May’s First Weekend Is Ripe for a Party

Don’t miss out on the Cinco-Derby swoop.

BY May 2, 2019
Pick your favorite drink (or two) during Rocco's Tacos Cinco de Mayo block party.

As if Neapolitans really needed an excuse to pop on a fascinator or kick back with a margarita, there are options en masse in the beginning days of May, as the 2019 Kentucky Derby races out of the gates Saturday, May 4, and Cinco de Mayo celebrations stretch before and after Sunday, May 5.

See our list of what’s in store for both, but keep in mind that many of the mint julep-charged Derby parties take flight well before the actual time the horses stampede around Churchill Downs (the most exciting two minutes in sports begins at 6:50 p.m. sharp). And while there’s no one prescription for how to do Cinco—some spots are offering discounted tacos and Mexican beer (Tijuana Flats), others full-blown fiestas with live music and free tequila shots (Rocco’s Tacos)—you have control over your party destiny.


KENTUCKY DERBY (all events May 4)

Naples Therapeutic Riding Center / Naples: 2019 Kentucky Derby Party at the NTRC; tickets ($75 per person or $125 per person for reserved seating) include hors d’oeuvres from Shula’s Naples and a drink ticket then cash bar, plus a hat contest (ladies) and crazy pants contest (gents) and a 50/50 raffle

Naples Junior Woman’s Club / Naples: 10th Annual Derby Dash 5-8 p.m. at The Naples Beach Hotel & Golf Club; tickets ($75 per person or $100 per VIP) include unlimited beer and wine and hors d’oeuvres, plus a silent auction

Gather / Cape Coral: free mint julep, 4-7 p.m., if wearing a Derby hat

The French Naples / Naples: Kentucky Derby Celebration—regular a la carte menu, with juleps and frosé for sale


CINCO DE MAYO (various dates)

Rocco’s Tacos / Naples / May 5: all-day party from 11 a.m. to 10 p.m., with live music, drink specials, tacos, prize giveaways and free tequila pours

Gather / Cape Coral / May 5: $35 Mexican brunch buffet with $8 bottomless micheladas, margaritas and bloody marias

Fort Myers Brewing Company / Fort Myers / May 3: Cinco de Mayo pre-party Taco Fest at 3 p.m. on Friday with live music and food trucks serving tacos

Tijuana Flats / various locations / May 3-5: two for $5 deals on tacos and beers

Felipe’s Taqueria / Naples / May 4: regular food and drink menu 2 p.m. to midnight, with live Mexican acts for music and dance throughout the afternoon and evening (3-9 p.m.)

Fleming’s Prime Steakhouse & Wine Bar / Naples / all month: “Prime Margarita” $100 specialty drink is on offer, mixing the ultra-premium single estate and single vintage Tequila Ocho with Grand Marnier Cuvee du Centenaire served in a take-home Baccarat Diamant Tumbler

Lucky’s Market / various locations / May 5: discounts and deals on avocados, salsa, tortilla chips and more to host your own fiesta, plus a taco pop-up in stores selling two for $5

Matanzas on the Bay / Fort Myers Beach / May 5: a la carte menu with some Mexican specials, house margaritas for $5 and buckets of Corona for $18

La Bamba Real Mexican Food Restaurant & Tequila Bar / May 5: food and drink specials and a 3 p.m. margarita crawl on-site at Miromar Outlets

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