Traveling to the southernmost US city is unlike any other vacation experience. Florida has always been an intriguing travel destination and Key West, Florida has been capturing the hearts of people for centuries.

This colorful city loves festivals, tourists, and one-of-a-kind occasions. While its reputation of being a “party town” is true, there are many family-friendly activities to enjoy as well.

The uniqueness and diversity of Florida can’t be beaten, and this iconic U.S destination doesn’t disappoint. The “key” to a fabulous experience in Key West is knowing exactly where to go, what to do, and what to eat like the best Key Lime pie!

Key West 3-Day Itinerary 

Here’s an exciting itinerary of natural beauty, tourist locations, outdoor fun, and hidden gems of the city. Feel free to mix up the three-day adventure however you please!

When’s the best time to visit?

The locals boast that they have the best year-round climate in the world with no fear of frost. 

It’s true. 

The warmest average temperatures hover in the 80s. Even in the coldest month of January, temps don’t dip below the 60s. The crowds are lower and the weather is the most blissful between the months of March and May.


Flying directly into Key West International Airport or catching a Greyhound Bus from Miami are popular modes of transportation. Cruise along the scenic Overseas Highway or jump on the Key West Express Ferry from Ft. Myers, Florida for breathtaking photo opportunities.

Check-In to Havana Cabana HotelHavana Cabana in Key West

Ready to escape from reality? 

If you’ve ever wanted a lush, oasis-style resort, you’ll be tickled when checking into Havana Cabana Resort. Take a step back in time when you are greeted with mid-century cars and Vespas in the welcoming front landscape. 

Nostalgic influences from the delightful culture of Cuba in the stunning lobby with winding staircases and Cuban wall art. One room option is a luxurious room facing the sweeping views of the gulf. The other option is a room with a balcony mere steps from the largest pool in Key West. 

Havana Cabana’s largest pool in Key West just happens to be a lagoon-style oasis surrounded by a cabana and palm trees. Unwind at any time during your stay at the Mojitos Pool Bar. 

The hotel also offers a wonderful free service of a shuttle van to and from the downtown area. Visitors also have the fun option to explore the town on a hotel bicycle or vintage Vespa.

Havana Cabana has a huge list of perks that are included with their resort fee.

  • 2 pair of Havana Cabana logo sunglasses upon check-in
  • 24-hour concierge service
  • Free on-site parking
  • Tesla charging stations
  • Shuttle service to Downtown Key West & airport pick-up on request
  • State-of-the-Art Fitness center
  • Wireless & wired internet
  • Poolside smoothies & popsicles 
  • Lobby churros & virgin mojitos
  • Tiki coffee 

Be a beach bum

If you are curious to explore Key West beaches, you don’t have to drive far to find one.

Although there are alarming rumors that beaches don’t exist in Key West, it’s not true. 

The truth is that one of the largest barrier reefs in the world runs alongside Key West. The reef causes the small landmass of Key West to be surrounded by a rocky barrier. But there are three public beaches that are clean with beautiful sand and water views.

Take a drive to the small Higgs Beach that includes a pier, dog park, and nearby African American cemetery monuments. It’s a great spot for shallow water snorkeling. 

Or visit my two favorite beaches, Fort Zachary Taylor Historic State Park and Smathers Beach. Each of these beaches showcases crystal clear turquoise waters and white, fluffy sand.

Visit Downtown Key WestDowntown Key West

Driving in Downtown Key West is somewhat intense with its narrow streets and expensive parking. Take advantage of the hotel’s free shuttle service! A friendly driver will take you to eccentric Downtown Key West and pick you up at a designated time.

Find the retro Cuban coffee sign for a selfie. Stroll around the marina and quirky shops. Stop by for a homemade Gladiators Ice Cream treat.

Experience Mallory Square & Its Famous SunsetMallory Square

Never heard about the Mallory Square Sunset Celebration? 

If not, you are in for a unique cultural experience! “See you at sunset” is a common phrase around these parts. Since the 1960s, people have been gathering a couple of hours before sunset to watch the pink and red set into the Gulf of Mexico. 

You’ll hear live music and see vendors selling trinkets and snacks as well as performers of every kind. Half of the fun is the surprise of which kind of entertainment will delight the crowds. Musicians, magicians, sword swallowers, high wire acts, or professional comedians are a few of the types of unforgettable entertainment.

Get Off the Hook 

Enjoy an upscale dinner at Off the Hook Bar & Grill. Specializing in American and seafood cuisine, this cozy bistro offers indoor and outdoor seating. You can’t go wrong with the surf and turf or stone crab claws.

Day one insider tip: Be sure to enjoy your hotel to the fullest by taking a dip in the lagoon pool at night!

DAY 2: EXPLORE THE CITY3-Day Key West Itinerary

Start the morning with a café con leche and a breakfast sandwich with the rich flavor combinations and relaxed atmosphere at Havana Cabana Resort’s on-site Floridita Food Truck.

Iconic Selfies

You can’t visit Key West and forget about the two most photographed places… the southernmost point and the Mile 0 Marker. 

Located at the corner of Whitehead and South Streets, the famous concrete buoy stands with the words “Southernmost point of the Continental U.S.A.” It’s a popular gathering place for tourists to photograph and meet other travelers.

Known as “the end of the road,” this famous green and white sign at the junction of Fleming and Whitehead Streets marks the final leg of US Highway 1. Typically there is a fun webcam there documenting all that visit, so wave to the camera!

Insider Tip: Arrive as early in the day to these two popular photo spots to avoid the crowds. If you don’t, you’ll be waiting in a long line no matter what time of year it is. 

Jet Ski around Key WestJet Ski Key West

For a once-in-a-lifetime adventure, check out Barefoot Billy’s tours

The most exciting tour is the one that allows you to circumnavigate the island of Key West on a two-hour guided jet ski tour! 

You won’t believe the view while gliding from the Atlantic Ocean to the Gulf of Mexico and back to the Atlantic. Barefoot Billy’s provides pick-up and drop-off from Havana Cabana as well.

Lobster Shack DinnerLobster Shack Key West

Experience a casual dinner at The Lobster Shack. What fun it is to try a traditional New England and Key West lobster roll to compare the two! If you prefer shrimp, they have a shrimp roll also.

Day two insider tip: You’ll do a lot of walking so carry a lightweight backpack with sunscreen, sunglasses & a change of shoes.


Heavenly BreakfastBlue Heaven Key West

Don’t leave this vacation destination without a quick breakfast at Blue Heaven

The whimsical decor may lead you to believe that they don’t take food seriously. But they do! Ask for the Rooster special and you certainly won’t leave hungry. 

Take a RideOld Town Trolley of Key West

Wind down on the last day with a leisurely ride on an Old Town Trolley sightseeing tour to explore some of the most iconic places in Key West. 

No pre-recorded information happens here! Each ride is as memorable as its professional guides that highlight the history and uniqueness of the city. Hop on and off to explore historical places that you don’t want to miss like Ernest Hemingway Home and Museum and the Butterfly and Nature Conservatory. 

Don’t miss a visit to the Key West Lighthouse and Keeper’s Quarters. Built-in 1848 and 88 steps tall, it has a rich history of a female lightkeeper and the storms it has survived through the years.

Shop until you drop

Friendly Caribbean-colored structures along the mile-long Duval Street will make you smile as you stroll for daytime shopping. 

Walk-in and out of one-of-a-kind shops that range from cheezy souvenir stores to designer boutiques. On your walk, you’ll see the Historic Strand Theater and are able to catch a selfie with the life-sized Marilyn Monroe statue in her iconic wind-blown dress. 

Don’t miss Kermit

You can’t travel to “the ends of the earth” and not experience authentic key lime pie!

The wait will be worth it to visit the Original Kermit’s on the historic Key West Bight waterfront. At this location, they also serve breakfast, lunch, and a light dinner from the cafe.

Don’t stop with a traditional slice of pie, however. Try a frozen slice of key lime pie on a stick that has been dipped in Belgian chocolate!

Day three insider Tip: Ask locals like your waiters and store owners about Key West and get an incredible new perspective.

You’ll be amazed at the vibrant energy and stunning scenery of Key West, Florida. It’s definitely a destination that must be visited at least once in every person’s lifetime.

Guest author bio: Shan Walker, The How to Guru, shares insider secrets that Women REALLY want to know about Georgia, Florida, & Carolina vacations – so YOU can focus on what matters most – making vacay memories with your people!

3-Day Key West Itinerary