Bachelorette Party Ideas: 14. Key West

It has been more than a few years since we last hit Key West, but after reading guest blogger
Lorena Crowley's post on her friend's bachelorette party, we're ready to book our flights!

Here's what Lorena has to say about their bachelorette party trip to Key West:

Does size really matter? The tiny two-by-four mile island of Key West weighs in on the eternal debate. Don’t be fooled by the Florida island’s small radius. There is plenty of fun to be had, and it’s an ideal destination for girls looking to feel a world away without needing a passport.

Destination Determined
Our bachelorette — my friend and former roommate —Lezlie, took the lead on planning her own celebration. The criteria: somewhere that would suit her sophisticated yet casual style.

After kicking around a few ideas like the Hamptons, the inspiration for Key West actually came from her fiancé. He had frequented Key West in past with his friends, and he knew we would love it. Unfortunately, his contribution didn’t prevent the bride from accidentally scheduling the festivities during his birthday. (ooops!)

So, at the end of March, we traded in our Pennsylvania sweaters and warm socks for sundresses and flip flops in honor of the bride. (Oh, the sacrifice)

Travel Time to Key West
Six of us made our way to the Philadelphia airport for a four-day getaway to the southernmost point in the continental U.S., and a seventh girlie joined us once we were in Florida. We took advantage of the super early flight to indulge in some Irish coffees at the airport because, let’s face it, we could.

We arrived to the Ft. Lauderdale airport, hopped into a stylish rental minivan and started the next leg of our journey— a 150-mile drive to the furthest island of the Florida Keys. We stopped for lunch and, of course, more drinks on Key Largo, the first and largest of the keys. It was an enjoyable drive, and while it’s often referred to as “the most scenic highway in America,” it made for a long day. Luckily, pulling up to our hotel made the trip worth it.

The Island City House Hotel was so charming. Its quaint old-Florida style, beautiful landscaping and our private wrap-around porch made it a great place to call home base for a few days. The fresh breakfast in the morning was a plus too!

A Few Blocks South
When booking a hotel, its location will make a big difference in how you experience the island. Key West is divided into Old Town and New Town. There is no doubt that Old Town in the place to be, especially for a bachelorette party.

Our hotel was a five-minute stroll from the infamous Duval St. Quaint small-town paradise by day and vibrant hot-spot by night, Duval St. and the blocks surrounding it claim most of a visitor’s time outside of the hotel.

Our hotel’s convenient location made our group size really manageable. Everyone felt comfortable coming and going as they pleased, which helped avoid drama.



Key West By Night
Our first stop after checking in to the hotel was Sloppy Joe’s. The historic bar features live music, great drinks and fun atmosphere where almost anything goes! We quickly realized that our Key West bachelorette weekend idea wasn’t the most original, as we were joined by at least two other groups also celebrating. But there was plenty of onstage time with the band for all the parties, and they made our bride feel special, even though she wasn’t the only one.

The remainder of the night we engaged in a self-led bar crawl, making our way in and out of some of the best-known hangouts on Duval, like Ricks, Fogarty’s and Fat Tuesday’s. Perhaps my favorite thing about Key West is its lack of an open container policy. That means no painfully rushed, last-minute chugs before leaving each bar. You can take your drink “to go” without fearing the wrath of law enforcement officials. And ladies, take advantage of this convenience and pace yourself for the night ahead of you.

There are so many bars off of Duval, and closing time does not come early. The atmosphere adds to the experience, as everyone is out to have a good time. In fact, as the night gets later, the party grows crazier. (For those unfamiliar with Key West’s liberal reputation, don’t be surprised to find yourself walking among crowds of drag queens before the night is over.)



Key West By Day
When all was said and done, we only ended up with two full days to soak in the sun and warmth of Key West. We spent the first day recovering and relaxing at our hotel’s pool after the previous evening's bar hopping. We planned an excursion the following day through a tour company called Fury. We selected the Ultimate Adventure package, which combined an all day catamaran trip with jet skis, parasailing, snorkeling and food/drinks for one flat rate—a recommendation for first time visitors to the island for sure! They even gave us a free sunset cruise that we took advantage of on another evening. And for the recessionistas out there, there is definitely room for negotiating pricing on these excursions, especially with a group.

Ironically, while Key West is surrounded by the Gulf of Mexico and the Atlantic, it’s not really known for its beaches. I think that came as a shock to some of the girls, but between all the boat trips available and the pools at hotels, there is plenty of water to go around.

In hindsight, it would have been ideal to have an extra day. Key West has some great historical sites, like the mansion once home to Hemingway while he wrote most of his best-known novels. It would have been nice to see some of those attractions and do some shopping along Duval.

The Atmosphere
I’ve never been anywhere quite as laid back as Key West. People of all ages were there to have fun, and everyone is friendly and outgoing. Our enthusiasm and celebration wasn’t only tolerated … it was encouraged!

As you talk to people in Key West, you quickly find they com from a little bit of everywhere. A lot of Floridians said they were regular visitors, but we also came across a welcomed number of Phillies fans and others from the northeast. Ironically, most of the people working at the bars and restaurants admit they initially came for a visit and never ever left. (I can’t say I blame them!)

Fab Food in Key West
For a seafood lover like me, Key West was just fabulous when it came to food. There are so many fresh seafood options at every restaurant, and I didn’t eat a single thing during our trip that I didn’t love.

We picked one night to splurge on a nice sit-down meal and were really impressed by the food and cocktails at Jack’s Seafood Shack. We had another great late lunch at the Rum Barrel, a pirate-themed restaurant just off of Duval. Rum fans can sneak a taste of its extensive rum list with the sampler.

And don’t forget to save room for key lime pie!

Quick Tips
Key West is such a great destination. Whether it’s for a relaxing getaway, a romantic trip for couples or the craziness of a bachelorette party, there is something for everyone. Overall, here are some things to consider:
• Think casual. For the most part, you’ll fit right in with a cute sundress and sandals. If you’re overdressed, you may feel out-of-place.
• If you can handle the extra expense, flying directly into the Key West airport saves a lot of travel time. The drive is scenic, but it’s still exhausting.
• Keep in mind that Key West can be a big spring break destination for college students. When making travel plans, it may be in you group’s best interest to schedule around that time of year. We cut in close!
• Try and find a hotel or bed and breakfast a comfortable walking distance from Duval St.
• Wear sun block.