Downtown Fort Myers is small enough that an anniversary plan tends to fit inside eight blocks. The River District runs along First and Second Street to the Caloosahatchee, and the restaurant most couples in this city name when they mean a real anniversary dinner is The Veranda, two joined 1902 houses on Second Street with a courtyard in the middle. The Luminary Hotel sits a few minutes away on Edwards Drive with the river directly in front of it, Hotel Indigo is a block off Broadway in the same district, and the whole area is walkable from the Sidney and Berne Davis Art Center and the Arcade Theatre where Florida Repertory Theatre performs. Three of our six shops — the Cleveland Avenue benches — are a ten-minute drive from all of it. That geography makes two mechanics easy if you know them. For a restaurant, send the arrangement in the early afternoon rather than at the reservation hour, and keep it small: a two-top in a historic dining room has room for a low compact piece and not for a tall vase, and the staff will place it on the table before you arrive. For a hotel, send it after check-in, because a front desk will hold a delivery for a guest who has not arrived and the point is for it to be in the room.
The other half of Lee County's anniversary trade happens with salt water in view, and the roads decide the timing. The Sanibel Harbour Marriott sits at Punta Rassa where the tolled Sanibel Causeway begins, looking across San Carlos Bay, and Ajs Florist Ftmyers at 15271-15 McGregor Blvd in 33908 is the closest bench to that end of the county. Fort Myers Beach is reached over the Matanzas Pass bridge on San Carlos Boulevard, and once a driver is on Estero Island there is essentially one road down its length, so a beach delivery is a longer commitment than the mileage suggests — Margaritaville and the Pink Shell are both on that stretch. One honest caution about this coastline: Hurricane Ian came ashore here on 28 September 2022 and the beach and the islands took the worst of it. Rebuilding has been uneven, property by property, and some addresses that existed in 2022 do not any more. If the anniversary is at a beach or island property, confirm with the property itself that it is open and receiving deliveries before you order, and give us a phone number for the front desk.
A very large share of the anniversaries we deliver in this county are fortieth, fiftieth and beyond, and they come with a problem nobody warns you about: both people are usually home. The classic anniversary surprise assumes one spouse is at work. Here the recipient may be on the lanai at eleven in the morning, which means a delivery van in the driveway gives the whole thing away. Three workarounds, in order of how well they tend to go. Time the delivery for a window when one of them is out — a tee time at the Fort Myers Country Club on McGregor, a standing hair appointment, the Wednesday grocery run — and tell us that window in the order notes. Or use a neighbor, which in a street of long-settled houses is usually easy to arrange. Or skip the ambush entirely and send it to arrive in the morning so it sits on the table all day, which for a fiftieth is frequently the better version of the gift. Gate-list addresses need the recipient's name as the association has it plus a lot or unit number; the Shell Point and Cypress Cove campuses route everything through a front desk, where a resident's full name and building is enough.