Rachel's Top Things to Do in Key West

Welcome to Key West! Whether it's for your wedding, a loved one's big day, or just to get away, there is so much to do and see on this island! And since there's so much, my photography clients and their guests often ask me for my list of can't-miss places. I absolutely love showcasing my home of over 11 years, so without further ado, here is my recommended list of what to do in the Conch Republic! 

Key West's Highlights

If you don't have much time in Key West outside of enjoying wedding festivities, never fear! You can cover the must-see places in a day! 

  • Hemingway Home. This is definitely at the top of the list! Built in 1851 in a Spanish Colonial style, Ernest and his wife Pauline bought it in 1931. Enjoy the dozens of polydactyl cats, the beautiful architecture, and some of Papa’s furniture while channeling your inner author; he wrote many of his famous books in the home, including For Whom the Bell Tolls.
  • Southernmost Point. This Key West icon is perfect for a photo op and bragging rights! The line just for pictures can get a bit long, so try to stop by in the morning. 
  • Sunset Celebration at Mallory Square. The center of Key West’s historic waterfront, Mallory Square’s Sunset Celebration is a nightly festival with arts and crafts, street performers, and food carts. The festivities start about 2 hours before the sun sets into the Gulf of Mexico.
  • Old Town Trolley. The Trolley is a great way to see most of Key West when your limited on time. In 90 minutes, you’ll cover the whole island and see 100 points of interest. 
  • Peruse Duval Street. Key West’s main drag is full of a wide variety of shops, art galleries, restaurants, and bars. But the best part of all is… people watching. From diverse tourists to quirky locals, you’ll see a wide range of characters while soaking in the spirit of the Conch Republic.

If you do have a bit more time to enjoy Key West, check out my recommended things to do, listed below by interest!

Site Seers

If you're a photo opportunist, you'll want to stop at these iconic Key West sites! 

  • Old Town Trolley. On the 90-minute trolley ride, you’ll cover the whole island and see 100 points of interest. I recommend doing this fun activity early in your trip since it might help you spot other places you'll want to check out.
  • Southernmost Point. This Key West icon is perfect for a photo op and bragging rights! The line just for pictures can get a bit long, so try to go there in the morning. 
  • Key West Postcard Mural. This painting is so beautiful, it's on the location list for my photography clients' Around Key West shoots! Snap a pic then go to the front of the building to grab food or refreshments from Cuban Coffee Queen!
  • Mile Marker 0 SignStop at this classic locale to commemorate that you made it to the end of US 1 then check out the “End of the Road” gift shop across the street for a memento.

History Buffs

Want to learn about the past? Key West has a rich and colorful history for you to explore!

  • Hemingway Home. This is definitely at the top of the list! Built in 1851 in a Spanish Colonial style, Ernest and his wife Pauline bought it in 1931. Enjoy the dozens of polydactyl cats, the beautiful architecture, and some of Papa’s furniture while channeling your inner author; he wrote many of his famous books in the home, including For Whom the Bell Tolls.
  • Key West Lighthouse and Keeper’s Quarters Museum. The tower and nearby Keeper’s Quarters have been faithfully restored and maintained as they were before the lighthouse was deactivated in 1969. It is the 15th oldest surviving lighthouse in the country and has 88 steps leading to the lighthouse deck. Make the climb for a great view! 
  • Harry S. Truman Little White House. Step back in time and into former President Truman’s era at Key West’s Little White House. Built for the Key West Naval Station officers in 1890, this incredible building began serving as Truman’s presidential winter retreat. In addition to Truman, the house has hosted six presidents and a king and is Florida’s only presidential museum.
  • Mel Fisher Maritime Heritage Museum. Mel was the local hero who searched for the wreck of the Spanish ship The Atocha for 16 years and found the motherlode in 1985. Learn about his $450 million find as well as fascinating information about Key West’s maritime history at this quality museum. 

Nature Lovers

With beautiful weather and the ocean on three sides, this island is the perfect place to commune with tropical flora and fauna.

  • Key West Butterfly and Nature Conservatory. This private, lush oasis perfectly captures the relaxed, magical feel of Key West. Take a breathtaking journey through the climate-controlled, glass-covered habitat and home to the magnificent world of over 50 species of butterflies.
  • Key West Garden Club/West Martello Tower. Stroll the brick pathways through graceful arched courtyards and lush, colorful foliage of the grounds of the West Martello Tower, a Civil War fort and a National Historic Site. The gardens feature a rare collection of native and exotic trees and plants, including blooming orchids and bromeliads. 
  • Audubon House & Tropical Gardens. Tour the historic home, built by Captain John Huling Geiger in the 1840s, learn about the naturalist John James Audubon’s visit to Key West to paint native birds, and enjoy the acre of lush gardens.
  • Fort Zachary Taylor State Park. Fort Zach is such a beautiful place, it’s where I do a lot of engagement and wedding photo shoots! Stroll the tropical forest then catch some rays on the sandy shore. 

Families with Kids

Do you have young ones in tow, or are you just young at heart?

  • Key West Aquarium. The Aquarium features thousands of fish native to the keys, including sea turtles! There's even a touch tank where kids can pet starfish, sea cucumbers, and crabs. It's also a blast to watch the shark feeding (no touching allowed!).
  • The Shipwreck Museum. You’ll learn all about Key West’s formerly booming wrecking industry from historical characters and fascinating exhibits. You can also climb the 65’ tower for a spectacular view of the harbor! 
  • Sunset Celebration at Mallory Square. The center of Key West’s historic waterfront, Mallory Square’s Sunset Celebration is a nightly festival. Kids and adults alike love watching the performers, from acrobats to jugglers to fire breathers. There are also arts and crafts for sale and food carts with tasty treats. 
  • Fort Zachary Taylor State Park. No family vacation in Key West is complete without some beach time! Make a splash, build a sand castle, or do some snorkling - no boat required! 

Mermaids and Mermen

Is the ocean calling you? There are tons of ways to pick up the phone. 

  • Pepe's Charters. Pepe is not only a great guy but also super knowledgeable about catching fish! His company offers a wide range of action-packed fishing charter options so you can catch all kinds of fish.
  • Laid Back Key West. Eric and his crew specialize in customizing private charter packages exactly to your needs, from fishing and lobstering to snorkeling and diving.
  • Fury Water Adventures. With Fury, you could do an island jet ski tour, go kayaking, snorkel at a coral reef, watch dolphins, or even parasail! 
  • Danger Charters’ Wind & Wine Sunset Sail.  Setting sail on this gorgeous schooner is an intrepid yet intimate way to experience Key West’s open waters. Book this one in advance!  
  • Dive Key West - Dive the Vandenberg. If you're a scuba diver, don't miss the Vandenberg! This WWII transport became an artificial reef and world-class diving site in 2009. Book your diving trip with Dive Key West, a friendly and high quality dive shop with over 40 years of experience.

R&R

If relaxation is the most important thing to you when on vacation, unwind with a massage, facial, or body treatment at one of these wonderful spas! 

  • Anahara Spa. Key West's newest day spa is conveniently located right on Duval Street!
  • Prana Spa. Prana is a lovely oasis with spa treatments inspired by travels to Thailand, India, and the South Pacific Islands. 
  • SpaTerre at Ocean Key. SpaTerre is the top-rated spa in Key West according to TripAdvisor!