Anna Maria City: The Island trolley is free and allows you to enjoy all parts of the island without having to worry about parking. You might want to take the north bound trolley to the Anna Maria City Pier and boardwalk. Pine Avenue has been transformed into a mecca of small boutique shops and there are several 'coffee or iced tea' stops along the way. The City Pier is at one end of Pine Avenue (on the Tampa Bay side) and the Studio at Gulf and Pine is at the opposite end (the Gulf of Mexico side). The Studio is owned by former Florida First Lady, Rhea Chiles, and always has an enchanting display of local art. Another favorite in Anna Maria City is Ginnie and Jane's on Gulf Drive (the trolley stop is right there), an antique store with a bakery - get your muffins and coffee and have a seat in one of the room displays. Be sure to stop by Rudy's Subs & More for a terrific breakfast or mouth-watering sub for lunch. Make sure you have a great Italian Meal at Vinny and Sheryl's Italian Kitchen.
Holmes Beach: The trolley continues south through Holmes Beach. If you want to do some shopping you can get off at the plaza where you'll find everything from art galleries, souvenier shops, clothing stores, restaurants, liquor stores and the Holmes Beach post office. If you're looking for some island night life and music, here is where you'll find it - the Tiki Bar at Island Flea or Lobsta's are both crowd pleasers. Or you might want to continue to the Manatee County Beach where you can enjoy the Gulf of Mexico and have lunch at the Cafe on the Beach. Further south is the island's only grocery store and several pharmacies along with the island's oddest restaurant... Mr. Bones, where BBQ is an art that has been perfected.
Bradenton Beach: Continuing south you'll come to Bradenton Beach. Make sure you take a walk down Bridge Street and enjoy the Bridge Street Pier that looks over the intracoastal waterway. If you have your fishing pole ready, you can catch your dinner off the pier. There are a lot of little boutique shops and places for lunch or dinner along the way. Along the route to Bridge Street you might have noticed the BeachHouse restaurant.. a lovely place to enjoy a sunset dinner on the deck. A little further down at the southern end of the island is Coquina Beach, a long stretch of white sugar sand that ends at the bridge to Longboat Key. One stop you might want to make in Bradenton Beach is Joe's Eats and Sweets.. a local favorite for ice cream treats.