April 27-May 1/KEY WEST – This multi-group (some 60 bands!) music festival is actually happening! It’s one of the first such festivals of this magnitude to return. Performances will occur at various venues, however, most shows will be at the outdoors Truman Waterfront Park Amphitheater.  It features Red Dirt & Americana music and the lineup is outstanding. The headliners are Lucinda Williams, Blackberry Smoke, the Randy Rogers Band, Pat Green, Shovels & Rope, Old 97’s, Wade Bowen, Roger Creager, Jack Ingram, Hayes Carll, Jason Boland & The Stragglers, Stoney LaRue and American Aquarium. VIP packages are sold out. Single-day tickets were due to go on sale sometime around the middle of March and organizers expect them to sell out quickly, especially because reduced capacity for all shows will be in effect. Masks are required. >MORE


May 1-9/WILDLIFE MANAGEMENT AREAS – Take part in a little outdoor competitive scavenger hunting, completely on your own or in groups, by participating in Florida WildQuest, hosted by the Florida Fish and Wildlife Conservation Commission. Download a free and easy-to-use app, pick a designated Wildlife Management Area such as Chinsegut or Tosohatchee, and take photos or videos of plants and animals to earn points while learning about Florida nature and history. You’ll see other players’ submissions in real time and be able to earn the chance to be entered into random prize drawings. Web: https://floridanaturetrackers.com/wildquest/


 May 1-17/DELRAY BEACH – Celebrate mom by giving her a beautiful orchid you can get for free by shopping in one of the prettiest downtowns in South Florida. You will receive one Phalaenopsis orchid for every $200 spent on items purchased at Delray Beach fashion boutiques, specialty stores, gift shops, art galleries, salons and fitness studios. You can also register to win a Mother’s Day prize package valued at more than $500. The package includes dining, spa, shopping and attractions certificates. Masks are required when inside businesses and also when you pick up your orchid.
When: May 1-8 for the shopping to be eligible to get the orchid, May 6-8 to pick up your free orchid and May 1-17 to register for the prize package
Web: downtowndelraybeach.com/mothersday


May 1-15/ST. AUGUSTINE – St. Augustine’s two-week, daily salute to the arts, culture, cuisine and heritage has more than 30 events, many of which are free. The festival’s headliners include Duo Beaux Arts, a husband and wife team of concert pianists (5/1); Mama Blue, a Jacksonville soul singer (5/9); Kaleidoscope of Dance (5/10); and Akia Uwanda, a Jacksonville jazz singer (5/15). Web: https://www.romanzafestivale.com


May 1-2/SANFORD Stroll the tree-lined, brick-paved streets of historic Sanford while checking out an array of artistic works including the festival’s “Art-in-Action” live artist demonstrations and chalk artists coloring the sidewalks. Create your own piece of artwork at one of the workshops and enjoy gourmet dishes at the Culinary Arts Court while acoustic performers play throughout the weekend. >MORE


May 2/LARGO – Spend a day enjoying the outdoors and strolling through a series of public and private gardens in either a docent-led small group tour or a self-guided journey of exceptional garden and landscape masterpieces throughout Pinellas County. It’s the perfect time of the year to get inspiration for planting or re-landscaping, and a fun little peek at other people’s creative use of native plants and flowers. >MORE

Key West Songwriters Festival

May 5-9/KEYWEST – This one features more than 100 performers spread over five days and nights. It features folks who have written songs for and/or performed with lots of A Listers, such as Garth Brooks, Tim McGraw, Reba McEntire, Sheryl Crow, Darius Rucker, Kacey Musgraves, Eric Clapton, Booker T & The M.G.s and the North Mississippi All Stars. The headliners are Lee Brice, Brandy Clark, Lori McKenna, Robert Randolph and Steve Cropper. Most of the shows are outdoors but masks and social distancing are still required. Web: keywestsongwritersfestival.com

St. Augustine Food & Wine Festival

May 6-9/St. AUGUSTINE – This annual festival is set to take place at the Renaissance World Golf Resort. The Festival will showcase the culinary, beverage, and culture of the area, and will feature celebrity guest chefs, local chefs, celebrity winemakers/proprietors, artisans, farmers, local craft spirits, and beers, along with renowned wine, spirits, and beer brands from around the globe. Tickets & packages for the festival are now on sale.


May 7, 22/DAYTONA BEACH – A time-honored tradition on one of Florida’s most famous beaches, this live weekend concert series kicks off in May with some great performance along the Atlantic Ocean – a precursor to the strong summer lineup. Country star Chris Janson headlines the first show followed by the soulful St. Paul & The Broken Bones later in the month. Buy tickets early! Due to COVID-19 protocols, attendance is limited and chairs will be provided. https://www.daytonabandshell.com/


May 8-9/LAKELAND – What began as a small crafts fair on the lawn of a public library nearly five decades ago has now grown into one of central Florida’s largest and oldest free outdoor art festivals, drawing tens of thousands to the shores of beautiful Lake Morton every year. Check out unique works of art from painters, sculptors, etchers, glass blowers, photographers and other artisans from all over the country and enjoy the beautiful lakeside atmosphere.
Web: https://www.mayfairebythelake.org/


May 13-16/BROOKSVILLE – Bring your RV or tent and set up camp at Sertoma Ranch for this five-day outdoor fest and friendly gathering filled with four days of Florida bands playing everything from rockabilly to funk to country and rock. Prepare your own meals at your campsite or buy food and beer from the many vendors on site while enjoying tunes from Uncle John’s Band, Led Zep, Wall of Echoes and other Sunshine State favorites.
Web: http://www.orangeblossomjamboree.com/


May 14-16/WINTER PARk – Known as one of the nation’s oldest and most prestigious juried outdoor art festivals, this 62-year-old event is returning downtown to Central Park after skipping last year, once again drawing hundreds of fine artists entering categories such as clay, digital, leather, printmaking, jewelry, wood and more. There’s also a schools exhibit of student art and interactive art activities for kids.
Web: https://www.wpsaf.org/


May 15/WEWAHITCHKA  Enjoy a day trip to “real” Florida in the one-stoplight town of Wewahitchka, known for a generation of beekeepers harvesting the liquid gold that’s also known as Tupelo honey. Purchase locally-made products featuring the honey, get a picture with the newly-crowned queen of the Miss Tupelo pageant and chill to live music. Also includes arts and crafts, food vendors and kids activities. >MORE


May 15/TALLAHASSEE – Located at the Kleman Plaza Although scaled back to only one day, Springtime Tallahassee is happening in 2021! Shop from arts, crafts and food vendors; cheer on the New Orleans-style krewes and floats during the Grand Parade; and let the little ones expend a lot of energy at the Children’s Park. The day concludes with an evening music festival.
Web: http://www.springtimetallahassee.com


May 18-31/ORLANDO – Held at various venues. This 14-day arts festival celebrates its 30th year as one of Orlando’s most unique cultural events, offering 850 un-juried, uncensored, and highly talented theatre, music, dance performances and artist displays of all genres. Kids Fringe for children and families also returns, bringing entertaining performances by Fringe artists, workshops, hands-on art activities. For those who cannot attend live, check out DigiFringe in June. >MORE


 May 20-23/MIAMI BEACH – Presented by the Food Network & Cooking Channel. The mouthfuls you will get at this four-day foodie extravaganza will be, as always, ginormous and delicious. The 20th anniversary edition of the affair will look a little different this year due to Covid, but there will be plenty of opportunities to experience great food and beverages. There will be a plethora of intimate dinner experiences hosted by some of the country’s most celebrated, critically acclaimed chefs. All but one of the events are outdoors and the organizers are determined to have as safe an environment as possible. Masks are required (except while eating or drinking) and there will temperature checks. Attendees can expect to provide proof and/or attestation of a negative PCR Covid-19 test dated no more than 72 hours prior to the events or alternatively proof of completed Covid-19 vaccination. This is a very popular event and there will be reduced capacities, so book early.
Web: sobewff.org for the complete schedule of events and sobewff.org/covid-guidelines for the Covid-19 measures


May 21/ST. PETERSBURG – It doesn’t get much better than tacos and cold beer on a waterfront setting in May. Located in the Albert Whitted Park.  Returning for a fourth time, this fiesta expands beyond those two delicious staples and includes two dozen gourmet food trucks serving special South American-inspired dishes along with their usual fare of everything from BBQ to sweets. Kids and pets are welcome, and bring your picnic chairs and blankets. The first 300 guests will get a free sombrero this year. >MORE


MAY 22-23/SAFETY HARBOR – Waterfront Park. Among one of the best spots to stroll an outdoor event, Safety Harbor is beginning to welcome back its springtime weekend offerings of fresh air, good food and beautiful artwork. This free fest combines a juried art show with a number of vendors serving delicious shrimp, fish and other seafood dishes along the beautiful waterfront and quaint downtown area. The artists’ work will include mixed media, paintings, 3-D artwork, photography, wood, metal, fiber and jewelry.
: https://www.safetyharborchamber.com/events/details/art-seafood-on-the-waterfront-2021-free-event-7579


May 20-23/COCOA BEACH – Returning in 2021 with some new event categories, this offshore boat racing event brings some of the world’s fastest speedboats and lots of adrenaline to the shores of the Space Coast. The five-day event draws bigger and bigger crowds each year, adding buzz to the live entertainment, dancing, parties and chances to see the impressive speed boats and racing teams up close at Race Village in Port Canaveral. Can’t catch it in person this year? Download the event’s app to live stream the races. https://www.thunderoncocoabeach.com/

The Hyundai Air & Sea Show

May 29-30/MIAMI BEACH – This event is part of the National Salute to America’s Heroes weekend. It features the United States Air Force A-10 and also showcases the men, women, technology and equipment from all five branches of the United States Military and police, firefighters and their first responder agencies. There are several VIP packages to consider. Masks are required except in open beach areas while seated and while seated in designated spaces to eat and drink. >MORE