Key West was made famous by Jimmy Buffett, but kept famous because after your first visit, you will be back! I did my fair share of exploring Key West throughout multiple trips myself after becoming based in Miami and below are my top recommendations for where to eat in Key West, what to do in Key West, AND where to stay in Key West.
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Key West: Best Time To GO
Look, there’s no bad time to go to Key West, but there’s definitely a better season. During the winter months, many snowbirds come here to escape the cold and enjoy the warm, dry season in Key West. March is probably the peak tourist season, as spring breakers flood in and hotel prices rise. During the summer months, it’s going to be much hotter, more humid and rainy. However, prices will be lower and crowds will be less.
Top Things To Do In Key West
This is my favorite part: Exploring! There are tons of unique things to do in Key West for every type of person. Here are a few of my favorites:
1. Edgar Allen Poe Speakeasy (New! $55+)
This 4-part cocktail experience is for my Edgar Allen Poe fans. Each cocktail is themed and paired with each story at The Key West Theater. Bring Poe’s tales to life this season and grab tickets to this experience while you can!
2. Open Bar SUnset Cruise Key West (69+)
Best place to be in Key West is out on the water! Watch the sun go down on a catamaran with a drink in hand on this sunset tour. An appetizer selection and live music is also included.
3. Afternoon Reef Snorkel With Drinks ($54+)
Looking to enjoy that afternoon sun? Sail to one of the third largest barrier reefs in the world. You’ll snorkel for an hour and see an abundance of wildlife, then hop back on the boat for a relaxing ocean ride with a cold beer in hand on this tour.
4. Dolphin Watching and SNorkeling Tour ($79+)
Snorkel in the Key West National Wildlife Refuge AND watch the dolphins play in their natural habitat on this tour. Draft beer and snorkel gear is also included.
5. Key West Conch Train Tour ($45+)
If you’re short on time, but still want to see as much as you can, this tour may be the one for you. Pass by iconic sights like Ernest Hemingway’s home and the Little White House while learning all of the fun facts around Key West. You’ll also get free admission to the Sails to Rails Museum and a chance to hop off on Duval Street for some shopping.
6. Parasailing Above the Island Paradise ($84+)
This is probably one of the best locations in the world to go parasailing because the water is SO clear. You can fit up to three people at once on this parasail adventure for a wonderful bird’s eye view. Keep an eye out for dolphins!
7. Jet Ski Tour ($128+)
Need a bit more adrenaline in your Key West itinerary? This 90-minute jet ski ride might do the trick. You’ll also have the chance to swim at a sand bar, spot dolphins and get all of those IG-worthy pics in.
8. Cuban & Caribbean Food Tour ($90+)
Foodies unite! This walking food tour in Key West includes 5 generous tastings at different secret locations around the historic neighborhoods. Try the freshest fish tacos, famous key lime pie, iconic conch fritters, and more.
9. Glass Bottom Boat Reef Tour ($69+)
Want to see the flourishing ecosystem within the reefs without getting your hair wet? This glass bottom boat tour will grant you access to a whole new world, without a single splash of salt water needed.
10. Key West Ghost Tour ($39+)
Islands can still be frightening! This ghost tour will take you through the strange past of multiple stops around Key West via trolley. P.s. You will not actually face Robert the Doll, but the stories of him will be told.
11. Guided Bicycle Tour with Key Lime Pie ($55+)
Burn your calories as you enjoy the iconic dessert of Key West on this bike tour. You’ll stop by the main attractions in a more local manner and, of course, enjoy a well-deserved slice of key lime pie afterward.
12. Truman Little White House ($25+)
This is the ONLY Presidential Museum in Florida and it was truly an interesting place to visit. Did you know Truman spent 175 days of his presidency working from here? Learn fun facts like that and more on a guided tour of the Little White House. P.s. This is a great thing to do on a rainy day in Key West!
13. Shark Viewing Catamaran Tour ($99+)
Experience the thrill of seeing sharks in their natural habitat on this eco-friendly catamaran tour. Don’t worry, your guides have 30+ years of experience navigating The Keys! You’ll also have the chance to spot turtles, dolphins, tropical birds and more.
Coolest Restaurants In Key West
Key West is truly a foodie haven, with local bites, fancy restaurants and hidden gems. I loved exploring more of the island with every bite. Here are some of the best restaurants in Key West:
1. Latitudes Key West- $$$$
Latitudes has made it on OpenTable’s 100 Most Romantic Restaurants in America AND their 100 Most Scenic Restaurants in America for good reason. The view was fantastic- we were seated basically on the sand and even saw dolphins jumping during our appetizers. Reservations need to be made in advance via OpenTable.
2. Nine One Five $$$
This is time after time known to be the best restaurant in Key West. It’s a bit more pricey, but the food, service and ambience is worth it. If you can’t get a reservation in time, you can also dine UPSTAIRS without a reservation, which is what most locals will do.
3. Mr.Z’s $
This late-night food spot is going to keep you coming back for more. Mr.Z’s is serving up the REAL DEAL, bringing the taste of authentic Philadelphia cheesesteaks to The Keys. Cash is preferred.
4. First Flight Island Restaurant & Brewery $$
This brewery is known for being the birthplace of Pan American World Airways and serves up beer, wine, cocktails and some delicious pub food. It’s a great place to go for lunch if you want something casual, reasonably priced and made well.
5. Santiago’s Bodega $$
Santiago’s is another go-to spot for locals and they have an awesome happy hour. From 3PM-6PM daily, you can get $5 tapas (they change daily), 1/2 off beer, wine & sangria AND $26 pitchers of Sangria. We split six different tapas here and each was even better than the last.
6. Cuban Coffee Queen $
Cuban Coffee Queen is often on the breakfast bucket list for visitors coming into town and remains a tradition each morning for the rest of their trip, as you will become addicted! Order authentic cuban coffee and dishes in this cafe in without long lines or reservations needed.
7. Better Than Sex $$
If you like dessert, you’re going to LOVE this place. Started by a couple, this desserts-only restaurant is perfect for date night. You really can’t go wrong with anything on the menu and their rimmed wine glasses are incredible. My favorite was the prosecco rimmed with salted caramel.
Where To Stay In Key West
Key West is a relatively small destination that gets a lot of visitors, especially during the cold months when spring breakers need, well, a break. With that being said, it’s not the most budget-friendly place to spend the night. However, there are multiple options available & here are my recommendations on where to stay in Key West:
Curry Mansion Key West
If you’re looking for a unique stay, this is it. The Curry Mansion comes with a legacy. Built back in 1869, you can still see the history in the 29 charming antique guest rooms. Located on Caroline Street, you’ll be right in the action downtown! However, I must note that this Victorian Mansion does have a bit of a haunted history, so if that’s not your thing, I’d choose another place to stay.
Hilton Garden Inn Key West
I had a very pleasant stay here myself! The Hilton Garden Inn is not in the downtown area, but a free shuttle service is included with your stay that will bring you down to the action of Key West and back home to a quiet stay. It’s a classic hotel, but very clean with great service and amenities.
Truman Hotel
This is a very conveniently-located and trendy hotel in Key West. The boutique hotel is modern and is especially great for couples. The Ernest Hemingway Home is just a 6 minute walk away and continental breakfast is served fresh each morning.
Casa Marina
This hotel has a private beach, pools and is walking distance to the southernmost point of the United States. It’s part of the Hilton collection and is a historic 1920’s resort, but still provides modern amenities, like flat-screen TV’s, Spa al Mare, and more.
The Reach
The Reach also has access to a private beachfront and is located conveniently downtown. This is a sister property of Casa Marina, so you have full access to their amenities, like the Spa al Mare, as well.
Pier House Resort & Spa
If you can afford it, Pier House is an excellent place to stay when in Key West. You’ll be on a private beach with a full-service spa right down in the action. Picture rain-style showers, an oceanfront view and top attractions just steps away.
I hope this quick guide gave you some insight on how to plan your next trip to Key West, whether it be where to stay, what to do and the best places to dine. If you plan on visiting Miami as well when you’re in Florida, make sure to check out these 100 fun things to do under $100 in Miami.
