Our Key West Trip + Engagement Story

Hi everyone! I'm back from a bit of radio silence...we just got back from Key West a week ago and I'm finally getting back to reality – although our reality is a little different now that we are ENGAGED (yay!!) and have been fully thrown into the excitement that it brings. 

I posted some photos on Instagram during our trip but there are plenty more to share. Key West exceeded our expectations and I wanted to share our experience and favorite spots in case you ever find yourself down at the very end of the U.S.!

Our beach for the week, at the Pier House Resort. We loved our stay here and couldn't beat the service, amenities, and the private beach. Key West is small and there are only a handful of public beaches on the island, so having a private place to enjoy the sun (and have cocktail service) was a must. And seriously...look at that ocean. We were actually right in this spot later in the trip when Jim proposed.

We had our first drink here after we landed – I forget the name of this bar but it was right next to our hotel. How fun is the bright painted furniture?!

The food in Key West was incredible – so much fresh seafood and tons of places to eat. Our first night there, we walked Duval Street from end to end (think Bourbon Street – lots of bars, live music, and no open container policy) and stopped for some street food from D.J.'s Clam Shack. The lobster roll was so good, and I know it wasn't just my beverage doing the talking ;)

We couldn't leave without visiting the Hemingway House. I am kind of obsessed with his style and did a little portrait of him, so it was really amazing to get to walk through his home and see his collectibles from years of traveling and living abroad. Above is the front entrance.

Here's the main parlor room and the master bedroom. 

The size of the property and the lush, beautiful grounds were just as impressive as his stately home. We walked through gardens of palms, sugar cane, banana trees, ferns...which offer shade to all of the six-toed cats that live on the property. 

And then there was THIS POOL. It's bliss. I wanted to jump in so bad.

We filled out the week with a snorkeling trip, plenty of bike riding, and tons of food. Key Lime pie basically has its own spot on the food pyramid down here (not complaining), so we had a very delicious week. We headed to Latitudes for dinner on our last night and we both agreed it was the best meal we've ever had. Not only was the food amazing, the atmosphere was so elegant and romantic...the tables are set up in the sand, right along the ocean, with candles flickering everywhere...we enjoyed every minute of that dinner and were really sad to be winding down the trip.

We hopped on the 11:00 ferry back to Key West and decided to hang out at the beach and drink some late-night beers. We did this every night in Maine last summer (there wasn't much nightlife!) so it's become a bit of a tradition to sit and talk on the beach late into the night. Jim filled up his backpack with some cans of Miller Lite (hey, we keep it classy guys) and unbeknownst to me, my ring. 

I set up a towel on the beach, and as we're getting settled, it slowly starts to drizzle. A little drip here, a little drop there...I'm thinking, shit, it's our last day here, I'm totally not ready to call it a night. Then it rains a little harder, my hair's really starting to get wet (of course I'm worried about this) but Jim insists we just wait it out, as this does happen a lot in Key West. A little rain cloud passes quickly here and there all the time. So we just kind of sit there, waiting for it to stop, which it soon does. It's dark out, sailboats are cruising by on the ocean, no one around, it's almost 2am already. Our conversation turns to our relationship, I'm not thinking much of it, and smooth as butter, this guy is casually popping the question right before my eyes. Immediately following were lots of tears, lots of excitement and freaking out, another round of beers, and the nice realization that no one at home was awake, and that we could enjoy this amongst ourselves until the next day.

Our flight home didn't leave Key West until 2:30, so we luckily had plenty of time to call our friends and family in the morning, while packing and getting ready to leave. We had time to hit up La Creperie for brunch and Bellinis, and took one last bike ride around the island to say goodbye.

We had a truly amazing trip, even aside from the proposal. It was just icing on a very delicious, very awesome cake, and I will never forget the many little moments we had together. I knew when I met Jim five years ago that he was the real deal, and we've been committed as partners ever since. We chose each other whole-heartedly. OKAY, not going to cry...there's no crying in blogging!

I'm thankful to be home and to still have a bit of a vacation high (and a tan). I'll be back to regular posting this week. Thanks for bearing with me, and please, do not ask me when the wedding is! ;)