10 Things I Loved About Key West


For my dad’s 60th birthday, we told him to pick anyplace to celebrate, and we’d all show up with our party pants on!  Ever a passion for beach music, deep sea fishing, and a toes-in-the-sand-drink-in-my-hand mentality, it was perfectly fitting that his destination of choice be Key West, Florida.  We spent a week there this winter (where I was thrilled to miss another NYC snow storm!), and really had the best time.  Here’s 10 things I loved about the island:

1. Cuban Coffee

572572031_571a55214c_bWe started each day with the stuff that fuels the locals: Cuban coffee.  It’s all over the island, but my very favorite place to get it was 5 Brothers.  Get yourself a small coffee and egg and cheese sammy, and you’ll be set for a full afternoon of lounging on the beach…or anything else that may come your way.

2. The Conch Train

unnamed-13I’ve shared with you guys my love of tours before, and how I always make a point of jumping on a tour when visiting a new place.  Key West’s tour de force is the Conch Train, a guided trolly tour that takes you all around the island, sharing bits of history, trivia, and insider’s knowledge along the way (how much do you love garbage cans used only for coconuts?!)  Bonus: with the temperature situated around 80 degrees, the open-air trolly provided a breezy and comfortable alternative to walking!

3. The Hemingway House

unnamed-14 unnamed-15The famed writer Ernest Hemingway spent many years on the island, nestled in his writing studio (pictured above) every morning at 6am, hitting 700 words or lunch, whichever came first.  A visit to the house comes with a guided tour, featuring lots of anecdotes on the writer’s life, and many wives, too!  You also get plenty of opportunities to pet descendants of his original 6 toe cats.  And yes, the offspring got the 6 toe gene, too!

4. Sidewalk Poets

unnamed-16Outside the Hemingway House sits local poets, who you can hire (at whatever donation you choose!) to compose a poem for you or a loved one on any topic you choose.  Such a cool concept (and the poet was REALLY good–I had her write a love poem to the hubs back in NYC, which is now framed in our living room!), and makes for a much more interesting souvenir than say, a Key West shot glass.

5. Key Lime Pie

unnamed-19 unnamed-18Like the coffee, this is something I indulged in EVERY DAY.  When in Key West, right?!  I tried all kinds of key lime things–chocolate dipped ice cream pies, key lime cocktails, key lime crepes, key lime cheesecake–but my favorite was the original key lime pie from the Six-Toed Cat cafe.  Hint: I asked local shop owners where the best pie on the island was, and this is where we were directed.  I couldn’t have agreed more!

6. The Southernmost Point

unnamed-17When in Paris, Eiffel Tower.  When in NYC, Empire State Building.  And when in Key West–the Southernmost Point Buoy!  This is the spot that marks as far south as you can go in the continental states (well, that tourists are actually allowed to visit–the true southernmost point is on a restricted naval base!)  There’s even a live streaming webcam that shows the incredible line of people waiting to take their photo by the buoy!

7. Smathers Beach

unnamed-20Unlike the Hamptons where a day pass on the beach can easily set you back $50, this gorgeous beach in Key West is absolutely free to the public.  Plenty of sun, and palm trees, as well, to enjoy a full day of swimming, reading, and napping.

8. Live Music, Everywhere

sloppyjoesphotoYou couldn’t walk down a main street in Key West without hearing bands and musicians playing–Duval Street being the most famous (complete with its own webcam, too!)  I really dug Sloppy Joes, but I promise, just follow the music and there’s no way to go wrong.

9. The Cutest Houses You Ever Did See

unnamed-10 unnamed-12Entire afternoons can be spent strolling up and down the residential streets in Key West, taking in the adorable gingerbread-like houses, complete with brightly painted shutters and orchids growing everywhere.  Rent a bike for an afternoon and take it all in!

10. Little White House

unnamed-22President Truman first started using this “little white house” as his winter retreat back in 1946, and today it’s been restored to its original glory (read: exactly how it looked when Truman was using it, so cool!), and opened as a museum to tourists and locals.

When booking flights, be sure to check out FlightCentre, who offers affordable flights for long haul travelers.  There is a tiny airport in Key West you can fly into with a connection, or if you have a zest for road trips, flying into Miami and driving the 4 hours to the island is stunningly beautiful and highly recommended!  Just think of all the beach music you can belt out on that drive!


Have you ever been to Key West?  What were your favorite things?

p.s. a very special thank you to the wonderful folks at Historic Tours of America!


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