One of the most amazing feelings in life is just taking off for the beach for a week! Whether you’re piling your bags in the car for a road trip or hopping on a plane with your favorite magazine and snacks, knowing that the beach is your final destination just adds another layer of excitement to the trip. When it’s Anna Maria Island you’re headed to, you’ll be in store for a week full of both thrills and relaxation, topped off with an excellent dining scene and constant ocean views. We have the perfect 7-day itinerary for your AMI vacation!

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Day One: Arrive on AMI and Spend Your Evening Out

Cross the bridge over onto the island, and you’ve arrived at your island vacation destination! No matter where you’re staying, you’ll never be far from the water, as the island is bordered by the azure blue waters of the Gulf of Mexico to the west and Tampa Bay (as well as some smaller bays) to the east. The north end of the island is the town of Anna Maria, then moves south to the lively Holmes Beach, and ends at Bradenton Beach. Each town offers a variety of stunning vacation homes both on and off the water, and you can’t go wrong with any choice!

After unpacking at your vacation rental, you can walk to the nearest beach and admire the sunset before heading out to dinner. For dining out, you have several options, from the bustling Bridge Street District in Bradenton Beach to the clusters of eateries and shops in Holmes Beach. Whether you’re looking for fresh seafood or ocean views you’ll find them here—try The Ugly Grouper for excellent island vibes and an array of seafood and burgers, or stop by the Beach House Waterfront Restaurant for an upscale vibe situated right on the shore.

Day Two: Get a Taste of Island Life

It’s time for the first full day of your weeklong trip to Anna Maria Island! If you’re an early riser head out to the beach at sunrise to find all sorts of unique shells in the morning, or wake up leisurely with your favorite brand of coffee. You can switch around the day’s activities schedule-wise, but take this loose itinerary as a guide!

On this day, it’s a great idea to rent a few bikes and cruise up and down the island yourself. You can experience several beaches all in one afternoon, and get a feel for each unique area of the island, from Manatee Beach in the heart of the island, all the way down to the action-packed Coquina Beach. Don’t forget that AMI has a free island trolley that will take you up and down the island with ease—there are stops within walking distance of most AMI vacation homes!

Day Three: Brunch Seaside and Shop on Pine Ave

On day three, it’s the perfect opportunity to indulge in a little brunch with a seaside view. Whether you’re a fan of a brunch with tons of options or just looking for an elegant brunch menu, you’ll have many options on AMI. Stop by Anna Maria Island Beach Café to dine with your feet in the sand, or check out Minnie’s Beach Café for breakfast classics.

When you’re done brunching, you can treat yourself to a little bit of shopping on Pine Ave on the north end of the island. You’ll find local stores selling everything from boutique beachwear to handmade soaps, and it’s the ideal place to pick up a little souvenir to commemorate your AMI getaway. There’s even nautical-themed home décor if you’d like to bring a little bit of the island to your own living room!

Day Four: Have a Bayside BBQ at Bayfront Park

This day is the perfect opportunity to check out Bayfront Park, a gorgeous city park that sits right on the tranquil waters of Tampa Bay with distant views of the iconic Sunshine Skyway Bridge that stretches over the bay. Bayfront Park offers a generous amount of amenities, including several coal BBQs available for use, making it effortless for you to have a cookout right on the bay! The park facilities also include restrooms, showers, and picnic tables, giving you all you need for a day on the bay.

With the proper license, you can fish in the shallow waters offshore, or stop by the nearby Rod and Reel Pier to fish—there’s also a cozy restaurant at the end of the pier, perfect for breakfast, lunch, or dinner as they’re open from 8 a.m. to 9 p.m. You might even catch a few dolphins playing around in the bay.

Day Five: Bridge Street District and a Night Out

In Bradenton Beach, you’ll find the Historic Bridge Street District, home to the Bridge Street Pier. As this area was the site of the first bridge built onto the island, you can find tons of history here in this walkable district that also includes countless opportunities for shopping and dining.

Walk to the end of the pier to admire the views, and maybe grab a cocktail and snack at the Anna Maria Oyster Bar—you can also fish off the pier if you obtain a license, which can easily be done online. Once you’ve dined out, you can continue the night at one of AMI’s many pubs, such as The Freckled Fin, or head back to your vacation home to get rested for your next day of adventure!

Day Six: Have the Ultimate Beach Day

Pack a picnic lunch and head out to the beach in the morning and stay as long as you’d like—the entire afternoon even! You’ll find many beaches on AMI that offer facilities such as coal grills, picnic tables, and restrooms, making it easy to spend the entire day out on the sugar-white sands of the island.

If you’re looking for something more low-key, you can find beaches that are a bit busy but may not have as many amenities, such as the breathtaking Bean Point, which sits on the northern tip of the island and offers unbeatable views of the Gulf and Tampa Bay. If you’d like to pair your beach day with another activity, consider renting some snorkeling gear, or even a kayak to explore the bays surrounding the island.

Day Seven: Relax and Wrap Up Your AMI Vacation

This day is the ideal day to catch up on any activity you missed, whether it was shopping for a souvenir or spending another day out on the sand. It’s also the perfect night to toast your epic vacation with a sunset happy hour. Whether you’re spending one final night taking advantage of all the five-star amenities in your vacation home, or heading home before the start of the new week, we hope this 7-day itinerary helps you plan out your AMI weeklong getaway!

Book Your Weeklong AMI Vacation Today!

It’s never too late to book your week-long getaway to Anna Maria Island! From beach cottages with private pools to trendy condos right by the shore, we offer an amazing selection of AMI vacation homes. Chat with us to learn more today!

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