The Gulf Of Mexico Meets Tampa Bay At This Paradisal Stretch Of Florida Coast With Total Caribbean Vibes

Total serenity is what many vacationers dream of, and there are few places more tropically serene in the U.S. than Southwest Florida. As the Gulf of Mexico meets the shoreline cities of Florida's west coast, some beautiful slivers of land offer amazing getaways. Among them is Anna Maria Island, a 7-mile-long barrier island with a taste of Old Florida that sits just west of Bradenton and south of the Tampa-St. Petersburg-Clearwater metro area. Though the island is just a bridge away, the feeling of seclusion here is unrivaled, with crystal blue waters and sugary white sand beaches reminiscent of the Caribbean.

Thanks to its inherent beauty and its locale in the Gulf waters, Anna Maria Island has become a popular beach day choice in Southwest Florida and a snowbird's winter playground. It's a destination that allows visitors to slow down compared to the pace of your average vacation, both literally and figuratively. This golf cart-centric community with beach access first came to popularity thanks to a man named Bean, and there's a connection to a popular cookie that tells the story of the paradise that is Anna Maria Island, Florida.

Though the island's first modern settler was Tampa mayor Madison Post, who named the island after his sister in-law Anna and his wife Maria, it was George Emerson Bean who was the first permanent resident. In 1892, Bean put down roots at the northern tip of the island, which is known to this day as Bean Point. When Bean passed away, he left the land to his son, who partnered with a man named Charles Roser to continue developing the island for future residents. Interestingly enough, Roser also became the creator of the Fig Newton cookie, which led to a financial windfall that further stimulated his ventures in the Sunshine State.

Today, Bean Point Beach is a cornerstone of any Anna Maria Island visit. The secluded beach is strewn with tiny dunes and bright white sand, which make for a picturesque setting. Facing west out to the Gulf, it provides a view of stunningly clear blue waters that rival the beaches of the Caribbean. Visitors claim this is one of the most beautiful and pristine beaches in the United States, but advise an early arrival if you're trying to park beachside. Watch the waves close to the shore, as dolphins often dance by the beach and seagulls swoop down to water level for fresh fish meals. The eastern side of Anna Maria Island faces toward Tampa Bay, and here you'll find the buzzier part of the island featuring the City Pier, where the shores often produce a variety of fish and sharks. Nearby are waterside restaurants, shops, and a Bayfront Park that offers views of the Sunshine Skyway Bridge on a clear day.

Once you arrive on Anna Maria Island, visitors are encouraged to slow down and use any transportation but a car. Golf cart rentals are readily available and the most common form of transport on the island, one that never stretches to more than 2 miles wide. There are also bikes for rent by the hour or day, and the island has a complimentary trolley service for a safe ride on the island. 

While neighboring islands along the Gulf Coast such as Longboat Key feature resorts, Anna Maria Island more modestly boasts a plethora of charming vacation rental homes and beachside cottages that accurately fit the relaxed vibe of the island. Pro tip: when staying at any of the top-rated islands in Florida to visit on vacation, a peak season trip between December and April will be pricier and much more crowded than an offseason venture to the island.

Fortunately, the convenience and diminutive nature of the island landscape make it a great place to hop from site to site while exploring the area. The Anna Maria Island Historical Museum is located right in the heart of Pine Avenue, where you can learn more about the origins of the land. Pine Avenue is filled with gift shops and great spots to purchase souvenirs, including the Shiny Fish Emporium, where you can decorate and glitter a sand dollar found on the beach. The entertainment on the island goes into the night, with local dives and restaurants regularly featuring live music. Locals recommend trying the fresh seafood and cocktails at The Waterfront Restaurant, next to the intersection of Spring Ave. and Bay Boulevard overlooking the bay. No matter what view you have on Anna Maria Island, the tropical feel is ever present.