An anniversary in this city usually has a table at the end of it, and the tables are spread out. Downtown holds Dudley's on Short in the old school building on West Short Street, Tony's on West Main, Coles on East Main, Carson's, the Lockbox room inside 21c and the Distillery District restaurants along Manchester Street. The southern half of town holds the Merrick Inn on Merrick Drive — a dining room in the former manor house of a thoroughbred farm, which is about as Lexington as a fortieth-anniversary dinner gets — plus Azur out at Beaumont Centre, the Malone's rooms, Jean Farris on Harrodsburg Road and Honeywood at the Summit on Nicholasville Road. Out past the county line are Holly Hill Inn in Midway and Wallace Station on the Versailles Road. Oram Flowers at 825 E Euclid Ave. in 40502 is 2.1 miles from downtown and sits roughly in the middle of that spread; Nicholasville Florist KY at 206 S Main St, 13.3 miles south, is the closer studio for anything below Man o' War or across the Jessamine County line.
Here is the practical advice that saves most anniversary orders: send the flowers to the house, not to the restaurant. A dining room takes a delivery at a hostess stand during setup, which means a vase sitting by a podium for two hours with nobody responsible for it, and if the reservation moves or the couple is seated on a patio the arrangement stays at the front. Flowers on the kitchen counter at four in the afternoon do the work you actually wanted — the moment happens before you leave, in private, and the arrangement is still there the next morning. If the dinner is the surprise and the house is not an option, a hotel front desk is the better intercept, because a desk logs a delivery, holds it and hands it to a named guest at check-in. Ask the restaurant first if you are set on a table drop; some will hold a piece in the back and bring it out at dessert, which is a different and much better plan than leaving it up front.
The hotel list is short and well-placed. The Hyatt Regency on West High sits against Rupp Arena and the Central Bank Center, which makes it the default for a concert or game weekend; the Hilton on West Vine is a block away in the same block of the convention core. 21c Museum Hotel occupies the old First National Bank building at 167 West Main and is the room most couples pick for a downtown anniversary, with the contemporary-art floors and the Lockbox dining room downstairs. Gratz Park Inn on West Second sits inside the historic Gratz Park district, a quieter and more traditional choice. South of downtown, the Campbell House on South Broadway has been the Lexington occasion hotel for generations; north of it, the Griffin Gate Marriott on Newtown Pike is the golf-resort option, with the antebellum Mansion restaurant on the property. For any of these, put the guest's surname and the arrival time on the order and let the desk hold it — a room delivery before check-in has nowhere to go.
Then the calendar, which in central Kentucky is more crowded than it looks. Keeneland's April and October meets fill downtown hotels and put a long afternoon load on Versailles Road and Man o' War for three weeks at a time; the Kentucky Horse Park's late-April three-day event does the same on Newtown Pike; and the first week of May empties every hotel room between here and Louisville. Local wedding season runs late April through October at the farm venues ringing the city, which is why so many Lexington anniversaries land in those same months — and why a same-day slot on a Saturday in May or October is the hardest one to get all year. Valentine's Day is its own animal at both studios. The 60-mile radius reaches the anniversary-weekend country too: The Kentucky Castle on the Versailles Road, Shaker Village at Pleasant Hill near Harrodsburg, the Beaumont Inn in Harrodsburg, Boone Tavern in Berea, and the distillery corridor at Woodford Reserve in Versailles, Buffalo Trace in Frankfort and Four Roses and Wild Turkey in Lawrenceburg.