Key West

Five Great Reasons to Visit Key West

We visited Key West recently on our first extended poker vacation. We’ve already reported on our visit to Miami and shared some of the things nobody tells you about the Florida Keys. We have also shared the craziness of playing poker in Southern Florida.  Our ultimate destination as we traveled down the Keys was, of course, Key West. After a wonderful stop on the island, here are our top reasons to visit Key West.

Five Great Reasons to Visit Key West

The Sun

Let’s start with the key. The most important reason, for us at least, to visit Key West is that is 75 degrees in February. We timed this trip specifically to get out of the chilly New England weather. Even in January, the coldest month of the year, Key West averages 75 degrees during the day. Few spots in the continental US can beat that. Not Los Angeles (high of 68 degrees in January). Or New Orleans (63 degrees). Not even San Diego (66 degrees). If you’re looking for some reliable warm sun in the middle of the winter, Key West is your best bet.

Five Great Reasons to Visit Key West

Key West is also one of the few points in the US where you can watch the sun both rise and set over the water. We’ll admit that we didn’t get up early enough to enjoy the sunrise, but the sunset celebration at Mallory Square can’t be beat. The festival begins every evening two hours before sunset and includes jugglers, musicians, magicians, artists, and food vendors. At sunset everyone pauses to watch the glorious sun sink into the Gulf of Mexico.

The Food

Key West has fabulous restaurants, decadent desserts, and unbelievable bakeries. We were only there for three days, but we had so many good meals. And don’t even get us started on the Key Lime pie!

La Grignote

We started each day with incredible croissants from La Grignote. At La Grignote, they make everything from scratch, and the croissants are so buttery and delicious that we had a hard time keeping ourselves to just one apiece.

Santiago’s Bodega

Our dinner at Santiago’s Bodega, a famed local tapas restaurant, brought fabulous food in a glorious setting.  The bar, tables, and floors are all beautifully hand designed with unique woods and the stained-glass doors add further dimension and style. We were fortunate to be seated out on the porch, where the evening breeze and neighborhood roosters added extra ambiance to our meal. Menu offerings range from soups and salads to hot and cold tapas dishes. Our favorites included the spicy shrimp bisque, croquettes, and patatas bravas. I would go back to Key West tomorrow just to eat at Santiago’s Bodega. Pro Tip: if you are visiting Key West in high season, reserve a table in advance. You’ll be unlikely to score a walk-in.

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Right down the street from Santiago’s Bodega lies Firefly, described on their website as “modern, chef driven cuisine.” After a long day of travel, we decided to have a casual dinner at Firefly’s lovely bar. The engaging bartender kept us laughing as we picked our way through what seemed like half of Firefly’s menu. We chose traditionally Southern items to share that evening, eating poblano and cheddar cornbread, shrimp and grits, and fried chicken. Setting aside Firefly’s diverse wine list (because who drinks wine at the bar?), we enjoyed a couple of local IPAs on draft. Score another win for Key West cuisine.

One of the best things about Key West is simply the overall sense of fun and adventure. Pretty much everyone is there to relax. Click To Tweet


When it’s time for treats, Key West has you covered. You can’t walk a block of Duval Street without passing an ice cream, praline, or Key Lime pie emporium. Our favorite was Mattheessen’s, which conveniently offers all three (along with home-made cookies and fudge). Key Lime pie is of course mandatory snacking in Key West, and Mattheessen’s frozen version will not disappoint.

The Drinks

While Paul and I don’t often drink hard alcohol (the occasional margarita excepted), Key West is all about the booze. If you’re looking for boat drinks, or want to start drinking beer at 10:00 in the morning on a Tuesday, this is the place for you. Key West has been matched in my experience only by New Orleans (a city we love so much we got married there) in the level of open day drinking on the street. Thanks to the legacy of Ernest Hemingway, Jimmy Buffett, and Hunter Thompson, Key West serves as a huge draw to the Baby Boomer set. Many are clearly on a mission to match those men at places like the Green Parrot, Sloppy Joe’s, and Captain Tony’s.

Green Parrot Key West

While day drinking wasn’t on our agenda, Paul and I can vouch for the number of excellent IPAs brewed by local Florida brewers such as the Florida Brewing Company, the Florida Keys Brewing Co., and Waterfront Brewery. If you are a fan of beer and come across one of these IPAs on draft, we strongly recommend you give it a try.

The Sights

Key West will not bore you. The island is replete with restaurants, shops, and water sports companies. You can take a trolley tour around town, visit the Southernmost Point in the US, wander through myriad art galleries, take a sunset cruise, visit the home of President Harry Truman, or climb the Key West lighthouse. There is even a literary walking tour where you can visit the former homes and favorite haunts of writers such as Tennessee Williams, Shel Silverstein, Elizabeth Bishop, and Robert Frost.

Hemmingway House Key West

We chose to take a tour of the Hemingway House, and were thrilled we did. Our charismatic guide JL told us story after story about Hemingway’s life and history with the house. In addition to original furnishings, the house is full of Hemingway memorabilia, most with thorough explanatory signs. After the tour, we were left to our own devices to wander the house and grounds, pet the 55 cats, or just relax in the garden.

Pro Tip: As with the restaurants, we strongly recommend that you reserve tickets to your chosen activities in advance. We had hoped to take the literary walking tour, but found it sold out for the length of our stay.

The Fun

One of the best things about Key West is simply the overall sense of fun and adventure. Pretty much everyone is there to relax. Whether due to the sun, the alcohol, or just a laid-back island spirit, the residents are friendly and welcoming. Even the traffic (while in a constant state of jam) seems friendlier than elsewhere in South Florida. Nonetheless, we recommend you avoid the traffic and park your car and walk, bike, or trolley your way around town.

If you find yourself in the middle of a dark cold winter and are looking for a little guaranteed sun, fun, and fine food, Key West is the place for you.

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