Bar guide · 9 picks · Updated August 2026

Best Bar Happy Hours in Brooksville, FL

Brooksville, FL has 9 bar spots with happy hour specials on the Brooksville happy hours page, part of 23 Brooksville menus with prices. Our #1 bar pick is Deep South Family BBQ, and deals start around $5 at Carrabba's Italian Grill. The 9 below count down from #9 to #1, each with its happy hour window, the deal, and a link to the full menu.

Bar spots

Happy hours

Menus with prices

Food deals

The 9 Best Bar Happy Hours in Brooksville, 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.

9. Outback Steakhouse

4 (13)Bar

14383 Cortez Blvd

See Outback Steakhouse menu →See the menu →

Bigun’s Bar-B-Que Brooksville, FL in Brooksville, FL

8. Bigun’s Bar-B-Que Brooksville, FL

4.5 (984)Barbecue Restaurant

7280 Sunshine Grove Rd

See Bigun’s Bar-B-Que Brooksville, FL menu →See the menu →

Bar

7. The Wheel-In

4.6 (68)Bar

10123 N Broad St

See The Wheel-In menu →See the menu →

Bar & Grill

6. The Office at the Crossroads

4.6 (462)Bar & Grill

25 W Dr Martin Luther King Jr Blvd

See The Office at the Crossroads menu →See the menu →

5. MISSION BBQ

4.6 (242)Barbecue Restaurant

14363 Cortez Blvd

See MISSION BBQ menu →See the menu →

Florida Cracker Tap Room and Bourbon Bar in Brooksville, FL

4. Florida Cracker Tap Room and Bourbon Bar

4.7 (864)Bar & Grill

962 E Jefferson St

See Florida Cracker Tap Room and Bourbon Bar menu →See the menu →

Tiki Bar

3. Andys Tiki Hut

5 (5)Tiki Bar

17375 Spring Hill Dr

See Andys Tiki Hut menu →See the menu →

Carrabba's Italian Grill in Brooksville, FL

2. Carrabba's Italian Grill

4.4 (3,356)Bar

12957 Cortez Blvd

Drinks

From 4 PM, Starting at $5, Until 6 PM Daily

3 items, 3 with prices

Select Items For Only$5Classic Red Sangria Blood Orange Margarita$5Bonizio Rosso Bonizio Bianco$5

See Carrabba's Italian Grill menu →See the menu →

Deep South Family BBQ in Brooksville, FL

#1 pick

1. Deep South Family BBQ

4.6 (1,450)Barbecue Restaurant

7247 Cedar Ln

48 items, 48 with prices

Florida Sampler$14Bacon-Wrapped Tots$6Fried Biscuits$6

See Deep South Family BBQ menu →See the menu →

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Happy Hours by Cuisine in Brooksville

Restaurant(27)Other(10)American(4)Italian(4)Japanese(2)Mexican(2)Seafood(1)

Frequently Asked Questions

Where are the best bar happy hours in Brooksville?

We found 9 bar restaurants with happy hour specials in Brooksville. Top picks include Andys Tiki Hut, Florida Cracker Tap Room and Bourbon Bar, MISSION BBQ.

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

Bar restaurants in Brooksville 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 bar restaurants in Brooksville?

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

Which Brooksville happy hours publish their menu with prices?

23 Brooksville venues on DiscoverHappyHours have a full menu with prices. From this list: Deep South Family BBQ (48 priced items). Open any venue page for the happy hour, food and drinks menus.