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About Key West
Key West is a popular place for watersports, diving and snorkeling, lively nightlife, and historic sightseeing. Walking through Key West, especially along Duval Street (its main 1.1 mile street), feels like a mix between New Orleans and Savannah. Old Town (where Duval Street is located) is lined with pastel, weathered, classic bungalows and guest mansions. Live music pours into the streets, beckoning passersby to stop in the various bars and restaurants for a refreshing drink and bite to eat.
The sunsets in Key West are priceless. In fact, they are so beautiful that they’re given a celebration each night in Mallory Square. Street performers, musicians, and food carts roll out the red carpet for this daily affair.
Key West is a very relaxed and casual spot...nothing feels rushed or fast-paced...everything is on island time. Expect strong Margaritaville-vibes in this Jimmy Buffet-approved destination. Perhaps that’s why the free-roaming chickens enjoy the island so much. Key West has a vibrant population of chickens that call Key West home, and it’s been that way for decades.
While tourism is now the island’s primary industry, the destination was once known for sponging, fishing, turling, salt manufacturing, and shipwreck recovery. Due to the island’s small size, cars are not the primary choice of transportation for tourists. Instead, you’ll see much more walking, bicycling, electric car rentals, mopeds, pedi-cabs, and trolleys.
When to Visit Key West
Key West has a subtropical climate - meaning hot and humid. I visited Key West in August - definitely not the best time of the year I would recommend visiting. Key West sees sunshine 76% of the year and has an average temperature of 77.7°F. On average, temperature highs are in the 70s and 80s year-round with lows in the 60s.
Regardless of what time of year you visit, you’ll never see snowfall. The record-low in Key West was 41°F, and it’s only happened twice in history - in 1873 and 1981.
The best time to visit Key West is between March and May because this is when the weather is still nice, winter crowds lessen, and prices decrease. Winter (December through February) is the island’s most popular time of the year, so expect more people, higher prices, and ideal weather at this time.
Note that hurricane season is from June to November, so check the forecast before your visit.
How to Get to Key West
Jordan and I were visiting family in Fort Lauderdale, so it made most economic sense to rent a car and drive down to Key West from there. Had we done it again, I would have chosen to fly directly into Key West International Airport from DFW instead. Yes that flight was definitely more expensive than a round trip out of DFW to Miami or Fort Lauderdale, but here’s why I’d suggest flying direct if you can for several reasons:
Key West is small, so rental cars are really not necessary to get around once you’re there.
The 4-hour road trip from Fort Lauderdale to Key West was rather monotonous. I know people like to make a road trip out of it and say that it’s a beautiful drive, but I don’t think it’s worth it (unless you’re trying to save money). In my opinion, a rental car road trip is much more worth it in places like Colorado and Arizona where the views are breathtaking.
Somehow, our rental car got a FLAT TIRE while we were in Key West, so we had to deal with that while on our short vacation. I’ve never had a flat tire on a rental car before. Frankly it could have been a lot worse than it was - we were able to air it up and trade it out at the Key West Airport. The ordeal took about 2 hours of our time, but it was just a hassle to deal with, especially when on vacation. If given the choice, I would’ve much preferred using that time to drink and relax by the pool instead!
American, Delta, United, and Silver serve Key West to 15 destinations, as well as HavanaAir, and on-demand charter services.
If you choose not to go by land or air, your final option is by sea. The Key West Express ferry service runs between Fort Myers and Key West or Marco Island and Key West (December-April). A round trip ranges from $140-$170 and is about 3.5 hours between ports.
Where to Stay in Key West
Key West’s Old Town is covered in private inns and bed & breakfast properties to offer you a more authentic island experience. I highly recommend going this route, even if you aren’t accustomed to staying in non-hotel properties.
Regardless of whether you opt for an inn, hotel, or Airbnb, Old Town is where all the action is at, so I recommend that you stay there; this way you can easily walk around everywhere. Key West has a TON of adult-only options, especially when it comes to the historic homes in and around Old Town, which is great news for childfree travelers! And here’s my top recommendation for where to stay in Key West - The Gardens Hotel.
This place is a HIDDEN GEM! For my full review of the property, see my post:
>>> Hotel Review: The Gardens Hotel in Key West, Florida <<<
Although this is my number one recommendation of where to stay, there are some other beautiful places to check out.
Here are a few other recommendations of where to stay in Key West, Florida:
The Gardens Hotel (My #1 Pick!) - 4-star, $$
Plantation-style rooms, suites and cottages are individually decorated and have wooden beds with Italian linens, as well as flat-screen TVs, CD players, minifridges and coffeemakers. Most rooms have either balconies or verandas, and some have whirlpool baths.
Breakfast is served on a porch overlooking the gardens. There’s a heated pool with a poolside bar, plus an aviary, fountains, ponds and a wine bar. Massage services and rental bikes are available. Children 16 years and older are welcome. Read more about this hotel here.
Photo credit: Saint Hotel Key West.
The Saint Hotel Key West, Autograph Collection - 3-star, $$
It is a 10-minute walk from the Ernest Hemingway House and 3 miles from lively Smathers Beach.
Featuring blue LED lighting and wood paneling, the contemporary rooms come with free Wi-Fi, flat-screen TVs and iPod docks. Upgraded rooms feature marble tubs. Monochrome suites with vaulted ceilings add sitting areas with sofas, and some have kitchenettes and/or balconies. Room service is available.
Amenities include a cozy Creole restaurant/bar and an outdoor pool with a waterfall.
Photo credit: Sunset Key Cottages.
Sunset Key Cottages - 4-star, $$$
Bright 1- to 4-bedroom cottages feature free Wi-Fi, flat-screen TVs, coffeemakers and pillow-top mattresses, as well as living and dining areas. Upgraded units add ocean-view balconies or patios; some have whirlpool tubs.
Boat transfers to Key West are complimentary. There's an informal restaurant/bar and a poolside bar. Other amenities include a gym and a spa, plus a beach and 2 whirlpools.
Photo credit: Simonton Court.
Simonton Court Hotel Key West - 4-star, $$
Upscale rooms are individually decorated, and feature unique touches such as spiral staircases, private balconies, whirlpool tubs and wetbars. Some cottages have kitchens or kitchenettes, and a 2-story townhouse offers secluded suites situated around a courtyard with a shared pool.
Free perks include Wi-Fi on the grounds, and continental breakfast served poolside. There are also 4 outdoor pools. Minimum stay requirements may apply.
Photo credit: Marquesa Hotel.
Marquesa Hotel - 4-star, $$
Housed across 4 distinct buildings without elevators, refined rooms and suites have free Wi-Fi, cable TV and marble bathrooms. Suites add pull-out sofas and covered porches. Turn-down service is standard, and in-room continental breakfast is available (fee).
Free perks include parking, and coffee and tea in the morning. Lush greenery surrounds 2 pools and a patio. There's a restaurant offering upscale American dishes, and a bar featuring light fare. Children 14 years of age and older are welcome.
La Mer & Dewey House. Photo credit: audleytravel.com.
La Mer & Dewey House - 4-star, $$
Stylish, individually decorated rooms all have private patios, iPod docks and Wi-Fi access. Some rooms add ocean views and whirlpool tubs.
The hotel has a bar and direct beach access and shares 3 pools with its adjacent partner hotels. Continental breakfast and afternoon tea are included. A resort fee covers property-wide Wi-Fi, parking, access to the fitness center and the use of beach towels and chairs.
What to Do in Key West
Southernmost Point
When: 24/7
Where: Whitehead St &, South St, Key West, FL 33040
How Much: Free!
You do get views of the Atlantic Ocean, but it’s more about being able to say you stood at the southernmost point of the Continental United States. This spot is also the lowest latitude of the contiguous North American states at 18 feet above sea level. Stop here in the morning to beat the line of people, then walk around the corner to the Key West Butterfly and Nature Conservatory - it’s 2 minutes away. From this point, Cuba is just 90 miles away. Fun Fact: Key West is geographically closer to Cuba than it is to mainland Florida and Miami, located 150 miles north.
Key West Butterfly & Nature Conservatory
When: Open daily from 9:00 AM to 5:00 PM (last admission at 4:30 PM)
Where: 1316 Duval St, Key West, FL 33040
How Much: $15.00 general admission
I’ve been to butterfly conservatories before, and while they’re all magical, this one felt especially so. After you walk into a small room, the Learning Center, with some background about butterflies and their lifecycle, you can enter the conservatory.
When you enter, there’s actual magical music playing which makes you feel like you’ve stepped into an enchanted garden or fairy wonderland. All around you are colorful butterflies - the bright blue and black ones were most prevalent. Overall there are over 60 species of butterflies from around the world housed here.
But don’t just look forward on the path; make sure to look both up and down. On the ground and in the trees are 20 species of exotic birds. Some are tiny and run across the path while others are colorful and singing in the trees. There are also two bright pink flamingos to visit - Rhett and Scarlett.
Although this is an attractive place to visit for families, it’s absolutely worth the visit for adults as well. I could’ve spent a whole day there just watching the butterflies dance around the glass-enclosed, climate-controlled conservatory. Because it’s a lush garden inside, it does feel like you’re in a greenhouse - it’s very humid. But occasionally you’ll walk by a big air vent and get a refreshing gust of air to cool you off.
The gift shop is also worth a look around - you can take your very own butterfly home displayed in clear acrylic cases. You can get a single one (like I did) or an amazing piece of artwork made by Sam Trophia who creates large wall and table mounted displays or butterflies. And you don’t have to worry about taking one of these beauties home - the butterflies are raised in select butterfly farms in South America, Africa, and Southeast Asia where they are only collected after they have completely lived out their short adult life cycles, which averages at about 1 month.
The Conservatory is open from 9:00 AM to 5:00 PM daily (last admission is at 4:30 PM). General admission is $15.00.
Ernest Hemingway Home & Museum
When: Open daily from 9:00 AM to 5:00 PM
Where: 907 Whitehead St, Key West, FL 33040
How Much: $17.00 general admission (includes optional guided tour)
Here you can actually walk through the former permanent residence of Ernest Hemingway and meet the polydactyl cats (6-toed cats) that live on the property. Even if you are not familiar with Ernest Hemingway’s works (e.g. The Old Man and the Sea, A Farewell to Arms, For Whom the Bell Tolls, The Sun Also Rises), you can still appreciate his strong influence on 20th century fiction. Hemingway was an American novelist, short-story writer, journalist, and sportsman.
The museum is open daily from 9:00 AM to 5:00 PM for walk-in visits, but it is cash only. General admission is $17.00. For the same price, you can choose to either walk the property at your own pace or you can go on the 20-30 minute guided tour.
We chose to just explore the home at our own pace. Unfortunately, I don’t know much history about Ernest Hemingway, so I’m sure the guided tour would have been helpful, but I still enjoyed wandering around the property.
The Hemingway Home was originally built in 1851 in the Spanish Colonial style. Ernest and his wife Pauline undertook a massive restoration in the 1930s to make the home what it is today. The home is decorated with European antiques as well as some souvenirs of Hemingway’s African safaris.
One of the most impressive features of the Hemingway home is the pool - built in 1937-1938. It cost $20,000 (which was an enormous amount back then) and it became the first in-ground pool in all of Key West. It was also the only pool within 100 miles.
Another interesting aspect of the Hemingway Home are all of the cats. According to the story, Hemingway met a sea captain who owned a polydactyl cat. The sea captain gave Hemingway this cat upon his departure. Today, there are approximately 60 polydactyl cats on the property! They freely roam the property both inside and outside of the house.
Key West Garden Club & African Refugee Cemetery
When: Open daily from 9:30 AM to 5 PM
Where: 1100 Atlantic Blvd, Key West, FL 33040
How Much: Free!
Another free spot to visit is the Key West Garden Club and African Refugee Cemetery at Higgs Beach. It’s a somewhat small and modest site but interesting nonetheless. The gardens grow within West Martello Tower, which was part of Fort Taylor, used during the Civil War. In 1861, Key West was the only southern city in the Federal government. The Fort continued to be used in the Spanish American War for quartering troops in 1898.
Instead of demolishing the site, the Club had it added to the National Register of Historic Places and turned it into a garden. I loved how the original brick is still preserved around the gardens, which are maintained by member-volunteers of the Garden Club. If I lived here, I’d visit often because it’s a very tranquil place with gazebos, a waterfall garden, and a labyrinth. An hour is about the maximum time you’ll likely spend there.
Just outside the old West Martello Tower ruins is the African Refugee Cemetery. In 1860, the U.S. Navy intercepted 3 ships bound for Cuba carrying 1,432 African men, women, and children. The refugees were rescued and brought to Key West for safe haven. Due to inhumane conditions on the boats, 294 of the refugees died within the first few months of arriving in Key West. They were buried at the African Refugee Cemetery, which was discovered in 2002 using ground-penetrating radar. It’s the only known African refugee cemetery in the United States.
Wind & Wine Sunset Sail with Danger Charters
When: Daily, 5:30 PM departures (times may vary)
Where: Opal Key Resort & Marina, 245 Front Street, Key West, FL 33040
How Much: $95 per person
Instead of seeing the sun set over Mallory Square, you can watch it set from the waters while sipping wine and enjoying nibbles on a 65-foot schooner. Though there’s not premium seating for everyone (we sat on the deckhouse), it’s still a very enjoyable experience and there are not many people on the boat (up to 30 guests max). (Make sure you have a good grip on your phone as it can easily go overboard if you’re not careful! I kept mine safe this time, luckily!)
What makes this experience really special are the crew onboard. Before setting sail, one crew member walks through all 8 wines. (They also have 5 premium beers for non-wine lovers.) After setting sail, two of the three crew members continue to circulate around the boat allowing you to try every wine as well as gourmet bites, like Havarti Dill, Smoked Gouda and Summer Sausage, Caprese Skewers, Water Crackers with Green Apple and a Honey Drizzle, and more. If you like certain wines, you can have more of it, and if you don’t like a certain wine, you can skip it.
The third member of the crew is steering the large skipjack sailing schooner. The cool breeze on the waters gives a welcome reprieve from the heat on land. The crew was attentive, the sailing was smooth, and the sunset was beautiful. Ages 13 and up are welcome (though we didn’t have any children on board.) Altogether it was about a 2 hour experience, starting at 5:30 PM. 10/10 experience!
Mallory Square & The Sunset Celebration
It’s a waterfront square surrounded by restaurants, shops, and art galleries. Within this area is the Shops at Mallory Square, a 26,000 square foot, air-conditioned emporium with artist shops, like Ocean Blue Studio. It’s a good place to try some authentic Cuban coffee from Cuban Coffee Queen.
Near Mallory Square, you can hop on an Old Town Trolley Tour or Conch Tour Train, visit the Key West Aquarium, or visit historic homes, like Harry S. Truman’s Little White House or the Audubon House & Gardens. Though we looked into a trolley/train tour, we felt that it was overpriced.
The most popular time to visit Mallory Square is for their daily Sunset Celebration. Starting two hours before sunset each evening, people gather to be entertained in the square by magicians, jugglers, clowns, psychics, musicians, artists, and food vendors - all in celebration of the famous Key West sunset.
Pub Crawl Down Duval Street
Duval Street is the main drag of Downtown Key West. It’s about a mile long, but it’s jam packed with restaurants, shops, and pubs, making Duval Street the place for pub crawls.
Here are some of the most popular spots for a pint:
Hogs Breath Saloon - a Key West staple for over 25 years, on the corner of Duval and Front Streets
The Green Parrot Bar - a 100-year old Key West dive bar where locals come to kick back some drinks and listen to some live music, off of Duval and Whitehead Street
Rick’s Bar - 8 bars in one across 3 stories, each with their own theme and experience, ranging from live rock to disco dancing
Sloppy Joe’s Bar - well-known bar who has hosted thousands of patrons through the years, the most celebrated being Ernest Hemingway
Photo credit: 24 North Hotel Key West’s “Best Drag Shows in Key West”.
Watch a Drag Queen Show
Key West has developed a reputation for some impressive Drag Queen performances. Key West and drag shows just go hand-in-hand. Here’s where you can catch a lively and fun show on the island:
801 Bourbon Bar - a less-traditional, comedic drag show with audience interaction
Aqua Bar & Nightclub - a local favorite for a traditional drag show with flashy costumes and lip-syncing
LaTeDa Cabaret - island’s most grandiose drag show (‘cabaret’) that pays homage to iconic women like Marilyn Monroe and Madonna, with actual singing
Mangoes Restaurant - host of the Drunken Drag Brunch for bottomless mimosas, signature menu items, drag queen performances, and a live DJ
Photo credit: 24 North Hotel Key West.
Rodriguez Cigar Factory
When: Monday through Saturday at 10:30 AM and 1:30 PM
Where: 113 Fitzpatrick St, Key West, FL 33040
How Much: $35.00 for tour
They preserve the historical cigar manufacturing industry which began in Key West in 1831. Rodriguez Cigars are constructed with vintage leaves aged through the traditional Cuban manufacturing process.
I didn’t have a chance to book a tour, but the Rodriguez Cigar Factory does offer a tour where you can learn the full process of manufacturing a cigar from an actual Master Cigar Roller. I’m not really keen on cigars but I would be interested in how they are made. Tours are offered Monday through Saturday at 10:30 AM and 1:30 PM. The tour is 1 hour and 15 minutes. The tour covers:
Key West’s cigar industry history
The Rodriguez family story
How to strip the central vein from the wrapper and binder leaves
How to blend the different tobacco and construct the filler
How to apply the final wrapper
The aging process in a humidor
Following this tour, you’ll receive one of their cigars and a complimentary Cuban espresso.
Photo credit: The Marker Key West.
Rum Tasting at Rum Distilleries
Rum plays an interesting role in Key West’s history. During the prohibition, Key West was one of the ports that hid smuggled spirits from Cuba. Today, there’s still a speakeasy from the Prohibition era on Duval Street - Speakeasy Inn. It’s one of the few buildings in Key West that has a basement and a secret room. If you’re a rum drinker and you enjoy learning more about rum running, you’ll have multiple distilleries to choose from while in Key West:
Key West First Legal Rum Distillery - get a free sample of rum and a 15-minute tour, offered every 20 minutes daily (or try a Mojito Class!)
Papa’s Pilar Rum Distillery - Made by the descendants of the Ernest Hemingway family, Papa’s Pilar wins the award for cutest shaped bottles; take a 45-minute distillery tour or try a cocktail class
Key West Trading Company - get a free tasting Thursday through Sunday from 5:00 to 9:00 PM
Photo credit: drytortugas.com.
Day Trip to Dry Tortugas National Park & Fort Jefferson
Most people get there by taking the Yankee Freedom III ferry, but if you’re looking for a more luxurious option, floatplanes are available.
Key West is home to the 3rd largest barrier coral reef in the world - the Florida Straits. It extends 150 miles north to Miami and 70 miles west to the Dry Tortugas. This is the largest coral reef in North America, so needless to say the snorkeling is excellent here.
Where to Eat in Key West
In my personal opinion, I would not peg Key West as a culinary hotspot. Don’t get me wrong - we ate very well in Key West, but I would not characterize Key West as a mecca for incredible food experiences.
That being said, Key West does have some really delicious places to eat - especially if you like seafood and/or Cuban food. Plus, it’s hard to beat the ocean views that many of the island restaurants offer.
Check out this related post to get a full round-up of the best places to eat in Key West for every meal.
Closing Thoughts About Key West
Key West is a great adult-friendly place to enjoy yourself and relax. There are quite a few adult-only properties to choose from as well as solo and couple-oriented activities for adults.
An overall casual and laid back destination, Key West is a place to be yourself and just get away from it all. It’s easy to see why Ernest Hemingway chose to put down roots in this tropical and irreverent setting. I loved how easy it was to get around the island, without having to rely on a car or Uber. It was also quite scenic with the tropical foliage combined with the pastel-hued, conch-style houses.
Between the water activities, the nightlife, and the rich history, Key West is a perfect place to have a long weekend getaway. Whether you want to let loose, recharge, or just spend some time by the water, Key West will deliver!
author bio
Known as The Jet Set Blonde, Brittany Ryan inspires others to add more adventure to their childfree travel experiences. Brittany has visited 23 countries (and counting!) Connect with her to get access to detailed childfree travel itineraries, travel guides for weekend getaways, and updates on adult-only hotels, resorts, cruises, and other travel amenities.
