Whether you’re a novice or budding sommelier, these Central Florida wine walks provide an opportunity to expand your palate and increase your knowledge of vino, often while perusing goods from local businesses and artists. Sip and stroll all over town from the Thornton Park District to Mount Dora and New Smyrna Beach and everywhere in between. Here are a few of our favorites for date nighters.

Update August 2024 by Meghan Roth.

MONTHLY WALKS

Thornton Park 2nd Thursday Wine and Art Walk

Orlandoans are no strangers to the monthly 2nd Thursday Wine and Art Walk in Thornton Park. More than 20 businesses participate, including area favorites like Soco, The Stubborn Mule, Dexter’s, and Maxine’s on Shine. There are also art vendors, DJs, and live music throughout the district in between tasting stops. The glass pick-up location changes each month, so be sure to check the Facebook event page before attending. The event is also cash only, so come prepared with $15 cash for your glass and map for the evening, but you can get your tickets online ahead of time for only $10.

Clermont Main Street Wine Strolls

Explore historic Downtown Clermont while sampling 25 different wines at participating shops. Rain or shine, head to Downtown Clermont for this monthly event and enjoy sampling a variety of red, white, and rose wines at over 20 participating local businesses. Wine sampling starts at 6:30pm at each of the 20+ locations. You will receive a map of participating locations at Check-In where you will receive your wine glass and wristband for the evening.

To Check-In for the event, head over to The Art Walk (between The Animal League & Black Bear Kitchen) where wine glasses & wristbands for each wine stroller are picked up to start your Downtown Clermont exploration. In-Person Ticket Sales & Check-In starts at 5:30pm on The Art Walk.

Maggie’s Attic Wine Tasting Events

There’s no need to wait for a festival to make your way to Mount Dora. Local wine shop and bar Maggie’s Attic hosts wine tastings on the 1st and 3rd Saturday of each month from 6-8pm. Throughout the evening, you’ll explore seven venues throughout Mount Dora offering tastings of 20+ wines from around the world. Bonus perks include appetizers throughout the walk, and live music at Maggie’s during the event. Tickets are $17 and can be purchased in advance. FYI: your wine glass/cup must be empty while you’re on city sidewalks and streets.

Flagler Avenue Wine Walks

Feel like hitting the coast? Flagler Avenue in New Smyrna Beach is a walkable strip full of restaurants, cute shops and bars lining the streets all the way to the beach. Every month, the streets become home base for the monthly Flagler Avenue Wine Walk. This lively event lasts for a whopping six hours (1-7pm) and invites you to taste up to 20 of the 100+ featured wines available for sampling.

Wine Walk tasting passports are $30 and include 20 tasting tickets along with a keepsake wine glass, map, and listing of each host locations wines for the month. During the event, locations offer both one and multi-ticket wines to sample of the 100+ featured wines for the month. Bonus: participating restaurants offer dinner specials for participants beginning at 6pm.

SEASONAL WALKS

Jingle Eve “12 Wines of Christmas”: November

Stroll the Ivanhoe Park district with a keepsake glass, sampling wines curated by Tim’s Wine Market during Jingle Eve's 12 Wines of Christmas. Guests will enjoy a pour of red or white wine at each retail stop. Wine walk tickets are $50 and include wine at 12 stops and a keepsake glass.

Winter Garden Wine Walk: June and November

Winter Garden is fast becoming one of our favorite locales for a date night away from the city thanks to an awesome weekend farmer’s market, Plant Street Market, the West Orange Trail and the unique businesses and restaurants lining Plant Street. The Winter Garden Wine Walks in June and November are another favorite featuring live music, wine tastings at multiple tasting stations, and food pairings. Tickets include a wine glass and guide to the tasting stations. Keep an eye on the Garden Choir Facebook page for upcoming events.

Bok Tower Gardens: Spring and Fall

Bok Tower Gardens may be a bit of a haul from Orlando, but it’s worth the drive, especially if you line up your visit to coincide with one of the fun seasonal events. Each spring and fall, the gardens host a seasonal wine walk where you’re invited to sample 10 curated wines and light bites. After the sampling ends, the after party, featuring live music and dinner specials, begins. Tickets are $50-65 for non-members.

Audubon Park Love Local Wine Walk

Support one of our beloved Orlando Main Street Districts and the small businesses that call the Audubon Park Garden District home. Enjoy trying different wines, district-wide, at multiple stops during their annual Love Local Wine Walk. Advance price for the wine walk with the souvenir wine glass is $20. Each wine glass is etched by hand in Audubon Park so quantities are limited. Advance price for the wine walk with standard plastic cup is $15.

Winter Park Sip, Shop & Stroll – March and November

A favorite among Orlando Date Night Guide readers, the twice annual Winter Park Sip, Shop and Stroll has been continuously voted in the top three for Best Periodic Event in our Annual Date Night Awards. The event invites you to stroll through Park Avenue visiting the area’s top restaurants and boutiques while sipping wine and sampling hors d’oeuvres. Tickets are $25. The fall 2024 Sip, Shop and Stroll is November 18, 202 from 5-8pm. Participating vendors this year include Cocina 214, 310 Park South, blu on the avenue, and Tabla among others. Feature image credit: WineART Wednesday

Sanford Wine Walk: Multiple Times per Year

Explore the vibrant streets of Downtown Sanford while indulging in an evening of hand-picked wines. From 6 PM to 9 PM, embark on a delightful tasting journey. Explore a dozen charming locations, each offering two unique and exciting wine samples. All proceeds benefit Theater West End, Sanford's first and only professional theater. Tickets range from $20-30. Tickets include a wine glass and printed guide to tasting stations