Florida 3-Day Weekend Getaway Itinerary for Anna Maria Island

Florida 3-Day Weekend Getaway Itinerary for Anna Maria Island

If you’re looking to get away for the weekend and enjoy a relaxing beach vacation or staycation on one of Florida’s more alluring islands, you’ve come to the right place. Booking a beachfront rental on Anna Maria Island is one of the best ways to see Florida’s stunning west coast and enjoy a weekend beach vacation. We have FL beachfront rentals for individuals, couples, and families looking to stay for any period of time but for this guide, we will focus on a weekend itinerary of 3 days.

There are plenty of reasons why you should choose Anna Maria Island for your next Florida vacation! Below, check out everything you need to know to make the most of your weekend-long visit to Anna Maria Island. There are too many attractions, activities, and places to visit to fit into a single 3-day weekend, so we will highlight some of our favorites to help you narrow it down. If you have questions, you can always contact the vacation experts at Island Real Estate if you need help planning your vacation or with booking one of our stunning beachfront house rentals or condo rentals in Florida.

Day 1 – Ride the Monkey Bus and See the Entire Island

Taking a ride on the “free-for-tips” Monkey bus is essential whenever you visit Anna Maria Island. The Monkey Bus travels all over Anna Maria Island, Cortez, and across the bridges by request. We recommend heading to Anna Maria City Pier to enjoy a walk on the boardwalk and some great fishing spots! The pier is free to visit and there is parking found along South Bay Boulevard. At the end of the pier, there is a restaurant, The City Pier Grill and Bait Shop, where you can enjoy food and some ice cream before heading back to the rental.

anna maria island monkey bus
Anna Maria Island Monkey Bus

Day 2 – Enjoy Popular Island Activities like Fishing, Kayaking, and Jet Skiing

If fishing is how you relax, then check out one of the 3 piers on Anna Maria Island instead. All of these are accessible from the free trolley. These piers are:

  • Rod and Reel Pier
  • Anna Maria Island City Pier (mentioned above)
  • Bridge Street Pier

If we had to pick the best spot to fish on Anna Maria Island, we recommend checking out Anna Maria City Pier. It has a beautiful boardwalk along with some great fishing spots! The pier is free to visit and there is parking found along South Bay Boulevard. At the end of the pier, there is a restaurant, The City Pier Grill and Bait Shop, where you can enjoy food and some ice cream before heading back to your Florida beach rental.

Day 3 – Take Some Time to Relax On the Beach

Anna Maria Island is home to any exclusive Florida beaches you can spend the day relaxing on. The beaches on Anna Maria Island are:

  • Coquina Beach
  • Bean Point Beach
  • Bradenton Beach
  • Manatee Public Beach
  • Beer Can Island Beach
  • Bayfront Park

Bean Point Beach is more than just a beach, it’s a historical landmark. We have some great rentals there that you might want to book so you’re just steps from this amazing landmark. Check out Latitude Adjustment, Rest A Shore, or Reel Paradise! Bean Point is the home of the founder of Anna Maria Island, George Emerson Bean. He founded the island in 1892 and chose the 160-acre northern tip of the island as his homestead. Though the homestead itself is no longer there, the area is still one of the most scenic parts of the island and great to visit as it has no obstructions to the gorgeous view of the clear, blue water. It should be noted there are no facilities on this part of the island, including no parking lots so be ready to walk. 

anna maria city jail
Anna Maria City Jail

While up here you can also visit Anna Maria Island Historical Society Museum and Old Jail, to learn about some of the island’s history. This is the “crescent Drive at Pine Avenue” stop on the AMI Trolley and is free admission!

Bradenton Beach is also a popular beach destination on the southern end of the island. This area can sometimes be a bit congested with traffic due to it being accessible only from Cortex Road or Longboat Key. However, don’t let this stop you from visiting as the beach itself is usually quiet and calm as it is away from the main stretch of road. While you’re here, definitely check out Bridge Street Market to enjoy fantastic food, beautiful art and jewelry, great local musicians, fresh produce, and much more!

On your walk, you can comb the beach for elusive and beautiful sand dollars. Don’t have beach equipment with you? Not a problem! There are plenty of beach equipment rentals where you can rent everything including beach chairs, towels, snorkels, fishing equipment, kayaks, wind surfboards, and even jet skis! 

Bradenton Beach is also a popular beach destination on the southern end of the island. This area can sometimes be a bit congested with traffic due to it being accessible only from Cortex Road or Longboat Key. However, don’t let this stop you from visiting as the beach itself is usually quiet and calm as it is away from the main stretch of road. While you’re here, definitely check out Bridge Street Market to enjoy fantastic food, beautiful art and jewelry, great local musicians, fresh produce, and much more!

bridge street market anna maria island
Bridge Street Market

Now that you have your bearings on the island, you’ll want to venture a little further out and visit Coquina Beach on the south end of the island. There is a free trolley that will take you there. While you are there, you can enjoy walking on the soft white sand boardwalks, which offer views of the Sarasota bay as well as tall pine trees lining the walks.

Need Help Planning and Booking Your Next Vacation Rental on Anna Maria Island?

If you are looking for the best week-long beach getaway, there is no better area to book your Florida beach vacation than Anna Maria Island. We have the best last-minute beach rental deals for those looking to get away soon. Or if planning for next year and beyond is more your thing, there is no better time to look, book, and lock in your rates than right now! Check out the rental calendar to see the number of rentals available for your desired dates. If you need help planning your itinerary, our vacation specialists are a phone call away to help with that and more. Call us at 877-778-6066.

Leave a Reply