Every bachelorette group chat hits the same wall about three weeks out. Everyone has flights, the house is booked, and the dinner reservations are made, but nobody has answered the question of how twelve people actually get around an island where parking is scarce, distances add up in heels, and rideshares split the crew into three cars every time.
Key West is small, but a weekend on it involves a lot of moving around. This is how experienced groups handle it.
Arrival day: land, regroup, disappear to the house
The crew never lands together. Someone arrives at noon, a few catch the 4 p.m., and the one flying standby appears at midnight. The answer is staggered airport pickups scheduled against a shared flight list, so each arrival gets met and nobody stands at EYW watching the rideshare app surge.
Flying into Miami instead to save on airfare? A private van down the Overseas Highway turns the drive into the weekend's opening event, with the playlist on and everyone together from hour one.
The big night: one vehicle, every stop
Dinner at the harbor, cocktails somewhere with a roof deck, then the Duval crawl. Twelve people in three rideshares arrive at three different times and someone is always texting a pin. One Sprinter with a dedicated chauffeur for the night means the whole crew arrives together, every photo has everyone in it, and the ride home at 1 a.m. is already at the curb.
It also settles the sober-driver question for the whole night, and there is no surge pricing waiting at closing time.
The slow day: beach, brunch, boat
Most itineraries put a recovery day in the middle for brunch, a beach afternoon, or a sunset sail. That day is where hourly service fits best: the vehicle and driver stay with the group, stage while you eat, and roll whenever everyone is ready, with nothing to re-book between stops.
What to sort out in advance
- The flight list: collect everyone's arrivals in one message and send it to your transportation company, so staggered pickups get scheduled once instead of negotiated all day.
- The big-night route: venues and rough times, so the vehicle is staged and waiting rather than summoned.
- The house address and its parking reality: many Old Town rentals have no parking at all, which is one more reason the crew should not bring cars.
- One point of contact: a single person texts the chauffeur; the group chat stays for photos.
Book the vehicle as soon as the dates are set. Bachelorette season is wedding season, and the 14-passenger Sprinters go first every weekend.
