Destination Wedding & TRAVEL Planner

The Ultimate Guide to Preparing for Your Stay in Key West

The stories of Duval Street are legendary and rival those of Vegas; everyone knows the sunset experience at Mallory Square is epic; and the city’s fathers include Ernest (as in Hemingway) and Jimmy (as in Buffet) with their unique personal stamps found all over town. The iconic Southernmost Point stands as the “Eiffel Tower” of the famed city and there is a seemingly seamless blend of military, marine, bohemian, parrotheads Alternative lifestylers/LGBTQ, modern-day pirates and treasure seekers, cruise ship shore trippers, family vacationers, honeymooners, spring breakers, dog lovers, cat lovers, adrenaline junkies, bikers — and everything in between. 

So where do you fit in and how can you be ready to make the most of your time in the Conch Republic? (pronounced “conk”)


• Read the little book “The Conch That Roared” by Gregory King, (1997). It is an easy read and will give you a true insight into the quirky history and mind set of the local culture.

• Key West is a city of festivals/events, so check calendars when planning (especially weekends). You may find one you want to attend … or at least be prepared. Some of the best known:  Key West Fishing Tournament (Jan); Songwriter Festival (May); Fantasy Fest (Oct.); Key West Holiday Fest (Dec). Source: – Great resource

• If you are a sportfisherman/woman or recreational boater, check those weather/tide/fishing guides in advance. Same thing goes for snorkelers and divers. BE safe, be happy.

 Key West is an Island – Not Just Old Town!

Dry Tortugas National Parkby boat or seaplane. Day trips and overnight camping, snorkeling; weddings and picnics, explore the fort

Fort Zachary State Park woods and beaches, picnics and weddings, watersports

Smathers Beach – One offew wide, sandy beaches you will find in the Florida Keys…. Open space everywhere. Concessions and rentals. Weddings.

At the End of the Day

No matter how you like to rest your head at night, The Southernmost City has you “covered”:

Airbnb, stay aboard a boat, luxury hotel, all-inclusive family style resorts, dive (literally) motel, adult hostel, lavish Victorian guest homes and cozy cottages of every style; camping in state parks, RV parks, funky little inns. There is something for everyone…. Book early!

If you’ve got kids or like it quiet… think about your proximity to the nightlife.

It is a dog friendly city but always check. Same thing goes for parking… it is not always a given and you may need to map it out and be creative. Depending on your style, youmay not even need a car. … especially if you flew into Key West airport. Pedicabs, pink taxi-vans, tourist trolleys and trams abound and of course the ever-present motor scooters and bikes.

What “Attracts You”

Here is just a brief sampling of “tourist-y” locales on the Key West Must See list:


History and Military

On the Water

In the Arts (everywhere)

Go for the statues, stay for the experience

For current events and other useful info visit:

What to Bring

It’s a walking city…. flips are great for a casual stroll, but your tired feet will appreciate this advice later: Bring sneakers, solid walking shoes or sandals or other athletic footwear for street exploration Footwear and fashion that are “boat” appropriate will come in handy. Along with sunscreen and a hat that won’t blow away. Of course, koozies and sports bottles are a must … or just buy one at “Fat Tuesday” to keep after you finish one of their famous daquiris.

Dress light as you walk about…. May – October you will fry. No see-ums come out at sunset along with the skeeters so have a good travel sized bug spray; everything is casual so don’t overpack (but do feel free to express your personal style!)

In town, there are corner markets and CVS is like a department store, but if you need to stock provisions, you will need to hit one of the shopping centers in New Town.

While some of this advice is common sense… there is nothing commonplace about Key West. Be prepared to see anything and everything. Newlyweds are everywhere {love is always in the air in this tropical paradise — as are weddings; do you see a pattern here?}.  Very easy to obtain a marriage license during business hours, in person at the courthouse. Please visit Monroe County Courthouse for complete details.


December 4, 2017

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