Sunshine, bikes, boats, live music, cocktails, the Super Bowl, and about 30 of our favorite people. This is the game plan — loose enough to be fun, organized enough that nobody misses the good stuff.
The goal is not to over-schedule everyone. Each day has one main thing we’d love the group to do together, with plenty of room for pool time, bars, food, shopping, wandering Duval, or doing absolutely nothing.
Turquoise water by day, ridiculous sunsets, and Duval Street after dark. Exactly the kind of place a 50th birthday should happen.
The short version — for when you just need to know where everybody is going.
Times and final reservations can be added as we lock them in. For now, this is the shape of the weekend.
Saturday is Shawnee’s night — sunset on the water, birthday dinner at Conch Republic, then Duval Street until we decide we’ve had enough. Or somebody makes us go home.
The big-group party choice — live music, dancing and classic Key West energy right on Duval.
The high-energy sing-along choice — live entertainment, crowd participation and plenty of noise.
The music-first choice — a legendary, no-frills Key West bar just off Duval with a serious live-music reputation.
There are a few ways to get here. Pick whatever works best for your schedule and budget — once you’re in Old Town, getting around is easy.
The easiest option. You land right on the island, then grab a taxi or rideshare to your hotel. If you’re staying in Old Town, there’s usually no reason to rent a car.
Often more flight choices and sometimes better fares. The Overseas Highway drive through the Keys is part of the experience. Allow roughly 3½–4+ hours from Miami and longer from Fort Lauderdale, depending on traffic.
Coming through southwest Florida? The high-speed ferry from the Fort Myers area is another fun option. Check the current schedule and fares directly with Key West Express when you’re ready to book.
If you fly directly into Key West and stay in Old Town, we’d skip it. Parking can be a hassle, and most of our weekend will be walking, biking or taking short taxi/rideshare trips.
We haven’t picked our hotel yet — and you don’t need to wait for us. Our recommendation is simple: find a place you like in Old Town and book it.
Most Old Town properties are small, so our group will probably be scattered around — that’s completely fine. Staying in the Historic District keeps you close to Duval Street, the Seaport, restaurants, bars and most of the weekend. Key West has tons of independent inns, guesthouses and cottages with real character. If you’re comfortable trying something different, explore them! If you prefer a familiar hotel brand, that works too — just pay attention to location.
Independent inns, guesthouses and cottages are a big part of the Old Town experience. These are just a few places to get you started — there are lots more worth exploring.
Three historic buildings, tropical gardens, a pool and studio through two-bedroom suites. A great example of the independent Key West experience.
A small tropical inn just a block from Duval Street. Great location and plenty of Key West character. It’s 21+, so it won’t work for everyone in our group.
Historic buildings and cottages tucked into lush tropical gardens in the heart of Old Town. Another great example of why it’s worth exploring the independent properties.
No problem. If you’re more comfortable with a familiar brand or a larger full-service property, these options keep you in or close to Old Town.
Right in Old Town near the marina, Duval Street and Mallory Square. A strong choice if you want a recognizable brand, resort amenities and the ability to walk almost everywhere.
A historic hotel right on Duval Street and part of Marriott’s Autograph Collection. Hard to beat if being in the middle of the action is the priority.
A larger historic resort on the Atlantic side with a private beach and two oceanfront pools. More resort-style and a little farther from the Seaport action.
A familiar, straightforward option on Simonton Street near Duval and the Southernmost Point. Pool, free breakfast and free parking without the full-resort setup.
A few practical things that will make the weekend easier. Don’t overthink it — this is Key West.
Key West is compact and very walkable. Bikes are great, golf carts are an option, and taxis/rideshare work well when you don’t feel like walking. For most of this weekend, you probably won’t need a car.
Shorts, T-shirts, swimsuit, sunglasses, sunscreen and comfortable shoes or flip-flops. Bring a light layer for breezy evenings and time on the water. Nothing we’re planning requires getting dressed up.
Expect warm days, comfortable evenings and plenty of sun, but Key West can get breezy or surprisingly cool after sunset — especially on a boat. We’ll update the site with the real forecast closer to the trip.
This website is the master itinerary. Final times, reservations, live-music schedules and changes will be updated here. We’ll also add the group text/chat details before the trip.
If you’re joining the Higgs Beach plunge, pack something you can get wet in plus a towel and dry clothes. The 2027 event time is still TBD, so watch the Sunday section for the final details.
Check back for final times, reservations, live music schedules, weather and last-minute updates. If something changes during the weekend, this is where we’ll put it.
Nothing here is scheduled. These are just good ways to spend some free time when you’re doing your own thing.
Classic Key West history, Hemingway’s home and writing studio, tropical gardens and the famous six-toed cats.
A surprisingly cool walk through a tropical habitat filled with free-flying butterflies, colorful birds and flamingos.
One of the best two-for-one stops: explore the historic fort, then swim, snorkel or relax at the beach.
Touristy? Absolutely. But if it’s your first trip to Key West, you pretty much have to get the picture.
Key West’s nightly sunset ritual with street performers, vendors, people-watching and a waterfront sunset.
Florida’s presidential museum and Truman’s Key West retreat. A good pick for anyone who enjoys American history.
Walk the Harborwalk, look at the boats, browse the shops, grab a drink or turn it into an easy waterfront lunch.
Sounds strange, but it’s a fascinating Old Town walk with local history, above-ground graves and famously quirky epitaphs.
Don’t overthink it. Some of the best sightseeing is just wandering around.
Key West has plenty of snorkeling, jet skis, parasailing, fishing, kayaking and boat trips. Pick what sounds fun and build your own adventure — no group schedule required.
Nothing here is scheduled — these are just some good Key West options when you’re hungry and doing your own thing.
From quick Cuban coffee to a full sit-down Key West morning.
Seafood shacks, Cuban food and easy places worth seeking out.
Think relaxed group trip, not field trip.
Join everything, join some things, or disappear for a few hours. Nobody is taking attendance.
Casual clothes, comfortable shoes, sunglasses, and enough stamina for at least one questionable late-night decision.
We’ll send final times, reservation details, meeting spots, and live-music updates as the weekend gets closer.
This is Shawnee’s 50th birthday in Key West. The objective is simple: spend time together, enjoy the island, and come home with stories that probably get better every time we tell them.