Whether you're grabbing a cold one, plotting a pizza-and-wings situation, or feeding a whole crew, Legends Bar And Grill keeps it simple…
3323 US-441 (Fruitland Park)
“Whether you're grabbing a cold one, plotting a pizza-and-wings situation, or feeding a whole crew, Legends Bar And Grill keeps it simple with starters, pizzas, pastas, sandwiches, and hearty platters. They also handle parties and catering, which is clutch when you promised food for the HOA meeting.”
From the Fruitland Park newsletter, October 14, 2026
Craving a proper pint and something hearty you didn’t microwave, The Bell Clermont pours classics like Guinness and Samuel Smith alongside…
637 8th St (Clermont)
“Craving a proper pint and something hearty you didn’t microwave, The Bell Clermont pours classics like Guinness and Samuel Smith alongside pub staples like bangers and mash, steak pie, and a killer sticky toffee pudding. Cozy, friendly, and delightfully transportive... basically your new midweek reset.”
Roasted Spirit pours fresh, inventive craft cocktails and boasts Clermont's largest selection of sipping spirits, perfect for a laid-back…
756 W Montrose St (Clermont)
“Roasted Spirit pours fresh, inventive craft cocktails and boasts Clermont's largest selection of sipping spirits, perfect for a laid-back night with friends. Pair it with scratch-made shareable tapas, catch some live music, maybe brunch if you're feeling it... a local's win this week.”
Your midweek unwind, sorted: Hamrick Family Vineyards brings a speakeasy vibe and a browse-worthy emporium to Leesburg, so you can sip,…
118 S 2nd St (Leesburg) · ✓ checked Aug 13
“Your midweek unwind, sorted: Hamrick Family Vineyards brings a speakeasy vibe and a browse-worthy emporium to Leesburg, so you can sip, chat, and poke around for something fun. Peek at their events calendar when you want an easy, local plan that feels a little special.”
An easy hang for Villagers who like their evenings social, Blondie's is the outdoor bar on Spanish Springs Town Square with regular live…
1051 Main St (The Villages) · ✓ checked Sep 3
“An easy hang for Villagers who like their evenings social, Blondie's is the outdoor bar on Spanish Springs Town Square with regular live entertainment, Blondies Trivia and Karaoke with Alan Ross, cheeky cocktails like the Dolly and Diana, and a house Blondie's Blonde Ale that goes down dangerously smooth.”
From the The Villages newsletter, September 7, 2026
Two Old Hags Wine Shoppe keeps Leesburg lively with a lineup of hard-to-find wines by the glass or bottle, cold beer for your wine-shy…
410 W Main St (Leesburg) · ✓ checked Aug 21
“Two Old Hags Wine Shoppe keeps Leesburg lively with a lineup of hard-to-find wines by the glass or bottle, cold beer for your wine-shy friends, and live music nights. Settle into The Lounge’s cozy cellar vibe, nibble local charcuterie, or bring your favorite takeout.”
Back 40 Wine Co is the kind of neighborhood wine bar where the list feels curated by a friend, not an algorithm, with pours that make you…
719 West Ave (Clermont)
“Back 40 Wine Co is the kind of neighborhood wine bar where the list feels curated by a friend, not an algorithm, with pours that make you linger and chat. Swing by when you want an easygoing spot to discover new favorites without leaving town.”
The Sipping Garden and Bistro is your low-key wine night upgrade, with charcuterie boards, wood fired flatbreads, truffle burrata, grilled…
605 W Magnolia St (Leesburg) · ✓ checked Aug 21
“The Sipping Garden and Bistro is your low-key wine night upgrade, with charcuterie boards, wood fired flatbreads, truffle burrata, grilled cheese and a homemade wine cake that winks at you. Settle in, pick a bottle, catch up with friends, call it your new midweek ritual.”
Locals, when you want Florida-inspired plates in a cozy 1921 house with legit museum vibes, 1921 Mount Dora delivers. Rotating art from the…
142 E 4th Ave (Mt Dora)
“Locals, when you want Florida-inspired plates in a cozy 1921 house with legit museum vibes, 1921 Mount Dora delivers. Rotating art from the Modernism Museum and a serious wine bar vibe make it feel special without trying too hard, perfect for a date night or a treat-yourself dinner.”
From the Winter Garden newsletter, September 5, 2026
If your week needs more sunshine and fewer spreadsheets, Tiki Bar & Grill at the historic Lake Minneola Inn serves easygoing bar-and-grill…
508 S Main Ave (Minneola)
“If your week needs more sunshine and fewer spreadsheets, Tiki Bar & Grill at the historic Lake Minneola Inn serves easygoing bar-and-grill comfort with water views and no fuss energy. Settle in by the lake, sip something cold, maybe snag a Tiki Boat rental for extra fun.”
Barons Creek Vineyards is now in The Villages, pouring award-winning wines sourced from premium vineyards in California, Texas, Washington,…
1171 Main St (The Villages) · ✓ checked Aug 6
“Barons Creek Vineyards is now in The Villages, pouring award-winning wines sourced from premium vineyards in California, Texas, Washington, and Spain. Swing by with your favorite porch-sitting friend, sip a little, find your style, then keep the good stuff coming with their wine club.”
From the The Villages newsletter, September 26, 2026
Pups Pub Clermont is an off-leash dog park meets sports bar where your pup makes friends while you catch the game. Think breed meetups,…
898 W Montrose St (Clermont)
“Pups Pub Clermont is an off-leash dog park meets sports bar where your pup makes friends while you catch the game. Think breed meetups, trivia nights, and bookable pawty packages with pupcakes, plus easy memberships or day passes so you can drop in this week.”
Whether you’re into crisp whites or sweet Muscadines, Lakeridge Winery & Vineyards keeps it local with tours, guided tastings, and weekend…
19239 US-27 (Clermont)
“Whether you’re into crisp whites or sweet Muscadines, Lakeridge Winery & Vineyards keeps it local with tours, guided tastings, and weekend festivals on a sprawling vineyard green. It’s the kind of spot where Clermont neighbors bump into each other, sample award winners, then stick around for live music and food.”
