4 Days in Key West, Florida: Travel Guide
Key West is the perfect destination if you want a tropical escape with breathtaking views, a bustling bar scene, and a rich history. From the beautiful beaches, nightlife (and daytime party scene!), fun activities, and the fact that it’s in the United States so you don’t need a passport or to fly, there’s truly nowhere like it!
I visited Key West on a mother-daughter trip so it’s definitely one of the best girl weekend getaways in Florida, but it’s also perfect for an adult trip with friends, a romantic getaway, or a family-friendly winter vacation!
My first impression of the Florida Keys was how stunning it is and that it felt like a tropical island with its beautiful, crystal clear blue water. Why go to the whole way to the Caribbean when you have Key West right here in the USA?
In this Key West travel guide, you’ll learn everything I did on my 4-day Key West itinerary, including where to eat and drink, what to see and do, where to stay, and more:
Traveling to & Getting Around Key West
Where to Stay in Key West, as well as the best beachfront hotels
Best Restaurants in Key West, including restaurants with a view for sunset and the best fine dining
Best Places to Drink in Key West, including the most famous bars plus the best espresso martini
Things to Do in Key West - since I traveled with my mom and sister, I’ll mostly cover things to do in Key West for adults, but many of the activities are family-friendly as well!
Let’s dive into our Key West travel guide so you can learn everything you need to plan your trip!
Traveling to Key West & Getting Around
Traveling to Key West
By far, the easiest way to get to Key West is by flying directly into the Key West airport. However, since it’s a smaller airport, flights are usually more expensive than other options and will likely not be nonstop.
The next easiest option is flying into Miami or Fort Lauderdale airports and then renting a car to drive the 3-4 hours to Key West. Before my trip, I read reviews that strongly encouraged flying into Fort Lauderdale instead of Miami because although the drive is 30 minutes longer than it is from Miami, getting through the airport to your rental car is significantly faster in Fort Lauderdale. But of course I thought I could beat the odds and save the 30 minutes… that was a mistake. Just getting from the gates at MIA to the rental car center took at least 30 minutes (and was very hectic), but then the wait to get our keys was over an hour. All that’s to say, I wish we flew into Fort Lauderdale and highly recommend you do the same! Flight prices were comparable and will be either the same amount of time, or faster, than flying into Miami.
Finally, if you live within driving distance, driving from home would be the most convenient! Plus, I promise it’ll be one of the most beautiful drives you ever experience.
Getting Around Key West
If you stay in downtown Key West, you do not need a car as you’ll have no issues walking everywhere! Golf carts are allowed on the roads downtown, so rent one for a unique way to explore the city with some extra fun! If you stay outside of downtown, you’ll need to travel by car to most places: either a rental, an Uber or Lyft, or the most economical: booking a hotel with a free shuttle to and from downtown.
Where to Stay in Key West
One thing that most people don’t know about Key West if they’ve never visited is that there aren’t many beaches or beachfront properties on the island. Almost all of the action in Key West happens downtown in the Historic Old Town, from exploring the city, partying on Duval Street, boating, and sightseeing, so I’d highly recommend staying downtown if that’s the type of vacation you’re looking for. But if the goal of your vacation is to relax on a sandy beach and you’re wondering if any hotels in Key West have a beach, don’t worry because the answer is yes!
We stayed at the Margaritaville Beach House Key West, which I HIGHLY recommend. It’s directly across from Smathers Beach (only a couple minute’s walk), which is known to be the best beach on the island for good reason (more details below under “What to Do in Key West”). Most of the (few) beachfront hotels were out of our price range, so with its convenient location near a public beach, Margaritaville Beach House is definitely one of the best Key West hotels with beach access on a budget.
The hotel also offers a shuttle to downtown that runs once an hour for most of the day, which makes going downtown every night a lot more affordable. The hotel itself had a resort feel with a pool, two outdoor bars (with delicious margaritas of course), hot tub, restaurant, gym, and huge lobby with a shop and concierge.
The room was by far one the cutest, best decorated rooms I’ve ever stayed in AND the cleanest. It had a very homey vibe with sliding doors between rooms, a mini kitchen, and tasteful Margaritaville-inspired décor. The suite-style rooms were perfect for our Florida mother-daughter trip. Truly our only complaints of the entire stay were that the pool wasn’t very relaxing because it’s a family-friendly resort and the hot tub was very small and crowded, so we never got to use it.
Other lodging options with great reviews are:
Havana Cabana At Key West - From my research, Havana Cabana looks to be the best, most affordable Key West hotel on the beach for adults only
Laureate Key West (waterfront)
Capitana Key West (beachfront)
Oceans Edge Resort & Marina Key West (waterfront)
The Perry Hotel Key West (waterfront)
Key West Beachside Hotel (waterfront)
Hilton Garden Inn Key West / The Keys Collection (waterfront)
Courtyard Key West Waterfront (small beach)
If you’re hoping to stay closer to popular tourist attractions or Duval Street’s nightlife, here are some of the best hotels on Duval Street, which are great for a trip with friends to Key West or a romantic getaway:
The Duval House (B&B)
Winslow's Bungalows - Key West Historic Inns - This inn even has private pools!
Or if you’re traveling as a family, I’d recommend these kid-friendly Key West hotels:
The Perry Hotel Key West (a bit further from Historic Old Town on Stock Island)
Find this ‘Greetings from Key West, Florida’ mural beside Cuban Coffee Queen’s waterfront location in Key West’s Historic Seaport
Best Restaurants in Key West
The town is full of fun restaurants, but here are the best restaurants in Key West in 2025!
Dinner -
Bel Mare Restaurant (pictured on right) - If you’re looking for a high-end dinner, Bel Mare is one of the best upscale restaurants Key West has to offer! It’s also waterfront with many windows, making it one of the best restaurants for sunset as well
A&B Lobster House - Make a reservation here if you’re looking for the best restaurant for seafood in Key West! A&B Lobster House is also one of the best fancy restaurants
Southernmost Beach Café - Stop here for some of the best cocktails in Key West and an incredible view of the sunset! Watching the sunset from the southernmost part of the USA was one of my favorite parts of my vacation and is definitely #1 on my list of what to do in Key West for a day!
Sunset Pier (pictured on left) - definitely one of the best Key West bars on the water for sunset (more details below under “Things to Do in Key West”)
Mangoes - One of the best restaurants in Key West’s Old Town downtown!
The Waterfront Brewery - Right along the dock, the Waterfront Brewery is one of the best restaurants in Key West on the water to watch the boats pull in and out!
Quick Bites, Coffee, or Desserts -
Cuban Coffee Queen - The best restaurant in Key West for lunch in my opinion! You can get delicious sandwiches to-go conveniently from their walk-up counters. We grabbed lunch here before boarding the boat for our snorkel excursion!
If you’re looking for other East Coast destinations with great food, check out Charleston, SC’s great restaurants
Best Places to Drink in Key West
Key West is known for having some of the most fun and famous bars in America, so going on a bar crawl is one of the most fun things to do in Key West for adults and is a must on your itinerary for an adult family vacation!
Virgilio’s (pictured on right) - With live music, amazing happy hour deals, and the best espresso martini in Key West, Virgilio’s is one of the best cocktail bars in Key West!
Willie T’s - check their website for their daily drink specials
Hard Rock Café (pictured on left) - A classic spot on any vacation, it’s always fun to cross another Hard Rock Café off of your bucket list. Plus, Key West’s location right on Duval Street is in a beautiful, picturesque building
Bull & Whistle Bar - we only drank at the first level (the Bull Bar) which felt like a very old-school bar with open air windows and live music. The Whistle Bar (on the second floor) has a balcony overlooking Duval St. There is a third floor, but it has “interesting” rules on clothing to say the least, so only make the journey to the top floor if you know what you’re getting into!
Sloppy Joe’s Bar (pictured on right) - Sloppy Joe’s is definitely one of the best Key West bars for young adults with a live band every night
Flying Monkeys Saloon - The perfect spot to get frozen drinks! We ate dinner here, which I wouldn’t necessarily recommend but is good if you’re in a crunch and need a meal fast!
Things to Do in Key West
Drive through the Keys - Before the trip even officially starts, one of my favorite parts of Key West was the drive down through the islands! Most of the archipelago is so narrow that you can see the ocean on one or both sides and there are tons of bridges to drive over the crystal clear ocean. This was such a unique experience that you can’t get anywhere else! Driving through the Keys and island hopping is also a great thing to do in Key West for free for a day
Spend a beach day at Smathers Beach (pictured on right), Key West’s best public beach for swimming and tanning! The ocean here is beautiful and pleasant to swim in, the beach is clean and not crowded, and the views are so peaceful with palm trees hanging over the sand. If you’re looking for cheap things to do in Key West for adults, visiting Smathers beach is perfect! You can also rent chairs, umbrellas, floats, and more right on the beach. Soaking up some sun on the beach was my family’s favorite part of our Key West girls trip so we spent 2 whole days of our 4-day itinerary at the beach!
Explore Key West’s historic downtown, Old Town, to see many of Key West’s popular tourist attractions, bars, restaurants, and shops, especially the bars on Duval Street. You can walk around on your own, which is a great free thing to do in Key West, or take a guided tour, like the Conch Tour Train, an Old Town Trolley Tour, or even a ghost tour. You can’t miss seeing this charming town and all its history, so if you’re wondering what to do in Key West for a day, this is it!
Go Snorkeling - Taking a catamaran to a reef for snorkeling was a highlight of our trip and perfect for a Key West family vacation! On our excursion, there was an open bar and live music, and we even saw dolphins! We booked through our hotel’s concierge, but there are tons of great options, like this snorkeling tour with an open bar or this snorkeling & dolphin watching tour led by a biologist
Go Boating - Getting out on the beautiful waters of the Keys is a must during your visit — whether it’s a sailboat, floating tiki bar, glass bottom kayak, paddleboard, speed boat, fishing boat, catamaran, or literally anything else that floats! To get even more Floridian vibes, this mangrove kayak eco tour is perfect. Or if you’re looking for romantic things to do in Key West, check out this sunset cruise with dinner and live music or this sunset sail on a classic Schooner
If you love being on the water while on vacation, head to Maine for your next trip to go boating in Portland or sailing in Camden
Watch the sunset at either Sunset Pier or Southernmost Beach Café, which are known to be some of the BEST Key West restaurants for sunset. I visited Sunset Pier which I can definitely attest is one of the best places to watch the sunset in Key West. Most seats along the long pier have a perfect view of the southern sunset over the ocean and can be enjoyed with live music and drinks or a meal from the Tiki Bar! We watched sailboats, schools of tarpons, and kayakers pass by in front of the beautiful setting sun.
Tip: Finding Sunset Pier was a little harder than expected because you have to walk through a parking garage to get to it. If you head toward the water, you’ll see signs that show you how to find Key West’s Sunset Pier!
Visit the Hemingway Home & Museum, where Ernest Hemingway wrote many of his famous books
Browse souvenir shops and fun attractions on Duval Street and Mallory Square
See the Southernmost Point Buoy - Probably the most popular tourist destination in Key West is the famous Buoy at the Southernmost Point of the USA. You should definitely see this while visiting, but beware there can be an incredibly long line of visitors waiting to take a picture. We stopped around lunch and only had a bit of time to spare so we just took a selfie from afar and skipped the wait for a better picture, but it’d be best to stop here early in the morning!
Make your own Key West Key Lime Pie Tour - Some of the most popular spots for Key Lime Pie in Key West are Pepe’s, Kermit’s Key Lime Shop, Blue Heaven, and Café Solé. Choose which bakeries you’d like to try and map them out to create a DIY Key West Key Lime Pie Tour!
If you have spare time on your drive to or from the Florida Keys, visit the Everglades National Park to hike the subtropical trails and see the wildlife, especially alligators!
Fun fact: Everglades National Park is the only place in the world where both alligators and crocodiles live!
Other fun attractions that I’ll make sure to see on my next trip are:
Mile Marker 0 Sign
Key West is one of the most fun places I’ve ever visited and I can’t wait to go back! Everyone should go here at least once in their life (if not many more!) and I’d highly recommend it for all types of travelers, including family vacations, a weekend trip with friends, or a couples’ trip! If you’re planning a visit, this Key West travel guide can be your one-stop shop for everything to do during your trip, including where to eat and drink, what to see, where to stay, and more.
If you’re still trying to pick your next travel destination, check out our guides for other East Coast destinations:
