Italian guide · 5 picks · Updated August 2026

Best Italian Happy Hours in Windermere, FL

Windermere, FL has 5 italian spots with happy hour specials on the Windermere happy hours page, part of 9 Windermere menus with prices. Our #1 italian pick is Bella Tuscany (happy hour Mon-Fri 3 PM-6 PM), and deals start around $5 at Flippers Pizza Co. - Windermere. The 5 below count down from #5 to #1, each with its happy hour window, the deal, and a link to the full menu.

Italian spots

Happy hours

Menus with prices

Food deals

The 5 Best Italian Happy Hours in Windermere, counting down to #1

Ranked by a confirmed happy hour window, menu depth, and Google rating. Every pick links to the venue's full menu on DiscoverHappyHours.

Piesanos Stone Fired Pizza - Windermere in Windermere, FL

5. Piesanos Stone Fired Pizza - Windermere

4.7 (1,121)Pizza Restaurant

7782 Winter Garden Vineland Rd #140

See Piesanos Stone Fired Pizza - Windermere menu →See the menu →

4. Pie Fection

4.7 (800)Pizza Restaurant

13211 Reams Rd Ste 108

14 items, 14 with prices

Romeo and Juliet$20Calabresa$21Five Cheese$24

See Pie Fection menu →See the menu →

3. Manzzo Cuisine

4.6 (584)Italian Restaurant

6506 Old Brick Rd #120

Happy hour

Monday To Friday · 5 PM - 7 PM

7 items, 7 with prices

Parma prosciutto$16Italian bread$19Shrimp$14

See Manzzo Cuisine menu →See the menu →

Flippers Pizza Co. - Windermere in Windermere, FL

2. Flippers Pizza Co. - Windermere

4.7 (1,883)Pizza Restaurant

6526 Old Brick Rd Suite 100

Happy hour

3PM - 6PM

Drinks

at Windermere MONDAY - FRIDAY, 3PM - 6PM GET $5 PINTS OF LOCAL BEER, $5 GLASSES OF WINE, AND $5 CRAFT BREADSTICKS WHEN YOU VISIT YOUR NEIGHBORHOOD FLIPPERS MONDAY THROUGH FRIDAY, 3PM - 6PM

4 items, 4 with prices

PIZZA & Half Italian or Caesar salad for only$11.99JOIN US FOR$5Pints Of Local Beer$5

See Flippers Pizza Co. - Windermere menu →See the menu →

#1 pick

1. Bella Tuscany

4.4 (1,536)Italian Restaurant

13424 Summerport Village Pkwy

Happy hour

Mon-Fri · 3 PM-6 PM

150 items, 149 with prices

Lentil Soup$13Herb-Marinated New Zealand Lamb Chops$21Crispy Beer-Battered Soft Shell Crab$20

See Bella Tuscany menu →See the menu →

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Happy Hours by Cuisine in Windermere

Restaurant(5)Other(5)Mexican(3)Asian(2)Japanese(2)Bar(1)Brewery(1)

Frequently Asked Questions

Where are the best italian happy hours in Windermere?

We found 5 italian restaurants with happy hour specials in Windermere. Top picks include Piesanos Stone Fired Pizza - Windermere, Flippers Pizza Co. - Windermere, Pie Fection.

What kind of italian food specials are available during happy hour?

Italian restaurants in Windermere typically offer discounted appetizers, tacos, small plates, and specialty items during happy hour, often at 30-50% off regular prices.

What time is happy hour at italian restaurants in Windermere?

Most italian restaurants in Windermere run happy hour between 3 PM and 7 PM on weekdays. Some offer daily or weekend specials too.

Which Windermere happy hours publish their menu with prices?

9 Windermere venues on DiscoverHappyHours have a full menu with prices. From this list: Bella Tuscany (149 priced items). Open any venue page for the happy hour, food and drinks menus.