Anna Maria Island may be small, but it’s packed with stuff to do from dawn till dusk. After a long day of hiking, exploring, boating or shopping, you’ll want to sit down and have a nice meal or a drink. Maybe you’ve spent the day casually on the beach and want a little nighttime excitement near your Holmes Beach vacation rental. Either way, the island has some unique charms that will keep you coming back.
Dining After Dark
Around Holmes Beach, The Ugly Grouper has great pub grub and seafood with outdoor seating in a friendly environment. Across the bridge in Cortez, The Swordfish Grill and Tiki has loads of great food as well. Check out their live music and famous crab races.
Hurricane Hanks is one of Anna Maria Island’s favorite restaurants and has a packed menu serving local favorites like shrimp and scallops and classics such as steak and risotto. Open until 12:30 am, or 2 am on weekends, they’re ready when you are for some late-night eats. Check their events schedule for craft liquor and beer tastings.
For a more fine dining experience, try Beach Bistro on Anna Maria Island. A staple of Anna Maria for decades, they’re committed to bringing you superb dining experience. Their menu is full of quality cuts, fresh fish, and decadent desserts. With beachside seating, it’s great for a romantic sunset dinner or a cozy nightcap.
Bar crawl Adventures
The strip along Bridge Street on Anna Maria Island has a lot of great bar crawl stops. A steady stream of locals and generously stocked bars keep these places bouncing. D Coy Ducks is a famed local watering hole in Holmes Beach which is open till 3 am. It’s a casual dive with game nights and poker tournaments that explodes into a sports bar at a moment’s notice.
The Kokonut Hut is the perfect after-party place at the Gulf Drive Cafe!
Enjoy a cocktail from this full-service bar or try one of their signature Frosty Factory Boozy Slushies while you take in the amazing views of the Gulf of Mexico. Grab some food and walk along the stunning beachfront before heading back to one of our Anna Maria Island vacation rentals.
All About the Ambience
The Doctor’s Office is a craft cocktail bar with a lively atmosphere and some ambitious offerings. True to its name, the menu focuses on a “medicinal” theme. Expert bartenders serve drinks with many different liquors and flavors: herbal, spicy, fruity, and interesting cocktails like the jalapeno margarita. Top off the menu with some fine local craft beers and it’s guaranteed to please any palate.
The Sandbar is a gorgeous beachside restaurant with a long history on the island. The energy is infectious, which you can tell it’s a popular venue for weddings and large events. Their Sunset Celebration is a perfect way to kick off your evening and bask in the moment. Guess the exact time of sunset to win a bottle of bubbly.
The Great Outdoors
All the places around here are just a few minutes’ drive away. If you want to mix it up there are plenty of companies that will help you rent a bicycle or even a golf cart. If you’re not up for walking but nobody in your group is fit to drive, there’s also a trolley bus. The bus runs up and down the island from 6 am to 10 pm. Plan ahead and make sure to check the schedule for holidays or other service interruptions.
A nighttime stroll will let you enjoy the little things you didn’t know you had. Bean Point on the north end of Anna Maria is a serene beach that overlooks Tampa Bay. There’s a faint echo of the city lights in the distance. It’s a wonderful spot to the cool sand and coastal breeze.
Plan Your Vacation
Anna Maria Island is a packed with things to do at all hours of the day. Check our listings of vacation rentals on Anna Maria and book your dream getaway!
A starry night at the beach is quite dreamy. The community has taken care to see that the island doesn’t get too built up. This means there is relatively little light pollution in the area – perfect for stargazing. You don’t have to go far after dinner and drinks to enjoy the night sky. Best of all, like many of nature’s bounties, it’s completely free.
Once you’ve had spent a good night out on the town, it’s time to head home to one of our many Anna Maria Island rentals. Hit the hay in a comfy cottage or a sleek lowrise condo. Either way, get a night of restful sleep and wake up knowing you’re right by the beach!
