It’s no secret that I favor more exotic locations over the typical beach vacation. 
When my husband suggested that we spend our second wedding anniversary in Key West, Florida, I wasn’t exactly thrilled (yawn…).  Although I would have been far more excited to travel somewhere “far away” and “exciting,” I had promised him that our annual anniversary trip would be a “Ryan trip” (Read: relaxing, preferably with a beach), and not a “Karisa trip” (Read: whirlwind adventure to a new country).  Try as I may to convince him that we should take advantage of a ridiculous flight deal that I found to Sweden, he wouldn’t budge.  I pictured myself spending our anniversary at Jimmy Buffet’s Margaritaville sipping fruity cocktails and cringed at the thought of the mundane.


Trying to muster up some excitement, I paged through one of my favorite travel inspiration books, “National Geographic 500 Trips of a Lifetime,” and found myself reading a two page spread highlighting the drive from Miami to Key West.  The article gave me a glimmer of hope – if National Geographic tells me it’s a trip not to miss, perhaps there’s some allure to the Keys that I’m not aware of.


Now, I’m female.  I’m Polish.  And, I’m a litigator.  So, by definition, I was pretty much born to be stubborn.  However, one of the fantastic things about getting older and growing up means that although I’m hard-headed, I can also admit when I am wrong.  And, my assumptions about Key West were WRONG!


I was surprised to find Key West such a quirky, alluring destination, which offers far more to do than simply sitting in the sun drinking fruity cocktails as I had assumed.  Key West has it all – history, culture, water sports, fun bars, and amazing restaurants.


Here are some of my recommendations for your trip to the Keys:

To Do & See: 

Hemingway House:  Tour Ernest Hemingway’s home that he lived in during his Key West days, which has been deemed a U.S. Historic National Landmark.  Stroll through the property and museum and search for the six toed cats wandering throughout.


Southernmost Point:  Head to the concrete buoy marked as the Continental US’s most Southernmost point, one of the most photographed attractions in Key West.  Although the buoy reads “90 miles to Cuba” this is, apparently, a rounded number as Cuba is actually something like 94 miles away (or 81 nautical miles), but who’s counting?


Customs House: The historic building houses the Key West Museum of Art and History and has a small, but impressive sculpture garden behind it.

Mallory Square Sunset Celebration: Tourists flock to Mallory Square to catch one of the sunsets that Key West has become legendary for.  While waiting to be impressed with the spectrum of beautiful colors that light up the sky, there are plenty of vendors and street performers to entertain you.  (And don’t worry, you’ll find outdoor bars serving up any libation you’d like, including Key Lime flavored cocktails).


Get out on the water!  Key West offers so many fun options to get off land and get wet.  You can chose from paddle boarding, snorkeling, jet skiing, diving, and more.  We chose to go out for a full day on a schooner sailboat with Danger Charters, and I couldn’t have been more pleased with the experience!


We spent the day sailing, snorkeling, and kayaking.  Lunch was fantastic, as were our beer and wine options.  Danger caters to their customers, and we couldn’t have asked for a better skipper and crew.  Besides that, we only had 10 others on the large boat, which didn’t seem to be the norm judging by competitor’s jam-packed boats we saw sailing around us.


To Eat:

Blue Heaven:  You can’t ask for restaurant recommendations in Key West without this one coming up.  Particularly known for their breakfast… and roosters walking about the grounds.

Cafe Sole:  This one is slightly off the beaten path and not right off Duval street, but its worth the walk for the chef’s innovative cuisine, which blend European and Island dishes.

Latitudes:  This restaurant WOW-ed me.  I’m no stranger to fine dining, but I’ve never had a dinner experience quite like this one.  You’re taken by boat to a small, private island, Sunset Key, to experience a spectacularly colorful sunset while dining on steak, lobster or fresh fish. (Entrees in the $30 to $75 range).


To Drink:

Hogsbreath Saloon: Fantastic music and cool libations in the heart of Old Town.

Captain Tony’s: We found ourselves continually ending up at this low key watering hole.  The skilled acoustic guitarists make up for the bras hanging from the rafters.  This bar used to house the Original Sloppy Joe’s where Hemmingway was a regular.

Jimmy Buffet’s Margaritaville: I know it sounded like I slammed this bar/restaurant in my post’s opening, but you can’t come to Key West without at least stopping in the original Margarittaville for a tequila libation.

Sloppy Joe’s: Famed for being Hemingway’s favorite Key West bar, the original location is actually the building that Captan Tony’s is housed in.  Outgrowing their former space, the new Sloppy’s is large, but came across sterile and lacking character to me.  This said, the bands playing were always top notch.


Marina Area: Although maybe not as popular with tourists, be sure to check out the equally character-filled bars off Duval Street in the marina area where you’ll find great happy hour specials.


I wouldn’t recommend that you stay anywhere in Key West but in Old Town.  Although prices are much higher in Old Town versus out by the airport, it’s worth it.  Part of the appeal of Key West is being able to walk everywhere and stroll past the historic homes.  Choose a B&B to call your Key West home and work your way into island time.

We chose to stay at Knowles House B&B, just a short walk away from Duvall Street.  The neighborhood was quiet (we weren’t even woken up by roosters, which I hear is nearly unheard of), but close to the bustle of Key West’s nightlife.  Our room was basic, but charming.  However, what the B&B lacked in 5 star luxury, they made up for with attention to details – a delicious morning breakfast, free wine and beer, a hot tub and pool that is always open, and a (clothing optional) sun-deck (!).  The employees were friendly and the service was fantastic!  We’ll be back to Key West in the near future, and I have a feeling we’ll be booking at Knowles House again.


Getting There:

So, are you ready to go?  If so, I would recommend driving from Miami to Key West, rather than flying into Key West directly.  The drive from Miami down Highway 1 is a mere 150 miles, but it will easily take you three and a half to four hours due to the fact that most of the highway is only one lane in each direction.  I’ve heard horror stories from people who were stuck on a bridge for 8+ hours unable to drive in any direction due to an accident, and it’s not uncommon for the drive to take much longer than 4 hours in the event of heavy traffic.

I’m not exactly selling you on the drive, am I?  So, why bother driving?

Because it’s gorgeous!

The further you get from Miami, the more beautiful the scenery and more colorful the water becomes.  Plus, you’ll get to drive across famed “7 Mile Bridge” which connects Knights Key to Little Duck Key.  When you find yourself somewhere near the middle of the seven miles, it’s quite the experience to look around you and realize that can’t see land in any direction…only bright teal water for miles.  Another benefit of driving is that you can “Key hop” your way down to Key West, stopping at some of the bars, seafood restaurants and attractions that the lesser known Keys have to offer.  I’d highly recommend that you set aside 90 minutes and stop at the Sea Turtle Hospital in Marathon – it’s worth the short detour!


I’ll leave you with one last piece of advice – splurge a bit and rent a convertible.  You just have to.  Trust me when I say that while the wind blows through your hair and your head is on a swivel taking in the gorgeous views around you, the 4+ hour drive will feel like merely a couple hours!

Related posts: 3 Reasons to Visit Miami (When You’re Over the Party Scene)Fort Lauderdale, You’ve Won Me Over and Saving Sea Turtles in Marathon, Florida.

Have you been to Key West?  What are your favorite spots?

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