Article originally written by Stephanie Patterson (November 14, 2017) | Updated by Nancy DeVault (May 12, 2025)
Most of us don’t have endless funds to spend on date night, but money doesn’t need to be a roadblock to spending quality time together. The following free walking tours in Orlando will expand your mind while you bond over a new shared experience.
Free Guided Walking Tours in Orlando
Central Florida Railroad Museum
Type of tour: Guided, indoors
Length: 15 minutes or so
Frequency: Daily during operating hours
Reservations required: No
The Central Florida Railroad Museum in Historic Winter Garden offers free admission and guided tours by volunteers, inviting residents and visitors alike to explore Central Florida's rich railroading history. Housed in a 1913 Tavares and Gulf Railroad depot, the museum showcases artifacts, photographs, and an extensive dining car china collection. This little gem is open Tuesday through Saturday, 11am-3pm.
Of course this locale makes for easy access to plenty of other Winter Garden based date nights.
Downtown Orlando Historic Walking Tour
Type of tour: Guided, outdoors
Length: 1.5 hours
Frequency: First Friday of each month at 9:30am, or download the map for self-guided
Reservations required: Yes
Couples eager to learn more about Orlando’s history while visiting historical sites should plan to do the free Downtown Historic Tour. Led by the City of Orlando Historic Preservation Board, this 1.5-hour informative walking tour highlights buildings of historical significance in our beloved Downtown Historic District.
This free walking tour is offered once monthly with a guide from October to early May each year. During the off-season, use the download the walking map for self-guided adventuring. There are nearly 30 historical buildings included in the walking map, each with accompanying historical information.
Lakeridge Winery Tour & Tasting
Type of tour: Guided, indoors
Length: 30-45 minutes
Frequency: Every 30 minutes daily
Reservations required: No
Located in Clermont on a 127-acre estate, Lakeridge Winery & Vineyards is a brief 30-minute drive from Downtown Orlando. You'll hardly feel like you're still in Florida as you sip a glass of wine while looking at the unexpected rolling hills and lush vineyards. Lakeridge Winery produces wine from muscadine grapes which are native to the Sunshine State and are best utilized for sweet wines.
The free winery tour and tasting is offered every 30 minutes or so during open hours, starting at 10am with the last tour at 4pm. The tour itself lasts about half-an-hour and begins with an introduction video about Florida wine, the winery itself, and the winemaking process. Afterwards, you'll get a peek at the vineyards as your tour guide shares more information about the winery and its sister site, San Sebastian Winery in St. Augustine. The best part of this free tour is saved for last… a guided tasting of nine wines, as well as suggested pairings.
I'd be remiss not to mention Lakeridge Winery's numerous yearly festivals. From the annual Harvest Grape Stomp to the regularly scheduled music line-up, there's usually something going on at this local winery at all times. Admission to the winery, tour, and tasting is always free, but festivals typically have a nominal fee. If you visit during a festival, the winery tour & tasting may have a slightly different format. Instead of doing the tasting at the bar, you'll receive a small tasting glass for sampling wines at seven stations throughout the winery.
Happy Hour Tour at The Alfond Inn
Type of tour: Guided, indoors
Length: 60 minutes
Frequency: First Wednesday of the Month at 6pm
Reservations required: Yes
While it’s totally worth it to splurge a little on a romantic staycation at The Alfond Inn, you can take a sneak peek at this boutique hotel without spending a penny. Along with luxurious furnishings, a romantic courtyard, and top-notch eats at Hamilton’s Kitchen, this stunning Winter Park hotel is also home to an impressive contemporary art collection.
The art is part of the Alfond Collection of Contemporary Art, started by Rollins College graduates Theodore & Barbara Alfond. Most all of the collection is on display at The Alfond Inn for you to see. Treat your eyes and your mind by attending the weekly tour, where adult beverages are available for purchase for those 21+.
Free Self-Guided Walking Tours in Orlando
Walking Tour at Greenwood Cemetery
Type of tour: Self-guided, outdoors
Length: You decide… the cemetery is four acres!
Reservations required: No
The Greenwood Cemetery used to offer one of the most popular free walking tours in Orlando with a grounds guide. However, this cemetery has since shifted to a self-guided digital format so wanders can come and go at their leisure (open 7am-7pm daily). Near the entrance gates, find a flyer with QR code information to get started.
During your mobile-guided meander, expect to be exposed to a treasure trove of information about Orlando’s past, as well as key figures that helped shape the city as we know it today. The cemetery opened in 1880 and, despite being a final resting place of hundreds of departed Orlandoans, this walk is indeed restful and enjoyable.
Structured walking tours used to span up to four miles within the 100-acre cemetery, which took about two hours to do. Now self-guided, do all or some as you wish.
Historic Walking Tour of Winter ParkType of tour: Self-guided, outdoors
Length: 20 stops to explore at your leisure
Frequency: Anytime
Reservations required: No
Date night on Park Avenue can be pricey, but it doesn’t have to cost a dime. Orlando Dater Night Guide suggests visit on a Saturday morning and take a stroll through Central Park, then wander through the Farmer’s Market and, lastly, embark on a free Historic Walking Tour.
Winter Park has a rich history and stunning architecture, and you’ll get a feel for that as you saunter on this self-guided walking tour. The tour includes more than 20 historical locations, with accompanying background information. Visit all of the stops, or choose your own adventure and explore the ones that intrigue you most.
There are four optional stops including Casa Feliz, a historic home museum open for tours on Tuesdays, Wednesday, and Thursdays (for the suggestion donation of $5). You can also download this brochure for a self-guided tour of Casa Feliz.
See Art Orlando Walking Tour
Type of tour: Self-guided, outdoors
Length: 8 public art sculptures to visit at your leisure
Frequency: Anytime
Reservations required: No
The arts are alive in Downtown Orlando thanks to monthly gallery hops, annual performance art events like IMMERSE, spectacular performances at the Dr. Phillips Center for the Performing Arts, live music venues, and more. Adding to our town's artsy culture, See Art Orlando makes for a lovely date night for couples.
This self-guided tour of eight public works of art permanently was installed by Orlando Mayor Buddy Dyer and the See Art Orlando Board of Directors. Almost all of the installations are located around Lake Eola; so, do this art stroll near sunset time for added romance. To experience the tour, just download the walking tour guide on your phone. The accompanying text for each installation provides insight on the work of each artist.
More Free Tour in Orlando
- A Day For The Arts: A self-guided itinerary by United Arts Central Florida and Visit Orlando, there are options for Downtown Orlando, Mills 50 District, and Winter Park.
- Mennello Museum of Art: On the first consecutive Saturday and Sunday of the month, this gem in Loch Haven Park offers free admission to holders of Bank of America or Merrill Lynch bank cards, as part of the Museums on Us Program. Guests should present their card and valid photo ID for admission.
- Rollins Museum of Art: Free docent-led museum tours are led on Saturdays at 1pm and 3 pm.
Check out our post on 75 Free Things to do in Orlando for even more ideas.
About the Author/Photographer:
Stephanie Patterson is the managing editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at www.spattersonphotography.com and www.traveltasteclick.com.
