How to Spend a Weekend in Key West
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If I had to pick any U.S. city to spend a weekend in, Key West would be it! As a summer baby, naturally, I LOVE the water! I might even be a part mermaid! I have visited Key West over five times in my life, and if you asked me to pick any city in the country to visit for a weekend adventure, I would, without a doubt, choose a weekend in Key West, Florida!
Key West is a U.S. Island city and is part of the Florida Keys archipelago, a string of tropical islands stretching about 120 miles off the southern tip of the U.S. state of Florida between the Atlantic Ocean and the Gulf of Mexico.
Did you know Key West is closer to Cuba than Miami?
There is no place in the world quite like Key West. This destination makes you feel both relaxed and alive all at once. The island can make you lose all sense of time in the most positive way. From the laid-back vibes to the beauty of the Atlantic Ocean, Key West is magical.
The Florida Keys, and Key West in particular, are so casual and have a come-as-you-are environment that most of the time, I will go from a water sports activity or excursion straight to dinner. No makeup or time spent getting ready? YES, PLEASE!
It’s no wonder Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, and Jimmy Buffett discovered inspiration in the tropical island city!
Here is everything you need to know to spend a weekend in Key West.
The Best Time to Visit Key West
The best time to visit Key West is March through May. These months offer the best weather and limited crowds. You’ll also have the least chance of rain during March, April, and May. I’ve been to Key West multiple times and have visited in either March or June each time, and in comparison, March definitely has the best weather!
If you love water sports and plan to spend most of your time in or on the water, June or any other summer month isn’t too bad. Also, if you are from Texas and are used to 100+ degree weather days in the summer, the weather in Key West will be a piece of cake. Just know it is extremely humid and hot when you are not in the water, snorkeling, or on a jet ski or boat.
Be sure to pack a sun hat, rash guard, and a lot of sunscreen!
How to Get to Key West
You have a couple of options when it comes to traveling to Key West:
Option 1: Fly directly into Key West International Airport (EYW)
This is my preferred option, and it is the most convenient too. The Key West airport serves major carriers such as American Airlines, Delta, and United. There are direct flights from Dallas, which is what I book when planning my trip to Key West. It’s easy to get an Uber from the airport and go straight to your hotel. The island is so small that there is no need for a rental car.
Pro tip: For your departing flight, remember that it’s an extremely small airport with limited food options and zero lounges. Be sure to buy snacks on the Island to pack with you before heading to the airport.
Option 2: Fly into Fort Lauderdale-Hollywood International Airport (FLL) or Miami International Airport (MIA), rent a car, and drive
From Fort Lauderdale, exit the airport and follow the signs for 595 West. Take 595 to the Florida Turnpike and follow the signs to Key West. From Miami, exit the airport and take the Florida Turnpike south toward Key West. The turnpike ends at US 1, so follow that as far as it goes, and you will arrive in Key West.
You may be wondering which option is best.
You can’t go wrong with either flying directly to Key West or flying into another airport and driving. I’ve done the drive more than once, and it is very beautiful and scenic, with lots of fun places to stop along the way. However, I don’t have to take too many days off work since most of my trips are on weekends. Therefore, option one is my preference. It saves so much time! You also save money by not having to rent a car, and you don’t have to pay for parking once you arrive in Key West. Parking in Key West can be very expensive!
You can’t go wrong with either option, but in saving time as a weekend traveler, option one is the way for me!
Where to Stay in Key West
On the last two trips to Key West, I’ve stayed at The Reach Key West, Curio Collection by Hilton. It offers the island’s only natural sand beach and is a great base for water sports such as snorkeling or jet skiing. It’s located at the island’s South end, which tends to be a bit quieter and more low-key. This part of the island is only a short walk to the Southernmost Point of the Continental U.S.A. buoy, a must-visit photo spot during your trip!
Visiting new hotels is something that I enjoy. For the next trip, I’m considering booking my stay at either the Hyatt Centric Key West Resort or the Kimpton Key West: Winslow’s Bungalows.
Where to Eat in Key West
Blue Heaven – Open for breakfast, lunch, and dinner and serves Floridian-Caribbean cuisine.
Two Friends – Open for breakfast, lunch, and dinner and serves a traditional American menu.
Garbo’s Grill – Open daily from 11:00 am to midnight and serves some of the best tacos and burgers I’ve ever had!
Kermit’s Key Lime Pie Shop – My favorite Key lime pie in all of Key West. Open from 10:00 am to 9:30 pm as of this writing, and they have locations at 200 Elizabeth Street and 335 Duval Street.
Latitude’s – An upscale restaurant with outdoor dining and sea views that serves contemporary cuisine. Be sure to make your reservation months in advance! You will be boated over to Sunset Key for dinner, and it is a true experience that you’ll certainly want to add to your Key West itinerary.
Mattheessen’s Bakery – Serves homemade cookies, fudge, ice cream, and key lime pie with multiple locations throughout Key West. I stopped here daily on the walk back to my hotel each night.
What to Do in Key West
There are so many fun things to do in Key West, Florida. My favorite activities involve water, such as visiting Dry Tortugas National Park, snorkeling, or a jet ski tour.
Here are some additional fun ideas of what to do in Key West, Florida.
- Visit Dry Tortugas National Park
- Book a snorkel trip
- Take a jet ski tour around the island
- Book a night kayaking tour
- Visit Smather’s Beach
- Go to the top of the Key West Lighthouse
- Visit The Hemingway Home and Museum
- Visit Truman Little White House
Weekend Itinerary
| Friday | Saturday | Sunday |
| ✈️ Land at EYW | 📸 Picture at the Southernmost Point of the Continental U.S.A. Sign | 🍳 Breakfast at Two Friends |
| 🚙 Call a Lyft or an Uber | ☕️ Grab a coffee at Cuban Coffee Queen | 🍰 One last Key lime pie from Kermit’s |
| 🏩 Check into the hotel | 🚤 Jet Ski tour at 10:00 am | 📸 Picture at US 1 Mile Marker 0 |
| ☀️ Watch the sunset in Mallory Square | 🌮 Lunch at Garbo’s Grill @ Hanks | 🐈 Visit The Hemingway Home and Museum |
| 🍔 Dinner at Blue Heaven | 🏝️ Visit Fort Zachary Taylor Historic State Park, Truman Little White House, or book an afternoon snorkel tour | 🏩 Grab luggage from the hotel |
| 🍰 Key lime pie from Kermit’s or Mattheessen’s | 🍽️ Dinner at Latitudes (make a reservation WELL in advance of your trip) & order Key lime pie for dessert | 🚙 Call a Lyft or an Uber |
| 🍹 Walk Duval Street | 🎭 Attend a Cabaret La te Da | ✈️ Depart home |
I can’t think of a better weekend destination than Key West, Florida. Taking weekend trips will always be a favorite of mine. It’s the perfect amount of time to explore a new place and lose all sense of time without being away from work and other responsibilities for too long. I often come back from weekend trips more recharged and extremely energized.
There can be many choices when deciding on a place to visit in the U.S., but few will match what Key West offers. This subtropical paradise offers some of the country’s best water sports, snorkeling, and fishing, and there is just nowhere else quite like it!
Let me know in the comments below what your favorite things to do in Key West are or when you plan on visiting for the first time!
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