Transportation is the part of a Key West wedding that nobody thinks about until the week of, and then it is suddenly everyone's question. Where do guests park in Old Town? How does the wedding party get from the hotel to photos to the ceremony on time? Who gets Grandma back to the hotel after the first dance?
The island is small, but a wedding day on it involves a lot of people moving between a lot of places on a tight schedule. Here is how to plan it so it simply works.
Start with the headcount and the map
Before you talk vehicles, write down three things: who needs a ride (the couple, the wedding party, the guests), where everyone is staying, and every stop on the day, from getting ready to the send-off. Guests spread across several hotels and rentals need a different plan than a group staying in one resort.
Then look honestly at parking. Much of Old Town has very little of it, beach and waterfront venues fill up, and guests in formal wear do not want to walk half a mile in the heat. That is why most Key West weddings move guests in shuttles rather than asking them to drive.
How many vehicles does a wedding need?
A simple rule of thumb: one luxury SUV for the couple, one Sprinter for the wedding party, and enough Sprinters to move your guests. Our Sprinters carry up to 14 passengers each, so a 40-guest wedding needs three to move everyone in a single wave, or fewer running loops.
Large weddings are routine for us. We run several vehicles on the same schedule, and the fleet can move 200+ guests at once, so a big guest list never means splitting the party across rideshares. Tell us your headcount and we will recommend the mix in our wedding transportation quote.
Guest shuttles: one wave or loops?
- One wave: enough vehicles to bring every guest at the same time. It costs more vehicles but guarantees everyone is seated before the processional. Best for ceremonies with a fixed start, like a sunset ceremony.
- Loops: fewer vehicles making repeat runs from the hotels. Works well for the reception, when guests arrive and leave over a longer window.
- Mixed: one wave to the ceremony, loops back to the hotels at the end of the night. This is the setup most couples land on.
A sample wedding-day timeline
Every wedding is different, but most follow the same shape. Build the transportation plan around it, with at least 15 minutes of buffer at every handoff:
- Getting ready: a vehicle collects the wedding party and delivers them to the getting-ready location.
- First look and photos: the couple's SUV moves them between photo spots while the photographer works.
- Guest arrival: shuttles bring guests to the ceremony 30 minutes before it starts.
- Ceremony to reception: guests ride over together while the couple takes a few minutes for portraits.
- The send-off and late night: the couple leaves in style, and the shuttles start loops back to the hotels for guests who leave early.
We work directly with your wedding planner on this schedule, so changes on the day go through one person and every driver hears about them.
Plan the whole wedding weekend
The wedding day is only part of it. Guests flying into Key West International need airport pickups, and guests who land in Miami or Fort Lauderdale to save on airfare can ride down together in a private van down the Overseas Highway. Add the welcome party, the rehearsal dinner and a day-after brunch, and you have a weekend of group transportation that is easiest to book all at once.
What to send your transportation company
- Date, ceremony time and venues, including the getting-ready location and the reception.
- Headcounts: the wedding party and the number of guests who need shuttles.
- Where guests are staying, so we can plan pickup points and loops.
- Your planner's contact, so the schedule has one owner.
Book as soon as you have a date and venue. Key West wedding season is busy, and the large vehicles are reserved first.
