Orlando One Block at a Time: Explore Historic Downtown Sanford

This charming small city, located adjacent to Orlando, offers visitors plenty to do.

The small city of Sanford lies just northeast of Orlando, but it feels worlds away. Here, you'll trade the hustle of the city and the bustle of the tourism corridor for a charming downtown district that gives way to Central Florida's natural side. Come with us as we explore and share a few highlights.


Hollerbach’s Willow Tree Cafe is one of the area’s most iconic eateries, a German restaurant beloved for its annual Oktoberfest celebration, authentic fare, and the Das Boot, a 2 or 3-liter glass boot filled with beer. At The Old Jailhouse, you can literally dine behind bars in what was once the county jail, now re-imagined as an upscale eatery serving cocktails and American cuisine. For a taste of everything, Sanford Food Tours offers 4-hour guided walking food tours visiting 4-5 notable establishments for hearty tastings with a side of local history.

Hollerbach’s Willow Tree Café: 205 E. 1st St., 407.321.2204

The Old Jailhouse: 113 S Palmetto Ave., 407.548.6964

Sanford Food Tours: 203.980.8774

A dish from Buster's Bistro courtesy Sanford Food Tours
(©April Amellin Photography)


Nestled within Tuffy’s Bottle Shop and Lounge, The Suffering Bastard is an immaculately decorated Tiki bar celebrating the Polynesian-inspired concoctions made popular in the late 1930s to 1950s. 

There are more than 40 drinks on the menu. Sip wine at the Sanford outpost of The Imperial at Washburn Imports, or immerse yourself in the local craft beer scene at one of the area’s four craft breweries, all within walking distance.

The Suffering Bastard: 200 Myrtle Ave.

The Imperial at Washburn Imports - Sanford: 116 E. 1st St., 407.732.6956

The Suffering Bastard Tiki Bar
(©J Hand Photography)


At Wondermade, satisfy your sweet tooth with handcrafted marshmallows (sold in boxes to take home), homemade ice cream in creative flavors, s’mores, waffles and other delectable treats. If it’s trinkets and art you’re after, peruse the eclectic goods at Magpies Modern General Store or wander through Jeanine Taylor Folk Art, a collective art gallery housing works for sale from multiple artists. 

Wondermade: 214 E. 1st St., 407.205.9569

Magpies Modern General Store: 215 E. 1st St., 407.495.8549

Jeanine Taylor Folk Art: 211 E. 1st St., 407.323.2774

Treats from Wondermade in Sanford Florida
(©Brooke Fehr)


Join the Alive After 5 street party in Historic Downtown Sanford on the second Thursday of each month (excluding July and August). Festivities include art, music, food, craft beer and shopping. For daily fun, head to the Central Florida Zoo for animal meet and greets and zip lining through the treetops, or take a stroll along the 1.8-mile Sanford Riverwalk, which meanders along Lake Monroe and offers stunning sunsets.

Alive After 5: 203 E. 1st St.

Central Florida Zoo and Botanical Gardens: 3755 W. Seminole Blvd., 407.323.4450

Sanford Riverwalk: E. Seminole Blvd.

Sanford Riverwalk at Sunset
(©Brooke Fehr)