A gorgeous escape with a laid-back attitude, you’ll most certainly leave your cares behind when visiting Key West, Florida. A perfect destination for those who want equal parts relaxation and fun, Key West attracts beachgoers, partiers, foodies, history buffs, families, couples, and just about everyone else. Known for mouthwatering Key Lime Pie, an unbeatable sunset, and charming Bahamian architecture that delights around every corner, you’re sure to love your time in the Conch Republic whether you’ve planned to stay an entire week or more, or can enjoy the island city for a day as a stop on a Caribbean cruise.
Like any destination, your day-to-day plans will be dictated by how you plan on getting around. Key West is very walkable, and you’ll find a mix of must-see tourist stops and hidden gems while taking in the scenery and laid-back vibe as you go. Walking or biking is a recommended way to explore Old Town, but if you want another way to tour the historic streets of this small city, booking a tour might be the way to start off your trip and get a lay of the land.
Key West is another location where Old Town Trolley Tours operates, and you might want to purchase a one- or two-day pass for your group if you’re worried about getting around in the hot and humid weather, or, if you want an efficient way to see the sights with a built-in tour guide. Ride through the entire hour-and-a-half trip, or hop off to further explore a landmark and catch a later trolley at your convenience. For a non-stop tour, book a ride on the Conch Tour Train, an open-air tram that lets you see the most iconic sites in less than two hours. Want to dodge the heat altogether? Opt-in for a haunted tour after dark with the Key West Ghosts and Gravestones Trolley Tour.
If you do decide that biking is the way you’d like to explore Key West, there are plenty of rental companies that you can order from during your stay. Just like Hilton Head, we’d recommend reserving your bicycles as soon as you possibly can!
The most iconic landmark that visitors always want to snap a photo in front of, is the Southernmost Point of the Continental USA. This monument, a large, brightly-painted buoy, signifies that you’ll not only be standing at the lowest latitude in the continental United States, but you’ll also be only 90 miles away from Cuba.
Around the corner, you’ll find the Key West Butterfly and Nature Conservatory. One of the best activities to plan for while in town—especially if you have children—you’ll get to take a walk through the climate-controlled, glass-enclosed conservatory amidst tropical plants, waterfalls, birds, and of course, 50 to 60 different kinds of butterfly species from around the world.
Great news—if you’re at the conservatory, you’ve already found the most iconic street of all Key West! Busy Duval Street starts beside the Gulf of Mexico near the cruise ship ports and continues south just over a mile until it reaches the Ponce De Leon Fishing Pier that juts out over the Atlantic Ocean. It’s along this street that you’ll find plenty of different bars and venues offering great vibes, company, music, and of course, delicious bites and drinks. Often considered the heart of Key West, there are as many good times to be had as there will be chickens roaming freely around you.
Another spot that you’ll want to check out is Mallory Square. A waterfront plaza in Old Town, it’s often the first stop for those disembarking for the day from cruise ships. Home to the Waterfront Playhouse Theater, a few souvenir shops, and where you’ll start your trolley or train tour, Mallory Square is also where the Sunset Celebration is held. Key West is known to have one of, if not the most beautiful sunsets in the world, so there’s a tradition to gather together nightly starting two hours before sunset and celebrate the gorgeous view with live music and other entertainment like magicians, psychics, and more.
The Key West Aquarium is also located within the plaza and allows you to see a wide variety of fish, see a shark or turtle feeding, and even experience the Touch Tank. You can purchase tickets ahead of time on the aquarium’s website, and choose to book a ticket package that includes admission to the nearby Shipwreck Treasure Museum, as well as a seat on a trolley tour.
Walk around the corner and you’ll find yourself standing in front of the impressive, red brick Custom House that is now the Key West Museum of Art & History. A building with quite a history itself, the now award-winning museum has two floors of exhibitions to discover that are run by the Art & Historical Society. This society also is in charge of other must-see museums and landmarks throughout Key West like the Key West Lighthouse & Keeper’s Quarters Museum, Fort East Martello Museum, and the Tennessee Williams Museum.
Another iconic site that you may just want to at least walk past, is Ernest Hemingway’s Home. Located catty-cornered from the Lighthouse Museum and just a block from Duval Street, there’s a good chance your tour guide will at least point out this significant landmark to you. The beautiful former residence of the great author, Ernest Hemingway, this museum is open every day and accepts walk-in visits. Take a tour of the home and gardens, and don’t forget to keep an eye out for one of the famous polydactyl (that means six-toed) cats that roam the grounds, descendants of Hemingway’s original cat, Snow White.
In addition to Hemingway’s residence, make sure to add a tour of President Harry S. Truman’s winter home to your to-do list as well. The Truman Little White House is Florida’s only Presidential Museum and offers guides tours and other seasonal and scheduled events. Just up the road, the farmers market is held every Thursday afternoon at the Truman Waterfront Park.
Keep heading south down the road and you’ll find a few more Key West gems to discover, like the Florida Keys Eco-Discovery Center where you’ll find a marine sanctuary that includes interactive exhibits and a 2,500-gallon reef tank. Next door sits the Key West Amphitheater, which is a popular waterfront outdoor music venue that features a sloping lawn where you can bring your own beach chairs to sit in. Make sure to check the schedule of events to see if you can catch a show while you’re in town!
This same road will eventually take you straight to the Fort Zachary Taylor Historic State Park, a popular destination for visitors who either want to learn about the pre-Civil War fortress, or, enjoy a relaxing day in the Florida sunshine on the white-sand beach area. This park offers water sport rentals, and nature trails, and is even dog-friendly!
If a day at the beach is what you’re after, Fort Zachary Taylor Historic Park is a great choice. Other options include Smathers Beach, Higgs Beach, and Dog Beach. However, what visitors really should do on their visit to Key West is get out on the water. Book a boat tour or some sort of water sport or snorkel tour to fully experience the beauty of the Keys. If you’re looking for an almost all-day affair, take a ferry to Dry Tortugas National Park to discover this remote area made up of crystal-clear water and various islands. An amazing location for snorkeling and diving, visitors can also explore Fort Jefferson on Garden Key, one of the nation’s largest 19th-century forts.
The best time to visit Key West, Florida, is during the spring season. You can almost count on lesser crowds and affordable accommodations from mid-March to May. For spring, prepare for a warm and comfortable climate, as the Florida Keys have a tropical climate that sees less rain and average highs in the high 70s and low-to-mid 80s. A great place to spend your Spring Break, there’s still time to visit after the students and their families are long gone if you’re looking for more of a quieter time. During this time, you’ll find a long list of fun events like the anniversary of Key West’s first settlement, the Conch Republic Independence Celebration, the Songwriter Festival, and more!
You also might consider the summer season if you’re dead set on visiting with fewer crowds and finding better deals on accommodations. Just make sure that you’re ok with the warmer temperatures and humidity since this is obviously the warmest time of the year in an already warm destination. There’s also a little thing called Hurricane Season that you’ll want to pay a lot of attention to but don’t let that be the only reason that stops you. While there might be a chance that a storm rolls through during your trip, you’ll have far fewer worries if you’ve purchased travel insurance. During the summer season, you won’t want to miss annual events like the Key Lime Festival, Hemingway Days, the Key West Mermaid Festival, and much more!
The most popular time to visit Key West is during the winter. Which, if you think about it, happens to any destination with a warm, tropical climate. Everyone loves escaping freezing temperatures and swapping winter jackets for light sweaters. So, enjoy average highs in the low-to-mid-70s during the winter season in the Keys–sounds like our kind of place! With it being so popular during this season, rates will tend to be on the higher side, and visitors arriving by cruise ship will certainly make the area a little more crowded than usual.
There are many beautiful resorts and hotels throughout Key West that you’ll be able to choose from that cover all traveler’s price points. Many visitors prefer staying right in the thick of the Historic Old Town, simply because they’ll be in walking distance of great restaurants, shopping, landmarks, and where other popular activities are located. The city itself isn’t very big, so if you do decide to stay on the eastern side of Key West, you’ll find that many hotels and resorts offer a waterfront view. Another popular type of accommodation is vacation rentals, which you can also find when planning your vacation using your Quest Travel Club Membership.
Below we’ve included a few examples completely at random that were featured on Quest Travel Club at the time this article was written:
Vacation Home Rentals
Resorts & Hotels
Prices and discounts subject to change.
