Anna Maria Island, a laid-back paradise nestled on Florida’s Gulf Coast, is the perfect place to unwind, relax, and immerse yourself in a tropical island atmosphere. Beyond its sugar-white sand beaches and crystal-clear waters, the island also boasts a vibrant bar and restaurant scene. From upscale cocktail lounges to beachfront tiki bars, Anna Maria Island has an impressive variety of spots to grab a drink and take advantage of unbeatable happy hour deals.
As your trusted luxury vacation rental agency, Once Upon A Beach is dedicated to making your island experience as memorable as possible. With this guide, we’re giving you an insider’s look at the 15 best bars and happy hours on Anna Maria Island, perfect for sipping cocktails, enjoying local craft beers, and soaking in the island’s best views.
1. The Sandbar Restaurant
- Location: 100 Spring Ave, Anna Maria
- Vibe: Beachfront, casual, and serene
No visit to Anna Maria Island is complete without a sunset cocktail at The Sandbar Restaurant. This iconic beachfront spot lets you enjoy a tropical drink while watching the sun melt into the Gulf of Mexico. While The Sandbar doesn’t have a daily happy hour, its stunning beachside setting, fresh seafood, and tropical cocktails make it an ideal place to relax.
Tip: Time your visit for sunset and snag a table on the patio for unbeatable sunset views.
2. The Doctor’s Office
- Location: 5312 Holmes Blvd, Holmes Beach
- Vibe: Cozy, upscale, and intimate
If you’re in the mood for craft cocktails, The Doctor’s Office in Holmes Beach is the go-to spot. Located in a former medical office, this speakeasy-style bar offers a cozy ambiance and a menu filled with creative, handcrafted cocktails. While there’s no traditional happy hour, the expertly crafted drinks and intimate atmosphere more than make up for it.
Tip: Ask the bartender for personalized drink recommendations based on your favorite flavors.
3. The Ugly Grouper
- Location: 5704 Marina Dr, Holmes Beach
- Vibe: Lively, outdoor, and family-friendly
A favorite among locals and tourists, The Ugly Grouper offers a lively open-air atmosphere with live music, yard games, and fun for the whole family. Their happy hour runs daily from 3 PM to 5 PM, offering discounted drinks and appetizers. The outdoor setting makes it a great spot for relaxing with a cold beer or margarita in hand.
Happy Hour: Daily from 3 PM to 5 PM
4. Daiquiri Deck Anna Maria Island
- Location: 107 Bridge St, Bradenton Beach
- Vibe: Tropical, colorful, and upbeat
Daiquiri Deck is the ultimate spot for frozen cocktails and a lively, beachy atmosphere. With over 30 flavors of daiquiris, this bar is perfect for cooling off after a day in the sun. Their daily happy hour from 3 PM to 7 PM includes discounts on their famous daiquiris, beer, and select appetizers.
Happy Hour: Daily from 3 PM to 7 PM
5. The Waterfront Restaurant & Craft Bar
- Location: 111 Bay Blvd S, Anna Maria
- Vibe: Upscale, waterfront dining
For a more refined experience, The Waterfront Restaurant & Craft Bar offers stunning views of Tampa Bay alongside an excellent craft cocktail menu. Their happy hour includes discounted appetizers, wine, beer, and cocktails, all served in a classy, waterfront setting. It’s perfect for a relaxing drink after exploring the island.
Happy Hour: Monday to Friday, 4 PM to 6 PM
6. The Freckled Fin Irish Pub
- Location: 5337 Gulf Dr, Holmes Beach
- Vibe: Irish pub meets beach bar
If you’re in the mood for an Irish pub with a beachy twist, head to The Freckled Fin Irish Pub. With its laid-back vibe, live music, and hearty pub fare, it’s a great spot to unwind with a pint of Guinness or a cold craft beer. Their happy hour features drink specials and discounted appetizers.
Happy Hour: Daily from 4 PM to 6 PM
7. Bridge Tender Inn & Dockside Bar
- Location: 135 Bridge St, Bradenton Beach
- Vibe: Old Florida charm, waterfront
Known for its Old Florida charm and waterfront views, Bridge Tender Inn & Dockside Bar is one of the island’s most beloved spots. Whether you’re enjoying a drink at the indoor bar or sitting by the water at the dockside bar, this spot offers great happy hour specials on drinks and food.
Happy Hour: Daily from 3 PM to 6 PM
8. Swordfish Grill & Tiki Bar
- Location: 4628 119th St W, Cortez (just off the island)
- Vibe: Laid-back, waterfront
Just a short drive from Anna Maria Island, Swordfish Grill & Tiki Bar offers a relaxed waterfront setting with fantastic views of Sarasota Bay. Their happy hour runs daily from 3 PM to 6 PM and features discounted drinks and appetizers. The tiki bar atmosphere and live music make it a great spot to kick back and enjoy the Florida lifestyle.
Happy Hour: Daily from 3 PM to 6 PM
9. Harry’s Grill & Bistro
- Location: 9903 Gulf Dr, Anna Maria
- Vibe: Friendly, casual, and inviting
Harry’s Grill & Bistro is a friendly, casual spot perfect for a laid-back happy hour experience. Offering live music, outdoor seating, and a welcoming atmosphere, Harry’s is a great place to enjoy discounted drinks and appetizers during their daily happy hour from 3 PM to 6 PM.
Happy Hour: Daily from 3 PM to 6 PM
10. Hurricane Hanks
- Location: 5346 Gulf Dr, Holmes Beach
- Vibe: Cozy, casual, and local favorite
Hurricane Hanks is a cozy neighborhood bar known for its great service, cold drinks, and hearty food. With a daily happy hour from 2 PM to 5 PM, you can enjoy discounted beer, wine, and cocktails. The friendly atmosphere and delicious food make it a go-to spot for both locals and visitors.
Happy Hour: Daily from 2 PM to 5 PM
11. The Beach House Restaurant
- Location: 200 Gulf Dr N, Bradenton Beach
- Vibe: Beachfront, relaxed, and family-friendly
If you’re looking for a beachfront bar with a laid-back vibe, The Beach House Restaurant is a fantastic choice. With gorgeous views of the Gulf of Mexico and a spacious outdoor seating area, it’s the perfect spot for a sunset drink. Their happy hour includes drink specials and discounted appetizers, perfect for a pre-dinner treat.
Happy Hour: Monday to Friday from 2 PM to 5 PM
12. Anna Maria Island Beach Café
- Location: 4000 Gulf Dr, Holmes Beach
- Vibe: Beachside, casual, and fun
Located right on the sand, Anna Maria Island Beach Café offers a fun, casual atmosphere for grabbing a drink by the beach. Enjoy their daily happy hour from 2 PM to 5 PM with discounted beers and cocktails, all while taking in the island’s beautiful scenery.
Happy Hour: Daily from 2 PM to 5 PM
13. Island Time Bar & Grill
- Location: 111 Gulf Dr S, Bradenton Beach
- Vibe: Island casual, upbeat
Located in the heart of Bradenton Beach, Island Time Bar & Grill offers a laid-back, island-style atmosphere with live music and great food. Their daily happy hour includes discounts on beer, wine, and cocktails, making it a perfect spot to relax after a day at the beach.
Happy Hour: Daily from 11:30 AM to 5 PM
14. Blue Marlin Seafood Restaurant and Grill
- Location: 121 Bridge St, Bradenton Beach
- Vibe: Cozy, nautical, and charming
For a more intimate, seafood-centric experience, head to Blue Marlin Seafood Restaurant and Grill. Known for its fresh seafood and charming, nautical-themed setting, this spot offers a cozy bar area where you can enjoy happy hour specials on select drinks and appetizers.
Happy Hour: Tuesday to Saturday, 4 PM to 6 PM
15. Wicked Cantina
- Location: 101 7th St N, Bradenton Beach
- Vibe: Tex-Mex, vibrant, and fun
For those craving margaritas and tacos, Wicked Cantina is the place to be. With a lively Tex-Mex atmosphere and a daily happy hour from 12 PM to 5 PM, you can enjoy discounted margaritas, beer, and appetizers. The casual, vibrant vibe and waterfront views make it a fun spot to unwind.
Happy Hour: Daily from 12 PM to 5 PM
Conclusion
Anna Maria Island is a paradise for beach lovers, but it’s also home to some fantastic bars and happy hours that offer everything from casual beachfront vibes to sophisticated cocktail lounges. Whether you’re looking to sip a margarita on the sand or enjoy a craft cocktail in a chic setting, the island has something for everyone. At Once Upon A Beach, we’re always happy to share our local recommendations to help you make the most of your island getaway. So, raise a glass, enjoy the sunset, and let the island’s best bars and happy hours enhance your Anna Maria Island experience!
