Last updated: May 5, 2026 at 12:46 PM
Best Happy Hours, Deals & Events in Orlando, FL — Tuesday, May 5, 2026
Orlando offers a vibrant happy hour scene, with spots like The Guesthouse and Hanson’s Shoe Repair providing great deals. Enjoy specials such as $4 drafts and half-priced cocktails in neighborhoods like Thornton Park and Downtown Orlando.
🍺 Happy Hours in Orlando, FL Tonight & This Week
Downtown Orlando
The Guesthouse
Address: 260 W Michigan St, Orlando, FL 32806
Happy Hour: Monday–Friday 4–7 PM
Deals: $4 domestic drafts, $5 well drinks, $6 house wines
Vibe: A relaxed neighborhood bar with a focus on craft beer and a friendly atmosphere.
Why go: This spot is perfect for unwinding after work with its solid selection of brews and affordable prices, especially nice during the mild spring evenings.
Hanson’s Shoe Repair
Address: 22 S Orange Ave, Orlando, FL 32801
Happy Hour: Tuesday–Saturday 5–7 PM
Deals: 50% off select cocktails, $3 select beers
Vibe: A speakeasy-style bar with expertly crafted cocktails and a sophisticated ambiance.
Why go: Experience expertly mixed drinks in an intimate setting. Their unique cocktail menu is a highlight, and the speakeasy feel is a great escape.
Wall Street Plaza
Address: 25 Wall St, Orlando, FL 32801
Happy Hour: Monday–Friday 3–7 PM
Deals: $3 domestics, $4 wells, $5 house shots
Vibe: A lively outdoor plaza with multiple bars, popular for its energetic atmosphere and regular events.
Why go: Enjoy the bustling atmosphere and varied drink specials, making it a go-to spot for groups looking for a fun night out in the heart of downtown.
The Other Bar
Address: 120 N Orange Ave, Orlando, FL 32801
Happy Hour: Monday–Friday 4–7 PM
Deals: $3 domestic bottles, $4 wells, $5 calls
Vibe: A casual, no-frills bar with a great jukebox and a friendly crowd.
Why go: Unbeatable prices on a wide range of drinks make this a local favorite for a laid-back evening.
Thornton Park
The Boheme at Grand Bohemian Hotel Orlando
Address: 325 N Magnolia Ave, Orlando, FL 32801
Happy Hour: Daily 5–7 PM
Deals: Half-priced appetizers, $7 signature cocktails, $5 select wines
Vibe: An elegant and artistic lounge offering craft cocktails and upscale small plates.
Why go: Indulge in sophisticated spring evenings with creative cocktails and a beautiful ambiance, perfect for a special night out.
World of Beer – Downtown Orlando
Address: 2731 E Colonial Dr, Orlando, FL 32803
Happy Hour: Monday–Friday 3–6 PM
Deals: $1 off all draft beers, $2 off appetizers
Vibe: A beer-lover’s paradise with a vast selection of craft beers on tap and a casual setting.
Why go: With over 500 beers, you’re sure to find a new favorite, and the spring weather is perfect for enjoying their outdoor patio.
Tactical Brewing Co.
Address: 417 Irvington Ave, Orlando, FL 32803
Happy Hour: Tuesday–Friday 4–6 PM
Deals: $1 off pints, $2 off flights
Vibe: A friendly, community-focused brewery known for its rotating selection of creative craft beers.
Why go: Sample a variety of local brews in a relaxed atmosphere. Their patio is ideal for enjoying a cool spring afternoon.
Milk District
Stardust Video and Coffee
Address: 4815 E Robinson St, Orlando, FL 32801
Happy Hour: Tuesday–Saturday 5–7 PM
Deals: $3 select beers, $5 wine by the glass
Vibe: A quirky, eclectic spot that combines a video rental store with a coffee shop and bar.
Why go: This unique venue offers a laid-back vibe and affordable drinks, making it a beloved local hangout.
The Crux
Address: 301 E. Colonial Drive, Orlando, FL 32801
Happy Hour: Monday-Friday 4pm-7pm
Deals: $4 draft beers, $5 well drinks, $6 house wine
Vibe: A modern, stylish bar with a focus on craft cocktails and a diverse beer selection.
Why go: Enjoy a trendy atmosphere and excellent drink specials, perfect for a spring evening out.
Bad Ass Coffee of Hawaii – Mills 50
Address: 1120 N Mills Ave, Orlando, FL 32803
Happy Hour: Weekdays 3 PM – 6 PM
Deals: $1 off all espresso drinks and teas, $3 select local craft beers
Vibe: A unique Hawaiian coffee shop that also offers local craft beers and a relaxed atmosphere.
Why go: Grab a refreshing coffee or a local brew in a fun, island-inspired setting, especially pleasant as the spring weather warms up.
Ivanhoe Village
The Hall on the Yard
Address: 1405 E Washington St, Orlando, FL 32801
Happy Hour: Monday-Friday 4pm-7pm
Deals: $4 draft beers, $5 well drinks, $6 house wine
Vibe: A vibrant food hall with multiple vendors and a lively bar area.
Why go: Offers a diverse range of food options alongside great drink specials, making it a versatile spot for any craving.
Ivanhoe Park Brewing Company
Address: 1305 Lauer Rd, Orlando, FL 32803
Happy Hour: Thursday 5 PM – 9 PM
Deals: $1 off all pints
Vibe: A spacious, dog-friendly brewery with a large outdoor area and a focus on creative, small-batch beers.
Why go: Enjoy Orlando’s pleasant spring weather in their expansive beer garden while trying a new craft brew.
| Venue | Days | Hours | Best Deal | Neighbourhood |
|---|---|---|---|---|
| The Guesthouse | Mon–Fri | 4–7 PM | $4 domestic drafts | Downtown Orlando |
| Hanson’s Shoe Repair | Tue–Sat | 5–7 PM | 50% off select cocktails | Downtown Orlando |
| Wall Street Plaza | Mon–Fri | 3–7 PM | $3 domestics | Downtown Orlando |
| The Other Bar | Mon–Fri | 4–7 PM | $3 domestic bottles | Downtown Orlando |
| The Boheme | Daily | 5–7 PM | Half-priced appetizers | Thornton Park |
| World of Beer | Mon–Fri | 3–6 PM | $1 off all drafts | Thornton Park |
| Tactical Brewing Co. | Tue–Fri | 4–6 PM | $1 off pints | Thornton Park |
| Stardust Video and Coffee | Tue–Sat | 5–7 PM | $3 select beers | Milk District |
| The Crux | Mon-Fri | 4pm-7pm | $4 draft beers | Milk District |
| Bad Ass Coffee of Hawaii – Mills 50 | Weekdays | 3 PM – 6 PM | $1 off all espresso drinks | Milk District |
| The Hall on the Yard | Mon-Friday | 4pm-7pm | $4 draft beers | Ivanhoe Village |
| Ivanhoe Park Brewing Company | Thursday | 5 PM – 9 PM | $1 off all pints | Ivanhoe Village |
🎁 Best Deals & Offers in Orlando, FL This Week
🍽️ Dining Deals
The Ravenous Pig
Address: 125 W Fairbanks Ave, Winter Park, FL 32789
Offer: Spring Prix-Fixe Menu
Details: Three-course menu featuring seasonal ingredients. Available nightly.
Why go: A chance to sample upscale, seasonal dishes at a fixed price during the beautiful spring dining season.
Se7en Bites
Address: 641 N Primrose Dr, Orlando, FL 32803
Offer: Lunch Specials
Details: Rotating lunch specials include dishes like shrimp and grits or fried chicken sandwiches. Served Tuesday-Friday until 3 PM.
Why go: Delicious Southern comfort food at approachable prices, perfect for a hearty spring lunch.
🍸 Drink Specials
The Parliament House Resort & Waterpark
Address: 410 N Orange Blossom Trail, Orlando, FL 32805
Offer: Martini Mondays
Details: All martinis are $7 all day, every Monday.
Why go: Kick off the week with a great deal on classic and creative martinis in a lively atmosphere.
Wine Bar Orlando
Address: 4015 Dr. Phillips Blvd, Suite 300, Orlando, FL 32819
Offer: Wine Wednesday
Details: Half-price bottles of wine and 25% off all glasses of wine every Wednesday.
Why go: An excellent opportunity to explore a wide selection of wines at a significant discount, ideal for sharing.
Sideward Brewing
Address: 210 N. Bumby Ave, Orlando, FL 32803
Offer: Craft Beer Tuesdays
Details: $1 off all craft beer pints every Tuesday.
Why go: Sample some of the best local craft beers at a reduced price, supporting a popular neighborhood brewery.
🎭 Entertainment Offers
Will’s Pub
Address: 1052 N Orange Ave, Orlando, FL 32801
Offer: Live Music
Details: Features local and touring bands regularly with varied cover charges. Check their schedule for specific nights.
Why go: Experience Orlando’s vibrant live music scene in an iconic, intimate venue.
Laughing Gas Comedy Club
Address: 100 W. Anderson Street, Orlando, FL 32801
Offer: Mid-Week Comedy Show
Details: Features local comedians on Wednesday nights. Tickets typically range from $10-$15.
Why go: Enjoy a night of laughs with up-and-coming talent in a dedicated comedy space.
📱 Loyalty & App Deals
Starbucks – Multiple Locations
Offer: Starbucks Rewards App
Details: Earn stars for every purchase, redeemable for free drinks and food. Occasional bonus star offers.
Why go: Save money on your daily coffee fix and enjoy exclusive member perks through their convenient app.
Moe’s Southwest Grill – Multiple Locations
Offer: Moe Rewards
Details: Earn points for every dollar spent, redeemable for free food. Includes a free queso or guac just for signing up.
Why go: A great way to get free burritos, bowls, and more by enjoying your favorite Tex-Mex meals.
🎉 Events & Parties in Orlando, FL — May 2026
📅 Tonight & Tomorrow
Trivia Night at The Guesthouse
Date & Time: Tuesday, May 5, 2026, 7:00 PM
Venue: The Guesthouse, 260 W Michigan St, Orlando, FL 32806
Tickets: Free to play
Don’t miss: Test your knowledge and enjoy happy hour specials during this fun weekly trivia event.
Live Music at Lil Indies
Date & Time: Wednesday, May 6, 2026, 8:00 PM
Venue: Lil’ Indies, 1036 N Mills Ave, Orlando, FL 32803
Tickets: $5 cover
Don’t miss: Catch local bands playing a mix of genres in this intimate and beloved neighborhood bar.
📆 This Weekend
Farmers Market at Lake Eola Park
Date & Time: Saturday, May 9, 2026, 8:00 AM – 1:00 PM
Venue: Lake Eola Park, 512 E Washington St, Orlando, FL 32801
Tickets: Free admission
Don’t miss: Stroll through a vibrant market offering fresh produce, local crafts, and delicious food while enjoying the spring sunshine.
Art & Wine Stroll – Ivanhoe Village
Date & Time: Saturday, May 9, 2026, 6:00 PM – 9:00 PM
Venue: Various galleries and shops along Ivanhoe Village
Tickets: $25 per person (includes wine tasting)
Don’t miss: Explore local art and enjoy wine tastings at participating businesses in the charming Ivanhoe Village district.
🗓️ Coming Up This Month
Orlando Beer Festival
Date & Time: Saturday, May 23, 2026, 1:00 PM – 5:00 PM
Venue: Lake Eola Park, 512 E Washington St, Orlando, FL 32801
Tickets: $45 – $65
Don’t miss: Sample a wide array of craft beers from local and national breweries, enjoy live music, and savor diverse food options.
Orlando Film Festival
Date & Time: May 15-24, 2026 (various screenings)
Venue: Enzian Theater and other locations
Tickets: Varies by screening and pass type
Don’t miss: Discover independent films, attend Q&A sessions with filmmakers, and celebrate cinematic creativity.
🆓 Free Events
Movies at Lake Eola Park
Date & Time: First Friday of each month (May 1st), starts at dusk
Venue: Lake Eola Park, 512 E Washington St, Orlando, FL 32801
Tickets: Free
Don’t miss: Enjoy a free outdoor movie screening under the stars at one of Orlando’s most iconic parks.
Live Jazz at Wall Street Plaza
Date & Time: Last Thursday of the month (May 28th), 7:00 PM
Venue: Wall Street Plaza, 25 Wall St, Orlando, FL 32801
Tickets: Free admission
Don’t miss: Enjoy smooth jazz music in a lively downtown setting, with plenty of surrounding bars and restaurants to explore.
| Event | Date | Venue | Ticket Price |
|---|---|---|---|
| Trivia Night at The Guesthouse | Tuesday, May 5, 2026 | The Guesthouse | Free |
| Live Music at Lil Indies | Wednesday, May 6, 2026 | Lil’ Indies | $5 |
| Farmers Market at Lake Eola Park | Saturday, May 9, 2026 | Lake Eola Park | Free |
| Art & Wine Stroll – Ivanhoe Village | Saturday, May 9, 2026 | Ivanhoe Village | $25 |
| Orlando Film Festival | May 15-24, 2026 | Enzian Theater | Varies |
| Orlando Beer Festival | Saturday, May 23, 2026 | Lake Eola Park | $45 – $65 |
| Live Jazz at Wall Street Plaza | Thursday, May 28, 2026 | Wall Street Plaza | Free |
| Movies at Lake Eola Park | Friday, May 1, 2026 | Lake Eola Park | Free |
❓ Frequently Asked Questions — Orlando, FL Happy Hours & Nightlife
Q: What time does happy hour start in Orlando?
Happy hour times in Orlando vary significantly by venue, but many start as early as 3 PM or 4 PM and run until 6 PM or 7 PM on weekdays. Some establishments offer extended or even daily happy hours.
Q: Which Orlando bars have the cheapest drinks?
Bars like The Other Bar in Downtown Orlando are known for consistently low prices, often featuring domestic bottles for $3 and wells for $4. Many neighborhood bars and breweries also offer affordable deals during their happy hours.
Q: What are the best neighbourhoods for nightlife in Orlando?
Downtown Orlando is a major hub with a high concentration of bars, clubs, and live music venues. Other popular areas include Thornton Park for a more relaxed, upscale vibe, the Milk District for eclectic bars and breweries, and Ivanhoe Village for a charming mix of pubs and unique spots.
Q: Are there free events in Orlando this month?
Yes, Orlando frequently hosts free events. Look out for free movie nights at Lake Eola Park, live music at various venues, and community gatherings. Checking local event listings for May 2026 will reveal specific free activities happening throughout the month.
Q: What are the best rooftop bars in Orlando?
For rooftop experiences in Orlando, check out The Rooftop at Topgolf for a lively atmosphere with golf simulators, or Cielo Sky Lounge for a more sophisticated setting with craft cocktails and city views. Many hotel rooftops also offer great vantage points and happy hour specials.