Key West Itinerary
Looking for the best things to do for your long weekend in Key West itinerary? This guide will ensure you get the most out of your short time in Key West, Florida.
With tropical weather, small-town vibe, great food & drink, history, and vibrant nightlife, a trip to Key West makes for a getaway you won’t soon forget! Key West has been home to pirates and presidents, famous authors and many-a-noteable mover and shaker. Key West is perfect for a couples getaway, friends trips, family vacation, and any mixture between – and you don’t even need a passport!
But before you pack your bags, you’ll want to know how to get the most of your time in Key West – or the types of things you’ll be able to fill your time there. This Key West Itinerary is written based on a 3 night Thursday – Sunday long weekend, but would work for any 3 night/4 day trip. You could also use this as the building blocks for essentials of a longer trip if you have more time (lucky you!) or slim it down with your favorites if you’ll have less time.
Here’s your ultimate itinerary for a 3 night long weekend in Key West.
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How to Get to Key West
Your method of transportation will undoubtedly impact your Key West Itinerary. If you’re wondering how to get to Key West, you’re not alone! Being an island at the southernmost point of the U.S., many people worry about accessibility.
Not to fear! There are plenty of options for getting to Key West depending on your time, budget, and personal travel preferences. I wrote a whole article on How to Get to Key West here, but this is the express version to get you started:
Fly direct to Key West International Airport
- How to do it: Book your flight itinerary to land at Key West International Airport, airport code EYW. From there, you can rent a car for your trip or take a short, inexpensive Uber or taxi ride to your accommodation.
- Best for: saving time and convenience
- The downsides: typically the most expensive option, and requires connecting flights for most itineraries
Drive the Overseas Highway to Key West
- How to do it: Fly into a mainland Florida airport that is most cost-effective and convenient for you. I highly recommend either Fort Lauderdale or Miami airports as they are typically the least expensive and the shortest drive. From there, you’ll rent a car and head for US-1 S then on to the magical Overseas Highway. The drive is about 3 1/2 hours of tropical ocean magic to Key West
- Best for: budget friendly, and scenic-route lovers that can arrive during the day.
- The downsides: takes more time, and not all accommodations offer street parking
Ferry to Key West
- How to do it: Fly into Fort Myers airport in Florida then take a taxi or shuttle to The Key West Express ferry. Ride the ferry in style all the way to Key West’s harbor, then Uber or taxi to your accommodation.
- Best for: those who love the scenic route and prefer to sit back and enjoy the ride. You’ll be able to relax and enjoy the view and even grab a drink from the bar. This is also a great budget/ time efficient option if Fort Myers offers the best airport rate, as the ferry from Fort Myers takes less time than driving at 3.5 hours versus 5.
- The downsides: the ferry only runs seasonally for weather safety reasons, and you’ll need to coordinate your travel with the ferry schedule.
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Thursday: Day 1 Arrival in Key West
Check-In
Whatever method you choose for getting to Key West, your first step is to check in to your accommodation. Get settled in your room, refresh from your journey, and check out the property amenities.
A note on arrival time: Most places are family-run bed and breakfasts, boutique hotels, or individual rentals, so if you’re arriving outside the normal check in times it’s a good measure to communicate this beforehand as it’s rare to find 24 hour desk service.
Dinner
Now that you’ve had to a chance to settle in and you’re ready to venture out, you’ve probably worked up an appetite. If you’re anything like me, you want something low-key and laid-back after arrival.
For this vibe plus some killer mahi mahi tacos head to Garbo’s Grill. It’s a permanent food truck kicked up a few notches and a popular go-to in Key West. It’s nothing fancy but great food and perfect for a low-key first night in Key West.
Key West Sunset Celebration at Mallory Square
If it’s not too late, head over to Mallory Square for the nightly Sunset Celebration. Beginning about 2 hours before sunset and lasting into the night, you’ll find live music, performers, and -of course- an exceptional sunset view in Mallory Square. Grab a drink to take in all the funky glory of Key West.
Nightcap
If you’re still up for more, check out Duval Street nearby for fun bars. You can bar hop and often find live music. For a stiff drink, check out The Rum Bar on Duval for my favorite – the Rum Runner.
Friday: Day 2 in Key West
Breakfast/ Brunch
Depending on how late you were out enjoying the sights and the many beverages of Key West, head out for your breakfast or brunch.
I recommend starting your day at Bagatelle where you can find brunch served until 4 pm. You can sit in the colorful airy inside or out on the balcony for some people watching on Duval. If you’re ready to roll (or still suffering from last night) they offer a “Hangover Happy Hour” from 9 – 11:30 am where brunch booze and breakfast tapas are $5! You may want to book ahead through OpenTable – Bagatelle is popular!
After Breakfast/ Brunch Snack
Hungry or not, stop by Glazed Donuts on Eaton St. to pick up a few of the most delicious donuts to grace the earth. Made from scratch daily, this unassuming bakery with robot paintings will fuel your soul and ruin your diet.
Note: Glazed Donuts is only open 7am – 3pm (or until they sell out) and closed all day Sunday.
Choose Your Own Adventure: Tours, Museums, and Beaches
After brunch, break away from the food and alcohol for a while to check out the other interesting features of Key West. You’ve got time for a few, so pick what calls to you! Here’s what I recommend adding to your Key West itinerary:
- Southernmost Point of the Continental US: [FREE] This is mostly a photo stop, but you can’t leave Key West without seeing it! This famous buoy marks the lowest latitude land of contiguous North American States. It’s pretty crazy to think, but Cuba is only 90 miles away from this marker.
- Smathers Beach: [FREE] Prefer to chill on the beach? I’m with you! Smathers Beach is the largest and best public-access beach on Key West. Enjoy the sun and the view, and you can find a few vendors for lunch or ice cream.
- Key West Aquarium: [$15.47 if purchased online here] Great for families,and lovers of all things aqueous, Key West’s aquarium has a touch tank and exhibits for alligators, sharks, turtles, and more. The best part, it’s super conveniently located in Mallory Square.
- Hemingway House Tour: [$14 tickets purchased in cash at the door] Check out the house that Ernest Hemingway called home. Some go as literary fans, others go to see the cats. We’re not big on tours, but I enjoyed having a look around the house and gardens and seeing all the six-toed kitties.
- The Key West Butterfly and Nature Conservatory: [$15 at door, but you can often find discounts from your hotel or vendors around Key West] It’s a beautiful tropical habitat for birds and butterflies. I personally haven’t had the pleasure, but people go nuts for this place.
- Truman Little White House: [$22.52, or reduced to $20.27 if you purchase online here] The former “Winter White House” has a lot of stories to tell, as it’s been inhabited by the likes of Thomas Edison, President William Howard Taft, and (obviously) President Harry Truman)
After your activities, you’ll likely want to make a stop back at your room, so plan a little time to unwind and refresh before dinner.
(Early-ish) Dinner
Now that you’ve done some looking around, it’s time to get back to that famous Key West eating a drinking. For dinner I recommend The Thirsty Mermaid. The food is locally sourced, the wine is flowing, and the ambiance is a sophisticated casual beachy chic.
HOT TIP: Try to make it to Thirsty Mermaid between 4-6 pm for their daily Happy Hour!
Nightcap
If you’re up for an after dinner drink or two (YOLO), head back out to Duval Street. Just be sure not to stay out too late – you’ll have an early day tomorrow!
For adult groups and couples I recommend stopping by Better Than Sex for a drink and dessert. This intimate dessert-and-drinks-only restaurant is famous for their sexy environment (nothing too gauche), decadent dishes, and adventurous drinks – like champagne with bruleed sugar, or a stout beer with dark chocolate rim.
This place is popular, so you may want to call ahead or make a reservation at Better Than Sex here to ensure your table.
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Saturday: Day Trip to Dry Tortugas National Park
[$180 for adults and $125 for children under 16 – includes boat transportation, breakfast, lunch, guided tour, snorkel equipment, and Dry Tortugas National Park / Fort Jefferson entrance fee]
Book your tickets online here.
What better way to spend your last full day in the keys than by ticking off this bucketlist-worthy local: Dry Tortugas National Park and Fort Jefferson. It’s one of the most remote National Parks in the U.S. and an absolute GEM.
Haven’t heard of it? The Dry Tortugas are a group of small islands off the coast of Key West where you’ll find undisturbed clear blue water ready for snorkeling with sea turtles and coral reef fish. Named for the turtles that call this place home, you’re likely to spot them nesting and swimming around the island. It’s also home to Fort Jefferson and it’s storied past. I’ve done this trip twice and it’s an absolute MUST for your Key West Itinerary.
You’ll wake up early and head straight to the Ferry Terminal to check in by 7:00 am. After boarding the Yankee Freedom III, you’ll eat breakfast and sip your coffee while you sail through the tropical waters toward the Garden Key of Dry Tortugas, watching for dolphins along the way.
Around 10 am you’ll arrive at the Dry Tortugas and have a little time to explore before a tour of Fort Jefferson is offered at 11:00 am.
Fort Jefferson Tour
I’ve said it before but I’ll say it again: I’m not one for a guided tour, and much less one about Civil War history. I skipped the tour on my first trip here but was dragged along by my husband on the second trip and was proven very wrong.
The history of this place is really interesting and the guide is excellent. I truly enjoyed it and would even go again on my next trip. That said, the tour is absolutely optional so if you’d rather spend the time on the beach – go for it!
Lunch
Whether you go for the tour or not, between 11 am – 1 pm you’ll head back to the docked Yankee Freedom III where you’ll find a buffet lunch laid out. You can choose to eat in the air conditioning on the boat, or take your lunch to-go and have a picnic somewhere on the island.
Beach Time and Exploring
After lunch until 3:00 pm, you’re free to explore the island, lie on the beach, or snorkel. Snorkel equipment is provided if you did not bring your own.
You’ll find fluffy white sand, clear blue-blue water, and undisturbed coral reef life all around the island. I highly recommend at least a little time in the water where you’re likely to spot sea turtles and lots of colorful fish.
Depart Dry Tortugas
Pry yourself away from this beautiful little island by 3 pm to board the boat again and head back to Key West. If you’re ready for a cocktail, the bar is open for the entire ride back. You’ll arrive back in Key West just after 5 pm.
Purchase your day trip tickets to Dry Tortugas National Park here.
What to bring with you to Dry Tortugas National Park
- Water – That tropical sun can get HOT. Be sure to stay hydrated!
- Snorkel – ‘Cause no matter how nice the tour, there’s always something nasty about putting your mouth on a well-used (and chewed) snorkel. Vom. You can pick up your own (much nicer) snorkel for cheap!
- Here’s a link to the snorkel I use for just $24 here.
- Reef-Safe Sunscreen – You’ll definitely need protection from the sun out there, but you don’t want to lather up in the stuff that kills the coral reefs you’ll be swimming around (learn more in this quick read). So pick up some reef-safe sunscreen!
- Here’s a brand I know, use daily, and trust – Raw Elements. If you use this link you can get 10% off with my coupon code “WHEREVERSOMEDAY10”.
- Seasickness Prevention – If you’re prone to seasickness, you’ll want to bring something along. You can use my link to pick up all-day formula Dramamine from Amazon here, and/or some nifty reusable seasickness wrist bands here.
Return to Key West and Refresh
After a day in the sand and sea, you’ll probably want to make a pit stop in your room once you make it back to Key West. So freshen up, and get ready for dinner!
Dinner
For your last dinner in Key West, live up all the goodness. You may or may not be wiped out after the day trip to Dry Tortugas, so here are a few great dinner options depending on your mood:
- Alanzo’s Oyster Bar – seafood place on the harbor. If you can make it there by 6:30 they have Happy Hour deals on drinks and tapas daily 4-6:30 pm
- Onlywood – stepped up italian and pizza place with a garden patio and extended wine list
- Seven Fish – well known bistro known for their locally caught fish, on the sophisticated side without being too stuffy
Sunday: Check Out and Return
You don’t have to go home but you can’t stay here! Well, you can (and many have), but in the off-chance you still plan on returning home – today will be your last day in Key West.
Grab a quick breakfast at Pepe’s before checking out and heading back home. It’s where the locals flock for changing daily specials and homemade breads!
We’d love to hear how your Key West adventures go! Tag us in your photos on Instagram as you check off our Key West Itinerary @Wherever.Someday for a chance to be featured!
