Key West is a tiny island located at the southern tip of the famed archipelago known as the Florida Keys. Renowned for its coral reefs, diving, snorkeling, and laid-back, vacation mode mentality, Key West attracts sun seekers from all over the world.
Key West is approximately 100 miles from Miami, and is only 90 miles to Havana, Cuba. Known as the southernmost city of the continental United States, Key West offers crystal clear waters, great weather, an array of watersports, excellent seafood, and a vibrant bar scene.
With Jimmy Buffet’s iconic song “Margaritaville” playing in my mind as the theme song, I had been dreaming of visiting this seemingly carefree destination for years. Key West is a perfect relaxed beach destination for couples, group trips, and families. It is truly a little island paradise, and and is easily accessible by car from Miami.
Here’s my ultimate guide to Key West with the best hotels, tours, beaches, nightlife, picturesque locations, hidden gems, and more!
My Experience In Key West
I once saw a photo of a chicken standing on a white sand beach next to a palm tree, with crystal blue water in the background. That image stuck in my mind as epitomizing Key West. I want to go there I said to myself. I want that laid-back island vibe to soak into my soul.
Ten years later, in February 2024, I arrived in Key West in the pouring rain. It was cold, overcast, and windy but the moment I stepped inside a colorful restaurant on Duval Street and saw frozen margaritas and shrimp and grits on the menu, all my worries began to fade away.
Key West is the opposite of pretentious. The vibe in Key West is: flip flops, beach bars, live music, chickens, cats, and horses in the street, salt in your hair, sun on your skin, the friendliest people, and the prettiest aqua-green ocean washing your worries away.
Key West is a destination centered around fun. It’s a tiny 2 x 4 mile island and yet there are over 300 bars to choose from! Around every turn, there is some new variation of fun going on and you can’t help but get caught up in the blissful mentality.
There are so many places to visit in the world, but Key West is a place I know I will return to. I love the laid-back island vibe it exudes and I can’t wait to visit in the balmy heat of summer when it’s so warm a bikini is the only thing I will need to pack. Paradise found.
Where I Stayed In Key West
Ideally situated, overlooking Sunset Pier and the crystal blue waters of the Gulf of Mexico, Ocean Key Resort & Spa is one of the island’s top luxury destinations. Raked ‘Top 10 Resorts in the Florida Keys’ by Condé Nast Traveler and ‘Top 15 Resorts in Florida’ by Travel + Leisure for 2023, Ocean Key Resort has been a favorite of locals and tourists for years.
Located next to Mallory Square in historic Old Town Key West, Ocean Key Resort provides the ideal home away from home to explore everything Key West has to offer. From the resort, you can easily explore downtown Key West on foot or walk down the street to Key West Harbor where an array of water tours await you.
All the rooms at Ocean Key Resort feature local art and eclectic hand-painted furnishings. Each room comes with a private balcony and view of the Gulf of Mexico or Key West’s historic Duval Street. Highlights include Sunset Pier, a high-end spa, the cute mini Rum Bar in the lobby, oversized showers, and delicious daily breakfasts. I loved how spotlessly clean the rooms and property were.
I also loved the dreamy Liquid Pool Bar & Lounge overlooking Sunset Pier and the ocean. This is the perfect place to spend an afternoon enjoying cocktails in the sunshine with a stunning view of the aqua sea. The decadent dinner I experienced at Ocean Key Resort’s upscale, romantic, oceanfront restaurant, Hot Tin Roof, was top-notch and not to be missed.
I would definitely stay at Ocean Key Resort & Spa again next time I visit the Keys. I highly recommend it as an ideal hotel to book for a special occasion and for exploring the best of Key West.
The Best Key West Hotels
There are a handful of upscale resorts in Key West, along with more affordable accommodations, making it an ideal destination for any budget. Here are 10 of the best hotels in and around Key West organized by luxury, mid-range, and budget-friendly.
Luxury Key West Hotels
- Ocean Key Resort – As mentioned above, this hotel provides the full resort experience with a poolside bar, stunning views, a superb location overlooking Sunset Pier, a full-service spa, and an excellent upscale restaurant on the property.
- Pier House Resort and Spa – Located across the street from Ocean Key Resort, set on Duval Street with serene sea views and an exclusive private beach. Pier House Resort is in an excellent location and offers great amenities and beachfront dining.
- The Marker Key West Harbor Resort – In the tropical setting of two acres of gardens, this harborfront property has 96 rooms and suites, an onsite restaurant, and three outdoor pools.
- The Marquesa Hotel Key West – This eco-certified, adults-only hotel offers three sparkling swimming pools, lush gardens, and a great American cuisine restaurant. Located close to the beach and only a two-minute walk to Duval Street, the guests say the property is first-rate.
Mid-range Key West Hotels
- Sunset Key Cottages – Located on a secluded private island a short boat ride away from the mainland, this aparthotel is perfect for couples. Think white sand beaches and your own private getaway. All apartments come fully furnished with all amenities and be sure to check out the on-site restaurant, Latitudes, too.
- H2O Suites – Close to the Southernmost Point and in the entertainment district, this highly-rated adults-only hotel is a favorite for its thoughtful touches and ideal location close to the action.
- The Gates Hotel, The Keys Collection – This stylish hotel combines a laidback island lifestyle with elegance and fun. It has a full program of entertainment and has a craft rum bar and cigar lounge.
Budget Key West Hotels
- Hilton Garden Inn Key West, The Keys Collection – This recently redesigned hotel is close to Smathers Beach and even has an on-site golf course.
- 24 degrees North, The Keys Collection – This hotel celebrates the fact that it’s on the same latitude as Havana, Cuba, and brings laid-back island vibes to its accommodation.
- Fairfield Inn and Suites, The Keys Collection – This family-friendly hotel is a convenient base for everything you’ll want to do in Key West.
Other Florida Keys Hotels
If you want to stay a little further afield, check out these hotels on other Keys. These two hotel options are just a scenic ocean drive away from Key West.
- Hawks Cay Resort, Marathon – This large, upscale resort oozes family holiday fun and is located on the nearby Duck Key, Marathon. It has a marina, a private beach with beach volleyball, five outdoor pools and restaurants, and its Calm Waters spa for all your pampering needs. Keys like Conch Key are only a short drive away and Key West takes just over an hour with stunning views along the journey.
- Little Palm Island Resort and Spa – Located off of Little Torch Key, this eco-certified luxury resort and spa has been newly refurbished and is said to be requisite! When staying here, you’ll check in at Little Torch Key, before boating over to this exclusive island resort. Expect white sand and crystal clear waters on the private beach and be sure to take advantage of the watersports on offer.
Top 12 Things To Do In Key West
Key West is a tiny island that is only 8 square miles. But there is a lot to do and see here. This is by no means a comprehensive list of attractions, but this will get you started. Here are my suggestions for 12 things not to miss in Key West.
1) Stroll Historic Oldtown Key West
The Key West Historic District encompasses approximately 4,000 acres and contains 187 historic buildings and one structure. Here you’ll find cute souvenir shops, museums, restaurants, and a sea of jam-packed bars offering island cocktails.
Duval Street is the main drag of downtown, running north and south from the Gulf of Mexico to the Atlantic Ocean. On Duval Street bustling frozen daiquiri bars can be found around almost every turn, set amidst eclectic shops, Victorian-style homes, back alley speakeasy bars, pubs, and seafood restaurants.
2) Watch the Sunset at Mallory Square
This iconic square becomes a festival of activity every evening, with street vendors, carnival performers, and a sea of restaurants and music all around. Mallory Square is the perfect place to enjoy a famous Key West sunset.
3) Take Photos at the Southernmost Point
To prove you’ve visited the most southerly point of the United States, get your camera out and have your photo taken at this commemorative monument. As with most Instagrammable places, you may want to skip this if you don’t like waiting in line for a photo op.
4) Take a Boat Trip
To get out on the water day or night, rent a boat or take a boat trip on Key West’s iconic waters. There are an array of tour operators to choose from but one good one to check out is Honest Eco Tours. They offer catamaran tours, power boat tours, and tours on a unique boat they built called the Squid.
5) Visit Dry Tortugas National Park
Accessible only by ferry ride or sea-plane, Dry Tortugas National Park, is located 70 miles from Key West, and comprises seven small islands teeming with life and natural beauty.
Snorkel or swim in the coral reef and take a historic tour of Fort Jefferson. Walking on the walls of this giant brick structure is a highlight.
6) Visit Historic Fort Zachary State Park
This is the southernmost state park in the United States and houses an impressive civil-war-era fort and one of the best beaches in the Keys. This beach is perfect for families as there are so many activities to do such as snorkeling and kayaking. It is also one of the prettiest beaches to sunbathe on.
7) Enjoy Live Music on Sunset Pier
Overlooking the crystal blue waters of the Gulf of Mexico, Sunset Pier is a relaxed dockside seafood eatery at the Ocean Key Resort with water views, drinks & live music.
8) Watersports
Offering the third largest coral reef system in the world and the year-round mild temperatures and sunshine, Key West is an ideal spot to do an array of watersports. You can kayak through the mangroves, jetski around islets, paddleboard, and snorkel in the crystal clear ocean.
This three hour snorkeling adventure tour takes you out on a catamaran to all the best spots around Key West. The Florida Keys National Marine Sanctuary protects North America’s only coral barrier reef.
9) Take a Tour of Ernest Hemingway’s House
Ernest Hemingway lived in this property from 1931 to 1939 and you can take a 30-minute tour of the house and grounds. Keep an eye out for descendants of Hemingway’s six-toed cat prowling around the grounds.
10) Relax on the beach
Key West is the perfect place for some rest and relaxation with white sand beaches, crystal clear waters to cool off in, and sunny weather. Some of the best beaches include the popular Smathers Beach, Higgs Beach, Rest Beach, and South Beach.
11) Visit Truman’s Little White House
This historic building was President Harry Truman’s ‘Winter White House’ and later served as a sunny retreat for Presidents Eisenhower, Kennedy, and Clinton. The admission price also includes a tour of the property.
12) Take a Ride on the Overseas Highway
Unless you take a boat to Key West, necessity will ensure you take a ride on this famous road at some point during your trip. This feat of engineering is an attraction in its own right. This stretch of road is often called “the highway that goes to sea.” It encompasses 113 miles of roadway and 42 bridges from Key Largo to Key West including the famous 7-mile bridge (pictured below).
For this trip, I booked a Daytrip private driver to take me from South Beach to Key West so that I could enjoy the amazing drive! The drive takes about 3.5 hours and you can expect breathtaking views as you hop from key to key and marvel at the coral islets and crystal-clear water.
The Best Tours in Key West
Key West offers a great number of fun tours for exploring the area, taking to the water and visiting natural wonders. Here are some great options:
- Sunset Party Cruise by Catamaran – Watch the famous Key West sunset as you enjoy complimentary hot and cold food, margaritas, beer, wine and champagne, whilst listening to live bands play your favorite tunes.
- Helicopter Tour – This 10 minute helicopter tour gives you spectacular views of all of Key West’s iconic landmarks and even offers the option of having the doors off!
- Full Day Tour of Key West National Wildlife Refuge – This all day tour takes you sailing, kayaking through the mangroves and snorkeling on backcountry reefs. Also includes an all-you-can-eat buffet .
- Parasailing Flights – Get the best panoramic views of the Keys on this exhilarating ride above the turquoise waters.
- Guided Bicycle Tour with Key Lime Pie – See the sights up close the eco-friendly way. Cycle around the Old Town, visit attractions and finish the trip with famous Key Lime Pie.
The Best Restaurants in Key West
Due to its island nature and proximity to Cuba and the Caribbean, Key West has developed a unique ‘Floribbean’ culinary style, combining classic American tastes and fresh seafood with Caribbean flavors. From roadside shacks to fine-dining restaurants, you’ll enjoy an array of fresh, flavorful dining options in Key West.
Here are our suggestions for 10 of the best restaurants in Key West.
- Hot Tin Roof – Located inside Ocean Key Resort, this popular oceanfront restaurant specializes in exquisite ‘Floribbean’ dishes that are a fusion of the best flavors that exemplify local cuisines. This Key’s staple is perfect for a romantic date night or special occasion, just be sure to book in advance as it gets busy. I dined here and it was exquisite. If you like mushrooms, the mushroom appetizer is amazing.
- Willie’s Chicken Shack – New Orleans’ staple fried chicken shack paired with frozen daiquiris on Duval Street, what’s not to love.
- Moondog Cafe and Bakery – This pretty bakery on Whitehead Street draws the crowds in with the delectable aromas of their gorgeous fresh bakes but you can also stay for brunch, lunch, dinner and happy hour!
- Seaside Cafe Key West – Located in the boutique hotel, The Mansion on the Sea, this cafe is famous for its iconic lobster pizza and epic mojitos.
- Glazed Donuts – Not quite a restaurant but not your average donut stand. Refined and elevated donuts with creative flavors are the norm here and donuts are usually sold out within a few hours. Make sure you try the key lime pie-flavored ones!
- Cafe Marquesa – This fine dining restaurant located in the Marquesa Hotel offers an exquisite setting for special occasion dinners. Don’t let the refined interior fool you though, the menu is down-to-earth with a perfect blend of innovation and classic.
- Blue Heaven – This laid-back joint was opened in 1992 by an artist and writer and it’s been a local institution ever since. Offering Caribbean flavors and colorful decor along with live music, it’s super romantic and the perfect place to relax and unwind.
- El Siboney – For authentic Cuban cuisine, this family-friendly restaurant in the heart of Old Town is the place to be. Try the Cuban Mix Sandwich and be transported to the Caribbean.
- Garbo’s Grill – This Korean BBQ street vendor has a small menu of classic and fusion dishes that packs a lot of punch.
- Alonzo’s Oyster Bar – This laidback seafood restaurant prides itself on being the only restaurant in Key West that has water on three sides, but we think it should boast more about its delicious crab – which is hands down the best crab I’ve had anywhere! I’m happy to confirm that they also live up to their name in the oyster department and have excellent Oysters Rockefeller. Visit between 4:30 and 6pm to take advantage of their famous daily happy hour.
The Best Bars in Key West
Key West is known to have some of the best bars in America! With over 300 bars to choose from there is truly something for everyone. On famed Duval Street, you’ll find live music joints, eclectic speakeasy bars, pubs, frozen daiquiri bars, beach bars, pool halls, dance clubs, and everything in between.
There’s a bar and a party in Key West for every theme and every day of your vacation. From my experience, here’s a list of 10 best of the best bars in Key West.
- Captain Tony’s Saloon – A quintessentially Key West bar steeped in history that’ll always have a barstool free for a cold one after a long day in the sun. If you’re feeling brave, try their signature Pirate Punch.
- General Horseplay – Priding themselves on craft cocktails, go there for the spicy margaritas and stay for the tomfoolery.
- Pickles Pub Sandbar – This modern sports bar serves cool drinks and comfort food, and showcases great live bands.
- The Roost – This sophisticated hidden gem has happy hour from 12-6pm and specializes in unique craft cocktails and is a welcome refresher from the chaos and liveliness of Duval Street.
- 22 & Co – If glitter, tutus and flamingoes are more your vibe, head to 22 & Co. This unicorn-inspired fun house offers fresh cocktails and magical vibes for a great night.
- Hog’s Breath Saloon – This pub is a favorite hang of the locals and offers classic drinks with a superb program of live music.
- Fogarty’s & The Flying Monkey Saloon – Located on Duval Street, this lively bar is well-known for its frozen cocktails – the frozen daiquiri isn’t for the faint-hearted.
- Mary Ellen’s Bar & Kitchen – This lively and eccentric bar serves comfort food like gourmet grilled cheese and always has something going on at night – its charity vibrator races are a real local event!
- Sunset Pier – Next to Mallory Square, this pier is a delight of music and festivities. Enjoy a Caribbean cocktail at the tiki bar and pull up a stool to enjoy the sunset view from the best seat in the house.
- White Tarpon – Here you can have the famous Key Lime Martini while admiring sweeping views of the harbor.
The Best Time To Visit to Key West
During the winter months (November – February) the weather is cooler but pleasant at around 75-80 degrees; the water is 70-74 degrees. During the summer months, the weather is very hot and humid and there’s always the risk of the odd hurricane or storm disrupting your vacation.
The water temperature can also get to a not-so-refreshing 86 degrees, but if you want to swim in a tropical bath with plenty of colorful sea life, then head to Key West during the summer.
Due to the excessive summer heat, (which I love, but know many find unappealing) high season in Key West is during the winter months. So in winter expect high season prices and lots of tourists.
March to May is a good time to visit Key West if you want to take advantage of warm weather and fewer crowds.
How to Get to Key West
You can fly into Key West International Airport, but this option can be pricey. As a more affordable alternative, you can fly into Miami International Airport (MIA), rent a car and drive to the Keys.
I chose to hire a driver from Daytrip to drive me from Miami to Key West so that I could fully enjoy the gorgeous views. The drive is easy and takes about 3.5 hours with no stops. But I recommend making a few stops along the way to explore other Keys and to take in the stunning scenery along the way.
Once in Key West, the city is very walkable but you can also cycle – many resorts have bicycles available to hire for you to do this. There’s also a hop-on, hop-off bus, and Uber. Or you can even rent a golf cart!
Key West Ultimate Guide Wrap Up
If you’re chasing a laid-back island vibe for your next vacation, I highly recommend checking out Key West. It’s a perfect long weekend getaway to add to your next Miami trip. Pack your flip-flops and your swimsuit and be ready for relaxed fun in the sun!
I hope you’ve found my Key West guide helpful. If you’re interested in visiting other areas in Florida you can check out all our Florida articles for inspiration or our US bachelorette party guides for other party destination ideas.
We hope that this article has inspired you to visit Key West! If you have questions about Key West or tips to share with our readers please leave these in the comments below.
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Read More About Florida
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- The Best Of Key West – Beyond Duval Street
- Dry Tortugas National Park: A Fortress In The Sea
- How To Have The Perfect Florida Keys Roadtrip
- The Best Things Central Florida Has To Offer
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