Key West, Florida is one of the most popular destinations in the USA.
With its beautiful beaches, charming old town area, and amazing tropical weather year round, many visitors have this southern Florida vacation on their bucket list!
Key West is rich in history and culture, with a diverse population that makes it an exciting place to visit.
Key West has plenty of attractions such as Ernest Hemingway’s Home & Museum, Duval Street with its eclectic stores, clubs, and restaurants, Historic Key West Seaport, southernmost point, the Key West lighthouse, and its beaches.
Our Key West itinerary takes you around the many amazing attractions the city has to offer.
Tourists can also enjoy many water attractions such as snorkeling, scuba diving, whale watching, dolphin watching, deep sea fishing, kayaking and guided tours by boat or airboat!
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Weekend in Key West Itinerary
Explore Key West in a weekend or 3 days by following our perfect Key West itinerary.
Enjoy the attractions and activities including pretty beaches, historic sites, and amazing restaurants.
If you find yourself in Key West for a weekend trip, here is what you should do to make the most of your visit:
Day 1: Old Town Key West
Start your day by exploring Old Town Key West and its historic buildings.
Next stop, Southernmost Point in Key West and eat some famous key lime pie.
End your day at Duval Street and Mallory Square.
Old Town Key West
There are lots of things to do and see in Old Town, making it a popular first stop on the Key West Weekend itinerary.
You can walk to see the historic buildings on a self guided tour and see attractions such as Railroad Depot and East Martello Fort.
You can also take the hop on hop off Old Town trolley tours which stop at all popular attractions.
See the hens walking down the streets, browse shops such as the Conch Shop, and stop at Sloppy Joe’s for some drinks.
Key West Southernmost Point Buoy
Key West’s Southernmost Point Buoy is a popular spot to visit in Key West.
This is the southernmost point in the continental United States.
The buoy is an iconic symbol for visitors to see while they are exploring Key West Southernmost Park and Pier.
Try some Key Lime Pie
One of the most popular things to do in Key West is to enjoy some delicious key lime pie!
This sweet & tart dessert tastes especially refreshing when you’re spending your day soaking up the sun while exploring this island paradise.
Key Lime Pie has been a staple in Key West for over 100 years and there are several restaurants famous for the delicacy.
Some of the best restaurants to try key lime pie include Ricky T’s, Florida Keys Café, Key Lime Pie Company, and Conch Republic Grille.
Definitely add this to your bucket list, while spending 2 days in Key West.
Sunset Celebration at Mallory Square
One of the most well-known events in Key West is the daily Sunset Celebration at Mallory Square.
Mallory Square is the heart of Key West. It is located right on the water and has an unobstructed view of the ocean!
Locals and tourists alike come here to enjoy stunning sunsets, live music, street performers, food stands, and souvenir shopping.
Watching the day end with a brilliant display of colors in the sky over the Gulf of Mexico at Mallory Square is an unforgettable experience.
The Mallory Square sunset celebration draws large crowds daily. We recommend arriving early for the best views.
Duval Street Shopping & NightLife
Buy amazing souvenirs for yourself and loved ones on Duval Street in Key West.
If you’re more interested in going out at night than buying key west souvenirs, then Duval Street also has an excellent nightlife scene with karaoke, DJs and live bands!
You can go bar hopping and paint the town red on your Key West trip.
Sleep and wake up early to finish your Key West itinerary 2 days.
Day 2: Museums and beaches
See your favorite museums before leaving Key West.
We recommend the Ernest Hemingway Home and Museum or Harry Truman White house.
If you have small kids, consider visiting the Key West aquarium.
Relax on the beaches near Fort Zachary Taylor and have a picnic on the sand – a must activity on the Key West itinerary 3 days.
End the day at the Historic Seaport admiring the docked boats and enjoying fresh seafood.
Harry S Truman Little White House
The Truman Little White House is a historic house museum in Key West, Florida. It was the winter White House for President Harry S. Truman.
The property includes a beautiful Victorian cottage) and grounds that offer spectacular views of Old Town Key West.
On guided historic tours of the property, visitors can see several artifacts including paintings by Norman Rockwell; period furniture such as writing desk used by Franklin Roosevelt and sofas given to Truman by Queen Elizabeth; books about Truman, as well as his personal items.
The Truman Little White House is a must for history lovers!
Ernest Hemingway Home Museum
Key West’s top attraction for literary lovers!
The Ernest Hemingway Home and Museum is a house museum in Key West, Florida.
The house has been carefully restored with original furnishings and offers historic tours to visitors.
Visitors can see his writing desk, first editions of Ernest Hemingway books on the walls as well as other personal items he used during his time there.
The house is a U.S. National Historic Landmark and popular for its architecture, gardens, six toed cats, and proximity to Duval Street.
Key West Aquarium
The Key West aquarium has a collection of more than 40,000 aquatic plants and animals for visitors to explore.
It’s a great resource for Key West visitors who want to learn about the incredible creatures that live in the waters of southern Florida.
Fort Zachary Taylor State Park
Fort Zachary Taylor State Park is one of the most popular tourist destinations for those visiting Key West.
Located on the coast, it offers a spectacular view of both the Atlantic Ocean and Gulf of Mexico.
This historic fort was built to defend Key West from pirates and foreign invaders. Today, it is home to a museum with exhibits on the history of Key West.
Visitors can also enjoy biking or hiking along the trails around the park. The park also has picnic tables with sweeping views of the ocean.
Key West Lighthouse
There are many reasons why the Key West Lighthouse is a tourist destination.
It’s situated on Fort Zachary Taylor and has been restored to its original condition.
On a tour, visitors can also explore the lighthouse and its grounds to see attractions such as an old cistern with a conch shell motif, cannons that date back to the 19th century, and beautiful views of Old Town Key West and the Atlantic Ocean.
The best time to visit this historical landmark is at sunset.
For many, the light is the highpoint of the weekend in Key West, Florida.
Key West Butterfly and Nature Conservancy
This beautiful conservancy is a must-see attraction in Key West – definitely visit it if you have the time on your Key West 2 day itinerary.
The Key West Butterfly and Nature conservatory features live exhibits with nearly two hundred species of native insects including many endangered or threatened species or butterflies.
The nature conservatory has lush tropical gardens that are beautiful to take a stroll and offers amazing views of the coastline.
Key West Historic Seaport
The Historic Seaport is a place that exhibits the unique history and architecture of Key West’s past.
You will find museums, historic buildings, ships in docks, buskers dressed as pirates, and people strolling on the boardwalk.
The historic Seaport also has many bars and restaurants and is the perfect place to eat fresh seafood including raw oysters and conch fritters or to gulp down an oyster shooter!
After enjoying two days in Key West, head back with awesome tropical memories in your head!
Day 3 in Key West
For those visiting Key West and looking for ways to extend your trip or explore this part of Florida, here are some day trips that can be done from this southern Florida city.
Dry Tortugas National Park
The Dry Tortugas National Park is a remote, uninhabited group of islands and reefs well-known for its rich natural beauty.
It consists of seven small islands (only six are open to visitors) and the surrounding marine area near Key West.
The national park is located at the end of the Florida Keys, 90 miles west of Key West.
Dry Tortugas National Park is accessible only via ferry boat – the Yankee Freedom III – or by sea plane tour – both which depart from Key West.
The park is often visited on a day trip by tourists who want to experience the unspoiled nature in an untouched environment.
The park’s main attraction is Fort Jefferson which was never completed but remains one of America’s most massive brick structures.
Visitors can explore the island on foot or by boat, camp out under the stars, see the massive Fort Jefferson, or take advantage of one of many water activities available such as fishing, snorkeling and kayaking.
Dry Tortugas has no lodging or campground facilities so visitors must bring their own food and water with them.
Bahia Honda State Park
There are several state parks in the Florida Keys, but the most popular one is Bahia Honda.
It’s about an hour north of Key West and includes a nature trail that will lead to one of the most beautiful beaches in Florida.
The road here goes over the Seven Mile Bridge and offers panoramic views of the islands.
Florida Keys Road Trip
Key West makes the perfect base for exploring the small islands of the Florida Keys, including Key Largo.
The Florida Keys have a unique culture and way of life. They are an island chain that is known for their laid-back attitude, beautiful beaches, coral reefs, and warm weather.
The Florida Keys also have some of the best fishing in the world!
The water here is home to many unique species such as manatees, iguanas, and sea turtles, making snorkeling and scuba diving popular activities.
You can extend your road trip on the popular Overseas Highway or US-1 all the way to Miami.
Apart from the Overseas Highway road trip, you can also enjoy other attractions such as Dolphin Research Center and state of the art Turtle Hospital on Marathon Key, John Pennekamp Coral Reef State Park, Florida’s first undersea park, which is home to a living coral reef, and the Islamorada artist community.
There are many other attractions near Key West such as the exclusive Sunset Key, Key Largo, and the Everglades!
Spend a day on the water
One of the most popular tours in Key West is kayaking to see marine life like manatees, Roseate Spoonbills, and dolphins.
Water Sports is also popular in Key West.
You can rent watercrafts like jet skis, fishing charters, and sailboats. Or enjoy parasailing to see the island city from above!
Romantic champagne sunset sail charter is popular with couples.
Dolphin cruises are preferred by families as are scuba diving and snorkeling excursions.
There are many dive shops around Key West that will take you on trips to see Key West shipwreck, treasures, and coral reefs.
You can create your own Key West sailing itinerary to explore the surrounding waters and reefs.
Key West 1 Day Itinerary
If you have less time, then use our one day itinerary for Key West.
Start your trip at the Southernmost Point Buoy and Mile Marker 0.
Then explore Old Town Key West and see historic buildings such as the Truman White House and Ernest Hemingway home.
Eat fresh seafood and key lime pie for lunch.
Spend a relaxing afternoon on the beach at Fort Zachary Taylor State Park.
End the day with watching the sunset in Mallory Square, followed by dinner on the Seaport.
If you love partying, enjoy the nightlife on Duval Street to wrap up your one day in Key West itinerary on a high note.
5 Days in Key West
If you have more time, you can also plan a Key West itinerary for 5 days.
Spend 2 days in Key West exploring the Old Town, museums, and beaches.
Then take a day trip to Dry Tortugas National Park and admire Historic Fort Jefferson.
Then rent a car and road trip the Florida Keys for 2 days.
Stop at attractions like Bahia Honda State Park, Islamorada, Marathon key, and Key Largo.
For Key West itinerary 4 days, skip the Dry Tortugas or spend just one day exploring the rest of the Keys.
Or if you like slow travel, spend all 4 days in Key West: 2 for the major attractions, 1 day on the water, and 1 day shopping and relaxing on the beach!
This relaxing alternative also works perfectly as a Key West honeymoon itinerary – you can enjoy quality time with your loved one in the charming city.
Or plan a Miami and Key West 4 day itinerary: spend 2 days each in both the cities!
You can also plan a Key West itinerary 7 days by driving all the way to Miami and spending time on South Beach, Ocean Drive, Wynwood Walls, and Little Havana.
Where to eat in Key West
There are many great restaurants, cafes, and seafood shacks serving delicious food in Key West.
Some of our favorites include Hogfish Bar & Grill, the Conch Republic Seafood Company, Blue Heaven, and Southernmost Beach Cafe.
Located in the heart of Key West, Blue Heaven Cafe serves amazing Caribbean food. This is a local favorite and Key West institution.
Blue Heaven Cafe is great for breakfast to dinner and has live music too!
Must eats in Key West include fresh seafood such as conch fritters, fried oysters, Cuban sandwich, fish tacos, fresh fruit juices, and the iconic key lime pie!
Best Time to Visit Key West
The Atlantic hurricane season runs from June 1 to November 30 each year. If you plan a trip during this time, be prepared for storms, rainy days, and unexpected delays.
One of the most well-known events in Key West Florida is the annual Fantasy Fest that takes place every October.
This is one of the busiest times in the city, especially Duval Street, and you will need advance reservations.
Winter is also the busy season: high crowds and expensive hotels!
Spring is a great time to Key West for warm weather and low crowds.
Summer in Key West can be hot and humid but you can spend all the time relaxing on the beach, making the most of your Key West vacation.
Essential travel tips to explore Key West
It is easy to get around Key West. You can get an inexpensive taxi or even rent a scooter or an electric bike to truly experience the beauty of this vibrant city!
The bikes are our favorites: the Key West vacation itinerary will have you covering a lot of ground, and it’s not worth getting stuck in traffic!
You can also sightsee Key West on the Conch Tour Train – a train ride that takes you around major attractions!
If planning to get a rental car, then be prepared for busy streets and almost no free parking, especially in downtown Key West.
Remember: there’s no cell phone reception whatsoever on the Dry Tortugas!
Don’t forget to bring your camera to capture the beauty of Key West.
We hope you liked our Weekend in Key West Itinerary.
More Southern Florida Travel Guides
Here are additional resources to help you plan your 3 Days in Key West weekend trip: