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Travel Guide to Key West, FL

By Courtesy of Court

The weather in Boston has been all over the place lately. I blogged a couple months ago about how excited I was that spring was almost here, and then just days later we got hit with freezing temps once again (spoke too soon, I guess!). Just this past weekend it was 82 one day and 52 the next. Mother Nature – what is up!?

Having lived in Boston for the past seven years, this is actually something that I’ve become accustomed to. Though let me be clear, it doesn’t get any easier. Thing is, you just have to make the best of it. Which I did! I packed up, and headed down South, where it was sunny and warm. Key West was the destination. What started off as a quick cold-weather escape, turned into an unforgettable getaway that spawned a yearly tradition.

I’ve been to Key West twice before. Once when I was 20. Me and a couple friends went down for Spring Break. Since I was underage, the experience was a bit different, but make no mistake, I still managed get into the bars!  The second time was during a cruise. We stopped there for a day, so not much time to do much of anything. Both times, I didn’t fly straight into Key West, but rather in another form (drove from Miami the first, and cruised in the second). But this time, we flew directly into Key West, and the flight was unbelievable. Absolutely breathtaking. It took me by total surprise! Not sure why, given that it’s an island, guess I just wasn’t expecting to see the incredible colors of the sea so up close and personal!

My friends and I stayed at Parrot Key Resort, a quaint waterfront property equipped with four (!!) pools, a bar/restaurant, a strip of beach and hammocks for days. Upon arrival, our room wasn’t yet ready, but we were greeted with an ice cold glass of Sangria (winning!). We spent the next hour hanging by the pool, sipping our Sangria. We may or may not have (we definitely did…), ordered another drink after that.

No makeup, pool hair – happy as a clam!

We stayed in the cutest one bedroom Villa that overlooked the garden leading into the adult-only pool. We had a private porch, and little palm to mark our entrance.

The resort was truly beautiful, and the staff was so incredibly friendly. We loved seeing the same people every day – it was such a pleasure! (Shout out to Georgi and our shuttle driver who we called “Brian” because we didn’t get a chance to ask, and we thought he looked like a Brian.)

The on-site restaurant, Cafe Blue, was clutch. They served breakfast, lunch and dinner, and had a kick-ass happy hour. Two for one drinks! For those that don’t know, Boston doesn’t have happy hour. It’s illegal to discount alcoholic beverages in Massachusetts for things like happy hour. So, sadly, we don’t get to enjoy what I consider, one of the “little things” in life.

These fish tacos were everything. In fact, they were so good that we ate them three times during our four night stay (ha!). You’d think we would have gotten sick of them, but no. Never. I mean, just look at them!! And the tots were the cherry on top of the proverbial sundae.

One of the many beautiful doors that lined the walkways and pools inside the tropical oasis.

While we could have easily stayed within the resort the entire vacation, and been happy that we did, we did venture out a few times.

Duval Street, Key West’s “downtown”, is filled with shops, bars, restaurants and boutiques. Given that you can walk around outside with an “open container”, it’s only fitting that you bar hop. Which is exactly what we did.

A couple faves: Irish Kevins, The Lazy Gecko (shout out to Karri Daley who has ridiculous pipes, and absolutely kills it on the guitar!) and Rick’s Bar (go upstairs for one of the best roof decks in KW!).

After our first night out, we stayed poolside all day. But the following day, we were up bright and early, and ready to hit the beach.

Smathers Beach is one of the only beaches in Key West. The island is surrounded by water, but has very little sand. Thankfully, Smathers is beautiful, so there isn’t really a need for another.

Of course, while in paradise…an impromptu photo shoot is a must.

The towel that I’m so professionally modeling (haha!) is from Sand Cloud. If you don’t know about these guys yet, you should! They’re on a mission to save marine life, and they’re doing it one stunningly beautiful towel at a time. 10% of all proceeds from each purchase go towards saving the fishies. If you want one, use my code COURTNEYOSG25 for 25% off!

Though the views from the beach were incredible, we were interested in seeing a slightly different view…

The crew at Sunset Water Sports hooked us up, and took us out on a private boat to go Parasailing. The views were AMAZING. Highly recommend.

All in all, the trip was nothing short of incredible. Once again, a reminder that it’s okay to take time off to relax, and do something for yourself. Every time I have the opportunity to unplug, I do. And I always come back to work feeling refreshed and bright-eyed. That’s a tell-tale sign if I’ve ever seen one!

On that note…

Key West…we’ll see you next year!


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