I feel that when most people think of Key West they envision a destination of bikers, rowdiness and everything that comes with being overserved. There are certain times of the year when it’s totally like that, I’m not going to lie. But to those of us that understand how to really enjoy Key West, it’s a tropical paradise full of color and quirkiness like none other. It’s also a perfect getaway when you want to be socially distanced outdoors enjoying nature. Let me show you how I do Key West:
Where to Stay
For such a small town, two miles wide by four miles long, Key West has a lot of accommodations from guest houses to luxury resorts. Unfortunately, there really isn’t a low season. With the wonderful weather, you can enjoy it year-round. This is also why you will find that lodging is quite pricey.
There are many hotels that I like in Key West but one of my faves that I recommend is the Margaritaville Beach House Key West. For all the beautiful water and reefs that surrounds the Florida Keys, there really aren’t very nice beaches, however, Margaritaville is directly in front of one of the few nice beaches in the area. The lively resort has an upscale beach house vibe with a poolside restaurant and bar.
Like most resorts throughout Florida, the hotel charges a nightly resort fee of $48 (plus tax) in addition to the nightly rate. This fee provides guests with exclusive access to the resort’s amenities, services, and activities, including:
- Daily parking for vehicles which in some hotel properties can cost $48 daily.
- Shuttle service to and from downtown and the Key West International Airport,
- Daily poolside refreshments including fresh blended fruit smoothies at noon and popsicles at 2pm
- Daily lobby refreshments including LavAzza brewed coffee from 6:30am to 11am and virgin mojitos with fresh-baked cookies between 3-7pm
- Pool towels
- Local calls & Wi-Fi
Part of the fun of Key West is exploring the island. So there are several options depending on your adventurous spirit. Besides being able to walk around anywhere, you can rent a bicycle, scooter, golf cart or electric car (FUV, Fun Electric Vehicle). Many shops will pick you up or bring it to you. You can also just take a hotel shuttle, trolley, bus, taxi or pedi-cab which is like a bicycle powered rickshaw.
Whichever you decide to do, just leave the car at the hotel because parking is not plentiful in Key West.
What to Do
While you are exploring, there are many touristy things to do in Key West like taking a picture by the Southernmost Point Buoy, marking the southernmost point in the continental United States or visiting a six-toed cat at the The Hemingway Home & Museum. I’m not making fun, if you enjoy that, by all means do it. But I think the best parts of Key West are not man-made.
Take time to visit Dry Tortugas National Park, one of the lesser known national parks of the U.S., the park is mostly water. The Dry Tortugas are 7 small coral islands in the Gulf of Mexico, located about 70 miles west of Key West.
The islands were first discovered by Juan Ponce de León in 1513. They would be used as the perfect location to defend the Straits of Florida and the Gulf of Mexico. Later, Fort Jefferson was built on Garden Key, modtly used to house a few high-profile prisoners in the 1860s.
The islands and marine ecosystems are protected and the National Park Sevices runs a ferry to visit the park, snorkel and explore. The waters are prestine and the most beautiful shade of turquoise. The tour includes snorkling equipment breakfast, lunch and snacks.
Get in the Water
There are many private charters and tours that will take you to have a fun-filled day in the water. Some offer jet-skis, trampolines, floaters, parasailing and lunch. Others can take you to secluded sand bars. Or you may want your own private catamaran to take you to exclusive spots where you can enjoy the water or just catch some rays while sipping on Rosé and sampling charcuterie.
Regardless your preference or your budget, you must spend some time on the beautiful Gulf of Mexico.
Key West it known for its spectacular sunsets. You may want to see it quiently or with a typical Key West celebration.
Mallory Square Dock has a daily celebration with art exhibitors and street performers.
The Sunset Pier at the Ocean Key Resort is also very popular, it’s by Mallory Square. Here you can grab some drinks and some food as you wait to see the most amazing sunset.
If you want to feel like a “conch”, natives from Key West, go to Lagerheads Beach Bar. Grab a lounge chair, order some beer and conch ceviche and listen to a local musician play some tunes while that sun is setting.
Latitudes is Sunset Key Cottage’s signature restaurant with gorgeous views of the Gulf of Mexico. Catch an early cocktail and dinner in the Ernest Hemingway dining room or dine al fresco while you watch the glorious Key West sunset. This option requires an advance reservation and a ferry ride.
Go Bar Hopping
When in Key West… you must experience the fun, casual, dive bars that are emplematic. Most of the best known bars are localed on Duval Street, the main street in Old Town. A good starting point is Rick’s Bar, with it’s eight-bars-in-one concept is more of an entertainment complex.
Sloppy Joe’s has been around since the 1930’s and always has some sort of entertainment going on. Then you have Hog’s Breath Saloon which is more like a pub with music and dancing. Last but not least, you have the Bull and Whistle Bar which is also a fun place for drinks, music and dancing.
There is no shortage of bars in Key West, these are just a few of the most iconic.
A few of my favorites are Hogfish Bar & Grill on Stock Island, it’s a great place to hang out a have some drink. It’s a huge Tiki hut on the marina. The Smokin’ Tuna Saloon has food and music in a courtyard and it’s just nice and chill.
You can really go bar hopping day or night but here are some night-time exclusive options that you may enjoy.
- La Te Da Cabaret is a drag cabaret show that is a bit on the naughty side but a lot of fun, if you like that sort of thing.
- Do a wine tasting with Stephanie at Grand Vin Wine Bar. She always has new wines to share.
- The bar at Nine One Fine Restaurant is great because they offer like 20 wines by the glass. The restaurants is also very good.
- Berlins is a little speakeasy that is a great escape from the madness of Key West. You can sip on a crisp martini while listening to some soft jazz.