Located about 90 miles from Cuba is a laid-back, 2-by-4-mile coral island known as Key West, Florida. It is a stunning area full of lively nightlife, water activities, history, culture, and pastel-inspired architecture. When you arrive at this beautiful destination, you’ll want more than a day or two to explore.
The trouble is that local transportation isn’t all that reliable. Many island residents use e-bikes or pay high ride-sharing costs due to the low number of available drivers. If you want to see everything in the area, you’ll need to either rent a car from the mainland or ship your personal vehicle.
Either way, it helps to research what to do in Key West, Florida, before planning a longer stay. Between the island drinks and sandy beaches, there’s a lot to take in.
Why Transportation Becomes More Important During a Longer Stay
The greater Key West area only has about 25,000 residents. For most, they download the Token Transit App and use city bus fares or ride-sharing to reach the historic Duval Loop or get to work, school, and medical appointments. While that app does help, it won’t get you everywhere you want to go.
Key West is next door to many neighboring islands, attractions, and hidden parks. There’s plenty to do “in town,” but you’ll also want to get out of the touristy spots for more personalized road tripping.
An extended stay full of stuff to do in Key West must include the comfort and familiarity of your personal vehicle. Once you’ve arranged for shipping your New York vehicle down to Florida for your vacation, you can then focus more on the Key West must-see items on your list and not worry about how you’ll get around.
Start With Key West's Historic Landmarks
Even though Key West became an “official” city in 1832, it can trace its history back to the indigenous people and the 1513 Spanish explorer Juan Ponce de Leon. That means there are all kinds of interesting places to visit.
Start with the Ernest Hemingway Home and Museum. You’ll see the home where the famous American author lived in the 1930s, set against tropical grounds and six-toed cats that feature prominently in the many photos of the controversial wordsmith.
You’ll also want to climb the Key West Lighthouse. It’s 88 steps to the top, where you’ll get grand views of the island and the surrounding turquoise waters, so bring your phone for some exceptional selfies.
Finally, there is Truman’s Little White House. This is the official Presidential Library tucked into the historic area, complete with the 1950 Cosmopolitan Lincoln Limousine parked right in front. Daily tours give you a deeper look into Harry S. Truman, including all the trips he took during his tenure.
Experience the Natural Side of Key West
Things to see in Key West, Florida, must include the natural world. This is a rare part of the earth, complete with waters, beaches, and local flora and fauna you won't want to miss. For example, the Key West Butterfly and Nature Conservatory features hundreds of free-flying butterflies, exotic birds, and 2 glorious flamingos in a glass-domed tropical habitat. Plenty of people who visit than make the move to Florida take friends and family to this destination.
You’ll really want your personal vehicle to head over to Fort Zachary Taylor State Park. Not only can you tour the fort, but you can also enjoy nearby outdoor adventures such as parasailing, jet skiing, paddleboarding, snorkeling, scuba diving, and more.
Explore Fun Things to Do in Key West Like a Local
As for moving around Key West locally, hit up Duval Street. There are numerous art galleries featuring nearby artists to decorate your home, as well as pastel architecture you cannot find elsewhere.
While you’re out and enjoying the shops, look for any café offering fresh and authentic key lime pie. This is the signature dessert and local tradition you’ll want to sample. As the day winds down, head to Mallory Square and watch the nightly sunset celebration. That’s when local performers, musicians, and food vendors gather around the waterfront as the sun sinks into the Gulf of Mexico.
After it’s dark, and depending on your age, hit up the local nightlife. Popular stops include Sloppy Joe’s Bar, Captain Tony’s Saloon, and the local favorite Green Parrot Bar.
Some of the Best Experiences Are Outside Key West
A significant reason to have your car shipped using safe, reliable enclosed delivery from Nexus Auto Transport is if you are outside the area. When you write down Key West, what do see and do, it must include day trips.
Visit the Turtle Hospital in nearby Marathon or take a scenic drive to No Name Pub in Big Pine Key and see the nearly $90,000 in one-dollar bills plastered all over the building. You’ll drive the Overseas Highway and see all kinds of stuff to do in Key West and beyond, just like a day trip to Dry Tortugas National Park.
Suggested 5-Day Key West Itinerary for Extended Visitors
| Day count | Morning | Afternoon | Evening | Transportation Notes |
|---|---|---|---|---|
Day 1 | Hemingway Home & Museum | Key West Lighthouse & Keeper's Quarters | Sunset Celebration at Mallory Square | Park and explore Old Town on foot |
Day 2 | Southernmost Point photo stop | Browse galleries and shops on Duval Street | Dinner and nightlife at Sloppy Joe's or Green Parrot | Personal vehicle useful for exploring beyond downtown |
Day 3 | Key West Butterfly & Nature Conservatory | Fort Zachary Taylor Beach for enjoy parasailing/jet skiing | Sunset picnic at Fort Zachary | Vehicle provides flexibility for beach gear |
Day 4 | Marathon and tour the Turtle Hospital | Big Pine Key and visit No Name Pub | Scenic return drive to Key West | Personal vehicle makes this easier |
Day 5 | Ferry or seaplane to Dry Tortugas National Park | Explore Fort Jefferson, snorkeling, and beaches | Farewell dinner and sunset in Key West | Vehicle remains parked |
Why Many Extended-Stay Visitors Bring Their Own Vehicle
From the moment you see that incredibly blue-green water, you’ll want to stay longer and experience what to do in Key West, Florida. Without a car, life gets a little more challenging. It’s not like all the destinations are in a two-block radius. Many of the top spots are spread out.
Having your vehicle on hand helps you get to the Lower Keys, grocery store, enjoy day trips, and avoid the long-term risk and expense of a local rental. The best way to make that happen is by having your vehicle shipped with Nexus Auto Transport. That nationwide coordinated support reduces your stress as you pack for your extended visit.
Nexus handles everything, offering an easy-to-use quote that includes pickup, delivery, pre- and post-inspections for your safety, optional shipping insurance, and so much more. With a vast network of professional carriers, you’ll easily find a delivery window that aligns with your trip and real-time communication in case heavy weather or congested highways get in the way.
Explore our complete guide to car shipping services to better understand your extended Key West options.
Make the Most of Your Time in Key West
Over a million tourists visit the Key West area each year. They flock to the islands to see beautiful ocean scenery, rare and exotic drinks, and local culture that blends many diverse nationalities and influences.
When you’re planning your trip of fun things to do in Key West, be sure to include shipping your personal vehicle. Having access to the SUV, family van, EV sedan, or custom Jeep helps you get around all the Keys. That’s how you’ll get the most value and create memories you’ll never forget.
FAQs
What is the best time of year to visit Key West for an extended stay?
April and May are the best times. That helps you avoid heavy crowds while still enjoying comfortable, sunny weather. You can also try late September into October for cheaper hotel rates, but you’ll be in hurricane season.
How many days do you need to see the major attractions in Key West?
It really depends. A solid trip should be 3 to 5 days, but if you want to take your time and use your personally shipped vehicle, plan for a full week.
Is Key West easy to explore without a car?
The Downtown Key West area is walkable, and there are trolleys and rental e-bikes. The farther you go, the more you’ll want a vehicle.
What are the most popular outdoor activities in Key West?
Always bring a bathing suit to Key West! There is snorkeling, scuba diving, parasailing, jet skiing, fishing, paddleboarding, beaches, and more. You absolutely can get outdoors in this area of the United States.
