Jailbreak 5K
Escape from St. Augustine! This one-way 5K takes you from the St. Augustine Old Jail across the Vilano Beach Bridge, through the Porpoise Point neighborhood and ends at the Vilano Beach ramp where a shuttle will bring you back to the start line. Proceeds benefit INK (Investing in Kids) and provide innovative programs, teacher support and classroom resources to promote the academic success of all St. Johns County public school students. Registration is $25-$45. 167 San Marco Ave., St. Augustine. www.runsignup.com/Race/FL/SaintAugustine/EscapeFromStAugustine
Location
Old Jail Museum
167 San Marco Ave.
St. Augustine, FL 32084
Why Go:
Lace up your running shoes for the Jailbreak 5K, an exciting one-way race that challenges participants to “Escape from St. Augustine!” Starting at the historic St. Augustine Old Jail on San Marco Avenue, runners will race across the scenic Vilano Beach Bridge, sprint through the beautiful Porpoise Point neighborhood, and cross the finish line at the Vilano Beach ramp, where a convenient shuttle service waits to return everyone to the starting line. Registration ranges from $25 to $45, with all event proceeds directly benefiting INK (Investing in Kids) to fund innovative public school programs and classroom resources throughout St. Johns County.
Wander & Rest Tip
Since this thrilling race literally finishes right at the Vilano Beach ramp, you are already just seconds away from your peaceful coastal sanctuary! After crossing the finish line and catching your breath, you can skip the return shuttle crowd entirely and head straight back to your neighborhood. Celebrate your fantastic finish by swinging past 180 Vilano Grill & Pizza for a hot, comforting post-race lunch, or take a quick drive into the historic district near 36 Granada to experience the French Pantry collective for a premium celebratory afternoon refreshment. Back at your private Wander & Rest retreat, transition from peak athletic performance into absolute coastal luxury. Deeply soothe your exhausted running muscles inside our private sauna, melt away any lingering physical tension in the bubbling hot tub, or enjoy a well-deserved, refreshing recovery swim in the pristine heated pool before curling up in our ultra-comfortable indoor lounge areas for a perfect afternoon rest.
Celebrate Cinco de Mayo all month long with the Salsa into a Fiesta Extravaganza, a guided culinary tour through St. Augustine from 12:30-3:30 p.m. Travel by open-air electric vehicle with a local guide and visit four Latino-inspired hotspots, enjoying bites like street tacos paired with cerveza, sangria, wine, and cocktails. Tickets are $145 and include all tastings, drinks, and transportation. 5 Palm Row, Ste. D, St. Augustine. www.thetastingtours.com
Location
The Tasting Tours
5 Palm Row, Ste. D
St. Augustine, FL 32084
Why Go:
Celebrate Cinco de Mayo all month long with the Fiesta De Mayo Tour, a vibrant culinary journey through the flavors of St. Augustine. Led by The Tasting Tours, this three-hour experience whisks you away in an open-air electric vehicle to four premier Latino-inspired hotspots for delicious street tacos and refreshing cocktails. It is the ultimate way to enjoy a festive afternoon of guided exploration, premium pairings, and authentic local culture without worrying about the transportation.
Wander & Rest Tip
Before your tasting adventure begins, take a stroll through the historic Plaza de la Constitución just a short walk from the meeting point. Once you return to your Wander & Rest sanctuary, keep the festive vibes going by lounging by the heated saltwater pool or detoxing in the private infrared sauna.