How to Spend a Weekend in Key West

Last updated on August 15, 2026

Located at the southern tip of the Florida Keys, Key West is an island of tropical sunshine, amazing water activities, and a lively downtown known for its haunting history and world-famous sunsets. Three days is the perfect amount of time to hit all the highlights.

We visit Key West often, so I have put together this itinerary for a fun and family-friendly Key West getaway to help you plan an amazing trip.

How Many Days in Key West Do You Need?

Though only four miles long, there are many fun things to do in Key West and lovely spots to do absolutely nothing.

Key West is worth a day trip, but the more time you have, the better! You could easily spend a week in Key West, but 3-4 days is optimal if you want to do it all and still have time to relax.

If you only have three days for a Key West weekend getaway, you’ll need to pack a lot into each day if you want to hit all the popular attractions. But it can absolutely be done!

Here’s a three days in Key West itinerary to help you get the most out of your stay.

Key West Itinerary

Day One: Explore Key West Historic Sites

The Florida Keys have a rich history and there are many Key West historic sites to check out. Most of these attractions can be easily reached on foot from most Key West hotels in town.

You can also take the Key West Hop-On-Hop-Off Trolley Tour, which I highly recommend! More than a tour, the trolley is fully narrated with interesting facts, history and legendary stories of Key West, all while providing transportation around the city. You can explore Key West at your own pace without having to worry about transportation or parking. Visit more than 100 points of interest and attractions around Key West  and hop off anytime you want.

► Explore Key West at your own pace on this highly-rated Hop-On-Hop-Off Trolley Tour

Hemingway Home & Museum

Start your Key West weekend by visiting Ernest Hemingway’s home. It is one of the most iconic things to do in Key West.

Not going to lie – I wanted to visit this iconic place to see the famous six-toed cats just as much as to see where Ernest Hemingway lived and worked during his years on Key West.

Nestled in the heart of Old Town Key West, this unique property was home for more than ten years to one of America’s most honored and respected authors. It’s where Hemingway worked on many of his literary masterpieces. The house is now a museum dedicated to the writer. Beautiful gardens surround the house.

The Hemingway Home & Museum is also home to approximately 40-50 polydactyl (six-toed) cats. A ship’s captain gave Ernest Hemingway a white six-toed cat. Some of the cats lounging around the museum grounds are descendants of that original cat, named Snow White.

The cats are well cared for and obviously used to visitors, so don’t hesitate to reach down and give the kitties some love if they look willing.

The Hemingway Home and Museum is located at 907 Whitehead Street.

Key West Lighthouse

After a visit to the Hemingway Home, take a quick walk to the Key West Lighthouse & Keeper’s Quarters. I On our first visit to Key West, I was surprised to find it is not located right on the water!

The Key West Lighthouse was built in 1848 by the U.S. Navy, who recognized the need because of the many coral reefs and shallow waters around the island.

Today the Key West Lighthouse serves as a museum dedicated to the lighthouse keepers who lived and worked there over the years. You can climb the 88 steps to the top for a fantastic view of the city, and go into the adjoining Keeper’s Quarters to view photographs and belongings of the former lighthouse keepers.

They Key West Lighthouse & Keeper’s Quarters is located at 938 Whitehead Street.

Key West Aquarium

When you’re done at the Key West Lighthouse, head back up to the Mallory Square area and have lunch! Then you are ready for a fun afternoon.

First stop: the Key West Aquarium.

The Key West Aquarium is located right next to Mallory Square in the heart of town. Originally built as an open-air aquarium in the 1930s, it is one of the oldest aquariums in Florida. Home to a variety of native sea creatures, visitors can get a good view of sea turtles, tropical fish, sharks, and alligators.

This aquarium is fairly small, and only took us about an hour to see everything. Educational talks and feedings occur every 30 minutes.

Although we weren’t sure if he’d be too old, my son really enjoyed the aquarium. He especially liked being able to feed the stingrays and sharks. Younger kids will like the touch tanks and craft table.

Shipwreck Treasure Museum

If you are visiting town with kids, the Shipwreck Treasure Museum is a must on your Key West itinerary!

Across from the Key West Aquarium is the Shipwreck Treasure Museum. This fun and unique museum takes visitors back to the mid-1800s, the era of the wreckers. It’s an interactive museum where kids can learn about Key West’s maritime history.

The Shipwreck Treasure Museum combines actors, films, and the actual artifacts from the wrecked vessel Isaac Allerton, which sank in 1856 in the Florida Keys.

Kids will especially enjoy the interactive exhibits and being able to climb up the 65’ tall lookout tower.

Discover Haunted Key West

Enjoy dinner (and perhaps a few drinks at Sloppy Joe’s) then end Day One of your Key West weekend getaway by exploring the darker side of town with a nighttime ghost tour.

My son and I went on the Ghosts & Gravestones Tour, which is a combo trolley and walking tour. The trolley took us past the city’s most notoriously haunted sites, and then into two buildings – the East Martello Fort and the Shipwreck Treasure Museum – to experience some haunts first-hand. Tours are led by “Ghost Hosts.”

The Ghosts & Gravestones Tour was cool and just moderately scary enough for my 13-year old. For older teens and the truly daring, make sure you borrow an electromagnetic meter from the tour guide to detect the presence of ghosts.

Day Two: In, On and Near the Water

With its tropical warm waters and some of the most amazing coral reefs in Florida, Key West is prime for snorkeling, jet skiing, parasailing, and other ocean adventures. Teens love being active, and this is an ideal option for the whole family.

There are several tour companies that offer fishing and watersport excursions in Key West.

We did a combo sailing and snorkeling tour with Sebago Watersports. If you prefer more action, you can request their Power Adventure excursion, with snorkeling, jet skiing, parasailing, kayaking, and paddle boarding. All tours provide food and drinks, and their staff is very attentive and friendly.

Another great option is to plan a visit to Dry Tortugas National Park, home to the magnificent 19th Century Fort Jefferson. Located about 70 miles from Key West, the cluster of seven small islands is only accessible by boat or seaplane.

The park is home to a wide range of tropical birds, marine life, coral reefs, and Fort Jefferson, which is surrounded by a moat and was formerly used as a prison during the Civil War. Guided tours are available.

When you return to shore, spend some time at Mallory Square. Facing the Gulf of Mexico, the waterfront plaza is a hub in Key West’s historic Old Town and world famous for its sunsets.

► Travel Insight

If you are headed to Mallory Square for the sunset, get there early! The area gets very crowded.

This nightly “Sunset Celebration” is one of the most popular things to see and do in Key West. This tradition began in the 1960s, and the celebration still takes place every day.

If you are headed to Mallory Square for the sunset, get there early! Every evening before the sun begins to set, hundreds of tourists gather at Mallory Square to watch the sunset and to enjoy exhibits of arts and crafts, live music and street performers. The area fills up fast!

You can also enjoy a Key West sunset sail and view the gorgeous sunset from a boat off shore.

Day Three: Butterflies and Beaches

Start your final day in Key West at the Key West Butterfly and Nature Conservatory.

More than 60 species of butterflies and 20 exotic birds fly freely throughout the glass-enclosed, tropical habitat within the Conservatory. It’s also home to a wide spectrum of bright and beautiful flowers, plants and bushes for the butterflies to land on, putting visitors quite literally in the center of all the action.

The Key West Butterfly and Nature Conservatory is located at 1316 Duval Street.

Just down the street from the Conservatory is the Southernmost Point, arguably Key West’s most famous landmark. A massive, colorful concrete buoy marks the Southernmost Point of the USA, which is closer to Cuba (90 miles) than mainland Florida.

This is one of the most photographed spots in all of Key West. As such, it also tends to get crowded as people line up to wait their turn to get a photo. It is not unusual to see upwards of 100 people in line.

On our visit we got lucky (if you can call it luck) to hop off the trolley at the site just as a torrential rainfall started. Armed in our rain ponchos, we were the only ones crazy enough to be at the shore. So while we didn’t have to wait in line to get a picture, we did get more than a little wet!

Rain or shine, don’t miss your chance to get a photo at the Southern Most Point in the United States.

End your Key West weekend getaway with some beach time and perhaps a fruity cocktail or slice of key lime pie. It is the perfect way to cap off the perfect weekend in Key West!

Key West Walking Tours

Key West is a destination best explored on foot! Consider adding a walking tour to your Key West itinerary if you’d like to see the major sights while getting some exercise and enjoying the fresh ocean air.

Key Wests offers a myriad of great walking tours – everything from pub crawls to historic walking tours to ghost hunts. You can search for free self-guided walking tour ideas online, or click here for a list of the best walking tours in Key West.

Key West Hotels: Where to Stay for Your Key West Weekend

Trying to decide where to stay in Key West? Here are our suggestions based on experience and reviews.

We made the Best Western Hibiscus Inn home base for our most recent weekend in Key West, and I highly recommend this hotel if you are on a budget.

Why?

The Best Western is conveniently located just one block from the popular Duval Street – Key West’s main drag – and within easy walking distance to beaches, shops, restaurants, entertainment and Key West’s top attractions. It has large rooms, a fantastic pool, and offers free breakfast every morning (a big money-saver, especially when traveling with kids!)

► Read our full review of the Best Western Hibiscus Motel in Key West.

Alternatively, here are a few other hotel options closer to the water in Key West:

Opal Key Resort & Marina has what many consider the best location, right next to Mallory Square on the marina. It features beautiful grounds and a nice outdoor pool, and is just steps away from all the area’s shops, restaurants, attractions and museums.

Margaritaville Beach House Key West is in a quiet area just steps away from Smathers Beach.

For a more budget-friendly option, check out the Marriott Fairfield Inn & Suites Key West. Located just a pinch away from downtown Key West but still right on the water, Fairfield Inn offers a complimentary breakfast and nice outdoor area.