The Florida Keys! Definitely one of my favorite places to visit in Florida. This gorgeous chain of islands in South Florida has that small town, vacation-everyday vibe. It’s home to laid back fishermen, ocean junkies, and ‘No Shirt, No Shoes, No Problem’ is their motto!

Each island has it’s own famous bars, restaurants, and gorgeous, must-see sites. They’re all known for their coral reefs, diving, snorkeling, fishing, boating, and breathtaking sunsets. They span about 110 miles and are connected by bridges so it’s very easy to road trip and explore all that the Keys has to offer.

Key West is not only the southernmost city in Florida, it’s also the southernmost point in the continental United States! It’s located about 90 miles north of Cuba and about a 3-4 hour drive from Miami. It’s known for its pastel, conch-style houses, its laid back atmosphere, its vibrant nightlife and amazing bars! It has a large LGBTQ community and is very welcoming towards all types of people. Key West is also home to Fantasy Fest, a yearly, week-long festival that attracts 100,000 people from all over the world for balls, parades, AIDS fundraisers, and more. Here’s my guide to a perfect weekend in Key West.

Guide to a perfect weekend in Key West

Where to stay:

We stayed in the Santa Maria Suites which was ranked #14 of the Top 25 Hotels in the USA from TripAdvisor last year. We had an amazing 2 story, 2 bedroom suite with a full kitchen, 2.5 bathrooms, and a pullout couch. It fit all 6 of us very comfortably and the highly modern finishes, sparkly pool, and daily happy hour made it that much better. It’s located about a block away from Duval Street and some of the beaches, so the location was walking distance to everything. It is a bit pricey but take advantage of the space and grab a group of friends to split the cost!

Where to stay: Santa Maria Suites

Guide to a perfect weekend in Key West

Things to do:

Duval Street

Duval Street is a famous downtown street in Key West. It runs north and south, a little over a mile from the Gulf of Mexico to the Atlantic Ocean. It’s Bahamian and Cuban influenced shops, restaurants, and bars line the street. It’s THE spot to shop, eat and drink in Key West.

Sunset Boat Tour

Friday night we went out on a boat cruise on the water as the sun set. There are many boat owners who offer chartering services in the Keys.


After a little shopping we walked over to South Beach to get some sun. Our reservation at the Santa Maria Suites included chairs, umbrellas, and towels for free at this beach. So we caught a few rays (and a few zz’s) before heading back to the hotel to get ready for the night.


We went to this amazing brunch spot, . We loaded up on their Bloody Mary’s, Blood Orange Mimosas, and Eggs Benedict before heading out to do some shopping on Duval street.


We went out to The Thirsty Mermaid for dinner that night. It was the cutest little mermaid/ocean themed restaurant with out of this world food!

TRAVEL TIP: Reserve a table or get there early because it’s a small place. It’s so worth the wait though!

Drag Show + Bar Hopping

You can’t have a Key West bachelorette weekend without going to a drag show! Key West is known for them. We went to 801 Bourbon which has two nighttime shows, 9pm and 11pm. This was actually my first drag show and I had so much fun! The show was entertaining, hilarious, and definitely the highlight of the night. After the show we headed out to Duval street again to hit up some more bars.

TRAVEL TIP: Reserve seats at 801 Bourbon before you go so you can sit right in the front!

Hemingway Home and Museum

Key West is known for once being the home to writer Ernest Hemingway. He produced some of his best work during his decade-long residence in the house that still stands today as the Hemingway Home and Museum. The famous six-toes cats that roam around are descendants of Hemingway’s own pets.

Key West Shipwreck Museum

The Key West Shipwreck Museum tells the story of 400 years of shipwrecks. Back in the 1800s, at least one ship per week would wreck along the Florida Reef and the waters were known as some of the most treacherous in the world. This museum has on display the gold and artifacts from those wrecks that once made Key West one of the richest cities in America.

Guide to a perfect weekend in Key West

What To Wear:

I headed to Key West in November and the weather was beautiful. It didn’t rain once. When heading to the Keys pack light and make sure to bring beachy dresses, bathing suits, coverups, sandals and of course, plenty of sunscreen!

STYLE TIP: The Keys are very laid back and casual so don’t worry about bringing out the 5 inch stilettos. Pack a pair of wedges or some cute gladiator sandals.


Florida is known for its unpredictable weather and 5 minute thunderstorms. Hurricane season runs from June 1st to November 30th but the storms are usually worse from August to October. So if you want to be safe, steer clear of Florida during those months.

Key West is truly one-of-a-kind. Head down there for a week of sun, ocean, and relaxation!

Author: Michelle is the owner of travel/style blog maps&muses. She has worked in the fashion industry for years but decided to quit the 9-6 life to live her dream and travel the world. Follow along on her fashionable adventures across the globe as she teaches you how to dress stylishly while traveling, and all on a budget.

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