taking it slow down US-1 is never a bad idea.
Afternoon: Hit the Sand and Sea
While it may be tempting to jump right into an afternoon of exploring Key West’s downtown, if you’re operating on a two-day time crunch, it’s important to build in some beach time where you can! Take advantage of having access to your hotel accommodations and hit the beach to embrace the island vibes immediately. If you’re staying at a beachfront resort like we did, it’s as easy as walking out the hotel doors. But if you’re staying in town, you’re best off visiting either Smathers Beach or Fort Zachary Taylor Park. The latter offers more powdery sand and is probably a bit more family-friendly, but costs $6.50 for admission. Smathers, on the other hand, is on the Atlantic side of the island with rockier sand, but more opportunities for free parking.
If you’re hoping to maximize your excitement, consider a jet ski tour with Barefoot Billy’s! We purchased our tickets spur-of-the-moment upon arrival for $160 for the two of us through our hotel concierge. This tour may be available at other hotels in the area (Margaritaville Beach House, for example, was offering shuttles to and from their property to the launch point for the tour). A boater’s license is required to operate the jet ski, but said license can be obtained online by taking a 25-question quiz (Which you can Google the answers to).
The tour departs from Casa Adina, located two doors down from The Reach along the southern side of the island. The tour includes a two-hour journey and takes you around the island of Key West with a few stops to point out some of the historical sites. And this isn’t some dinky guided tour where you barely make a wake; our instructor had us hitting speeds of 70 mph while flying over the ocean waves and encouraged us to “pull 180s” during 20 minutes of open water play. As novices at best, we found this tour exhilarating and totally worth our time. You can book online HERE.
Late Afternoon: Sunset at Mallory Square
Mallory Square is THE place to be for sunset on Key West. Situated on the northwest corner of the island for a beautiful view of the sunset over the Gulf of Mexico. Plan to arrive an hour ahead of sunset to scope out the optimal viewing location. Even if you’re not trying to park yourselves in front of a sunset for an hour, there’s plenty to explore in this bustling part of town. Street performers line the square including acrobats and musicians (and also a really odd mime of sorts that we sat in front of... I'm not sure I’d recommend that performance). There are also food carts offering local delicacies like conch fritters and shaved ice as appetizers before dinner. Local artisans, fortune tellers, and face painters entail some of the other offerings at the Square.
If you have some extra cash to spend, you may opt to enjoy the sunset from the water on a sunset sail. Dozens of tour operators offer this excursion, but I’d recommend Barefoot Billy’s based on the amazing customer service I experienced with them or Schooner Jolly II Rover for sailing the Seven Seas experience.
EmmExplorer Extras:
Pre-game at one of the nearby bars before heading to the square; we had a hard time finding alcohol vendors near the best sunset views.
Dinner: Hot Tin Roof
For an elevated dining experience with stunning views, plan to swing by Hot Tin Roof, located inside Ocean Key Resort. This upscale eatery offers a variety of Floribbean (Florida + Caribbean) flavors with an emphasis on seafood. My partner and I ordered several small plates and found each of them to be spectacular. Highlights include the decadent lobster bisque (The best I’ve ever had) and the rich Shrimp Macaroni and Cheese. I also adored my Hemingway Daiquiri and our key lime pie dessert. We loved the restaurant’s convenient proximity to the activity on Duval Street, and tranquil location perched above the ocean adjacent to Mallory Square. Make reservations if you plan to dine, and request outdoor seating for the best views around.
EmmExplorer Extras:
If you’re looking to skip the hustle and bustle of Mallory Square, Hot Tin Roof’s outdoor terrace offers stunning sunset views.
Evening: Crawl Duval
Alright, it’s the moment you’ve been waiting for… It’s time to bar crawl down Duval Street! Duval Street infamously hosts countless bars on its stretch from north to south on the island, enticing legendary guests like Ernest Hemingway, Jimmy Buffett, and Kenny Chesney. A fusion of the Caribbean islands and New Orleans’ French Quarter, Duval caters to a 21+ guest looking for a no-frills good time. There are several “institution” bars that are considered must-visits. During our recent stop, my boyfriend and I managed to visit eight of the Duvall haunts, making for the single most ambitious bar crawl of my life. Highlights include Sloppy Joe’s, Irish Kevin’s, and Captain Tony’s. Curious to know my power rankings? Check them out in this blog post!
EmmExplorer Extras:
Keep an eye out for local flavors on the bar menus! Enjoy a Key Lime flavored cocktail or a Hemingway Daiquiri to pay homage to Key West’s most famous attributes.
Take it easy and keep yourself hydrated; a long day in the sun can sneak up on you in the evening!
Day Two in Key West
Morning: Smile for Snapshots at the Southern Most Point
Touristy or not, you can’t visit Key West without stopping by the Southernmost Point. But be warned; the lines can get long! I recommend getting there as early as possible in the morning to take advantage of slower lines. How early is up to you (and dependent upon how your post-Duval Crawl is treating you). We visited around 11 am on the Monday of a holiday weekend and waited around 10 minutes to take our photos.
Mid- Morning: Visit the Hemingway House
Ernest Hemingway’s stunning estate makes for an informative and entertaining stop during the day in Key West. Located near the center of the island close to the stunning lighthouse, the Hemingway House offers guided tours of the grounds daily. The 40-minute tour includes a guide and access to the interior of the home, as well as its surrounding gardens. Keep an eye out for six-toed cats which are direct descendants of Hemingway’s own cat, Snow White. Nearly 60 cats roam the grounds and even have their own mini Hemingway House that they call home. For brides-to-be, the home hosts countless weddings and even offers affordable elopement packages. We loved our tour of the grounds and fell in love with the home’s stunning architecture and rich history. We will definitely be back to visit again.
EmmExplorer Extras:
For fellow collectors of souvenir art, the Hemingway House gift shop offers some unique art prints in addition to cat-themed gifts and collector’s editions of Hemingway’s novels.
Lunch: Waste Away in Margaritaville
A parrot head’s pilgrimage to Key West isn’t complete without a stop at Jimmy Buffett’s original Margaritaville Restaurant. My partner and I bonded over our mutual love for Jimmy and were fortunate to attend Jimmy’s last show together, so this visit to the storied establishment was a big driver in our desire to visit Key West. The Key West Margaritaville location offers a slightly more intimate feel than some of the larger, more corporate locations you may visit in other tourist destinations. The menu is largely familiar staples (Cheeseburgers in Paradise, seafood, margaritas, and boat drinks) and I won’t claim to say it’s the best food in the world. But you’re not here for the food; you’re here to raise a glass to Jimmy’s legacy and his contribution to Key West’s culture.
EmmExplorer Extras:
Can’t get enough cheeseburgers in paradise? Parrot heads can flock to the Margaritaville Beach House in Key West for their accommodations and continue their search for that lost shaker of salt.
Late-Afternoon: Explore the Streets of the Keys
Beyond the bars of Duval, there are countless unique art galleries, antique dealers, beachy boutiques, and souvenir shacks along the street that are worth exploring. My favorite gallery is the Waylan Gallery located a few steps away from Margaritaville. There are plenty of casual locations to stop for snacks along the way like Flaming Crossing Ice Cream, a delicious ice cream shop that offers some boozy flavors for those seeking the hair of the dog. And of course, you can’t visit Key West without a slice of Key Lime Pie! Consider swinging by Blue Haven or Kermit's for some of the best pie on the island. Plan to spend a couple of hours enjoying town before heading back to the mainland in the late afternoon to complete your two-day Key West adventure.
Calculating the Cost of Two Days in Key West
Here are my hard costs from this exact itinerary so you can get a rough estimate of the total costs for the experience. Costs are for two people traveling over MLK Weekend in 2025:
Activities:
Barefoot Billy’s Jet Ski Tour (One Jet Ski): $180
Florida Boater’s License for Jet Ski Tour: $15
Tour of the Hemingway House: $60
Food
Brunch at Cuban Coffee Queen: $30
Drinks at the Hotel: $60
Dinner at Hot Tin Roof: $200
Drinks at Various Duvall Bars (We visited 8 total): $200
Breakfast at the Hotel: $50
Lunch at Margaritaville: $75
Transportation & Accommodation
Two Day of Car Rental (Mid-Sized Sedan): $296
One Night at The Reach: $700 (We redeemed 95,000 Hilton Points / 47,500 AMEX points for our stay)
Gas (Estimated): $50
GRAND TOTAL: $1,916
Wrapping It Up!
Whether you’re hoping to soak up the sun or add some adventure to your Florida itinerary, Key West is the perfect destination for your island escape. Even after visiting five times over the years, I can confidently say that no two trips to Key West will be the same. This itinerary only scratches the surface of all of the amazing things to do on the island. What are you most excited to explore in Key West?
If you’re planning a trip to Florida, check out some of the linked blog posts below. I completed my “Great Florida Road Trip” and have plenty of tips and itineraries to share!
Until next time, keep on exploring!
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