Local’s Choice Tips: Janessa Silvestri
Author: Laura Myers, November 2025
Janessa Silvestri – a lifelong Key Largo resident, realtor, mother of a 2.5-year-old son and gourmet cook – oversees The Armory Speakeasy, an off-the-beaten-path Upper Keys watering hole with gourmet dining.
Janessa Silvestri (l, in hat) enjoys lunch with mother Jeanette Silvestri at Janessa’s favorite restaurant, Latitudes on Sunset Key, located just off Key West. Courtesy: Janessa Silvestri
She’s the owner of a business partnership with VFW Post 10211, which owns The Armory Speakeasy’s building at 102255 Overseas Highway, at mile marker 102, in Key Largo.
On November 10, Silvestri and The Armory Speakeasy hosted 250th birthday festivities, open to the public, honoring United States Marine Corps members. The Marine Corps was founded Nov. 10, 1775, in Philadelphia, Pennsylvania.
Janessa Silvestri walks the Cheeca Lodge pier, to enjoy a cocktail, in Islamorada in 2020. Courtesy: Janessa Silvestri
Silvestri was born in Red Bank, New Jersey. Father JR, then a skilled tradesman worker, and mother Jeanette, then a cosmetologist, moved to Key Largo when Janessa was a year old. Today, JR owns a construction company and Jeanette is a realtor.
As a teenager, Silvestri attended Coral Shores High School and graduated from Montverde Academy, a college prep boarding school in Central Florida near Orlando.
Janessa Silvestri, with husband Jose Rodriguez and son Wave, age 2.5. Courtesy: Janessa Silvestri
She attended college at Florida International University in Tallahassee, at Cabrini College in Radnor, Pennsylvania, and at Valencia College in Orlando before training in culinary arts at Le Cordon Bleu Orlando.
She returned home to work as a realtor for a decade, and two years ago, learned of a leasing opportunity with the VFW facility from veteran John Donnelly, a VFW Post 10211 trustee.
Janessa Silvestri (r), enjoys cold-weather shrimping with brother Joe Joe (l) at Adams Cut in Key Largo. Courtesy: Janessa Silvestri
The restaurant’s concept was created by Silvestri, who worked closely with her father on its interior transformation.
The military-themed The Armory Speakeasy, fully remodeled and unveiled in November 2024, pays homage to veterans of foreign wars.
A secret code, which must be obtained through Instagram or The Armory Speakeasy’s website, is needed for entrance.
Janessa Silvestri with son Wave at the opening of The Armory Speakeasy in November 2024 in Key Largo. Courtesy: Janessa Silvestri
Once inside a darkened sophisticated atmosphere, patrons can “sip with rebels, dine in style…the drinks are tactical, the food is commanding,” its website states. “This is not just a bar. It’s a mission.”
That mission is a theme of “service, sacrifice and celebration.” Military weaponry, shell casings and photos of service men and women line the walls as décor.
Janessa Silvestri (c) with mother Jeanette Silvestri (foreground) and Mary Bianchini (r), who runs the Key Largo Civic Club, celebrating its 76th birthday this year. The Sons and Daughters of Italy host Friday night Bingo, enjoyed by Janessa, at the club house. Courtesy: Janessa Silvestri.
Artist Wyland – the conservationist artist known in the Keys for his giant Whaling Wall paintings – donated a military-themed work to The Armory Speakeasy earlier this month. The art depicts a 1945 photograph of Marines raising a U.S. flag.
At the venue, patrons’ favorite fare – far beyond a typical Keys fish, rice or fries and coleslaw meal – is crafted for sharing and includes carpacchio, bunker or steak bites, and ‘shock wave’ tuna. A ‘lamb of command’ features char-grilled lamb with minted chimichurri, paired with fennel slaw.
Silvestri’s future goals includes the possibility of opening another Speakeasy. And because of her interests in culinary arts and growing healthy food, farming is another consideration.
“I love the Keys and I love real estate, so I feel like this is me giving back to the community,” Silvestri said. “Change is always inevitable.”
Silvestri, her husband Jose, a professional basketball player who also manages The Armory Speakeasy, live with son Wave in the Upper Keys.
Motto: "Lead with purpose. Build with passion. Leave a legacy that inspires."
Where she dines: “My absolute favorite is Latitudes at Sunset Key (located just off Key West.) The entire experience is exceptional, from the boat ride over to the breathtaking sunset views and thoughtfully-crafted cuisine. It truly captures the essence of the Keys in the most elegant way.”
Where she explores: “On the water, whether it’s paddleboarding through the mangroves, shrimping during cold fronts at night, or enjoying a sunset cruise surrounded by the beauty of the islands.”
How she relaxes: Spending quality time with family, hosting intimate home dinner parties at home, and taking in the beauty of sunrises and sunsets. “You can often find me at Bingo Night on Fridays at the Key Largo Civic Club.”
