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.
Lodging:
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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November 9, 2014
I have written a few posts about the Florida Keys. Some of my favorites include:
– Card Sound Road.
– Mrs. Mac’s in Key Largo
– Sombrero Beach
– turtle hospital (glad you went there!)
– Key West Cemetery
– El Siboney (authentic Cuban food popular with locals)
– El Meson de Pepe (the touristy Cuban place at Mallory Square)
November 9, 2014
Thank you – I’ll have to check out your recommendations on my next trip there!
November 10, 2014
Years ago I had one day in Keg West on a cruise and it was by far my favorite stop of any cruise I’ve ever taken. We have always talked about going back for a weekend getaway and after reading your post, I think we will definitely drive down from Miami. Thanks for the recommendation!
November 10, 2014
Have a GREAT trip! And please, let me know if you have any recommendations after you’re back! 🙂
November 10, 2014
Well, Key West sounds a whole lot more interested than I expected! I’ll have to save this for someday travels. Thanks for sharing!
November 10, 2014
I was really surprised and can’t wait to get back soon!
November 11, 2014
I’ve been to Key West once but am currently planning a trip for April because a friend is getting married there. I was so excited she told me they chose Key West! Your clothing optional B and B pool area made me laugh!
November 11, 2014
Enjoy! You’ll have a fantastic time! 🙂
November 14, 2014
I really enjoyed this post
December 16, 2014
I definitely tend to prefer more exotic trips, but that said, it doesn’t take too much persuasion to get me to a low-key beach locale either. Key West is high on my list and based on this, I may bump it up even a few notches more. Thanks for all the recommendations!
December 17, 2014
I was surprised how much I loved KW! I will warn you, there aren’t a ton of beaches, but you can find them if that’s on your agenda. Otherwise, there are plenty of other activities to get out on the water!
January 25, 2015
Just goes to show you, there are still a lot of great places right here in the good old US of A! Great post! The keys are amazing!
January 25, 2015
Absolutely! The Keys were a pleasant surprise to me!
March 19, 2015
looks great and love the pics, thanks
July 20, 2015
My husband and I visited Key West in early March with a few of his cousins from WI. You know where I’m going with this, they wanted to bar hop. They did and we got to check out the finer points on the island. We loved our hotel, The Cabana Inn. It was a block off of Duvall, not too loud even during spring break. The Green Parrot is a must for live music, an entertaining mixed aged crowd, even the locals were hanging out here. This was also a block off of Duvall. Next time we’ll drive down, we took a boat from Fort Meyers and left the convertible at his cousins : (
July 21, 2015
That sounds like a great trip, Amy! And, I bet the boat was nice too. I am dying to get back to Key West!
August 3, 2015
Enjoyed The article. Good timing for me, Going in the end of August to Miami and will spend a day in key west.
August 3, 2015
You’ll love Key West! I would try to spend a few days there if you can!
October 7, 2015
Great post! We are heading to Key West next month and will use this to help guide us on things to do. We’ve only been once before for a short time on a cruise so we are excited to get back there. Can’t wait get out on the water. Any specific places for snorkeling?
October 7, 2015
SO jealous, Angela! I actually didn’t pick the snorkeling spots – the charter captains did. (But he chose great ones)!
October 10, 2015
We absolutely love The Keys!!!! We live in Florida and did the drive down there, which was GORGEOUS! When we got there we set up a tent Oceanside at one of the camp sites, highly recommend trying that out for a night or two. Glad you enjoyed it there too!!!
October 11, 2015
Camping sounds like a great time, Megan!