We have had more weekend trips to Key West than we can possibly count. And while a weekend isn’t as much time as we would like to have in Key West, any amount of time in Key West is better than no time. And a weekend still gives you a lot of time to explore Key West.
After countless trips, I think I’ve almost perfected how to spend a weekend in Key West. I’m sharing that itinerary with you so that you can make the most of your Key West vacation.
Day One of Your Weekend in Key West
I find that day one of vacations can go one of two ways. Either I’m tired and I want to just settle in or I’m super excited to get out and explore. One of the things that makes Key West so great is that you can find things to do either way. And honestly you cannot go wrong with whichever you choose to do. Feel free to go with the flow, you’re on island time now!
No matter what you do on your first day in Key West, you’ll need to eat. Key West has so many options for delicious food. Here are a few quick picks for your first night:
- For a fast and laid back option, check out Garbo’s Grill (a food truck that serves Asian fusion/tacos/burgers)
- And for somewhere in the middle, hit up Hogfish Grill in Stock Island. This is my favorite choice. Hogfish Grill is such a quintessential Key West restaurant. From the fresh seafood to the “old Florida” tropical decor to the open-air restaurant, this place immediately puts me into vacation mode. This is also where Jimmy Buffett used to visit when he came to town.
- For a fancier dinner, Louie’s is a great place overlooking the water.
If you want to relax and settle in, you can spend the evening wherever you are staying. A lot of the resorts in Key West have the kind of pools that you never want to leave.
If you’re staying at an airbnb without a pool, or if the beach is more your style, then you could also relax at the beach. The beach at Fort Zachary Taylor State Park is my favorite and as a bonus, you could check out the historic fort there on your way. Smathers Beach is a good option too, with palm trees right on the beach.
If you want to go the exploring route, Duval is a great place to do it. Duval Street runs north and south through the island from the Gulf of Mexico to the Atlantic Ocean. It’s filled with small shops, restaurants, and bars. You can spend your evening hopping from one place to the next, grabbing a drink if that’s your thing, and listening to live music. Duval is a must in Key West and it’s so much fun!
If you go this route, make sure to catch the sunset celebration at Mallory Square. It starts around 90 minutes before sunset every night. Street performers and vendors gather to watch the sun set behind Sunset Key.
Day Two of Your Weekend in Key West
First, start your morning with coffee (if that’s your thing). Cuban Coffee Queen is one of the most recommended coffee shops in Key West. Pro tip – go to the Margaret Street location and take a picture by the Welcome to Key West mural while you are there. If you have time, stroll the historic seaport while you drink your coffee.
Locals in Key West will tell you that you need to get out on the water to truly experience the Florida Keys and its natural beauty. So that’s exactly what we are going to do.
The Florida Keys are home to the only live coral reef in the continental United States. Snorkeling in the Florida Keys is one of my absolute favorite things to do. There are a lot of different options for snorkeling tours in Key West. We have gone on several, and this snorkel tour is a great option that’s more cost-effective. We have always had a great experience.
If you can afford it, though, it’s worth it to hire your own boat. If you have a group of people, your own boat can actually come out to be around the same price per person.
While snorkeling is my favorite choice, there are tons of water activities available. Some other popular options are:
- Dolphin watching cruises
- Jet skiing
- Kayaking (kayaking through the mangroves is a very unique experience!)
- Sunset cruise
- Parasailing
Any of these options are amazing!
If you didn’t get a chance to check out the ever-famous Duval Street on your first night, consider hitting it up after your day on the water. You could also relax at the beach, catch a gorgeous Key West sunset, or rent bikes.
I love renting bikes, a scooter, or a golf cart (it just kind of depends who I’m visiting Key West with). It’s the best way to explore all the different streets in Key West. All of the historic homes in Key West are so much fun to look at – no two are quite the same.
For dinner, consider some of my favorite options:
- El Siboney for some of the best Cuban food you’ll ever eat.
- Salute! is on Higgs Beach and a bit more upscale for Key West standards. It is a sister restaurant to Blue Heaven.
- Seaside Mansion at the Cafe is famous for their lobster pizza for good reason. It is incredible, but I actually like their lobster biscuits even more. It’s waterfront with some of the most beautiful views.
And if you haven’t gotten a slice of key lime pie yet, make sure you grab one. I personally love grabbing a chocolate covered key lime pie from Kermit’s.
Day Three of Your Weekend in Key West
Even though it’s the end of your weekend in Key West, hopefully you can leave a little later in the day so that you can still have some fun. Start your last morning in Key West with breakfast. I have so many favorite breakfast spots in Key West that it’s so hard to choose which one. Most people say that Banana Cafe or Blue Heaven are the best places for breakfast in Key West but I think Breakfast Club Too is my favorite.
After breakfast, take some time to check out a museum. There are a lot to choose from! The Shipwreck Museum has a lookout tour with incredible views of Key West and Sunset Key. Or you could check out the Hemingway House to learn more about Ernest Hemingway and his life, plus see some of the descendants of his six-toed cats.
Another favorite of mine is the Key West Butterfly and Nature Conservatory where you’ll see various butterflies (it’s magical seeing so many flying all around) as well as two flamingoes, tropical birds, foliage, and more. The Key West Lighthouse is another good option. Did I mention there are a lot of options for museums in Key West? It’s hard to choose which one is the best.
Instead of visiting a museum, you could also ride the Conch Tour Train or the hop-on, hop-off trolley. Both options take you around town to some of the best spots in Key West. On the way, you’ll hear about each place as well as history of the island. Since both are hop-on, hop-off so you can get off at any of the stops as well. This is a great option to see a lot of the island when you’re only there for a short time.
And if you have time, you can always swing by the Southernmost Point for a quick picture. Is it touristy? Yep. Is it a must-do while you’re in Key West? That depends on what you like. There tends to be a line but it moves quickly.
I really hope you found this Key West itinerary to be helpful. Of course, feel free to adjust the itinerary to fit your preferences. While you can’t fit in absolutely everything from my Key West bucket list into one weekend trip, it gives you a total list of options to choose from if some of the activities on this list doesn’t fit what you’re looking for.
Key West can be a perfect weekend getaway, especially if you’re lucky enough to live close by or have access to direct flights. I love helping people learn about all of the fun things to do in Key West because there is so much! Enjoy Key West, I know you’re going to have the best time!
