Key West Getaway

Living with a teacher has made me more aware of “breaks” and definitely more prone to travel. I feel like we have to take advantage of her paid time off. For some strange reason, the corporate world doesn’t have spring, summer, Thanksgiving or Christmas breaks. Is there a petition I can sign? It’s been 6 years since I graduated college and I still haven’t accepted that I don’t have that schedule anymore. (And I sort of hope I never do!) For the past several years, my dad’s side of the family has been traveling together over the holidays. We spent New Year’s Eve in Las Vegas a couple of times and had a blast. The last time we went (perhaps after losing a ton of money in the high limit room) we decided to do something more low-key. We didn’t want to leave the country but we were craving warm weather and relaxation. Where else can you get that in December other than the southernmost point in the continental US? Key West it is. Check out my list of restaurants, best places to stay, and things to do in Key West, Florida!

[where to STAY]

We wanted a little bit of privacy so we opted to rent a house on the island. Y’all, this house was incredible. I highly recommend Vacation Homes of Key West. They have named each of their rental properties and we stayed in “Tropical Tranquility.” (Who doesn’t want to stay there with a name like that?!) There were plenty of bedrooms and bathrooms for everyone and we had our own private pool and courtyard. They have tons of different rental properties based on your needs  – bungalows and cottages, townhouses and condos, suites, compounds, penthouses, and estates.

Check out some of the pictures of our house!

If you want to stay somewhere close to all the action, I recommend the Westin Key West Resort & Marina. It was only a block away from Duval Street making it within walking distance to shopping, restaurants, and all the nightlife Key West has to offer.

[what to DO]

Rent a gold cart | Now I’m not just saying this because I grew up in Peachtree City. You really do need to transfer into something smaller if you plan on being out and about. These streets are narrow and most of the island is parallel parking. It would be a total nightmare if you were in anything other than a Smart Car. Key West is so small that you can ride around the entire island all day without needing to recharge your cart. We paid a weekly rate for a 6-passenger golf cart from Tropical Rentals and didn’t give our SUV a second glance all week.

Flagship Lilly Pulitzer store | Fun fact: The company’s fabrics originated from Key West Hand Print Fabrics located in Key West. The colors are bright, the patterns are bold, and I LOVE every square inch of this store.

Visit the famous Southernmost Point buoy and the US 1 Mile Marker 0 sign. The continental US begins in Key West so you have to be a cheesy tourist and document these spots! I recommend going late in the afternoon and watching the sunset here.

The Duval Crawl | This is like the Vegas strip or the Times Square of Key West! All the action happens on Duval including live music, shopping, and people watching. You can find everything from trendy swimwear shops to funky art galleries. Be sure to check out the live music at the famous Sloppy Joe’s or Hog’s Breath Saloon. The crowds can get rowdy but it’s oh so entertaining!


Ernest Hemingway Home | Ernest Hemingway himself called Key West home from 1931 – 1939. It was in this house that he did some of his best work. Fun fact: Hemingway was given a 6-toed cat when he lived in the house and to this day you can still find 6 and 7-toed cats roaming the grounds that are descendants of Hemingway’s feline pets. Tours are offered daily.

[where to EAT]

Sarabeth’s | I first found this little gem at Chelsea Market in New York City. When I spotted Sarabeth’s on my Trip Advisor app I knew we’d find ourselves there a morning or two.

Key Lime Pie Factory | This little corner of heaven makes the most delicious homemade key lime pies. They also sell slices on a stick…dipped in chocolate. I assume that’s all you need to hear, right?

Blue Heaven | This place was so hip and so tasty that we ended up here two nights in a row. Blue Heaven featured al fresco dining with a quirky Caribbean vibe. The live entertainment and cuisine have made this place a MUST when in Key West. I ordered the Caribbean BBQ Shrimp on both visits because it was just. that. good. And if I haven’t sold you yet, if you do nothing else in Key West, order a slice of Key Lime Pie at Blue Heaven. Check out that meringue mountain!

Just writing this post has me daydreaming about my next visit to the Conch Republic! Hmm…Spring Break applies to me right?

Happy Friday!