Looking to hit a warm, sunny beach, sip on an umbrella drink and have a fantastic vacation? Why not visit Key West? In this article, you’ll find the best four day weekend itinerary for visiting Key West – full of fun things to do, places to stay, and great places to eat!
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Key West is an eclectic town. It’s Old Florida meets Bourbon Street.
As the most southern city in the continental US, Key West is located about 160 miles south of Miami and only 90 miles north of Cuba.
Known for its nightlife, beautiful beaches, historical sites, and relaxing go-with-the-flow vibe, a vacation spent in Key West should be on every traveler’s bucket list.
With a fun-filled, exciting vacation in mind, here’s the best four day weekend itinerary for Key West!
Fun Fact: There are actually 800 keys in Florida, and 42 bridges. The longest bridge is Seven Mile Bridge and links the Florida mainland to the Keys
GETTING THERE
There are a several ways to get to Key West.
You can fly into Key West International Airport (EYW) directly. Most airports in Florida offer connecting flights.
For a one day excursion, there are several tour operators that offer day trips from Miami to Key West. These are usually 13 hours or so in length. It takes approximately 3-4 hours one way from Miami to Key West depending on traffic and time of year. For tours, check out TRIP.COM
You can also fly into Miami (MIA) or Fort Myers (RSW), grab a rental car and drive to Key West. (Roughly 5 hours from Fort Myers, and 3 hours from Miami with light traffic.)
Want to know the best way to get to Key West?
Fly into Fort Myers and from the pier at Fort Myers Beach, take the Key West Express to Key West.
The Express leaves at 8:00 am and arrives in Key West about 4 hours later.
The passenger-only ferry offers a full-service galley, bar, and satellite TVs to enjoy during the ride.
Relax and enjoy the views on the water knowing you don’t have to deal with the traffic along the Overseas Highway. You can book tickets here.
ACCOMMODATIONS
Key West has tons of amazing options for lodging. Hotels for all budgets, bed and breakfasts, vacation rentals and more.
Here’s a list to check out!
Opal Key Resort & Marina – Beautiful resort on the water just one block from Duval Street in Old Town. They also offer specials for guests booking with the Key West Express!
Margaritaville Beach House – Rated one of the top resorts in the Florida Keys, The Margaritaville offers fun and relaxation. Located just across the street from Smathers Beach, it’s a great location for families.
Bed & Breakfast – If B&Bs are more your style, check out The Artist House. This beautifully decorated house has seven suites and is located just off Duval Street, and within walking distance to the Southernmost Point landmark.
VRBO – If you prefer your own home away from home, check out the Vacation Rental By Owner option. Dozens of townhomes, condos, bungalows, old Floridian houses just off Duval Street, and even accommodations aboard sailing vessels! Check out availability here.
DAY 1
However you choose to arrive in Key West, celebrate your arrival!
Once you arrive and check into your accommodations, get out and explore! Visit Duval Street – the heart of Key West.
Then, head over to Mallory Square to watch the sunset while having dinner at Bistro 245 (located at the Opal Key Resort).
Mallory Square also has lively entertainment and street performers that are fun to watch. Check out their webcam!
DAY 2
For your first full day on the key, explore the true essence of Key West by getting out and experiencing it at its best.
Book a sportfishing trip, go kayaking and explore the island’s mangroves, or wander up and down Duval Street.
Whatever your preference, you won’t be disappointed!
Sport Fishing
Spend the day with Corsair 2 Sportfishing. One of the best fishing charters in Key West, Corsair 2 is a 50′ Hatteras fishing boat that will take you up to 25 miles off shore to find Mahi Mahi, Snapper, Grouper, Sailfish and Marlin.
They provide all the gear and tackle, you just bring snacks, drinks and sunscreen!
Kayaking & Sailing
Reserve the Full-Day Island Eco-Tour. This six-hour tour is a favorite that takes you sailing, snorkeling, kayaking and dolphin watching.
Breakfast and lunch are included and don’t forget to try their homemade sangria!
Tip: They offer a discount if you book online directly from their website.
Kayak through the mangroves.
If you prefer to a more relaxing day of just kayaking among the mangroves and learning about this amazing ecosystem, try the Mangrove Kayak Eco Tour by Lazy Dog Adventures.
This excursion is only two hours and the guide is very informative!
Visit Duval Street
Duval Street is a must visit with so many interesting shops, art galleries, bars and plenty of shaded areas to sit and people watch.
Some of the finest artists have galleries on Duval Street including Peter Lik, Wyland and James Coleman.
Many shops feature items made by local artists and residents, while others offer tempting treats.
Speaking of tempting treats, don’t miss the best key lime pie in Key West!
Stop by the Seaside Cafe at the Mansion for a truly amazing slice of key lime pie (and their world famous lobster pizza).
Dinner: If you’re looking for a great place for dinner, I recommend trying the Seaside Cafe at the Mansion, or the Hogs Breath Saloon where you’ll find live entertainment, often performed by nationally known bands!
DAY 3
For your third day in Key West, explore the U.S.’s most remote national park, Dry Tortugas and Fort Jefferson National Park.
It is only accessible by boat or seaplane and encompasses a total of seven islands.
Catch the Yankee Freedom ferry from the terminal on Grinnell Street and sail just over two hours to Fort Jefferson.
Explore the fort and surrounding area, or soak up some sun at one of four beaches in Dry Tortugas until the ferry leaves on the return trip at 3:00 pm.
The Dry Tortugas have some of the best snorkeling in all the Florida Keys. The waters are shallow, crystal clear, and full of marine life.
Included with your ferry reservation is breakfast and lunch, snorkeling equipment, and the entrance fee to the Dry Tortugas National Park.
The ferry arrives back in Key West just after 5:00 pm.
After arriving back in Key West, you’ll be just in time for dinner and after a full day of exploring I guarantee you’ll be starving!
I recommend having dinner at Jimmy Buffet’s Margaritaville. Delicious food, great entertainment, and happy hour from 5-7pm…who doesn’t want to enjoy a cheeseburger in paradise?
DAY 4
For the last day in Key West (unless you decide to not leave paradise, then by all means party on!) take the opportunity to explore some other favorite destinations in Key West.
The return ferry to Fort Myers doesn’t leave until 6:00pm so you have plenty of time to get in some last-minute sight-seeing.
You could enjoy some downtime by relaxing and digging your toes in the sand on one of Key West’s beautiful beaches.
Smathers Beach is one of the largest public beaches on the key and there you can rent paddle boats and jet skis. Be sure to bring your own food and drinks as there are no concessions on the beach.
Fort Zachary Taylor Historic State Park Beach is another local favorite popular for fishing, swimming, and snorkeling.
For history lovers, a trip to the Truman Little White House may be in order.
Located on Front Street, the house is where President Truman visited 11 times during his presidency and five more times after leaving office.
While visiting, President Truman discussed the Marshall Plan, and met with the Joint Chiefs to create the Department of Defense through the Key West Accord in 1948. Tickets can be ordered online here.
Don’t forget to take a stroll past the Southernmost Marker before you leave! A picture in front of the iconic marker is a must for anyone’s first time to Key West.
There is so much to do and see in Key West that you’ll soon be making plans for your next trip!
If you plan to return to Fort Myers via the Key West Express, boarding begins at 4:30 pm. The ferry departs Key West at 6:00 pm arriving in Fort Myers around 9:30 pm.
Whether you spend one day or a week, this four day weekend itinerary for visiting Key West can be altered to fit any schedule.
From relaxing on a soft, sandy beach to exploring one of Florida’s three national parks, to a myriad of outdoor activities for the adventure-lover, Key West truly has something for everyone.
So make your reservations, enjoy some fun in the sun, and embrace your inner dragonfly!
Check out these 5 Hidden Gems In Florida you don’t want to miss! Heading to Florida soon? Leave us a comment below sharing your favorite Florida destination!
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