It's FINALLY time to PLAY in Orlando this May!

Sip & Stroll at Pioneer Village

May 1


Take a stroll through history and enjoy an evening of food and refreshments during the May Day Sip & Stroll at Pioneer Village. This event is a fundraiser for Osceola's history and includes live music and a silent auction!


St. Johns River Festival of the Arts

May 1 - May 2

Join in the fun Saturday, May 1st from 10 a.m. – 6 p.m. and Sunday, May 2nd from 10 a.m.-5 p.m., 2021 in Historic Downtown Sanford, Florida as the brick streets get transformed into an artist mecca for the 10th Annual St. Johns River Festival of the Arts – A Fine Arts & Fine Crafts event with artwork from some of the best artists in the country!

See Art-in-Action from live artist demonstrations and create your own piece of artwork at workshops scheduled during the weekend. Enjoy gourmet tastes at our ‘Culinary Arts Court’ while you listen to the sounds of acoustic performers.

Come spend the day in beautiful Historic Downtown Sanford and take home a beautiful piece of art to add to your art collection.


Mayfaire by the Lake

May 8 - 9

Held on Mother’s Day Weekend each year, this event has blossomed into one of Central Florida’s largest outdoor arts festivals.

Around 165 artists display creations from clay to jewelry and painters of all categories. There is a hands-on children’s Art Tent where the kids can create a unique gift to give to Mom for Mother’s Day.

Food and beverage vendors will offer an endless supply of everyone’s favorites. Corn dogs and funnel cakes will keep the kids (and some Moms and Dads) happy.

On Saturday, May 11th, the fun continues into the night at Lake Mirror, just two blocks north of Lake Morton, with live music, picnics, food trucks, a bouncy castle, a 5K run, and a fireworks show.

Free parking and shuttle service are available, and entrance is free.


Orlando Taco Week

May 1 - 4



It's been known for some time that Orlando is an innovative culinary hot spot. We are celebrating the city's most creative creations - Tacos! Each restaurateur and Chef will prepare their unique take on a taco with a taco special. The idea is to get people to embrace the food, culture, and Orlando-love while getting out to eat, drink, and try new places! Download your taco passport to print and get it stamped at participating locations. Taco Week will draw hardcore taco fanatics and people that appreciate a deliciously crafted meal.


The Winter Park Sidewalk Art Festival

May 14-16


The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest and most prestigious outdoor art festivals. The Festival debuted in March 1960 as a community project to bring local artists and art lovers together. It is produced by an all-volunteer board and draws more than 350,000 visitors each year. Over 1,100 artists from around the world apply for the Festival each year. An independent panel of three judges select the 225 artists who will exhibit their works. The Festival consistently ranks as one of the top juried fine art festivals in the country with high rankings in Art Fair Calendar’s “2019 Best Art Fairs”, Art Fair Source Book’s rankings and Sunshine Artist Magazine’s “Top 100” lists. The 2021 Artists Application is by invitation only this year and is being extended to the final 2020 accepted artists.


The Orlando International Fringe Theatre Festival

May 18 - May 31


The Orlando International Fringe Theatre Festival is a 14-day immersive cultural experience held annually, featuring 850 ticketed theatrical performances and a free outdoor music festival. Loch Haven Park serves as the main campus for the festival, though in recent years programming has expanded to venues in nearby Ivanhoe Village and Winter Park. The festival unites local, national, and international artists with the Central Florida community, creating a uniquely diverse arts experience.



Bok Tower Gardens

All Year Round


If Mom loves flowers, plants, and nature, you can’t go far wrong with a Mother’s Day trip to one of Central Florida’s awesome botanical and natural gardens. Explore lush backdrops of flowering foliage with sweet aromas filling the air. It’s FREE admission for Mom’s on Sunday, May 10th, 2020 at both Bok Tower Gardens and Harry P Leu Gardens. This 250-acre woodland setting offers a totally tranquil setting where Mom can get some real peace and quiet. Bok Tower Gardens is a designated site of the Great Florida Bird and Wildlife Trail.


We hope our list has helped you plan your spring vacation!