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 plane or passport, there’s truly nowhere like it! I visited on a mother-daughter trip in Key West as it’s one of the best girl weekend getaways in Florida, but it’s also perfect for an adult trip with friends, a romantic getaway, and a family-friendly winter vacation!
My first impression of the Florida Keys was how stunning it is and how it felt like we were on a tropical island abroad. Why go to the Caribbean when you have Key West right here in the US? The water is the beautiful, crystal clear blue that you dream about all winter.
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:
Getting Around Key West
Where to Stay in Key West, as well as the best beachfront hotels in Key West, especially on a mother-daughter Key West trip
Best Restaurants in Key West, including the best Key West restaurants for sunset with a view and the best fine dining Key West restaurants
Best Places to Drink in Key West, including the most famous bars in Key West plus where to get the best espresso martini in Key West
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 as perfect things to do in Key West for couples!
Let’s dive into our free Key West travel guide to learn everything you need to know to plan a trip to Key West!
Traveling to Key West & Getting Around
By far, the easiest way to get to Key West is flying directly to the Key West airport. However, since it’s a smaller airport, flights will usually be 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 visit to Key West, I had read reviews that strongly encouraged flying into Fort Lauderdale instead of Miami because even though the drive is 30 minutes longer than from Miami, getting through the airport to your rental car is significantly faster than at Miami. But silly me thought I’d beat the odds and get to my car so fast and save the 30 minutes… that was a mistake. Just getting from the gates to the rental car center at Miami airport took at least 30 minutes (and was very hectic), but then we waited in line for our rental car for over an hour. All that to say, I wish we flew into Fort Lauderdale and would highly recommend you do the same! Flight prices were very comparable and will be either the same amount of time, or faster, than 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.
If you stay downtown, you do not need a car in Key West as you’ll have no issues walking everywhere! Golf carts are allowed on the roads downtown, so rent one for a really fun way to explore the city with some extra fun! If you stay outside of downtown, you’ll need to travel to most places by car: 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 about Key West that most people don’t know if they’ve never visited is 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 as it’ll be the most convenient and fun. But if your goal for visiting Key West is to relax on a sandy beach and you’re asking yourself “do 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”)! The few beachfront hotels in Key West were all 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 mini 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 room I’ve ever stayed in AND the cleanest. It had a very homey feel with sliding doors between rooms, a mini kitchen, and tasteful Margaritaville-inspired decor. The suite-style rooms were perfect for our Florida mother-daughter trip. Truly our only complaint of our entire stay was that the pool wasn’t very relaxing as it’s a family friendly resort and the hot tub was very small and crowded, so we never got to use it.
Other beachfront options that had great reviews that we considered staying at were:
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
Capitana Key West - beach
Oceans Edge Resort & Marina Key West - waterfront, but no beach
The Perry Hotel Key West - waterfront, but no beach
Key West Beachside Hotel - waterfront, but no beach
Hilton Garden Inn Key West / The Keys Collection - waterfront, but no beach
Courtyard Key West Waterfront - small beach area
If you’re hoping to stay closer to Key West’s most popular tourist attractions and Duval Street’s nightlife, here are some of the best hotels on Key West’s Duval Street, which are great for a trip with friends to Key West or a Key West 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 (bit further from Historic Old Port on Stock Island)
Best Restaurants in Key West
Key West 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 high end restaurants in Key West, 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 Key West restaurants for sunset on the water as well
A&B Lobster House - Make a reservation here if you’re looking for the best restaurant in Key West for seafood! A&B Lobster House is also one of the most popular options for the best fancy restaurants Key West has
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 Key West vacation and is definitely #1 on my list for 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!
Blue Heaven
Kermit’s Key Lime Shop
Key Lime Pie Bakery
Best Places to Drink in Key West
Key West is known for having some of the most fun and famous bars in America, so if everyone is of age, 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 Key West itinerary for an adult family vacation!
Virgilio’s (pictured right) - With live music, amazing happy hour deals, 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 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 very old-school Key West 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, so only make the journey to the top floor if you’re okay with that!
Sloppy Joe’s Bar (pictured right) - In my opinion, Sloppy Joe’s is 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 chain of 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, which is one of the most unique things to do in Key West that you can’t experience anywhere else! If you’re wondering what to do in Key West for a day for free, driving through the Florida Keys and island hopping is worth it!
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 jutting over the ocean. If you’re looking for cheap things to do in Key West for adults, visiting Smathers beach is perfect! You can rent chairs, umbrellas, floats, etc. right on the beach or just bring your own. Soaking up some sun on the beach was my family’s favorite part of our Key West girls trip 4-day itinerary that we spent 2 whole days 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 and attractions on Duval Street. You can walk around on your own, which is one of the best free things 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 for adults, this is it!
Go Snorkeling - Taking a catamaran to a reef to snorkel was a highlight of our trip and perfect for a Key West family vacation! We booked the excursion through our hotel’s concierge, but there are many other great options, like this one with an open bar or this tour with dolphin watching led by a biologist
Go Boating - Among 1,700 islands, there are of course just as many options to get out on the water! The Florida Keys waters are so beautiful that you definitely need to get out on the water sometime during your visit! Whether it be a floating tiki bar, glass bottom kayaking, sailboat, paddleboard, kayak, speed boat, fishing boat, catamaran, or literally anything else! On our snorkel catamaran excursion, there was an open bar and live music on the trip back, and we even saw dolphins!
Visit the Hemingway Home & Museum, where Ernest Hemingway wrote many of his famous books
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 drinks or a meal from the Tiki Bar and live music! We watched sailboats, schools of tarpons, and kayakers pass by in front of the beautiful scene.
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 Sunset Pier!
Browse fun souvenir shops and 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 the best DIY Key West Key Lime Pie Tour!
If you’re driving from the Florida Keys and have spare time, 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 to Key West:
Mile Marker 0 Sign
Key West Lighthouse
Old Town Ghost Tour
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 trip, this Key West travel guide can be your one-stop shop for everything to do during your visit, 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:
