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One Day in Key West Florida

A One Day Key West Florida No Holds Barred Adventure Guide!

Author Mary Chong
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Treasure, trains, pirates, ghosts, margaritas, sunsets and pie, oh my! In Key West, Florida, there is so much to do, and given that we only had one day in this sunny beach city, we just had to do it ALL.

You see, we were staying up in Ducks Key at the ultra-relaxing Hawks Cay Resort, but since we were only approximately 1-hour north of Key West, we couldn’t resist the additional Florida Keys adventure. So, we left our resort hotel bright and early one morning, hopped into our car, turned left onto Highway 1 and headed further south for a day in Key West!

PRO TRAVEL TIP: If you are travelling to Key West as a port stop on a Caribbean Island cruise and therefore have a lot less than 24 hours in Key West, you can certainly do almost all of these same activities, but of course, you will start at the historic seaport.

A One Day Key West Florida No Holds Barred Adventure! - Highway 1

Here’s what we did in one day in Key West Florida

A One Day Key West Florida No Holds Barred Adventure!

When it comes to the “must do in Key West,” first things first–getting around the city.

Most of the parking spaces on the streets of Key West are permit only, and if you can find a meter, you’ll have to keep feeding it coins all day. Best to look for an all-day parking garage with one flat fee to avoid the stress of watching the clock.

Conch Tour Train by Old Town Trolley

A One Day Key West Florida No Holds Barred Adventure! - Conch Tour Train

Hop-on hop-off Key West tours, whether on a bus or a tram, are an excellent way to get acclimatised to a city. They usually include narration either by way of a recording or by the driver. Our little ride on the Conch Tour Train was especially good because while we were riding, a sun shower started, and we were thankful that we were still able to see the sights and stay dry at the same time. Our driver also offered us complimentary rain ponchos.

Four train stops in popular centralised locations to the various tourist sites make it the perfect activity to see Key West in one day.

PRO TRAVEL TIP: Hop-on Hop-off tours are also perfect when you are tired and don’t want to walk. They are an ideal thing to do in Key West for seniors or families with young children.

Ernest Hemingway Home and Museum

A One Day Key West Florida No Holds Barred Adventure! - Hemingway Home

Address: 907 Whitehead St, Key West, FL 33040
Open 9-5, 365 days a year

A One Day Key West Florida No Holds Barred Adventure! - Hemingway Home

Acclaimed author Ernest Hemingway lived in Key West during his most productive years, and his home provides great insight into his life and work. Notable things to see here are his office and the cats that roam the property. The 40+ cats are polydactyl since they either have six toes on their paws or they carry the polydactyl gene within their DNA.

A One Day Key West Florida No Holds Barred Adventure! - Hemingway Cats


  • If you’re allergic to cats like I am, make sure you come prepared with allergy medication.
  • To get the most out of your visit, make sure you join the 30-minute guided tour included with admission.

Photo time at the Southernmost Point

A One Day Key West Florida No Holds Barred Adventure! - Southern Most Point

Address: Whitehead Street & South Street
Fee: Free

Key West is 90 miles away from Cuba and is the southernmost point in the continental US. It’s an excellent spot for that photo opportunity and an absolute must-do for first-time visitors, but be warned that there will be a long queue.

Waste away at Jimmy Buffett’s Margaritaville Cafe

A One Day Key West Florida No Holds Barred Adventure! - exterior view Margaritaville

Address: 500 Duval St, Key West, FL 33040

Located on famous Duval Street, full of restaurants, shops, and historic buildings, lies the famous Margaritaville Cafe owned by singer/songwriter Jimmy Buffett. A great place (albeit touristy) to listen to live music, eat some Caribbean-inspired food, cool off with cold frozen cocktails, and of course, a margarita!

Find peace at St Paul’s Episcopal Church

St Paul’s Episcopal Church Key West Florida

Address: 401 Duval St, Key West, FL 33040

Open daily from 7:30 to dusk, St Paul’s Episcopal Church welcomes anyone and everyone to visit. The first church, made of coral rock, began construction in 1838, a few years after the City Council of Key West requested a priest be sent and for the Parish of St Paul’s to be established. The current church is the fourth, the previous three destroyed by hurricanes and fires alike. Despite these disasters, the churches were always rebuilt promptly and today, it continues to offer its services. 

Whether you want to stop by for a prayer or look in awe at the stained glass windows, the church is a great spot to gather a couple of moments of peace when travelling. 

Also, if you want to sit in on service each Sunday at 7:30 am and 10:00 am, Holy Eucharist Rite II services are always offered.

PRO TRAVEL TIP: There are some benches outside with trees for shade and a nice breeze if you need a rest break.

Hellings House Museum and the Key West Woman’s Club

Hellings House Key West Florida

Address: 319 Duval St, Key West, FL 33040

Formed in 1915, the Key West Woman’s Club is a volunteer service organization who do everything they can to help better their community. 

The Hellings House, where they’re located, also functions as a museum open to the public—but make sure to check their hours or call ahead of time to ensure they are open! The house was originally built in 1892 by Captain Martin Helling and his wife Eleanor (whose father was Florida’s first millionaire). Due to Key West’s rocky history, the Hellings did what they could to keep families in the community. In 1940, the Key West Woman’s Club took over and continues to maintain the house today, trying to keep the Hellings’ generosity alive. 

The Shops at Mallory Square in the Old Naval Depot and Storehouses

The Shops at Mallory Square Key West Florida

Address: 291 Front St, Key West, FL 33040

If you’re looking for an incredibly unique shopping locale, then the Shops at Mallory Square is your stop. Located inside the former Naval Depot and Storehouse (as well as one of the US Coast Guard Headquarters!), this shopping centre isn’t what you would typically expect. Built between 1856 and 1861, the building is the oldest brick building on the entire Key West. 

The inside of the building does not disappoint either; filled with shops and exhibits from a wide range, make sure to dig into some frozen custard, explore some stunning art, and maybe even buy a thing or two (or three).

Find Treasure at the Mel Fisher Maritime Heritage Museum

A One Day Key West Florida No Holds Barred Adventure! - Mel Fisher Museum

Address: 200 Greene St, Key West, FL 33040

There be gold in the keys, and this maritime museum is the place to see it.

For 16 years, Mel Fisher and his crew set off in search of treasure off the coast of Key West. In 1985 all that searching paid off when he discovered the Nuestra Senora de Atocha and the Santa Margarita, two Spanish galleons that sank during a hurricane in 1622.

The $450 million treasure cache includes 40+ tonnes of silver and gold, 100,000+ Spanish silver and gold coins, and 1000+ silver bars.

A One Day Key West Florida No Holds Barred Adventure! - Mel Fisher Museum gold bars

This fascinating museum shows off the discoveries and the details of the expedition. The gift shop showcases genuine artefacts, and reproductions are available for purchase.

PRO TRAVEL TIP: There is a free bag check as no bags are permitted inside. An audio tour is available.

Become a Pirate at the Key West Shipwreck Treasure Museum

Key West Florida Shipwreck Treasures Museum

Address: 1 Whitehead St, Key West, FL 33040

The Key West Shipwreck Treasure Museum is located in a recreated 19th-century mast salvage warehouse. It is also the perfect spot for a fantastic view of Key West if you dare to climb to the top of the 65-foot lookout tower. This guided tour is ideal for the kids in that a costumed “actor” escorts you through the various displays and explains the history of Key West in the age of pirates and shipwrecks. The museum also provides a fascinating look into the history of the slave trade.

Get Wet at the Key West Aquarium

Exterior view Key West Aquarium

Address: 1 Whitehead St, Key West, FL 33040

The small Key West Aquarium, built in the early 1930s, is directly next to Mallory Square. Including exhibits indoors and out, the highlight of the Aquarium is the touch tanks, which children (and my man-child) seem to love.

Key West Aquarium touch tank

PRO TRAVEL TIP: Key West Aquarium and Shipwreck Museum combo admission tickets are available.

People watch at Mallory Square

Mallory Square Key West Florida

Fee: Free

Mallory Square was the original location of the slave auctions back in the early 1820s, but now this centre of Key West is known for its live performances, buskers, and famous Sunset Celebration when locals and tourists come to toast the sun going down.

Mallory Square is the spot to take a break on one of the benches; people watch and see the cruise ships leave port while enjoying the ocean breeze.

History at Key West Memorial Sculpture Garden

Key West Sculpture Garden

Address: 401 Wall St, Key West, FL 33040

Any local history fans here? If so, the Key West Memorial Sculpture Garden is a must-visit. Recounting the island’s history through its most influential men and women, you’ll be riveted by their stories. The garden includes sculptures of people you’ll be surprised to recognize—Ernest Hemingway, anyone?—as well as those you may not know but will surely still inspire. 

In addition to their founding stories, the 36 bronze sculptures and surrounding area are beautiful, and you’ll want to stay awhile.

PRO TRAVEL TIP: There are public restrooms between the sculpture garden and Mallory Square

Sunset Sail on the Schooner America 2

Schooner 2 and Calculated Traveller

Standing on the shore at Mallory Square at dusk is a fabulous way to enjoy a Key West Sunset but experiencing it on a schooner with your honey is the ultimate when it comes to creating a romantic memory.

If you are a regular reader, you know that we frequently travel by cruise ship, but we’ve never been on a sailboat before, and we loved it. The Schooner America 2 does it right. With drinks and hors-d’oeuvres included, we sailed the harbour and watched the sunset in style!

Sailing onboard the Schooner 2 Key West Florida

Ghosts and Gravestones Frightseeing Tour

Ghosts and Gravestones Tour Key West Florida

Address: 501 Front St. – Conch Train depot; corner of Front & Duval Sts.

Spooky good. This 1.5-hour Ghosts and Gravestone Frightseeing bus tour takes you through the streets of Key West on a ghoulish tour in search of ghosts. With a city full of historic homes, you just know there will be some tales to be told. The highlight of this tour is a visit with Robert the doll at the haunted Fort East Martello Museum.

A One Day Key West Florida No Holds Barred Adventure! - Robert the Doll

Robert is a handmade doll gifted to local artist Gene Otto in 1906 by a household servant who practised black magic and voodoo. Whenever Gene did anything bad, which apparently was quite often, and would get caught, he would blame it on Robert. It is said that Robert will move by himself or will cause ill will if you aren’t polite during your visit with him. So, don’t forget to ask permission from Robert before taking his photo and remember to thank him for the pleasure afterwards or face the consequences [insert evil laugh here].

As the night ended, we drove our tired bodies back to Hawks Cay Resort and collapsed into bed exhausted.

A One Day Key West Florida No Holds Barred Adventure! by Calculated Traveller

What a whirlwind adventure of Key West all in one single day! We hope you enjoyed these Key West travel tips and suggestions and find them helpful when planning your day in Key West.

Did you visit any of these sites on your vacation? What did you think of them?

What places do you suggest as the best things to do in Key West in one day?

Travel assistance provided by The Florida Keys and Key West. All opinions are entirely my own.

These adventures and travel guides nearby may interest you:
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11 Things to do in Miami Florida
Florida Keys Onion-Encrusted Yellowtail and Key Lime Pie
A Traveller’s Guide to St Augustine Florida – History and Fun

There are a variety of active excursions in the area of Key West – snorkelling, jet ski tours, bike tours etc. check some out here.