Anna Maria Island, FL, is a hidden gem on the Gulf Coast of Florida. Known for its pristine beaches, laid-back atmosphere, and charming community, Anna Maria Island is the perfect destination for a memorable girls’ trip.
And what better way to experience all that this island has to offer than by staying in one of the luxurious vacation rentals on Anna Maria Island?
At Duncan Real Estate, we pride ourselves on providing personalized service and expert knowledge of the island and its surrounding areas as well as premier Anna Maria Island vacation homes with enough space for your whole group. Let us help you plan the perfect Anna Maria Island girl’s trip that promises unforgettable memories from beginning to end!
Instagrammable Spots
Capture picture-perfect moments at Anna Maria Island’s most Instagrammable spots. From stunning sunsets to quaint historic sites, Anna Maria Island does not lack Instagrammable spots. These locations will provide a beautiful backdrop for your vacation photos.
Rod & Reel Pier
Tucked away on the far North end of Anna Maria Island, the Rod & Reel Pier is a hidden treasure dining experience. This two-story, newly renovated restaurant offers traditional fare, local favorites, and famous fish specials since 1947. Whether you choose to dine upstairs with a view of the Gulf of Mexico or enjoy a casual drink at the bar downstairs, a visit to the Rod & Reel Pier is an authentic Old Florida experience. Don’t forget to bring your camera to take a picture of your entire group from the dock while enjoying spectacular views of the Gulf of Mexico, Anna Maria Island’s beautiful beaches, and the Sunshine Skyway Bridge.
Old City Jail
Immerse yourself in the island’s history by visiting the Old City Jail, now home to the Anna Maria Island Historical Society. Housed in a building that was originally constructed as an icehouse in 1920, the museum showcases the story of the island’s first settlers, their legacy, and the island’s fishing and baseball history. Explore the exhibits, including archives of records and newspapers, and gain a deeper understanding of the island’s rich heritage.
Wine Tastings
Indulge in a delightful experience of wine tastings at any of these charming wineries near Anna Maria Island. Indulging in a decadent wine tasting while on your girl’s trip is the perfect activity to make lifelong memories.
Manasota Vineyards
Located about an hour from Anna Maria Island in East Bradenton, Manasota Vineyards is a must-visit for wine lovers. This wonderful winery offers tours, wine tastings, and a lovely pavilion area that serves as a picturesque venue for weddings and events. Take a tour and stroll through the vineyards, witness the winery’s operations, and treat yourself to their fantastic selection of wines. For an elevated experience, opt for the more comprehensive tour, which includes a delicious lunch in the pavilion. Additionally, Manasota Vineyards hosts special events throughout the year, such as the enthralling Murder Mystery Dinner & Show.
Mademoiselle Paris
Embark on a delightful journey to France on Anna Maria Island at Mademoiselle Paris. This charming establishment specializes in French wine paired with traditional French dishes. Owned by Jean and Chef Arnaud, the restaurant invites you to savor a four-course meal paired with four glasses of wine. Indulge in appetizers and gougères, delight in live music, and enjoy a live presentation by Jean, the wine connoisseur. As an added bonus, you even have a chance to win a bottle of wine! Experience a taste of France in the heart of Anna Maria Island.
Fiorelli Winery & Vineyard
For a wine-tasting experience closer to Anna Maria Island, visit Fiorelli Winery & Vineyard. With humble beginnings in 1998, Fiorelli Winery has grown into a beloved establishment that shares its love of wine with guests, who are considered part of the family. Aside from their winemaking expertise, they offer wine tastings and private tours. This winery also hosts a wide range of private events, making it the perfect venue for weddings, birthday parties, and corporate gatherings. Immerse yourself in their winery’s history, enjoy an overview of each wine you sample, and create unforgettable memories at Fiorelli Winery & Vineyard.
Plan Your Visit
The ultimate girls trip is just clicks away! Browse our full inventory of Anna Maria Island rentals to find your perfect accommodations!
Nightlife
Anna Maria Island offers a vibrant and lively nightlife scene where you can enjoy good drinks, great conversation, and live entertainment.
Bortell’s Lounge
Bortell’s Lounge is an Anna Maria City staple with a long history dating back to 1977. Serving as a gathering place for locals and tourists, this piece of island history has recently undergone renovations, offering a new and improved experience. The lounge boasts one of the best locations on the island to sit back and relax with a drink in hand, and continues its legacy of serving excellent drinks and providing a friendly ambiance. Step into Bortell’s Lounge and immerse yourself in the island’s vibrant nightlife scene.
Island Time Bar & Grill
When it comes to island dining and entertainment, Island Time Bar & Grill sets the standard. Offering a relaxed tropical setting and the area’s best live entertainment, this establishment will make your nights on Anna Maria Island genuinely unforgettable. Indulge in a varied menu that includes fresh ingredients and made-from-scratch recipes by Chef Jimmy Lopatinski. Sip on the island’s best margarita or enjoy a cold beer while listening to some of the best local acts performing live music from 7:00 p.m. to 10:00 p.m. Island Time Bar & Grill is more than just a restaurant; it’s an experience.
Stay With Duncan Real Estate
To ensure your ultimate girl’s trip experience on Anna Maria Island, stay with Duncan Real Estate. As your personal guide to the island, we offer a wide selection of Anna Maria Island vacation rentals, guaranteeing you find the perfect home away from home. With our local expertise and connections, we can assist you in planning activities, events, and excursions tailored to your preferences. Whether you’re seeking serene beachfront properties or charming vacation homes lodged in the island’s vibrant community, Duncan Real Estate has the perfect option for you. Trust our personalized service and make your stay on Anna Maria Island truly unforgettable. Book your stay with Duncan Real Estate today and be one step closer to the ultimate getaway!
