Exploring Sanford's Food, Culture, and Downtown Charm
There is no shortage of ways to get out and find an adventure around Orlando. Many times we are asked, "What are some of the best day trips from Windermere?" For longtime Windermere residents, Sanford is always near the top of the list. This waterside town has a true mix of historic downtown charm and a thriving food and craft beer scene, offering visitors an eclectic experience. Many times locals find themselves at the Sanford Airport, whether it be for a pick up or drop off, making it a perfect excuse to head downtown and escape for the afternoon. One of the advantages of living in Southwest Orlando is being so close to many vibrant Central Florida destinations.

How Far is Sanford from Windermere?
From downtown Windermere, heading up the 429 makes it a fairly straightforward route directly to downtown. This route is approximately 40 miles and will take about 50 minutes to an hour or so, depending on traffic. You can also take I-4, or even the 417 (especially if you're heading to or from the Sanford Airport). This is why we love planning a half-day or even a full-day visit. Parking is available street-side, and you'll find several public parking lots within excellent proximity to the downtown hub along 1st Street. Visitors can hop on the free trolley service that provides transportation with multiple stops around downtown Monday through Saturday. The Trolley also connects with Sunrail Monday - Friday starting at noon.
What can you do in Sanford in a day?
The downtown area is compact and easy to explore. With many restaurants, breweries, and shops located close together, it's not a challenge to park in one location to access many of the highlights. Some of our favorite things to do in downtown is ducking in the quaint shops like the Spellbound Bookstore, perfect for the book lover in your family. Think modern-day Shop Around the Corner for all the You've Got Mail fans out there. This cozy, independent bookstore features tons of curated book collections, gifts, stickers, and more.
Afterwards, head around the corner onto 1st Street and you'll find plenty of places to grab a bite to eat or a pint. If you're seeking an evening outing, be sure to check out which shows are being performed at the Theater West End. Whether it be a stand-up comedy series, musical, or play, there is something for the whole family.

For first-time visitors, you can't miss a stop at Hollerbach's German Restaurant. A staple in downtown Sanford known for their authentic German experience. From the moment you walk in, you're immediately greeted by long tables lined up around the center stage. If you've been seeking a traditional bratwurst, kase spatzle, or our favorite, the giant Bavarian pretzel, with a side of sweet mustard and a scoop of Hollerbach's tasty Obazda spread, you've hit the German jackpot. Anybody else drooling right now? Oh, and if you are picturing a giant 3-liter draft beer stein filled to the brim, they have you covered. Wrap it all up with a live in-house German Folk band and you'll be singing Zicke-Zacke, Zicke-Zacke, Hoi, Hoi, Hoi right along with the whole restaurant. Don't sleep on the craft root beer, it's not to be missed.
Afterwards, make your way over to the Hollerbach's German Market for snacks, meats, and all the Haribo gummy bears you can dream of. In between, the charming German giftstore, Hollerbach's Outfitters, has your full supply of Lederhosen, traditional Drindl dresses, and a selection of Christmas decor and gifts, perfect to commemorate your visit. Another favorite is Wondermade, featuring locally made, unique-flavored marshmallows. Take a sweet treat home with so many options to choose from, including seasonal flavors, Florida flavors, and so many more. In fact, The Funk Collection partners with Wondermade for a special custom treat that goes out in our closing gifts, so the team is no stranger to the magic of the marshmallow. You can also find them at Disney Springs at their outdoor kiosk near Paddlefish.
Experience the Sanford Riverwalk
Before you head out of town, a stop at The Sanford Riverwalk is perfect for a stroll along the shores of Lake Monroe. The Veterans Memorial Park is a must-visit, dedicated to those who have served in the military. There, you can read informational kiosks and see the towering monument, dedicated to the memory of those who served in the First World War. A peaceful location to reflect and a prime spot to catch the sunset across the water.
Final Takeaway | Why is Sanford one of the best Day trips near Orlando?
If we haven't convinced you with the small but mighty sampling of our favorites, there is so much more to see and do in Sanford. A mecca for all things craft brewery, be sure to check out one of the many local brews throughout the city. There is even a Craft Beer & History Tour available on weekends, so that you can hit the highlights, all while learning a bit out the history of prohibition in Sanford. River tours, ghost tours, and even airboat tours are also offered. Did we mention events? From the Annual Sanford Jazz in the Park Festival to the monthly Sanford Food Truck Fiesta or weekly Saturday Farmers Market, there is no shortage of fun to be had, making Sanford a repeat visit.

For those who have called Southwest Orlando home for decades or are considering a move, The Funk Collection team is well-rooted in local knowledge to help you find your next home with easy access around our great Orlando region. Curious about available homes in Windermere or surrounding Orlando? Start browsing today.
Posted by Jeffrey G. Funk P.A. on
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