Florida

Key West

One of the most tropical destinations in the U.S. and the closest you can get to the Caribbean without leaving the country. The place you wish to be when skies are gray and you’ve had enough of winter.

I call it “the land of misfit toys” because the culture in Key West is eccletic and eccentric. You’ll find parrots and Parrotheads. The locals are often people who just chose not to color inside the lines of mainstream life and that is what gives Key West its flair.

It is smaller than most think, actually a very small town and just a handful of beaches. This is a boater’s paradise. Each marina is a window shop for yachts. But there are so many riches hiding in this pirates haven, you just have to be willing to treasure hunt.

Getting There

Key West has an airport. If you are lucky, you can fly in direct. But for most, you will need to connect. The only other option is to fly into Miami and drive the entire length of the Florida Keys. A fantastic trip, but its a 4 hour drive that always takes much longer because there is so much to see along the way.

Where To Stay

There are several resorts, lots of timeshares and Air B&Bs. Totally depends on your budget. For me, I wanted to have a beach on site because I knew that beach space is limited in Key West. They have a great public beach, but there are only 2 hotels that have actual beachfront properties.

I stayed at Casa Marina, A Waldorf Astoria resort. Gorgeous place with a petite private beach. It has a very interesting history having been the concept of a railroad tycoon who intended to build a luxury hotel for his most important customers of the overseas railroad from Key West to Miami. It was designed by the same man that did the Metropolitan Opera House, the New York Public Library and the Senate and House building in Washington D.C. The 6 1/2 acres of beachfront were purchased for just $1000 in 1918. The resort opened on New Year’s Eve 1920.

In 1942 it was purchase by the Navy and used as officers quarters during WWII and then re-opened as a luxury hotel in the 1950s. It was then again used as a barracks during the Cuban Missile Crisis after which it fell into a period of decline. It got a complete overhaul in 2008.

The rooms were definitely dated and not the standard you’d expect at a Waldorf Astoria property by a landslide. I stayed in 2014, and it was clean for the most part, but I’d check reviews and shop around. The beach itself wasn’t that great, so perhaps an Air B&B walking distance to the public beach would be a better investment unless you are burning up Marriott reward points like I was.

Things To Do

On your first day I’m guessing you’re heading straight to the beach. You have two choices in Key West, the Gulf of Mexico side or the Atlantic side. I think the better beaches are on the Atlantic side, so expect darker water than the Gulf. Grab a towel, a good book, some suntan lotion and a couple of cold ones and head to the public beach. Let the towering queen palms lull you into a good beach nap.

Once you get a little crisp, clean up and head to Duval street and Mallory Square to start getting the lay of the land. Wear comfy shoes, there’s more walking than it seems like for a small area. Time to start window shopping for souvenirs and restaurants.

Take advantage of the open air spaces when you can. That’s why your here, right? Take advantage of the freshest local seafood, whether you prefer ceviche, crab or lobster. Thirsty? No problem. This is Margaritaville.

Key West Cemetery

This is a nice diversion from beaches and shopping, and it’s free. Located in the center of Old Town, this cemetery was originally founded in 1847 after a hurricane washed away the old cemetery, scattering tombstones and remains throughout the area. Now built on the highest point in Key West, many of the tombstones are older than the cemetery itself. Get a walking guide book or take a guided tour. There is some fascinating history here and some hysterical grave markers. Cemeteries are not normally my idea of a fun vacation outing, but this was worth the visit.

Kino’s Sandal Factory

I found this place many years ago when my cruise ship spent a short afternoon in Key West. I bought a handmade pair of sandals for $5 that day, and those sandals were still with me 20 years later. They’re a bit pricier now, but as quality as I remember. They are indestructible and a must-have. They are hand-made right there in the store and they now have many more cute styles to choose from for men, women and children.

Dry Tortugas National Park

This is one of my best-kept-secret recommendations on any of my travel pages.

About 70 miles West of Key West lie the ruins of 19th century Fort Jefferson. While the park is over 100 square miles, most of that is water. There are 7 small islands, only accessibly by boat or seaplane, and the main island is open for visitors.

There are two options to get there. You can take a big, stinky ferry with a huge crowd of other tourists for a 2.5 hour ride, get less than 2 hours at the Fort and another 2.5 hour ride back. Or…..

You can go by seaplane!!!

If you haven’t ever been on a seaplane, this is a great virgin flight. A guy wearing flip flops takes you and only about 8 other people on a short, 35 minute flight to the park. On the way, you have headphones that narrate a very interesting history of the Fort while your seaplane glides along at only 500 ft altitude (which is low enough for you to see the turtles swimming in the Gulf below you). You glide to a stop at the dock, and your free to explore for about 2 hours. Guide optional.

Because you chose to splurge just a little and take this route, you have the place essentially to yourself. I’m definitely NOT a fort person and would normally skip this on a trip. But it was SO worth it. Got some great photos, learned a little history AND had time to snorkel around the dock and have a picnic lunch (they can rent you snorkels and sell you lunch, I packed a picnic ) before we took off to return to Key West. Best part? While your seaplane is kicking up the last drops of water, you’ll fly right over that stinky ferry with the 500 people that are just arriving….and you’ll be back on the beach with umbrella drink in hand and 2 hours into a good nap before they get back.

Where To Eat

Casa Marina Resort did have excellent food, but unless your staying there you probably wouldn’t go out of your way to eat there. For the basic eater, there are an unlimited number of places to get steak and lobster. For the more refined palate, here are the other places I can recommend:

Salute! On the Beach: This was at the property next door to Casa Marina. Had a great grilled fish sandwich here for lunch.

Blackfin Bistro: On Duval Street, excellent dinner, romantic courtyard.

El Siboney: No trip to Key West is complete without authentic Cuban food. Check out this mom-n-pop place on Catherine Street.

Lattitude’s at Sunset Key Cottages: This is a special dinner spot. Located on Sunset Key, the restaurant provides boat shuttle service for customers with reservations. Schedule so you can be there during sunset of course, as the island is named because it has totally unobstructed views of the western sky.

Turtle Kraals: This was a recommendation of friends that know Key West well. It is off the beaten path at a marina and they had absolutely fantastic ceviche. Top 3 ceviches ever, and several to choose from. The memory of that lunch is what calls me back to Key West.

Getting There/Where To Stay

Fly into Miami International. Research the neighborhoods of Miami – most will head toward South Beach where you can have beachfront accommodations in a variety of prices and qualities.

I chose to stay at the InterContinental in the Brickell neighborhood. It had a nice pool area and a modest spa but other than that it was about location.

The Brickell is the financial center of Miami overlooking Biscayne Bay. There were lots of shops and galleries in walking distance, also a good variety of restaurants.

It was also walking distance to Bayside Park which had more reasonable shopping and food, a sort of boardwalk feel. I wandered around here my first night but it felt a little too touristy for me so I headed into the Brickell in search of dinner.

Had two meals total – El Farolito Peruvian which had great drinks and decent but authentic food. Also ate at Cvi. Che 105 which was only good for the ceviche.

Little Havana

A short taxi ride from the Brickell area brings you to Little Havana, an old Cuban neighborhood. Come around lunchtime and stroll the streets – its just a few blocks in each direction. Have some Cuban food and people watch.

Be sure to hit the Domino Park to see a game in action.

Come back at night after you’ve freshened up and take in the nightlife. Here’s a few ideas:

• El Cristo for lunch-had a huge Cuban lunch and it was ridiculously cheap considering how much I ate plus a couple cold beers
• Start at the Ball & Chain for pre-dinner drinks, appetizers and entertainment. Try their Old Fashioned – they make it with a smoky house bourbon and a tobacco leaf. Check out the outdoor shell stage for live entertainment. They were hand rolling cigars in the front and had different musicians there.
• Visit Guantanemera Cigars. Not just a cigar shop. They had live Cuban salsa music, wine and appetizers. Go early to get a spot and stay as late as you can. It was a highlight of my trip – the musicians just kept coming and coming and the band got bigger and bigger. I was mesmerized by the dancing and the spirit of the people.