Your 3-Day Key West Vacation Plan

Whether it's for your wedding, a loved one's big day, or just to get away, Key West is a wonderful island to stay for a few days - or in my case - over 11 years! Many of my photography clients and their guests ask me what they should do and see when they're not participating in wedding festivities. Showcasing my island home is one of my favorite things, so without further ado, here is my recommended itinerary for getting the most out of three days in Key West!

Day 1

Good morning! Start your first day in paradise off right with a visit to the Southernmost Point! Just 90 miles from Cuba, it’s a popular spot for photos, so the morning is a good time to go. Then, head north on Whitehead street for breakfast at Six Toed Cat. They have classic options like French toast, omelets, and Benedicts. It’s right next to the Hemingway Home and named after his famous polydactyl felines. 

Next, check out the Hemingway Home itself! Built in 1851 in a Spanish Colonial style, Ernest and his wife Pauline bought it in 1931. Enjoy the dozens of 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. Afterwards, cross the street to tour the Lighthouse and Keeper’s Quarters. Can you make it up the 88 steps to the top?

If climbing all those stairs made you work up an appetite, walk two blocks to Blue Heaven for some incredible Key Lime Pie. It’s an iconic restaurant beloved by locals and visitors alike, and its KLP is out of this world! You might also notice some chickens roaming around - they're a common sight in Key West! Then, four blocks away is another classic locale - the Mile Marker 0 sign for US 1! Snap a pic, then make a stop at the “End of the Road” gift shop across the street for a memento.

Next, walk further north on Whitehead Street and choose your track:

Kids Track: Check out the Key West Aquarium and/or the Shipwreck Museum, depending on your family's pace and how much time you have. They’re very close to each other, and both are fantastically fun for families. The Aquarium features thousands of fish native to the keys, including sea turtles! At the Shipwreck museum, you’ll learn all about Key West’s formerly booming wrecking industry. You can also climb the 65’ tower for a spectacular view of the harbor! For dinner, stop at the nearby Red Fish Blue Fish. It has great seafood, a nice outdoor patio, and kids love the little paper boats their meals come in!

Grown-ups Track: Head east on Front Street to Alonzo’s Oyster Bar for their happy hour between 4:00 and 6:00 PM! All drinks (except bottles of wine) are half off, as is the entire page of their menu with appetizers and sides. Try some incredible fresh seafood such as oysters, clams, shrimp, and conch!

End your first day in the Conch Republic at Mallory Square’s Sunset Celebration. Enjoy the street performers, artisans, and most of all, a glorious Key West Sunset!

Grown-ups, not ready for bed? Go to The Green Parrot Bar, an institution since 1890. They host fantastic live music almost every night of the week! 

Day 2

Breakfast is the most important meal of the day. Head to Harpoon Harry’s for some chow in a delightfully retro diner setting.

Next, choose your track:

Presidential Track: Stop by the Harry S. Truman Little White House. Built for the Key West Naval Station officers in 1890, this incredible building began serving as President Truman’s winter retreat while president. 

Natural Track: Go to the 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.

Treasure Hunting Track: Head to the 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 and fascinating information about Key West’s maritime history at this quality museum. 

Now that you’ve had a history lesson, time for some shopping! Peruse Duval Street’s multitude of stores for keepsakes, clothing, homewares, fine art... you name it! I really love Mario Sanchez’s works, which are featured at Gallery on Green

It’s time to set sail! Danger Charters’ Wind & Wine Sunset Sail on a gorgeous schooner is an intrepid yet intimate way to experience Key West’s open waters. Book this one in advance! Finally, end your day with a romantic dinner at Santiago’s Bodega. One of my absolute favorite restaurants here, it’s a cozy tapas bar that serves an array of delectable small plates with house-specialty sangria.

Day 3

You’ve covered so much ground on land, so today is the day to dip your toes in the water! Head to Blue Heaven again for some island vibes and a spectacular breakfast. My personal favorite is the Lobster Benny, or, if you’re not into seafood, the Rooster Special. Also, another slice of that amazing Key Lime Pie wouldn’t hurt!

While you digest, hop on the Old Town Trolley at its nearby Bahama Village stop. For the next 90 minutes, you’ll cover the whole island and see 100 points of interest. 

Next, choose your track:

Adventurous: Jump in with Fury Water Adventures! You could do an island jet ski tour, go on a snorkeling trip, or even parasail! Keep in mind that depending of the timing of the excursion you choose, you might want to save the above trolley tour for afterward.

Relaxing: It’s time to hit the beach! Head to Fort Zachary Taylor State Park. It’s such a beautiful beach that it’s where I do a lot of engagement and wedding photo shoots. It’s also a great spot for some snorkeling - no boat required! Hungry? Call Cuban Coffee Queen for a delivery of amazing Cuban fare.

Finally, enjoy one last Key West sunset during dinner. For a view of the Gulf of Mexico and wonderful island-inspired cuisine, try HarbourView Café, a part of the elegant Pier House Resort & Spa. Or, for a very special treat, go to Latitudes! Book in advance and then ride the ferry from the Westin to Sunset Key for an unforgettable dining experience.


Special thanks to my past wedding photography client and fellow Key West resident Kara Gladish and her company Kahunify for collaborating on this guide!