Key West is total paradise – with crystal-clear waters, gorgeous beaches, and the ultimate laid-back vibe. Whether you’re in the mood to chill or explore, this island has something for everyone. But with so much to do, planning a trip can feel overwhelming. That’s why I’ve put together this Key West itinerary to help you make the most of your time here. From the best places to eat and drink to all the must-do activities, I’ve got everything you need for an amazing long weekend in Key West.
So, let’s get started!
Getting to Key West
There are several ways to get to Key West. If you prefer to fly in, you have several options to choose from. However, the most convenient airport is Key West International Airport. If you’re looking for more flight options, Miami and Ft. Lauderdale are also great choices, but take up a considerable chunk of your trip if you’re only staying for a weekend (each way is approximately 3-4 hours).
Another option is to take the Key West Express ferry from Marco Island or Ft. Myers. The ferry ride takes about 3-4 hours (depending on weather), but it has a full bar and galley, allowing you to start your vacation as soon as you board. Plus, the ferry is air-conditioned, and it has a sundeck, making it an enjoyable way to travel to Key West.
Getting Around
Getting around Key West is easy and convenient. Since the island is only about 4 miles long and less than two miles wide, walking or biking is a great way to explore the area. Many attractions, restaurants, and shops are within walking distance of each other, so you don’t have to have a car to get around. Additionally, scooter and golf car rentals provide a fun way to get around. If you want to travel a bit further, there are plenty of options. Taxis, Uber, and Lyft are readily available but if you plan on exploring north of Stock Island, I recommend renting a car for the day.
Where to Stay
If it’s your first time in Key West, I highly recommend staying at the Southernmost Beach Resort. This waterfront property is located in a quieter part of Duval Street, which makes it the perfect home base. Plus, it’s within walking distance of most of the island’s top attractions, so you won’t have to worry about transportation. The resort has ocean views and a wide range of amenities, including three pools, a poolside and beach bar, and direct access to the beach.
Click here for my guide on the best places to stay in Key West
Day One
Once you’ve checked into your hotel, head over to the Seaside Café at the Mansion on the Sea (the pink house) next door.
With its prime location just steps from the ocean and tables scattered between palm trees, it’s the perfect spot to relax with a drink and appetizer. They have my favorite mojitos and conch fritters, and they are famous for their lobster biscuits. This is one of my favorite restaurants in Key West and I go multiple times each visit. Just keep in mind that there is only outdoor seating, so dress appropriately for the weather. If it’s too hot, there is plenty of seating available under a pavilion.
After, take a stroll down Duval Street and check out some of the local shops. You won’t want to miss The Green Pineapple, Low Key, and Shaddow and Fish, which are some of my personal favorites.
If you’re in the mood for some live music, there are plenty of bars along the way where you can grab a drink and enjoy some tunes. From jazz to classic rock, you’ll find a variety of music genres being played at different bars. The Green Parrot, Sloppy Joe’s (yes, a bit touristy, but it’s still a classic), and Hank’s Hair of the Dog are some of my favorite bars for music.
If you happen to reach the end of Duval Street before the sun sets, you should definitely make your way to Mallory Square to watch the sunset.
Head over to the marina for dinner. There are plenty of great restaurants to choose from, but I highly recommend the A&B Lobster House for a more upscale dinner. Their menu features fresh seafood and steak, paired with an extensive wine list. If you’re looking food recommendation, I love to get the lobster bisque and filet.
The view of the marina is just as good as the food, offering a chance to watch the yachts and fishermen come in for the night.
After dinner, be sure to stop by Hank’s Hair of the Dog or one of the many bars in the area and listen to some more live music. It’s the perfect way to end your day in Key West!
Day Two
Start your morning off right with breakfast at Blue Heaven. Don’t be deterred by the chickens and cats running around- it’s all part of the charm!
This place can get pretty busy, so make sure to get there early. But trust me, it’s worth the hype! If you have to wait for a table, head to their bar across the street for a mimosa and some live music.
I’ve heard that their Lobster Benedict is amazing, but I have to admit, I’m pretty basic with my breakfast and usually go for eggs, potatoes, and bacon, but their homemade bread makes my meal delicious. Oh, and you can’t leave without having a slice of their key lime pie, even if it’s early in the day!
For your second day in Key West, you should plan a fun water activity. There are so many to choose from, but I like to either snorkel among the coral reefs or kayak through the mangroves.
I haven’t had a chance to try a charter myself because my family had boats and kayaks, but I’ve heard great things about the following options:
- For snorkeling, Island Jane Charters offer a 3-hour snorkeling and sailing charter for $79. The price includes all necessary equipment, as well as water, soda, white wine, beer, margaritas, and champagne.
- If you’re interested in kayaking, the Lazy Dog kayak tour offers a 2-hour kayak tour through mangrove tunnels for $60.
There are plenty of companies that offer these activities, so you’re sure to find one that fits your schedule.
For dinner, keep it casual and head to DJ’s Clam Shack. Order your food at the window and pick spot at the front counter to watch people roam down Duval Street (it can be pretty entertaining), or head to one of the picnic tables in the back for a quieter dinner. Their lobster rolls are seriously the best I’ve ever had, and I’ve tried them all up and down the East Coast!
If lobster rolls aren’t your thing, give the Thirsty Mermaid a try. It has a cozy atmosphere with nautical décor and their happy hour and dinner menu are pretty great. The mussels and clam chowder are my favorite and I like to pair them with a glass of white wine!
Day Three
On your third day, take some time to relax and enjoy the beach or one of the resort’s three pools.
Personally, if I’m not at the beach, I love hanging out at the Shores Pool because it overlooks the ocean, has a full bar, and offers food from the Southernmost Beach Café, which makes for an easy lunch. It’s the perfect spot to soak up some sun and enjoy the ocean breeze. If you decide not to stay at The Southernmost Resort, you can still access the pool and all their amenities by purchasing a resort pass for $50 per person.
Stop by the Cuban Coffee Queen for a midday pick-me-up. The menu features a variety of Cuban-inspired beverages, including Cafecito, cortadito, and café con leche.
For your final dinner in Key West, make it a special one and head to Louie’s Backyard. It’s on the pricier side, but the stunning waterfront views make it worth every penny. If you can arrive early, grab a glass of champagne and take some pictures on their lower deck that extends over the ocean. It’s an experience you won’t forget! Just don’t forget to make a reservation in advance. I haven’t had it myself, but everyone raves about the Shrimp & Grits.
If you’re looking for a classy spot to have after-dinner drinks, I highly recommend checking out The Canary Room at the Casa Marina. I went there three times during my last trip to Key West, and every drink I had was amazing, but my favorite drinks were the Hemingway Daiquiri and the Clover Club. They’ve seriously got the best craft cocktails in town. The atmosphere is really nice too, so it’s a great place to unwind after a long day in the sun. Definitely worth checking out!
Departure
Departure day is always bittersweet, but you can still end your trip to Key West on a high note! Before you head to the airport or start your drive back home, make sure to stop at Salute! On the Beach for an early lunch. This beachfront restaurant is located on Higgs Beach and offers Italian-inspired dishes with stunning views of the ocean. The combination of great food and a beautiful setting will leave you with a lasting memory of your time here in Key West.
And there you have it! I hope this Key West itinerary helps you plan an unforgettable trip. Safe travels, and have a blast!
For even more tips on making the most of your time in Key West, check out my Ultimate Key West Guide. It’s packed with everything you need to plan a memorable trip! And if you’re short on time, don’t miss my One Day in Key West Itinerary for a perfect 24 hours in Key West!
