You landed. Your bags didn't. It happens more than you'd think at Key West International Airport (EYW) — a small regional airport served by American, Delta, United, and Silver Airways, where bags are routinely delayed, especially on Silver regional connections. Here's the thing though: Key West is probably the single easiest place in the world to deal with this situation. The island is 4 miles long. Everything you need is within a 5-minute golf cart ride. You do not need your luggage to start enjoying yourself. You just need a plan — and that's what this is.
Step 1 File the PIR at the Airport Before You Leave
Before you walk out of that terminal, go directly to the airline baggage office. File a Property Irregularity Report (PIR). This is the official record of your delayed bag — without it, the airline has no obligation to deliver to your hotel, and tracking becomes much harder.
EYW is a small airport. The baggage office is open during flight arrival windows and is easy to find. The process takes about 5 minutes:
- Give them your bag tag receipt (the sticker on your boarding pass)
- Provide your hotel name and address
- Get a reference number — write it down or screenshot it
Key point: Don't assume the airline will find you. They won't. Filing the PIR is what triggers the delivery-to-hotel workflow. Most delayed bags at EYW arrive on the next scheduled flight — often within 4–6 hours.
Step 2 Get a Golf Cart — Because This Island Is Tiny
Here's where your delayed bag situation quietly becomes a non-issue. Key West's entire navigable area is about 4 miles end to end. What would be a logistical nightmare in Miami or Atlanta is a 20-minute errand loop here — if you have wheels.
Our carts are Scan & Go: no reservation required, no deposit, no paperwork. Open the app to see the cart location on Stock Island, head over, scan the QR code on the interior rearview mirror using the Conch Cart Rentals app, and you're moving. Walgreens, Duval Street shops, back to your hotel — done in under half an hour. Compare that to a $25 taxi ride or a 30-minute walk in the Florida heat carrying nothing.
Open the app, see the cart on Stock Island, scan the QR code on the mirror, ride. 4-pass from $180/day. No deposit, no holds, no surprises.
Step 3 Essentials Stop — Walgreens on Duval
Walgreens: 734 Duval St, Key West FL 33040. Open 8am–10pm most days. This is your first stop. For overnight basics, you're looking at $30–$50:
- Toothbrush and toothpaste
- Deodorant
- Sunscreen (mandatory in Key West)
- A basic swimsuit if they have one in your size — they usually do
- A phone charger cable if yours is in the checked bag
If Walgreens is out of something, your backup is CVS at 530 Truman Ave, about 5 minutes away by cart. There is no big-box store on the island — the nearest Walmart or Target is in Marathon, about 50 miles north on US-1. For one night's worth of basics, you don't need it.
Step 4 Clothing on Duval Street
If you need something to wear tonight — and not just a swimsuit — Duval Street has you covered. It's not fashion week, but it's functional. Conch Republic Clothing Co., Basic Gear, and a dozen other tourist shops along Duval sell shirts, shorts, and sundresses for $20–$40 a piece.
A 4-passenger cart makes Walgreens, Duval Street, and your hotel a 20-minute loop instead of a 30-minute sweaty walk.
Budget $40–$60 for a full outfit. You'll probably wear it again — Key West has a casual dress code for basically every venue on the island. This is not a problem you need to stress about.
Step 5 Contact the Airline for a Delivery ETA
Once you've filed the PIR and grabbed your essentials, check in with the airline on timing:
- Delta, American, United: All have app-based bag tracking — you can watch your bag's location in real time
- Silver Airways: You'll likely need to call directly; their bag tracking is less automated. Save the reference number from your PIR and be specific about your hotel name and address
Most airlines will provide an amenity kit or a $50–$100 voucher if your bags are delayed 12 or more hours. Ask — it's standard policy on most carriers, though it varies. Most delayed bags at EYW arrive on the next scheduled flight, which is often within 4–6 hours. The hotel concierge can receive the delivery on your behalf.
The Marathon Option (24+ Hours, Bags Truly Lost)
If it's been 24 hours or more and your bags are genuinely lost rather than just delayed, the calculus changes. Walmart is in Marathon, about 50 miles north on US-1 — roughly a 45-minute drive. This is a car or taxi trip, not a golf cart trip. Call a taxi (figure $20–$30 each way), rent a car for the day, or ask your hotel about shuttle options.
But to be clear: this scenario is rare at EYW. The airport handles a small volume of flights. Truly lost bags — not just delayed — are uncommon. File the PIR, track the bag through the airline's system, and give it 24 hours before escalating to this level.
The Short Version
A delayed bag is a minor inconvenience in most cities. In Key West, with a golf cart and $40 at Walgreens, you're back on the beach in 90 minutes. The island is small. The stores are close. The vibe doesn't require checked luggage to enjoy.
File the PIR before you leave the terminal. Grab a cart. Hit Walgreens. Get back to your hotel and let the airline deliver. You've lost maybe 90 minutes of vacation — not the whole trip.
Key West's only keyless golf cart rental. All-black Cushman carts in 4, 6, and 8-passenger configurations. No deposit. No holds. Book online or walk up — the cart starts the moment you scan.
Already in Key West? Open the app to see the cart location on Stock Island — no reservation needed. The QR code is on the interior rearview mirror of every cart.