My first trip to Key West, but certainly not my last. Such a unique place which satisfies your inner pirate with rum and island vibes, provides you with cultural fulfillment yet still awakens your inner party animal when the night arrives! Also a great place for seafood loving foodies!
And so, seven ladies, and an oversized vehicle packed to the brim with bachelorette paraphernalia, make-up bags, and oversized suitcases containing all the necessities, and we were off to Key West from Miami for a fun filled Bachelorette weekend! The beautiful bride to be, Sarah, (and also my very special younger cousin) was soon to marry her teenage sweet heart after 10+ years.
Here is our short, but sweet laundry list for planning an unforgettable Key West Bachelorette Weekend.
1. Stay on Duval Street
Our timing was impeccable. Arriving into the beautiful lobby of the Duval Street La Concha Hotel right as happy hour (aka wine o’clock) began made for a perfect grand entrance. Our itinerary did not consist of much sleep, but for the few hours we’d get, it made a difference to rest of tired eyes in a stylish and very centrally located hotel, where we could walk everywhere we needed to.
2. Party with Drag Queens
Talk about impeccable timing once again. Our weekend in Key West also happened to fall on Pride Weekend. The city was buzzing, and the drag queens were ready to put on a show. Think confetti, strobe lights, rainbows, questionable makeup, platform shoes, raunchy dance moves – the full works! It was the ultimate entertainment, especially when our bride to be was dragged on stage to be apart of all the action at 801 Bourbon Street.
3. Matchy Matchy Shirts
It’s a bachelorette, so queue very “punny” matching shirts with wine slogans (and our matching hats). “Rose All Day” “Hakuna Moscato” “Everything happens for a Riesling” “Chill the wine His Last name is mine”. So corny and but yet so necessary! No one could miss us strutting down Duval Street!
4. Eat all the sea food
Key West is a small 4-mile long by 1-mile wide peninsula surrounded by the sea, explaining why it boasts delicious and fresh seafood. Our favourite place to indulge was the low key, unassuming DJ’s Clam Shack. Our weekend menu consisted of conch, crab, fish, oysters, mussels, and all things from the sea! We weren’t short on excellent meals the entire weekend, just the way I like it! Some highlights (to name a few) were the crab cakes at La Te Da Restaurant, Happy Hour Oysters and Key Lime Pie at Two Friends Patio Restuarant, and mojitos at the Southernmost Hotel Bar!
5. Bar Crawl on Duval Street
What’s a bachelorette without a drink or several to celebrate the soon to be life-long union. Duval St. is the perfect place to day drink. We started at Fat Tuesday’s for Pina Coladas before wandering from bar to bar making our way to Mallory Square for sunset. There’s a bar for every mood on Duval street, and we embraced them all.
· Pour yourself a frozen drink at Fat Tuesday’s – that’s if you can make a choice from the many options.
· Sign a dollar and staple it to the bar at Willie T’s
· Listen to live music at Irish Kevins
6. Enjoy a Key West Sunset
The skies light on fire in Key West at sunset, boasting bright pinks, yellows, reds and blues. Be sure to stop and take it in (with a drink in hand, obviously).
7. Search for your Key West Style Dream house
Whether you’re a lover of architecture or not, there’s no denying Key West homes are some of the most adorable. With their shady porches, pastel colors, quaint design and island vibe, it is hard not to walk by and picture yourself sitting on your favourite veranda with a book in one hand and wine in the other!
8. Bird’s Eye View of Key West
In the midst of the bar hopping and eating all the seafood, we managed to fit in a few cultural pieces. We made the 88 step climb to admire the scenic view the lighthouse keepers watched over for more than 120 years. It’s now a museum and worth the visit. Speaking of a bird’s view, we also stopped in at Nancy’s Forresters’ Secret Garden for a very fun and informative visit with her piano playing cockatoos, and colorful dancing macaws. Her lifelong dedication to rescuing, studying and training birds is impressive.
9. Beach it!
On our last morning, the Bride to be and I took a leisurely early morning stroll (coffee in hand obviously after a late night), to Fort Zachary Taylor Beach. We were in Key west after all so it only makes sense to take a dip in the bright blue waters (nearly as pristine as ours in Cayman! 😊 )
10. Southernmost point
Carrying on with the cultural activities on our final afternoon, we made our way to the southernmost point buoy, otherwise known as the lowest latitude land of the North American continent. The large painted buoy is a must-do photo-op in Key West! We wrapped up the trip with a yummy low key lunch and mojitos at the Southernmost Hotel Bar!
11. Indulge in Key Lime Pie
This one goes without saying. You’re in Key West, which means you must eat Key Lime pie! Our search for the best key lime pie is ongoing, but we tried one from The Original Key Lime Pie bakery and one from the Two Friends Patio Restaurant, the later having a slight edge.
And just like that, our weekend of love, laughter, good eats, drinks and drag queens came to an end far too quickly. There’s so much of Key West left be explored, and I can’t wait to return!
