It’s been 18 years since myself and my two colleagues-turned-friends quit our media jobs, sold our belongings, left New York City, and backpacked the world together for a year. Jen, Amanda, and I got to know each other extremely well after sleeping head-to-toe in hostels, hotels, tents and overnight sleeper trains for 365 days. (After our round-the-world trip, we wrote a book about our adventure called The Lost Girls: Three Friends. Four Continents. One Conventional Detour Around The World.)
Not only did we continue to stay friends, but upon our return, we made a pact that the three of us would travel together once a year for the rest of our lives. We’ve held true to that promise to each other, even when things got busy and big life changes happened–from having kids to switching jobs to moving cities (me).
For our 2024 girls getaway, we followed in Hemingway’s footsteps and escaped to Key West. To me, Key West felt like a laid-back Caribbean island meets the magic of New Orleans meets the soundtrack of Nashville.
Key West is the southernmost city in the continental U.S., mixing adventure and intrigue with relaxation and nature. The mix of cultures such as Cuban, Bahamian, and American, along with the vibrant art and music scene, makes it so much more than your typical beach town. So, when we heard the Keys’ locals share their favorite saying that “We’re here, because we’re not all there!” we paused and thought…yep, sounds like a Lost Girls destination to us. Here are highlights of how we spent 48 hours in Key West.
Where to Stay in Key West: The Pier House Resort & Spa
Having never been to Key West before, Amanda selected the Pier House Resort & Spa based on three things: Location, pool, and beach. It turned out to be the best decision, because it was on the main Duval Street and steps away from the famous pier where locals gather every night to toast to the sunset with a cocktail.
Now that we’ve visited the island, I would absolutely go back to this resort again for many reasons. One is I loved that it had its own private beach with an area for swimming. I was surprised to learn that hotels with beaches were actually rare on Key West despite its island location.
Though I do advise swimming in the ocean with a friend. During my morning laps, I discovered I may be a fast enough swimmer to qualify for the Olympics after spotting a 12-foot brown sea creature swimming directly underneath me, and torpedoing straight back to shore. It wasn’t until I fell in the sand in front of Jen and Amanda, chest heaving, while they lazily sunned themselves on lounge chairs, that I realized what I saw must have been a gentle manatee (a.k.a. “sea cow”), calming my heart rate. To which my friends told me I needed to relax more, and sent me this meme (an extremely inaccurate comparison to myself, I swear).
In addition to manatee sightings, The Pier House Resort had everything we wanted for a girlfriend getaway, from an onsite spa to a hot tub to a gym. There were also three dining options. The onsite Chart Room bar is said to be where Bob Marley and Jimmy Buffet launched their musical careers. Rather than a high-rise hotel, this 119-guest-room-and-23-suite resort integrates the island feel by incorporating both architecture and nature into the design with its collection of buildings connected by palm tree-lined walkways.
Friday
1. Sunset Cocktails & Music I 5 p.m.
After making the 15-minute drive in a taxi from the airport to The Pier House, Jen, Amanda and I quickly changed into our sundresses and walked about one minute to the aptly-named Sunset Pier. We ordered a Sunset Margarita, watched the sun languidly sink below the horizon in bursts of pink and gold, and danced to live music.
2. Dining Al Fresco I 7 p.m.
We walked a few steps back to The Pier House for more stunning ocean views as stars began to dust the sky while dining on the deck of One Duval. Chef Maria’s menu changes according to what’s in season, and we dined on seafood such as coconut curry snapper and seared ahi tuna. This is one of the top restaurants in Key West, as the service is wonderful and the ingredients fresh. Breakfast, lunch and dinner are served either in the elegant indoor dining room or ocean-side on the deck.
3. A Haunted Ride I 9:30 p.m.
Key West has a dark side. When the sun goes down, the spirits come out, according to our ghost host, Lulu Fortuna, during the Ghosts & Graveyards Trolley tour. From learning about a maid who used VooDoo to cast a spell on the creepy Robert the Doll to stopping at the Shipwreck Museum and daring tour participants to touch the cursed silver bar from a shipwreck in 1656, this experience will have you imagining you’re seeing ghosts. The locals even get in on the action, with passersby yelling “You are doomed!” to trolley riders, who yell back, “We are doomed!” If you’re traveling with kids under 13, I’d suggest skipping this tour and doing the daytime Old Town Trolley Tour instead to avoid nightmares interrupting your vacation sleep. Rates start at $38 for a one-hour tour.
Saturday
4. Breakfast on the Beach I 8:30 a.m.
Roosters free roam on the island (supposedly descendents of fowl found throughout the Caribbean), and we were awakened early to a “cock-a-doodle-doo.” Since the aptly-named Beach Bar wasn’t yet serving food, the three of us ordered eggs, toast and coffee from One Duval and ate it under an umbrella on the lounge chairs set on the beach.
5. Paddle Board Adventure I 10 a.m.
We paddled our way through the mangroves in the backcountry of Key West on a paddleboard eco-tour with Lazy Dog Adventures at Hurricane Hole Marina. If you like moving your body and being in nature, these tours are an adventurous way to learn about the local ecosystem and marine life (just be sure to wear a lot of sunscreen). While we did not see any manatees on this tour, we did spot sea stars, frigate birds and even got to hold a jellyfish that didn’t sting. Two-hour paddleboard eco-tours start at $70.
6. Island Escape I 2 p.m.
After working our bodies, we headed to the 27-acre private island at Sunset Key Cottages, where we plopped ourselves into the white sand and spent a relaxing afternoon reading on the beach and ordering drinks from the pool bar, much to Amanda and Jen’s delight. To get there, we took a private boat shuttle from Opal Key Resort, which has its own marina, for an eight-minute ride to the island.
As dusk neared, we swapped our bathing suits for sun dresses in the onsite locker rooms and ate dinner on the island at the elegant Latitudes restaurant. The setting was as memorable as the food, being seated on the outdoor verandah to witness another breathtaking Key West sunset. We shared plates so we can sample more of the menu, such as Korean barbecued wagyu beef skirt steak with sesame potato puree and Caribbean lobster risotto. The boat leaves the marina at Opal Key at the 15- and 45-minute mark of every hour from 6:45 a.m. to 10:45 p.m.
7. Famous Nightlight I 9 p.m.
After a sunset dinner at Latitudes, Jen, Amanda and I hopped the shuttle boat back to the main island and found ourselves pulled to the celebratory energy of Duval street.
We heard the most incredible voice coming from a rooftop bar, and decided to follow the music to find the source. We walked up the steps to the Halo Rooftop Lounge, facing Duval Street on the roof of The Saint Hotel. We spent a magical hour captivated by a live performance from American Idol contestant and singer songwriter Kristen McNamara, who sang both popular hits and her own original music, one of which was named after the place where we found ourselves, “Duval Street.”
Next we headed to the local dive bar Green Parrot on the corner of Southard and Whitehead Streets, which opened in 1890. You can practically feel the history, with a wooden bar, wooden stools and musical paraphernalia from eras past hanging on the walls. It’s known for its live music but there weren’t any bands playing the night we stopped in. Instead, we stayed for the colorful conversations with the locals and the unlimited free popcorn, which only made us thirstier.
Sunday
8. Pancakes and Cats I 10 a.m.
Blue Heaven, two blocks from Duval Street on Petronia and Thomas Streets, is a famous brunch spot also known for the cats and chickens that wander freely in the eclectic outdoor dining area. No surprise that live music is also a staple of the establishment. Come hungry as the menu includes shrimp and grits, Betty’s banana bread, blueberry pancakes, and famous Key Lime Pie.
9. Hemingway House I 11 a.m.
Our visit to Key West wouldn’t be complete without a visit to the Hemingway House with its 60 six-toed cats. The famous writer and member of the “The Lost Generation” visited Key West and made it his home in 1931. Hemingway fell in love with the sunny weather, the ocean fishing, and the laid-back bar scene. Famous for novels such as Farewell to Arms and For Whom the Bell Tolls, Hemingway wrote part or all of his books and two of his most famous short stories in Key West.
Tours run daily, take about 30 minutes and cost $19.
10. Poolside Party I 12:30 p.m.
We’d experienced the nightlife, swam in the ocean, and paddled our way through the mangroves. Jen, Amanda and I ended our trip with a pool day in style with a reserved cabana and lunch at the Margaritaville Beach House Key West. Located directly across the street from Smathers Beach, which is the largest public beach in Key West, visitors can choose to take a stroll by the ocean. But we preferred to stretch out on the lounge chairs, sip on a Tropical Hurricane, and watch the resident iguanas sun themselves. At the end of the day, and at end of the trip, the three of us could agree that we are still each others’ best travel partners.
To read more about The Lost Girls original trip, check out our blog, book and read more about it on We Said Go Travel!
