How to Spend a Weekend in Key West

Unique history, beautiful historic homes, incredible blue water, and amazing nightlife make Key West the perfect spot for a weekend trip.

When my friend decided to get married at Little Palm Island, right near Key West, and invited us to her small, beautiful ceremony, I knew we had to come. Key West is truly so different than other parts of Florida I’d been to, I’m so glad we went! It gave us the chance to explore a spot I’ve always wanted to visit, and now I get to share with you how to spend a weekend in Key West.

Table of Contents

Where to Stay

There are many different spots to stay in Key West, including some really cute Airbnb’s and hotels along the water. My boyfriend had a bunch of Hilton points (we basically funded this whole trip on points), so we decided to stay at the gorgeous Casa Marina: A Waldorf Astoria Resort.

The Waldorf Astoria and Curio Collection Hotel next door (both Hiltons) are the only two resorts with a private beach in Key West. This was a huge win for us because we wanted some relaxed beach time without fighting with lots of people, especially during the current situation. Safety is important! The rooms were spacious and we loved spending time laying out by the adult pool. Would definitely recommend it!

Getting to Key West

To get to Key West, Florida, you have a few transportation options. Choose the option that best suits your preferences and travel plans. Safe travels!

By Air

The Key West International Airport (EYW) serves the area. You can book a direct flight to Key West from various cities in Florida and some other major U.S. cities.

However, this airport is often expensive. An alternative option is flying into Miami or Fort Lauderdale, renting a car, and driving to Key West. We did this and saved about $200 a person on the trip.

By Car

The road in and out of Key West is Overseas Highway (U.S. Route 1). The drive is approximately 160 miles and offers breathtaking views of the ocean. You can easily rent a car and make several stops at gorgeous places along the way. It takes about 3-4 hours to make the drive. Key West is at the very end of Route 1.

By Bus

There are also bus services that connect Miami to Key West. Check with local bus companies for schedules and routes.

By Ferry

Some companies operate ferry services between Key West and nearby locations, such as Fort Myers or Marco Island.

Friday Night

Dinner, Drinks, and Key Lime Pie on Duval Street

You can’t come to Key West without enjoying some time on Duval Street in Key West! Duvall Street is famous for the 43 bars that fit on this two-mile street that stretches from the Atlantic Ocean to the Gulf. There’s a lot of history packed into this street too!

It’s worth spending an evening hopping from one live music spot to the next. Drag Queens are a regular sight here on the weekends (sometimes weekdays, too, depending on the season), and it can be fun to check out a show while there!

We opted for live music, drinks, and food at Viva Argentinian Steakhouse where we could enjoy a good rum cocktail with some chill live music. That’s something about Duvall I think everyone can appreciate it – there’s something for everyone!

While on Duval, make sure you stop for Key Lime Pie at one of the shops! You can’t come to Key West without trying the Key Limes.

Saturday

Snorkeling Trip

I was surprised to learn that the Florida Keys are home to the only live coral reef left in the continental United States. That makes visiting a gorgeous reef a must while here. We decided to go on a snorkel trip with Saltwater Seafari and are so glad we did!

We went to Looe Key Reef with Saltwater Seafari and it was incredible! We were the only ones there snorkeling and had the whole place to ourselves. Their trips are really affordable and they were so kind to accommodate us however possible while on our trip.

Visibility was 60 feet and the water was a crystal clear blue you don’t even need a filter on. I absolutely loved it! We saw sea turtles, dolphins, tons of fish, nurse sharks, lobsters, and more. Couldn’t ask for a better way to spend a Saturday!

I know coming to a new place then immediately leaving can be tricky, but I honestly found this to be the highlight of our whole trip and if you love the water, you’ll love this. If you can, do this on Sunday instead of Sunday and explore Key West on Saturday! Either way works, but I know I wouldn’t want to be salty the whole plane ride home…

Fort Zachary Taylor State Park

On the southern edge of Key West, you’ll find Fort Zachary Taylor. Fort Taylor predates the Civil War and is a National Historic Monument housing the largest cache of Civil War armament in the world. Beyond its historical importance, the park is the southernmost state park in the continental United States and has a great public beach.

The fortress itself is huge and you’ll find lots of corridors and historical information to discover. In the afternoon it can get really got here, so come prepared with plenty of water!

It has a beautiful beach you can relax at, is the perfect spot for finding iguanas, and offers amazing views of the beautiful blue Key West waters. We spent about an hour here without visiting the beach. If you choose not to stay at Casa Marina or The Reach, you could spend the afternoon hanging out here at the beach.

Relaxing at your Resort

We choose to head back to our resort after this for some afternoon drinks, private beach, and pool time. The Casa Marina has a beautiful beach area that is closed to the public with large comfy day beds to lounge between the palm trees.

Casa Marina also had two pools. A family pool and an adult-only pool. We chose to relax at the adults-only pool which we had almost all to ourselves. It as a really relaxing afternoon!

Drinks and Dinner

End your Saturday with an awesome happy hour on the water. Waterfront Brewery has awesome views, fun games, and beer you’ll want to try. They also offer great views.

Then, it’s time for some awesome food! One of the things Key West is known for is its awesome Cuban food, it’s the perfect way to start off your weekend in Key West!

El Siboney is a family-friendly, traditional Cuban restaurant near historic downtown. The portions are huge and the food is delicious. I would highly recommend it if you want some authentic and delicious Cuban food. I’ve been to Cuba and I can tell you the food here is amazing!

Sunday

Key West Sites 4 hours

CLICK HERE FOR MY GOOGLE MAPS VERSION OF THE BELOW

On Sunday morning, take yourself on a walking tour of Key West! There’s a lot to see, especially when it comes to historical sites. We started off near Casa Marina, but you could start on the other side of Key West as well and walk across to see the sites too. Key West is only 2 miles wide so you can see a lot in a day.

Start off at Cuban Coffee Queen where you can grab an awesome coffee and pastry to fuel you for your morning. Once you’ve got your coffee, head off walking toward the water. The marina is beautiful and you’re sure to see fish swimming around under you as you walk.

Walk along the water until you reach Greene Street. Greene Street is home to some cute shops and cafes. We enjoyed walking through the little streets and checking out shops!

From there, walk on to Mallory Square. Mallory Square is home to street performers, shopping, museums, and great views. When COVID is not happening, there’s a nightly sunset celebration. Right now, there are no performers, etc to be found. Shops and restaurants are open and this is still a historic square worth a visit!

After Mallory Square, walk to the Truman Little White House. The Little White House was the winter White House for President Harry S Truman for 175 days during 11 visits.

Other presidents, including Presidents William Taft, John F. Kennedy, Dwight Eisenhower,

Jimmy Carter and Bill Clinton have used the house for important presidential business during their terms as president, too. It’s now a museum and worth a stop on your walk through Key West.

$15 for tours

Whitehead Street

From there, start to walk down Whitehead Street where you’ll reach the US 1, 0 Mile Marker at the corner of Whitehead and Fleming.

Another two blocks and you’ll hit the colorful Bahama Village neighborhood sign at the corner of Petronia Street and Duval. This is a cute spot in an even cuter neighborhood. Walking these streets and you will find some of the cutest houses in Key West!

Continue down Whitehead Street and you’ll be greeted with the Key West Lighthouse and Ernest Hemingway’s house. They are right across the street from each other and back in the day, were waterfront property! The Navy has built up the area and it’s no longer on the water.

Ernest Hemingway wrote 80% of his works while living in the house and his cat’s descendants still live on the grounds! This was our favorite site in Key West and a tour only takes 30 minutes. Definitely worth it.

$17 to visit Ernest Hemmingway’s House, $17 to visit the Lighthouse.

After the tour, head to the Southernmost Point. I personally found this a bit of a tourist trap, it’s not actually the Southernmost Point of the US, that is on the military base in Key West. To be fair it does make a nice photo and the view is great! Just prepare to wait in line if you want a picture.

Lobster Rolls on Duvall Street

Two blocks away from the Southernmost Point is a cute little lobster roll spot called The Lobster Shack. It’s only open during the day (closes at 2 pm) so make sure you make it in time to enjoy a lobster roll! Lobster is amazingly delicious and fresh lobster is easy to find in Key West, making it a must while there.

After all that walking, we were tired and ready to do some relaxing. We picked up our car and headed outside Key West to our friend’s wedding happening on Little Palm Island. If you’re looking for more to do, I’d recommend spending time at more museums, visiting the beach again, or stopping in at the distillery in town.

A weekend in Key West was such an incredible and unique experience. We felt at times like we were outside the US and the water was just incredible. I can’t recommend spending a weekend in Key West enough!

Plan a memorable weekend in Key West with this ultimate travel guide. Explore the historic homes, beautiful beaches, and lively nightlife.
Plan a memorable weekend in Key West with this ultimate travel guide. Explore the historic homes, beautiful beaches, and lively nightlife.
Meghan

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