Sanford will surprise you with charm, beer, food and nearby biking and kayaking

I’ve seen this historic riverfront town a half hour from Orlando called a “hidden gem” or “Central Florida’s best kept secret.” Turns out, it’s not hype, it’s true. Sanford is having a renaissance. When I visited recently for a long weekend, I was surprised how lively and fun Sanford is today.

There are tons of things to do in Sanford, Florida. There’s a beautiful riverfront where you can walk or bicycle for miles. Within a half hour, there are two wild and wonderful rivers to kayak and numerous hiking trails.  Sanford has a charming brick-paved downtown filled with preserved historic buildings enlivened with restaurants, breweries and bars. 

I’ve lived in Florida long enough to know this wasn’t always the case with Sanford. When the Navy airbase closed in 1969 and Disney World opened in 1971, the city went into a slump.

Eventually, those decades where economic activity waned in Sanford meant there weren’t a lot of reasons to tear down old houses and buildings.

Today, that old A&P store in downtown Sanford is Dees Brothers Brewery. The old police station and jail is the Old Jailhouse Kitchen and Spirits. The train station is Henry’s Depot Culinary Collective, a popular food hall.

The nearby residential historic district is a splendid neighborhood shaded by hundred-year-old live oaks arching over carefully restored homes where golf carts are used to buzz around town.

With its proximity to Orlando, just a half hour away, Sanford is more young, hip and artsy than the old Southern town some might have expected.

Give it three days, and the many things to do in Sanford Florida will reward you with a great weekend.

Here are 10 reasons I fell in love with Sanford, Florida

Lake Monroe and our houseboat Airbnb

Lake Monroe, part of the St. Johns River system, is big (roughly 5 miles long and 4 miles across) and beautiful. It’s popular with manatees, fishermen, sailboats, power boats, pontoon boats and, to our delight, houseboats.

We rented a houseboat in the Downtown Sanford Marina for three nights and loved staying on the water, surrounded by other boats, a block from the lively downtown.

 There are a handful of houseboats for rent via Airbnb or VRBO, all of which are kept at the dock. (No cruising.) They’re in the $150-$200 a night price range, plus the various fees and taxes. If you want to take a boat out on the water, the marina’s Buzz Boats rents pontoons for $240 for a half day plus yachts and fishing boats for more.

There is also a popular and picturesque paddlewheel lunch or dinner cruise aboard the St. John’s Rivership, which is reminiscent of the days when steamships originally put Sanford on the map.

Sanford’s RiverWalk along Lake Monroe for biking and walking

For five miles along Lake Monroe, a paved path 12 to 14 feet wide hugs the shore. In the city, the RiverWalk is popular for walking and watching sunrise and sunset views over the lake. It’s lined with signs telling the area’s history and appealing swinging benches.

An extension to the RiverWalk completed in 2021 takes the pathway west to the Central Florida Zoo near I-4. The extended path makes it a great bike trail where you can do 9.5 miles out and back. It will connect to the 250 mile Coast-to-Coast trail from Titusville to St. Petersburg, which is under development. (Rambler tip: The trail is big on pretty scenery views the lake, but is low on shade, making it a better ride in early mornings. )

You can rent bikes in downtown Sanford at Bicikleta Bike Shop. (Only $15 for two hours.) You can also rent surreys for a family or group there.

Historic downtown Sanford Florida: Walkable and well-preserved

The downtown, about eight blocks square next to Lake Monroe, is a national historic district with 25 notable historic buildings. Many have been painstakingly restored, with stucco removed to reveal the bricks and windows returned to the original appearance. The wide sidewalks and paving are brick – some historic; some made to match.

The center of the downtown is a charming square at Magnolia and First Street, where a fountain and historic clock anchor a space where a farmers and artisan market is held every Saturday.

If you’re interested in learning more about the town, we recommend a walking tour from Sanford Tours and Experiences. We took the Downtown Sanford History and Architecture Tour, which was excellent. There’s also a Craft Beer and History Tour, where you sample  beer at three establishments and are guided by a certified beer judge.

Sanford Florida’s wonderful craft beer scene

Instead of viewing other breweries as competition, people in Sanford’s craft beer business talk about how more breweries in the city is a win-win for everyone, making Sanford a beer lover’s destination and increasing every brewery’s customer base.

When we were in Sanford, we tried one brewery at happy hour and then strolled to another brewery, a few blocks away, for dinner and another beer. All of the breweries will provide small servings so you can sample multiple beers. It’s easy to chart your own Sanford brewery tour.

The breweries are:

• Community Brewhouse, 115 Magnolia Ave., Sanford, FL 32771, which opened in 2012 as the Sanford Homebrew Shop.
• Deviant Wolfe Brewing, 121 W. First St., Sanford, FL 32771
• Dees Brothers Brewery, 210 Magnolia Ave., Sanford, FL 32771
• Sanford Brewing Company, 400 Sanford Ave., Sanford, FL 32771
• Wop’s Hops Brewing Company, 419 Sanford Ave., Sanford, FL 32771, which was Sanford’s first craft brewery.

There’s more, too: There’s  a cidery, Tuffy’s Bottle Shop/ Lounge, 200 S. Myrtle Ave., Sanford, Florida 32771, with a big beer garden and a live music venue with ticketed shows.

There’s a craft distillery, Loggerhead Distillery, 124 W. Second St., Sanford, FL 32771, also in the historic district, where you can sample and buy interesting liquors, including a key lime gin.

And there are many bars and restaurants with craft beers on tap, including a big craft beer garden, Celery City and a café specializing in Belgian beers (and foods!), Buster’s Bistro, 300 Sanford Ave., Sanford, FL 32771

Sanford is becoming a foodie haven

The walkable downtown historic district also offers a remarkable number of dining choices as Sanford has become a magnet for foodies.

The original downtown draw starting in 2001 was the large and popular family-run German restaurant Hollerbach’s Willow Tree Café, now with three stories including a rooftop garden. It’s at 201-205 E. First St., Sanford, FL 32771. Highly rated on Yelp and Trip Advisor, it draws people from across Central Florida and we saw lines of people waiting for a table. There are often polka bands. (Rambler tip: Mark this down as a great Oktoberfest destination.)

But there are also chef-driven farm-to-table restaurants (The Tennessee Truffle, 125 W. First St., Sanford, FL 32771, and The District, 112 W. Second St., Sanford, FL 32771, among others) plus a whole range of cuisines  – Jamaican, Korean, Belgian, Italian, Greek, Southern, barbecue, pizza, Irish, Mexican, Soul Food and more. In addition, all the breweries serve food, often excellent and affordable.

There are also affordable Sanford classics — The Colonial Room, a cozy spot popular for breakfasts and comfort food, and the Original Christo’s, a casual family owned spot for pizza, burgers, salads, sandwiches and more.

Strolling Sanford’s beautiful historic residential district

The live oak trees won my heart immediately – such magnificent specimens, one more beautiful than the next, lining the streets in this second historic district. The area has 434 homes built between 1886 and the 1920s on the National Register of Historic Places.

If you enjoy historic homes and buildings, just wander south of the downtown. The district is bounded by Sanford Avenue, 14th Street, Elm Avenue, and Third Street.

A good place to start is Touhy Park at Sixth Street and Elm Avenue, or “the tree park,” as it is nicknamed. There are more than 80 varieties of trees that come from seedlings from historic places, such as Mount Vernon, Valley Forge, Ellis Island, Antietam and Gettysburg. 

If you walk in any direction from this park, you’ll pass historic schools, churches and homes, many landscaped beautifully. When a building in the historic district has to be replaced (like after a fire), its replacement has to be one of a specific set of styles to blend into the district.

Sanford Porchfest, Sanford, every February
Lively music-filled Sanford has a one day free music festival described this way: “17 porches; over 70 bands.” This town fills its beautiful oak-shaded historic district with free concerts you attend by strolling from block to block all afternoon.

Sanford is 20 minutes from Katie’s Landing on the wild and scenic Wekiva River

This outing from Sanford will take you into a different world nearby. We loved the fact that our stay in Sanford included paddling a wilderness that we had had all to ourselves followed by a stroll in a friendly small-town downtown for dinner and drinks.

The Wekiva River is one of only two designated National Wild and Scenic Rivers in Florida. (The other is the Loxahatchee in Jupiter.) The famous and most popular part is 17 miles upstream where the Wekiva originates at stunning Kelly Park/Rock Springs Run.  (Here’s a Florida Rambler story on the Wekiva there.)

The Wekiva at Katie’s Landing is also beautiful, although it isn’t the clear sand-bottom spring run that is so stunning at its start. It is also much less crowded and busy.

Katie’s Landing, part of the Florida State Park system, is the only launch site for canoes and kayaks on the river inside Lower Wekiva River Preserve State Park.

You can arrange for kayaks and livery back to Katie’s Landing for a 10-mile downstream trip through Adventures in Florida, which also offers guided tours.

You also can launch your own kayak or canoe, as we did, and paddle up or downstream and back again. (Just leave enough energy to paddle back if you start downstream with the current.)

On our November paddle trip, my husband and I paddled downstream and were thrilled to see splashes of fall color in the native red maple trees and golden bald cypress trees, as well as to see sandhill cranes, alligators and a variety of birds.

Across the street from the kayak launch is the start of the Sand Hill Nature Trail, one of several hiking trails in the area.

Katie’s Landing has restrooms, picnic tables and grills; however, there is no potable water.

There’s much more to explore along the Wekiva. Here’s a guide from Florida Rambler: Wekiva River Basin’s stunning beauty invites paddlers, campers, hikers and bikers

Sanford is 30 minutes from places to paddle the stunning Econlockhatchee River

Here’s another terrific kayak trip we built into our Sanford getaway.

The Econlockhatchee  — let’s just call it the Econ, OK? — is an exceptionally pretty river that flows through a wild corridor. It is a designated as one of three dozen Outstanding Florida Waters. For miles, it is lined with large, old live oaks whose limbs are covered with air plants and resurrection ferns. There are various places to launch and take out, and you can use an outfitter to paddle downstream on a one-way trip.

We did an 11 mile paddle ending at the St. Johns River. An alternative is an 8.5 mile trip that starts upstream from where we paddled. You can also do it as an out-and-back too.

This is a river for beauty and solitude: On our trip, we saw exactly one other boat in 12 miles.

What we did see: Many alligators, most of whom plunged into the water the instant they heard or saw us, and a variety of birds, including a spectacular roseate spoonbill that let us get close enough for good photos.

We’ll return to paddle more of the Econ!

More from Florida Ramber about kayaking the Econlockhatchee.

Scenic and wild hiking trail in Black Bear Wilderness Area

We haven’t hiked this, but next time we’re in the area, we will. The Black Bear Wilderness Area Trail is a seven-mile hike and it offers some great scenery along the St. Johns River, some boardwalks, but also sections that are quite challenging. Here’s some information from All Trails.

Hotels and lodging in Sanford

Sanford needs a downtown hotel; with all its appeal, such an accommodation is sorely lacking.

Alternatives are the houseboats and other houses and cottages you can rent on Airbnb or VRBO.

In the historic district, you’ll also find Park Place Inn and Cottages, 1301 S. Park Ave., Sanford, FL 32771, which gets good reviews. This small complex of cottages and apartments was built in 1924.

Beyond these options, you’ll find a variety of standard chain hotels in Lake Mary near I-4 and near the Orlando Sanford Airport.

Transportation: Auto-train, Sanford airport, SunRail and trolley

Sanford got its start as a transportation hub, and it still is. In the 19^th century, people arrived by steamship on the river and then could take trains on the Henry Plant (not Henry Flagler) railroads to “South Florida,” which meant Tampa Bay and Punta Gorda, not Miami.

Trains are still a reason a lot of people visit Sanford. We first came to Sanford to take the Auto Train, an Amtrak service that takes you and your car (same train, but on different cars) from Sanford to the Virginia suburbs of Washington DC. The Auto Train station is located about two miles west of historic downtown Sanford.

The Orlando Sanford International Airport, the site of the Navy air base that closed in 1969, is located about five miles south of downtown. It gets its international status from flights to and from Canada.

Sun-Rail, a commuter rail system in the Orlando area, has service to Sanford. The station is about two miles west of downtown.

From the Sun Rail station, there is a free trolley to downtown Sanford, which then loops through the historic district about a dozen times daily (except Sunday.)

Those coming by car will probably do so on I-4; nearby exits are about five miles from downtown Sanford.

Things to do in Sanford Florida region from Florida Rambler

• A half hour away is a community where we’ve enjoyed a weekend, charming historic town, Winter Park.
• We love a terrific nearby beach town, New Smyrna Beach, 45 minutes east.
• We have lots of ideas for natural adventures in the area in this article: Eight natural places to enjoy in Orlando area