Favorite Places: Key West, FL

If you really want to get away, get the tropical island experience but not leave the country, then Key West, FL is the place. It’s closer to Cuba than it is to Miami, bicycles are the most efficient mode of transportation and everyone is laid back…really laid back.

Fortunately for the locals and the semi-locals, many people who visit Key West only skim the town’s surface, leaving the majority of the island to be enjoyed without the drunken, loud-mouthed tourists. The tourists mosey off a cruise ship in packs or out of one of the big fancy hotels, do the Duval crawl the majority of their time in Key West and maybe hit up the Sunset Celebration. That’s nothing! Many visitors to Key West never wander around the little alleys, seek out the local spots or even sober up long enough to eat something other than the famed ‘cheeseburger in paradise.’ Thanks to my parents (who used to be full-time Key Westers and now are part-timers) I have discovered all the best tourist-less spots in this little island town and I’m about to share them with you!

Closer to Havana than Miami

Favorite Key West Places Map I created– click to explore!

Usually I start a day in Key West with a run. Its way too hot to run once the sun is high in the sky and I enjoy seeing how the rest of the island is waking up. There’s not that much terrain to cover being that the island is only about 4 miles long and 2 miles wide. So, if you are a runner you can cover the entire town on your daily morning run—from Old Town, Smathers Beach, the wharf and back.

Tropical plants of Key West

For breakfast I like to indulge in a big bowl of fresh fruit and a café con leche from 5 Brothers on Grinnell and Southard. But I also suggest Azur for a fancy brunch or La Creperie for some real South of France crepes.

By the time I eat breakfast the sun is usually strong and the humidity is getting thicker. Most Key Westers do not go to the beach that often and instead lay out in a pool, read in the shade or go boating. It’s usually too hot to sit on the beach all day but for those vacationing and antsy for the real tropical getaway experience I recommend Fort Zachary Taylor on the island’s southwest side. There is a fee but it is the most maintained beach on the island. Also, since it’s a state park you can camp there with an RV and there are benches under trees to escape the heat, grill up some food or kick back with a good book.

If I’ve had enough of the Key West sun, then I like to take advantage of the island’s slow pace and bicycle around all the tiny roads. The tropical flowers, huge Victorian houses and quirky island shacks (and the characters that live in them) will keep you entertained for an afternoon. Don’t worry about getting lost, there are no bad neighborhoods and remember it’s only an 8 sq. mile island. Do watch out for the cats, chickens and iguanas, which freely roam the island.

Bo’s Fish Wagon


For a late afternoon drink I suggest hitting up the Conch Republic’s 2 for 1 happy hour over on the wharf. Nothing like watching the sun lower over all the boats with a warm evening breeze and some reggae music. There is also the famous Sunset Celebration but that has become such a tourist trap. The sunset view is gorgeous but the crowds can be too much.

Sunset view from Mallory Sq.

So far this ‘ideal’ day has been very laid back which should leave your well rested for some nightlife. First you need to prep the liver with a big dinner. There are many restaurants to choose from on the island but some can be outrageously priced and overrated. My favorite ones are:

La Trattorria on Duval- Just as good as my North End favorites, but on a tropical island.

Conch Republic on the Wharf- Definitely try the Conch Fritters.

Old Town Mexican Café on Duval- Cali-Mexican served alfresco so you can people-watch the craziness of Duval St.

The Café– A ‘mostly’ vegetarian restaurant that even my meat-eating friends and family enjoy.

Mangia-Mangia on Southard- Not as good as La Trat but still delicious. They make their pasta.
After a nice meal it’s time to hit the parties. Duval is worth seeing for one night if partying in Key West is on your vacation to-do list. However, it can be much. As much as Boston likes to believe they drink a lot, Southerners are on a whole other level.

For a more low-key, well I wouldn’t really call any of the drinking saloons in Key West low-key, establishment you may want to try the wharf area. There is also a hidden lounge behind La Trattorria called Virgilio’s that has excellent  (and strong) martinis, live music and a tree in the middle of the lounge. Also, Louie’s Backyardis essential for a romantic evening cocktail on the back deck overlooking the water (the house Jimmy Buffet used to live in and wrote some his most famous songs while living there is right next door).

There are also fun boat tours, kayaking rentals, Bahia Honda State Park (which is gorgeous) up road in the Keys, and an indie movie theatre Tropic Cinema with a concession stand stocked with wine, beer, sushi, fine cheeses and gourmet candy. For a small and somewhat isolated island, there is plenty to see and do—even if you plan to avoid Duval at all costs.

Whenever I go down to Key West I never want to leave…which is how a lot of people become locals!


One thought on “Favorite Places: Key West, FL

  1. Pingback: Slowing down in the Keys « BeachyBrunette

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