Key West may be known as the southernmost city in the lower 48, but it feels a million miles from the typical USA. This laid-back tropical island destination is at the top of the list for domestic girls’ getaways and bachelorette parties. Planning a Key West bachelorette party is easy because the island is basically made for fun in the sun. There’s incredible food, great weather and so many things to do in a concentrated area.
Thinking about a Key West bachelorette? Grab your gals, order your beach-themed party goodies on Etsy and check out our suggestions for things to do, restaurants and resorts in the Florida Keys.
It won’t come as a surprise but I am a huge fan of the destination bachelorette party. I had two myself; a surprise, shark-themed party in Bonaire with my girls Alex and Kristin and a star-studded shenanigan-fest in Las Vegas with Rae and Britney Spears. When Rae and Ben got engaged in Paris back in December and I became Matron-of-Honor and member of the official Party Planning Committee, I was pumped to outdo all my fabulous bachelorette festivities with the destination party to end all parties.
But it’s 2020, so nothing has gone according to plan. Rae initially had her heart set on a bachelorette party in the Greek Isles, so if I had to find a silver lining to the pandemic, it’s that I didn’t have to spend 6 months’ mortgage on that trip. Say what you will about Florida’s incoherent COVID response (and I have A LOT TO SAY), I’m grateful we live so close to the Florida Keys at a time like this. It was a destination we felt would not only be fun, but as safe as it could be – something we have to consider now when choosing where to travel.
I’m not lying when I tell you the last time I was in the car with Rachel and her BFFs Jessi and Cheyanne, they were teenagers acting up in the backseat. I distinctly remember shouting, “Don’t make me turn this car around!” Happy to report they were better behaved this time!
There were only four of us on this Key West bachelorette adventure, and that was just the right number for me. I don’t know how people manage to coordinate with 15 people on these massive girls’ weekends, especially during COVID. Four was a great, manageable, fun number.
Where to Stay for a Bachelorette Party in Key West
The Perry Hotel, Stock Island
One of my favorite hotels in the Florida Keys! The Perry Hotel has everything you could possibly want for a girls getaway – yachts, pools, key lime pie martinis – and it’s just a bridge away from Old Town Key West. Why’s that important? Because if you want to mix crazy nights out with chill, quiet days by the pool, being a bit outside the hustle and bustle is not a bad idea.
Plus, The Perry has a free, beautifully air-conditioned shuttle that runs throughout the day. We took it every time we went into town and never had to pay for parking or worry about who was designated driver. Easy peasy.
The complimentary Champagne at check-in was exactly what we needed after our drive from Orlando. As we sipped, the concierge told us about all the property’s amenities, from the sunset lounge on top of the hotel to the state-of-the-art gym we had no intention of using during bachelorette weekend. It was well appointed, to be fair, but we had other fitness activities in mind. Like boogying all night, obviously.
Key West is a big Navy town, so it makes sense that The Perry Hotel derives its inspiration from Commodore Perry, the father of the US Navy. Key West’s seafaring roots are on display in the 288-slip marina and the decor, a mix of nautical touches and ocean artifacts.
Inside our spacious double queen overlooking the main pool and the marina, we had a mini-fridge perfect for snacks and White Claw, a closet with cozy bathrobes, a large bathroom and spa products within. You never know if your hotel room is going to be a squeeze, but we never felt boxed in – even with four of us and our bags and bags of wigs, dresses, balloons and candy.
The Perry had all new protocols in place due to COVID. Only one family allowed on the elevator at a time; hand sanitizer all around; socially distanced tables in the restaurant; housekeeping only by request vs. every day.
Do I love wearing a mask in the Florida heat? Friends, I do not. Sweaty face is not awesome. Is it mildly inconvenient to wait for the next elevator instead of cramming on with a bunch of strangers? Kinda. But it’s a small price to pay to be able to start traveling again, so I’m willing to do what it takes to protect me and others.
Three nights was not enough to experience all that The Perry has to offer and all that Key West has going on. We didn’t get to rent bikes or Arcimoto electric vehicles and we didn’t have time to track down the the Perry’s onsite distillery. AND! We left Sheba at home, but The Perry is pet friendly so next time she will be the Pup of Honor.
A whole week would be much more reasonable if you want to fit a ton in. But for a long girls’ weekend, it had all we needed and more.
Click here for more details on The Perry Hotel.
Other Resorts in Key West We Love:
- Family friendly: The Laureate
- Great villas: Parrot Key Resort
- Party atmosphere: Margaritaville Key West
- Beautiful ocean views: Southernmost Beach Resort
- RELATED: 21 of My Favorite Hotels in All of Florida
Where to Eat in Key West
Matt’s Stock Island
One of the best reasons to stay at The Perry is Matt’s Stock Island, the main restaurant onsite. The food is ridiculously good. You think I’m joking? We ate there for almost all of our meals — and we KNOW about how great Key West’s restaurants are. It was just so convenient to plan breakfast and dinner at home base before venturing out. And a reservation was just a quick phone call to the concierge away.
Our favorite menu items:
- Cornbread mash (I could drive back to the Keys right now for more of this)
- Avocado salad
- Ribeye with house made steak sauce
- Shrimp & Grits
- Key Lime Pie Martini
- Banana Bread Pancakes
Other Favorite Key West Restaurants
Rae’s favorite skirt steak! We try to get out to Latitudes on Sunset Key every visit to Key West. It’s an ideal location for sunset dinner if you can get a reservation timed just right, but they also have a lovely brunch. Can’t go wrong, just don’t forget to make a reservation as it’s a very popular spot.
A&B Lobster House
Fancy a splashy night out? I love the A&B Lobster House for fresh seafood and a fancier dining experience. It’s still Key West casual, but the ambiance is a bit more upscale.
Cuban Coffee Queen
We just discovered the Cuban Coffee Queen this trip and I am still fantasizing about the fresh, warm, flaky bread! I’ve never had such an incredible breakfast sandwich. The coffee is strong and there are a ton of options, but get there early – especially if you’re planning to grab breakfast before hopping on a boat excursion nearby – because the line gets long and you don’t want to be left on the dock.
Less of a cuisine destination and more of a pool party with bar food, you can’t go wrong with Dante’s for an afternoon of pool time with mostly socially distant strangers.
Fun Things to Do at a Key West Bachelorette Party
When in the Keys, I’m a big fan of doing active, outdoor activities during the day, relaxing by the pool or on a boat in the afternoons and then going out for dinner, required key lime pie and shenanigans on Duval Street afterward. Here are some of our most favorite things to do in Key West.
We had such an easy breezy day out with HonestEco, an environmentally savvy your company in Key West. We chose the All of the Above tour, with kayaking, snorkeling and dolphin watching – some of my favorite things to do in Key West!
The snorkel spot was shallow with clear, greenish water, decent visibility and fish, lobster and even a stingray. I didn’t bring my underwater camera setups and I didn’t need to — the crew snapped some great shots of stingrays and lobsters as we were snorkeling and sent them to us before we even finished the tour. WOW!
After kayaking around a mangrove island, birdwatching and snorkeling, we were excited to try organic lunch provided from a local spot, Date & Thyme. I super appreciated HonestEco’s commitment to local food and environmental sustainability – no plastic water bottles! Everyone gets a reusable stainless water bottle to refill throughout the trip so there’s a real reduction in waste compared to some other tours. Even the boat – the Squid – is electric, the first of its kind in the US.
Kayaking and snorkeling are always fun, but my favorite part was getting to see the dolphins. There are about 300 dolphins living year round in the waters surrounding Key West. They’re full time residents, not tourists, so you have a great chance of finding them when you go out with HonestEco.
Immediately after snorkeling and lunch, Capt. Brady took us right to them – well, not too close. HonestEco doesn’t get too close to the dolphins, taking great care not to disturb their day. But, if they are feeling curious, they might get close to the boat. Lucky for us, that’s what happened! They were quite frisky and we managed to see quite a few, including a baby.
We swapped quotes from The Office with Capt. Brady – fortunately it was not an abandon ship situation like the Booze Cruise episode!
For more information on booking an HonestEco tour, visit their website.
For the bachelorette bunch who wants to try new things! Fury’s 65′ catamaran Ultimate Adventure is an all-inclusive experience with a ton of activities – jet skis, parasailing, snorkeling and access to an inflatable water park floating in the shallow turquoise sea.
It’s so much fun, we try to do it every time we’re in Key West. Breakfast and lunch included!
Click here for details on the Fury Ultimate Adventure.
Sunset is Key West’s time to shine! If you have the time, check out Mallory Square for one sundown and hop onboard a catamaran with Sebago for another. Sebago’s sunset sail features all-you-can-drink beer, wine and sangria with light appetizers.
We didn’t even need a full dinner afterward and it’s a great pre-Duval Street activity to get you pumped for a night the town.
Learn more about the Sebago Sunset Sail here.
Key West Food Tour
Key West is an amazing spot for a food tour because there are so many unique influences, from Cuban to South American to Caribbean. And all the fresh seafood is just a bonus. Key West has incredible walking tours through historic Old Town where you might taste Key West staples like Cuban food, conch fritters, fish tacos, key lime pie and rum. Doesn’t that sound delicious? Learn more here.
Whether you’re an expert or a beginner, you’ll love a guided SUP tour of the mangroves with Lazy Dog. Learn all about non-stinging jellyfish, the sponge industry, manatee and turtle grass conservation and the strength of the mangroves. It’s a great way to see the eco-system and earn an extra fish taco from all the burned calories! Click here for more details on booking a Lazy Dog tour!
Ernest Hemingway Home and Museum
You don’t have to walk too far in Key West to find a spot where Hemingway lived, wrote or drank. He lived on the island for 10 years and his home still houses famous 6-toed cats. The trolley tour passes right by his house and is a great way to see a lot of Key West’s top tourist attractions.
Also check out:
- Key West Helicopter Adventure
- Key West Craft Cocktail Tour
- Key West Ghost Tour
- Key West Conch Train Tour
More Bachelorette Fun Around the Florida Keys
If you’ve ever been to the Florida Keys, you know Key West is just a small part of the island chain. Key West vacations are heaven on earth, and just about eight hours from my front door. I do like to stop about halfway down the line to explore the rest of the archipelago. Whether you’re planning an epic tropical bachelorette party, a chill island-style girls’ getaway or any other vacation, you may want to consider other islands as part of your itinerary.
Robbie’s of Islamorada
Robbie’s is a family tradition when we go to the Florida Keys! There’s so much to do at this little roadside outpost along the Overseas Highway and yes, t’s a great place for bachelorette shenanigans. There’s a tiki bar with all the tasty tropical drinks you could want, parasailing, jet ski rentals, fishing charters, hungry tarpon to feed and shopping from local vendors. A Florida Keys bucket list item you have to check off with your girls!
We stopped at Robbie’s on the way to Key West and intended to stop again for lunch on the way home, but traffic was as bad as I’ve ever seen. It was Labor Day weekend after all, so it was no surprise, but we were disappointed we didn’t get to stop for more conch fritters and one last tropical beverage of the trip. We will be back!
Spas in the Florida Keys
I’ve been very fortunate to check out several of the best spas in the Florida Keys over the years, so if you are planning a girls’ getaway, you’ve got to check out some of my favorites.
Cheeca Lodge on Islamorada
I had one of the most incredible massages of my life at the spa at Cheeca Lodge, a luxurious beachfront hotel on Islamorada. Using hot tiger clam shells, I was massaged into a pile of vacation bliss. Check it out if you’re in Islamorada!
Learn more about Cheeca Lodge here.
Hawks Cay on Duck Cay
A bit closer to Key West is Hawks Cay, a resort with both hotel-style accommodations and large family villas. They recently completed a $50 million renovation of the 60-acre property, with 250 villas and 177 guest rooms.
We love Angler & Ale, one of many onsite restaurants, but it’s the spa that gets my attention after a day out deep sea fishing with Two Conchs.
Kayaks and stand-up paddleboards are free in the saltwater lagoon, and there’s an adults-only pool area, too. You can book fishing, diving and water sports in addition to spa time.
Learn more about Hawks Cay here.
Bachelorette Party Planning: What to Pack for a Bachelorette Party in Key West
Besides the obvious stuff you should bring anytime you’re in Florida – swimsuits, polarized sunglasses, reef safe, high SPF sunscreen and wide-brimmed hats, here’s a list of things to consider packing for a Key West bachelorette party:
Every good bachelorette party needs a theme… or two. We went with two separate themes for Rae’s bachelorette weekend so there would be multiple days of fun. First, the obvious “Beach Bach,” with special koozies, custom signs and all the beachy puns.
*Be sure to pack Scotch tape so you can safely hang the decorations on the wall or balcony.*
Then, of course, because it’s us, we had a whole slew of themed goodies from our favorite show. Did we watch The Office in bed while recovering from our sunny day out with HonestEco? You bet we did.
- Party Planning Committee Shirts
- Kelly’s AGT Party Mug with Rae’s face
- It Is Your Bachelorette Sign
- Custom Beers, Beets, Bachelorette Hair Ties
- Customized matching T-shirts (some with no minimum!)
Do you ever travel with a dedicated bag of wigs? I mean, unless you’re Moira Rose, probably not. This trip, we had my whole wig collection. Why do you have a giant wig collection, Angie? Ewww, David. Mind your own business.
Even in masks, you gotta go all out when you bachelorette. We had a couple different themed evenings, but my favorite was bridesmaids-in-black and bride-in-white… plus wigs.
Pro tip: leave your high heels at home and bring comfy shoes. You can thank me later.
Duval Street and the main party area of the island is walkable but not tiny, and if you’re anything like us, you may spend more time walking up and down in search of food, drinks and dancing than you actually do eating, drinking or dancing. Comfy shoes are a must, and you won’t be the only one wearing them!
We themed each day of Rae’s bachelorette getaway, so every morning she had new presents to open and a new surprise to be excited about.
We did a lingerie shower where she had to guess who bought what (yes, the cozy jammies are from me!) and other little goodie bags throughout the weekend.
Jessi and Cheyanne coordinated bachelorette games for the weekend, so when we weren’t snorkeling or searching for dolphins in the sea, we played such a fun variety of games. My favorite was the He Said/She Said game where we had to guess Ben’s answers to a list of questions he received in advance.
You think I’m kidding? The combination of hot sun and alcoholic bevvies can be a shock to the system, especially if you’re not from around these hot and humid parts. I barely boozed at all and I still brought my square bottle of electrolytes around with me. Cheers!
Bachelorette Party Playlist
If I have any regrets about this bachelorette weekend in the Keys, it’s that WAP is a very popular song and I heard it for the first time, and then the 100th time, on the way there and back. (If you don’t know about WAP, please for the love of your ears, don’t Google it.)
Make a sassy playlist with Beyonce, Taylor Swift, Shakira and J. Lo before you go, share it with all attendees and prepare to hear the same female empowerment jams (minus WAP) all weekend.
Ironically, my last trip before the pandemic was a Disney Cruise stopping in – where else – Key West?! So in a year of significantly less travel than I’m used to, Key West is getting a lot of our attention. I don’t see that ending anytime soon as every visit endears the Florida Keys to us that much more as we make family memories.
I miss international travel like crazy, but visiting the Florida Keys is the taste of the Caribbean I needed after six months of going nowhere. I never forget how lucky I am to live so close to paradise!