Best Weekend in Key West (that won’t cost a fortune)

A weekend in Key West has something for everyone. I recently explored this quaint and picturesque town with the laid-back vibe.

Key West has it all; natural beauty, history, a great foodie scene, water sports, a killer sunset and a rooster cemetery. Wait…what?! A rooster cemetery? Read on.

At 90 miles northwest of Havana, Key West is closer to Cuba than it is to Miami. It is the most popular of the towns in the Florida Keys archipelago. On this weekend in Key West you’ll discover some of the most popular activities as well as some hidden gems of Key West.

Day one of your weekend in Key West

Hop-on-hop-off train

Those who follow my blog know I am a great advocate of the Hop-on-Hop-off concept.

Getting on any one of these bus, trolley or train tours lets you get the lay of the land quickly. This lets you decide where you want to spend your limited time based on what is of interest to you.

In Key West the Key West Conch Tour Train is the way to go. The train offers a 75-minute tour stopping at the most important and visited sights. They’ve been around for over 65 years so they must be doing something right.

Hop on and listen to the fun and knowledgeable guides give you an engrossing – and perhaps a little irrelevant – history of Key West.

Use the 75 minutes to just relax and be entertained or jump off at your favorite spot and hop back on next time the train passes bay to go to your next stop.

Explore Duval Street

Duval is the most trafficked street in Old Town Key West. It’s got iconic bars like Sloppy Joes, one of Ernest Hemingway’s old watering holes and Hogs Breath, another drinking spot and restaurant whose motto is “Hog’s breath is better than no breath at all.”

You’ll also find quirky shops selling unique artisanal products and restaurants in all price brackets.

Visit the Hemingway House

If you love history and are a fan of Ernest Hemingway, you’ll love a visit to the Hemingway Home.

Hemingway purchased this house in 1931. He finished his masterpiece, “A Farewell to Arms” here and started another work of art, “For Whom the Bell Tolls.”

Wander on your own or take one of the tours to learn interesting tidbits about Hemingway and the house itself. For example, Hemingway complained that one of his ex wives took his last penny and to emphasize that point, the penny was embedded in the pool where it can still be seen today.

You’ll enjoy seeing the period furnishings and Hemingway’s personal possessions in the home and the wildly lush gardens. The best part of the tour is seeing all the six-toed cats that live there, all descendants of the original kitties. There are over 50 of them!

The Lighthouse

Right across the Hemingway Home is the majestic Key West Lighthouse built in 1825. Climb to the top for amazing views of Key West.

There is also a nice little exhibit there displaying the nautical tools and maps that were used in the bygone days.

Wander Bahama Village

The Lighthouse and Hemingways Home is just a few steps from Bahama Village. This residential neighborhood is packed with colorful Key West architecture with its wooden homes, garden exteriors and decorative porches.

Petronia Street is the heart of the Bahama Village neighborhood. It features open-air restaurants, yummy seafood and unusual cocktails that will make you very happy. As the name implies, the area was founded by Bahamian immigrants and that flavor still prevails.

Have a delicious brunch at any of the local restaurants in the area like Blue Heaven where the Rooster Cemetery is located, and experience the Key West laid-back vibe.

Watch the sunset at Mallory Square

The one activity that everyone in Key West enjoys be they locals or visitors is experiencing the Sunset Celebration on Mallory Square. People start gathering a couple of hours before-hand to check out the local street performers and get the prime spot to view the sunset.

Once the Sunset Celebration is over, head to the many restaurants in the docks area for authentic Key West fare of seafood and tasty cocktails. We asked locals where we could eat and they pointed us to The Boat House saying it was the best deal in town. The drinks and tasty small plates are half price during Happy Hour.

Go on a Ghost Tour

If you still have the energy after your first day of your weekend in Key West, indulge in a Ghost Tour. There are many in Key West but the Key West Ghosts and Gravestones Tour is one of the oldest. There is also a Haunted Pub Crawl.

There are several ghost tours you can take in Key West.

Day two of your Key West weekend

The Audubon House and Gardens

This is such a magical, interesting historical house. A real pleasure to experience. Believe it or not, no one knows why it is called the Audubon House. John James Audubon, the famous naturalist and illustrator of Birds of America stopped by Key West and used the prolific flora and fauna of the location to depict his iconic drawings. But the Audubon House was not even built yet!

The beautifully maintained home belonged to the Geiger family for many years. When the last member of the Geiger family, an eccentric recluse, passed away, the home was purchased by the Wolfson family who opened it to the public and have maintained it since then. And a lovely job they’ve done, indeed.

The home is beautifully maintained as a museum displaying what life was like during the home’s heyday.

Key West Aquariaum

The Key West Aquarium is a true delight! Maybe you’re interested in the world beneath the sea, maybe you’re not, regardless you will find your time in this aquarium to be well spent.

The Key West Aquarium is a wonderful place to see all the native species; alligators, hermit and horseshoe crabs, mysterious jellyfish and the ever interesting sharks. In fact, this is the best place to witness an actual shark feeding!

Water sports

Can you really say you visited Key West if you didn’t indulge in the areas water sports? Maybe, but I preferred not to because it’s so much fun. My choice was Fury Water Adventures and my experience was the most fun I’ve had on water…EVER!

They have lots of different water based activities from a simple cruise to a rough and tumble combination of waterski, snorkeling, dolphin watching and more…including parasailing.

I chose the dolphin watching and snorkeling tour and it was a blast. First we were picked up at the dock and taken to a comfortable and sturdy ship which transported us to distant waters.

The ship Captain, Nicole, and the First Mate, Caitlyn, were professional. They were very safety conscious and regaled us with interesting, useful and amusing stories about their experiences on the water.

I was surprised to see the amount of dolphins we saw. I learned many dolphin facts I was not familiar with; many of them have names, dolphins mate for fun as well as reproductive reasons, just like humans.

They have personalities and social structures that are remarkably similar to our own, families, social hierarchies, and more. And we saw a bunch of them!

But the best was still to come! After an extensive dolphin watch we donned wet suits to explore the depths (actually it wasn’t THAT deep) of the Gulf of Mexico. We saw horseshoe crabs, a sea of sponges and a kaleidoscope of fish in indescribable colors.

Indulging in a water sport with Fury Water Adventures is a memorable experience and highly recommended.

Party the night away on Duval Street

Wash up from your aquatic adventure and head to Duval Street for a night of karaoke, music and fun.

There are any number of bars, restaurants and music venues to people watch, listen to live music and just hang out. Among them is Hog’s Breath, Sloppy Joes and Captain Tony’s to mention just a few. Just walk up and down the street and see what appeals to you.

Day three of a weekend in Key West

Little White House

There are still so many things left to do on your weekend in Key West, but you have to narrow it down. Here are three recommendations.

First, visit the Little White House, where President Harry Truman escaped to during his presidency. He loved the area so much he spent 175 days of his presidency there. The home is beautifully maintained and an interesting stop for history lovers like myself.

Custom House Museum

Here is a charming, engaging, informative and well curated museum that definitely doesn’t get the respect it deserves.

Completed at the end of the 19th Century, this amazing structure was originally a Customs House. The building passed through many hands, mostly U.S. government until 1991 when the State of Florida leased it to the Key West Art and Historical Society for a museum.

The museum features two floors of temporary and permanent exhibits as well as a large selection of local artists’ works. It is an excellent place to learn more about the history and culture of Key West.

Visit the Key West Cemetery

If you’ve read my posts at all, you know I’m a cemetery aficionado. I don’t know why. I guess I love the history and peace one finds in cemeteries. If you too enjoy learning about cemeteries of the United Sates, you’ll love this one.

This particular boneyard in Key West did not disappoint. It is a historically significant, beautifully landscaped cemetery with lots of history and iguanas scattered along the tombs.

Among the tombs you’ll find humorous inscriptions on tombstones like “I told you I was sick” and “I’m only resting my eyes” or “Here lies a devoted fan of Julio Iglesias.”

You’ll find monuments to heroes of various military encounters like the Civil War, the sinking of the Battleship Maine, WWI, The Cuban War of Independence from Spain, WWII, and others.

If you really want to learn more about the history of Key West, this lovely, bucolic and interesting cemetery is the place to do it.

Don’t miss the cemetery’s regular walking historical tours. And check out the amazing giant iguanas while you’re there!

Where to stay in Key West

Key West has a wide range of accommodations for every budget and style.

There are plenty of upscale accommodations, even more mid-range places to stay and a good amount of budget accommodations and hostels.

You’ll also find adult only and LGBTQ friendly accommodations.

Please note that accommodation expenses in Key West is all about seasonality.

Hotel prices are highest from January to May peaking in February/March. June to September rates are lower by a third – it’s also hurricane season. October to December rates begin to perk up again.

The best places to eat in Key West

There is an abundance of places to eat in Key West. Here is one little delight that I found by accident near the docks, The Breakfast Club. They had the most amazing salads and burgers! I love little surprises like this; finding a great restaurant by accident.

More inland off Duval Street the Thirsty Mermaid was recommended to me and boy, am I glad it was! The seafood and service here were exemplary.

Now here is a surprise. Most restaurants in really touristy spots are not ideal. The Boat House, however, was a very good touristy restaurant that delivered on its reputation as the Best Happy Hour in town. All cocktails AND small plates were half priced during Happy Hour. But the surprise is that the half priced dishes are delightful; peel and eat shrimp, conch fritters, chicken wings, and lots more.

Honestly, there really are tons of places to eat in Key West. These I’ve mentioned are just a few we got around to.

How to get to Key West

The different ways to get to Key West depend on how much time you have, Most people take the legendary US 1 all the way down to Key West stopping along the way in interesting little towns like Key Largo of Bogart and Bacall fame, Islamorada, Marathon and the Lower Keys.

Driving from Miami, such a trip can take a few hours, days, or a lifetime depending on your interests.

If you are short on time, Key West has an airport you can fly into. Airlines that fly into Key West from major U.S. cities include American Airlines, Delta, United, Jet Blue and others.

The best time to visit Key West

Similar to Miami, the best time to go to Key West is winter because of the spectacular weather.

If you want to know more about Key West, explore the area with a good reference book in our hands, like these.

What are YOUR thoughts about the best things to do in Key West and the ideal Key West Weekend? Let us know n the comments.

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