Three days in Key West featuring sunset sails, historic forts, and adventurous tours. This is the perfect guide for your Key West and Florida Keys vacation!

A Florida Keys vacation of three days in Key West is something everyone should do at least once (predictive text said once a year, it’s not wrong). Key West is a historic town with a colorful past, and the people who live there enjoy life. Just what you would expect from an island that’s survived hurricanes and pirates for the last 500 years, all while seemingly being at the end of the world.

We’ll be covering a full three days in Key West, not including travel time. Miami to Key West is about a 4-hour drive, all dependent on traffic of course. Getting to the island, checking into your hotel, and getting settled in will take most of the day. If you get in early enough you can get a nice meal and watch a great sunset.

Day One in Key West: Exploring the Island

Key West is divided into distinct neighborhoods that offer unique experiences. Old Town is the heart of Key West and is filled with culturally influenced architecture from bungalows of the Victorian era settlers to Bahamian style cottages. It is on the southeast corner of the island and is very walkable. You can find a lot of things to do in this small walkable area. Shopping, restaurants, art galleries, and historic homes and areas are in this neighborhood.

The Hemingway Home and Museum

Get there early and beat the crowd, grab a tour guide and stroll through the immaculately preserved house with pictures of the great American author Ernest Hemingway’s life including his love of deep-sea fishing. Descendants of his famous six-toed cats are still prowling around the premises where he wrote A Farewell to Arms, To Have and Have Not, and For Whom the Bell Tolls along with many others.

The Hemingway Home and Museum is located at 907 Whitehead Street and open from 9 am to 5 pm. Tours start at 9:15 with a new one every 15 minutes, they last about 30 minutes and are included with admission. Admission is $19/$7 for adult/children and tickets are only available at the main gate.

Key West Lighthouse and Keepers Quarters

Right across the street from the Hemingway Home is the Key West Lighthouse, it won’t be hard to miss. The Florida Keys are an extremely hard area to navigate due to the shallow reefs in the area. The lighthouse has been helping mariners navigate the area since it opened in 1848 and was a working light house for the next 121 years.

Not only can you climb the 88 steps to the top of the lighthouse and get fantastic views of Key West, but you can also tour the Keepers Quarters. Explore the history of the workers who dedicated their lives to the safe passage of mariners. Interesting fact – the first keeper was a woman, which was totally unusual in the 1800s.

The lighthouse and museum are open from 10 am to 5 pm. Admission is $15.50/$11.50/$7.50/Free, for adults/senior citizens, locals, retired military and college/children/active-duty military.

Lunch

Head over to Ana’s Cafe and the Southernmost Grocery Store for a delicious Cuban sandwich. Grab some chips, a cold drink, and eat it out on the covered front porch while you people watch. It’s just a short walk from the Lighthouse down Duval Street. When you’re done take a block and a half walk to the Southernmost Point of the United States.

The Southernmost Point of the United States

You know you want this photo so you can flex on all your northern friends. At the time of this writing the Southernmost Buoy and South Street are being repaired and won’t be open until late 2026. The good news is that you can still get your selfie fix at a full-scale replica temporary marker just a block from the original. The new location is at the Duval Street Pocket Park at 1400 Duval Street. Pro Tip: if there’s a line to get a photo (there usually is) come back early in the morning or later in the evening when there’s fewer people, plus the lighting is better for pictures.

Key West Butterfly Conservatory

Have you ever had the experience of walking amongst tropical plants and cascading waterfalls with 100s of butterflies and exotic birds flying around? Well, now’s your chance. Not only that, but there are also two pink flamingos squawking in the background to complete the experience. Continuously voted as a Key West top attraction, the Butterfly Conservatory is the place to learn about butterflies, how they migrate, and what parts of the world that they’re found in.

Admission is $15.50/$14.50/$12.50 for adults/military/child and the hours are 9 am – 5 pm.

Schooner Wharf Bar and Mallory Square

Grab some spectacular seafood at Schooner Wharf Bar while you have great views of the marina. With live music nightly, Schooner is always voted one of the best bars by the locals.

After dinner head on over to Mallory Square and enjoy the sunset celebration and happenings. Fun for all ages the celebration includes stunt performers, comedy shows, live music, and local vendors.

Day Two in Key West: Explore the Ocean

Climb aboard a sailboat and sail to the Keys backcountry. The Key West National Wildlife Refuge is home to 14 islands and is filled with manatees, dolphins, hundreds of species of birds, and sea turtles in a 375-mile stretch of ocean.

Danger Charter Sail Snorkel and Kayak Tour

Danger Charters, great name, great tour. You’ll sail to the backcountry in one of their shallow-draft schooners. On the way you’ll get to know all about the Key West National Wildlife Refuge thanks to the knowledgeable guides.

Snorkeling

First up is snorkeling, in the water you’ll see stingrays, and other marine life among the coral reefs. If you’ve never snorkeled before, it’s okay because the Danger Charters guides are experienced and will help you with whatever you’re concerned about.

There’s a full buffet lunch with drinks for you when you get back, you can eat and mingle with the other 19 people on your cruise.

Kayaking

Next is the cruise to a mangrove island, here is where you get into the kayaks and you’ll paddle around the island. You’ll learn about how mangroves form as well as about the birds and marine life that inhabit them as you kayak under the canopy of the trees.

Once you’re done kayaking and the kayaks are loaded back on the boat, it’s time to pull up anchor and head to a sandbar (weather permitting). Relax on the boat under the canopy, hang out and socialize on the sandbar, it’s up to you. Drinks are provided in the form of wine, beer, soft drinks, and water, along with healthy snacks. After your stay at the sandbar is over, it’s time to head back to Key West, so relax and enjoy the rest of the cruise.

A full day tour is $134/$109 for adults/children and lasts 6.5 hours. If you’re pressed for time or want a little less time on the water, they have 1/2-day trips leaving in the morning and early afternoon that are 4.5 hours and cost $99/$79. Just a heads up before you book, they automatically put on a 12% trip insurance fee for easy cancellation if you can’t make it. If you’re positive that you’re going to be there, unclick the trip protection fee and save yourself some money.

---

---

Duval Street Dinner and Night Life

There is everything from fine dining to tiki huts with walls covered in dollar bills on Duval Street. If you’re looking for more upscale, try Ocean Grill and Bar, or Milagro Grill and Bar. Both have delicious seafood in a classy setting. For a more casual experience try Old Town Tavern and Beer Garden or wander on down to Sloppy Joes and hang out with all the other Hemingway fans.

After dinner be sure to walk around Duval Street and people watch. Stop in any of the bars/restaurants that line the street and grab a drink to cool you off as you enjoy the parade of people up and down the street. And if you’re brave enough, make a stop at the Garden of Eden and hang with the locals, naked. Don’t worry, if you’re shy, you don’t have to take your clothes off, it’s a clothing optional bar.

Day Three in Key West: Relax on the Beach

Most people don’t understand this, but for as much shoreline as there is in the Florida Keys, there’s not a lot of good beaches to hang out at. Fortunately, Key West has three really nice beaches, all on the south side. Some type of water shoes are recommended as the beaches are sand over fossilized coral and it’s extremely hard on the feet.

Fort Zachery Taylor Historic Fort and Beach

Take a tour through this Civil War era fort and after you’re done hit the beach. Only one floor of Fort Taylor is intact, but you’ll get a feel for what it was like living there. Original Civil War era canons are still in position. After you’re done touring the fort, head on over to the beach where you can snorkel, swim, and just relax on the shore. Just be sure to bring your beach shoes, the beach itself has sand, but you do walk on coral as you’re getting into the water.

There are plenty of grills and picnic tables scattered throughout the property, so bring a picnic lunch, or catch dinner with your fishing pole and enjoy. The Chickee Hut rents snorkel gear, beach chairs, umbrellas, and inflatable rafts. If you have the energy, hike around the property’s nature trail. Finally, if you stay long enough, catch a gorgeous sunset while you lounge on the beach.

Higgs Beach Park

Higgs Beach is a small strip of sandy beach with a pier. If you want to stretch your legs, they have a volleyball court and across the street there are pickle ball and tennis courts. There’s a restaurant nearby for lunch and there are showers and a restroom available.

Chair rentals are available, and there are tables and grills scattered around, some even are under tiki huts. If you bring Rusty with you there’s a dog park nearby.

Smathers Beach

The largest public beach in Key West, Smathers Beach is 1/2 mile long. While it doesn’t have all the amenities of the other beaches, it does have restrooms, showers, and volleyball courts. If you want to get a little bit of air between you and the beach, Sunset Watersports is right there, and they’ll take you parasailing.

Enjoy the Key West Sunset One Last Time

Grab a drink, sit in one of the brightly painted chairs at the Sunset Pier, and enjoy the sunset one last time with other sunset enthusiasts. Head on over to Mallory Square and hang out with the other sunset revelers. Or if you’re still up for another adventure, book a sunset cruise. Whether you want private and romantic, or party boat, there is no shortage of sunset cruise vendors, so pick one that matches your personality. Our favorite is Commotion on the Ocean with Fury.

Commotion on the Ocean

Complimentary margaritas, beer, champagne, and wine, or water and soft drinks if you’re a tea-totaler. Cruise the high seas on a catamaran and watch the sun dip below the horizon as a band plays in the background. The two-hour tour includes snacks, drinks, and breathtaking views. The cruise leaves from the historic seaport and costs $79.95/$59.95 for adults/children.

Getting around for Three Days in Key West

Parking can get crazy expensive in Key West. Some places offer free parking while others will have a small charge for parking, and some might not even have any parking at all. The public parking lot charges $48 per day, so keep that in mind if the place that you want to stay doesn’t have any.

Key West is pretty much a park it and forget it town. If your hotel has parking, you’re in luck, even better if it’s free parking. You can get around using one of the many services available. If you’re too far to walk, pedicabs, bike rentals, golf cart rentals, and public transportation are all easily accessible. Pro Tip: Download the “Key West Rides on Demand” app and have the buses at your beck and call. It works similar to other ride sharing services but with the local buses. You and up to four friends can request a pickup and drop off at any bus stop in Key West and Stock Island. Get a seven-day pass for $25/$15, you can purchase it directly from the bus driver.

Where to Stay for Three Days in Key West

Key West has two distinct sides, Old Town and New Town. Old Town is filled with history, historic homes, bars, and there are plenty of things to do that are in walking distance. New Town is where you’ll find resorts, condos, and shopping. Which side to choose depends on what kind of stay that you’re looking for.

Bed and Breakfast Rentals

There is no shortage of bed and breakfast rentals in Key West. Most B&Bs offer a cozy room, a lot of facilities have pools, some even have rooftop decks, and Old Town is filled with them. Near the festivities on Duval Street, close to plenty of attractions, Mallory Square, and beaches, there are many B&B’s that will suit your needs.

Any place that you stay in Old Town is convenient to the popular attractions. Be careful about staying right on Duval Street, it might get a little noisy. We like to stay three or four blocks off Duval Street; you don’t have to worry about noise and it’s close enough to walk there when we want to.

Retro Art Deco Motels

There are a few of these, they’re clean, comfortable, and roomy. They don’t have the “romantic” feel of the B&Bs, but they’re usually a lot cheaper. The Seashell Motel, El Patio Motel, and the Blue Marlin Motel are all definitely worth a look.

Resort Style Motels

You’ll find these along the shoreline of Key West. Big hotels, plenty of amenities, pools, and restaurants. You’ll find these on the north end of the island, Beachside Resort, Coconut Mallory Resort, DoubleTree Resort. Or if you want to stay closer to Old Town on the southern end of the island, there’s The Southernmost Resort, Pier House Resort, and the Hyatt Resort among others. These are great places to stay if you have kids or a big group.

When to Go

Spring is the best time weather-wise to go with comfortable days and nights. It’s not as busy as winter and the temps are perfect for watersports.

Summer is generally hot and rainy, but it’s considered off season, so the rooms might be a little cheaper.

Fall the weather is nice except for the occasional hurricane. If you don’t mind a possible sudden change of plans you could score a great deal on accommodations.

Winter is the high season, all those snowbirds have to go somewhere, and Key West is a favorite destination. If you don’t mind crowds, the weather is perfect, but it will be crowded.

Everybody should try to get to Key West at least once in their lives. This quirky little outpost at the end of the world is just waiting for you.

• Florida Keys
• Islamorada
• Key Largo
• Key West
• Marathon
• Uncategorized