The ultimate Anna Maria Island girl’s trip features a blend of historic sightseeing at the Rod & Reel Pier, French-inspired wine tastings, and live music at open-air bars like Island Time Bar & Grill. To accommodate groups, Duncan Real Estate provides high-capacity vacation homes that offer the privacy and space needed for a collective retreat while remaining close to the island’s most “Instagrammable” locations.
What are the best activities for a girl’s trip on Anna Maria Island?
Groups typically focus on a mix of social dining, photography, and evening entertainment.
Live Music: Visit Island Time Bar & Grill for nightly performances and outdoor dining.
Sightseeing: Capture group photos at the Old City Jail or the scenic Rod & Reel Pier.
Wine Pairings: Experience traditional French wine courses at Mademoiselle Paris or tour local vineyards at Fiorelli Winery.
Most Instagrammable Spots on the Island
Rod & Reel Pier
Located at the far North end, this 1947 landmark provides panoramic views of the Gulf of Mexico and the Sunshine Skyway Bridge.
Group Activity: Dine on the second floor for elevated views or take group photos from the end of the dock.
Old City Jail
Part of the Anna Maria Island Historical Society, this roofless structure was originally an icehouse built in 1920.
- Best For: Quirky historical photos and learning about the island’s first settlers and fishing heritage.
Top Wine Tasting Experiences
Mademoiselle Paris
An authentic French bistro that offers curated four-course meals paired with specific French wines.
- Key Features: Live music, presentations by wine connoisseurs, and a menu developed by Chef Arnaud.
Fiorelli Winery & Vineyard
Established in 1998, this winery offers a traditional vineyard experience close to the island.
- Highlights: Private group tours and structured tastings of their diverse wine selection.
Manasota Vineyards
Located in East Bradenton (approx. 1 hour away), this venue is ideal for a dedicated day trip.
- Highlights: Extensive vineyard tours and seasonal events like the Murder Mystery Dinner & Show.
Where to Find the Best Nightlife
Island Time Bar & Grill
This venue is the island standard for live entertainment and tropical dining.
- Schedule: Live local acts perform nightly from 7:00 p.m. to 10:00 p.m.
- Signature Item: Made-from-scratch recipes and a popular margarita menu.
Bortell’s Lounge
A recently renovated Anna Maria City staple that has served locals and tourists since 1977.
Highlight: A classic “Old Florida” lounge environment perfect for late-night cocktails and social gathering.
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!
How do I find a rental for a large group?
For the best experience, search the Duncan Real Estate website using filters for “Multi-Bedroom” and “Private Pool.” Booking a single large home rather than multiple smaller units allows your group to stay together in a central, private location.
