48 (Walkable) Hours in Historic Downtown Sanford

The city of Sanford, which dates back to the mid-1800s and was incorporated in 1874, preserved its downtown so well that it earned a spot on the National Historic Register in 1976. The area includes 26 buildings dating from 1877-1924.

But you don’t have to be a history buff to absolutely love a weekend stay in Sanford.

Those centuries-old buildings now make up an absolutely charming and eminently walkable district that includes craft breweries; a riverwalk with an adjacent park; quirky boutiques, galleries, bookstores and thrift shops; and a collection of eclectic, independently owned restaurants — all contained within a few square blocks. You’ll experience old and new Florida at the same time.

Sanford, which is just 30 minutes from Orlando, is easily accessed via Orlando International Airport and Daytona International Airport, but the best option is Orlando Sanford International Airport, which is less than five miles from downtown. And, of course, with its location in the center of the Sunshine State, the city is easily reached by car from all directions.

Visitors to Sanford can make trips to Orlando North’s many natural wonders — all of them within a short drive — or take a jaunt down to theme parks near Orlando. But we’ve designed this 48-hour Sanford visit so you can leave your car parked and never have to hail a ride-share service.

Ready for a walkable weekend experience in one of Florida’s most unique cities? Here we go:

Friday

There are numerous options for brand-name hotels in Sanford and nearby Lake Mary, all of them clean, comfortable, and affordable. But for this visit, try something unique. Book a room at the Higgins House B&B, a 126-year-old Queen Anne Victorian near the historic district. Each of the three guest rooms is unique, with cozy, vintage appointments. Just be careful — the covered front porch, with its comfy wicker chairs and an old-fashioned swing, might be a little too inviting.

Time for a drink, don’t you think? If you happen to be a craft beer aficionado, you’re in luck. Downtown has three highly regarded microbreweries — Sanford Brewing Company, Wop’s Hops Brewing Company and Kitchen (which are in the same block and both serve food) and Deviant Wolfe Brewing (six blocks away, with a lively tasting room). Celery City Craft doesn’t make its own beer, but it has 50 taps with plenty of Florida-made brews and an expansive outdoor area filled with picnic tables.

Of course, if a sudsy good time isn’t your thing, Bitters & Brass, with its British-style interior of dark woods, serves magnificent craft cocktails. And most of Sanford’s restaurants serve wine and liquor.

Yes, it’s time for dinner. You have a bevy of choices, ranging from fine dining to inexpensive ethnic cuisine — all within the radius of a few blocks, and many with large outdoor dining and drinking spaces. Here’s a sampler: Buster’s Bistro, The District Eatery Tap & Barrel, The Breezeway, The Smiling Bison, The Original Christo’s and Negril Spice (Jamaican cuisine). Also: The Old Jailhouse Kitchen & Spirits is situated in an 1890 building that was previously a blacksmith, a livery feed store and acted as the Seminole County Jail from 1914-1959. (You can even eat behind bars!) Shantell’s, owned by Shantell Williams — a mother of 10 who tools around town on a Harley — does soul food with a healthy approach.

If taking in some live music is on your to-do list, Tuffy’s Bottle Shop has a vast courtyard that presents some of the area’s best regional bands and national touring acts as well as other fun stuff like shuffleboard tournaments. The West End Trading Co., five blocks east, has an outdoor courtyard that features local, regional and national acts.

(Note: As of late September 2020, when this post was written, live entertainment at these venues was limited.)

This is a walking visit, but feel free to hop aboard our free trolley that runs through downtown. It has 10 stops and operates Monday through Saturday from early afternoon until 7:45 p.m.

Saturday

Get up — no time to waste. Or go ahead and sleep in. You’re on holiday — the choice is yours!  When it's time to chow, take advantage of the Higgins House full breakfast, or head out to a nearby restaurant for a robust starter meal. Several eateries serve brunch, but let us recommend The Tennessee Truffle, a “farm-to-fork” place that specializes in Southern-inspired cuisine.

To get your Saturday underway, stroll through the Sanford Marketplace at Magnolia, where you can view and buy cool wares from local vendors.

Time to check out Sanford’s waterfront on beautiful Lake Monroe. Stroll the Sanford Riverwalk (it runs 1.8 miles) and amble through Fort Mellon Park. On the park’s western edge sits the Sanford Museum, which houses an archive chronicling the city’s rich past and tells the story of founder Henry Shelton Sanford. For an alternative perspective, stop in at the small Goldsboro Museum, which chronicles the second Black incorporated city in the U.S. (1891). Twenty years later, a bill pushed through the Florida legislature forcibly annexed the town into the City of Sanford, making room for expansion. Goldsboro residents sued for four decades to restore the town’s charter, but were unsuccessful.

How about a truly unique lunch? Board an authentic, 105-foot “sternwheeler” paddleboat called the Barbara-Lee for a three-hour excursion that includes a full-course meal and a jaunt across Lake Monroe and along the St. Johns river. You can lean on the wrought-iron railings and take in the sights, sun and breezes, or gaze from climate-controlled rooms and covered decks.

Afterward, you may want to stop back at the Higgins House for a quick refresh, lounge on the porch or brick-pathed garden, or spend a few minutes in the parlor listening to an authentic 1895 Edison cylinder phonograph.

You have a wealth of choices for Saturday happy hour. Washburn Imports is a cool store selling unique furniture and furnishings accumulated from Asia and the Pacific Rim. But wait — the space also houses the Imperial Wine Bar, which serves boutique wines, classic cocktails and craft beers.

For something livelier, check out Hollerbach’s Willow Tree Cafe, a Sanford institution. Set right in the heart of historic downtown, it’s a German-themed restaurant and bar with a large indoor dining area and expansive outdoor decks. The place can get boisterous when the live oom-pah music and singalongs kick in. What launched as a single-room German eatery in 2001 now includes Magnolia Street Market — an authentic German deli, bakery and shop — and Hollerbach’s Outfitters, which sells all kinds of Teutonic garb, just in case you really want to get in the spirit.

Stay for a hearty, meat-and-potatoes dinner if you like, or consider something a bit more laid back. On the water you’ll find St. Johns River Steak & Seafood, which features plenty of tables (some covered, some open-air) that overlook Lake Monroe. If you’re looking for a sweet dessert treat, pop over to Wondermade, where you can delight in homemade marshmallows with flavors like Key Lime, Root Beer and Bourbon, and ice creams, including Cornbread and Maple Bacon.

Like many cities a century-and-a-half old, Sanford has its spooky past. Try the Historical Ghost Walking Tour, a jaunt through downtown where a guide will regale you with stories of ghostly happenings from the city’s yore, culminating in a walk to a haunted house.

Sunday

We’re pretty certain you slept well. Have a sit-down breakfast on white tablecloths in the Higgins House’s lovely dining room. It just might be that your legs are a little fatigued, so give our fair city another once-over by hopping on Ride Lime, a service that takes you around town on large, bright-green golf carts. It’s like an open-air ride-share — and it’s free! Your driver will point out local landmarks and provide some history. Ride Lime serves only downtown Sanford.

If you’re not too tired to walk, take a stroll through the Old Sanford Residential District, which borders downtown to the south. Listed on the National Register in 1989, this area contains 434 homes and other buildings in a wide range of architectural styles, among them Craftsman, Prairie, Queen Anne, Folk Victorian, National, Colonial Revival, Spanish Eclectic, and Mission. It runs 12 blocks north-and-south, five blocks east-and-west, and includes four small, lovely parks, ideal places to take a load off and relax.

Your 48 hours are up! No doubt you had so much fun they flew by. We can’t wait to see you again, so until next time, farewell from your friends in Historic Sanford!