February 2025
Our Long Weekend Itinerary for Anna Maria Island, Florida
I have had a visit to Anna Maria Island on my mind for awhile ever since I learned about it from none other than an Orlando theme park vlogger, TimTracker. They featured their vacations there on their YouTube channel and it really looked like a wonderful place to visit and relax. It is super family friendly with an old Florida charm and white sanded beaches touching clear blue water – I knew this would be a great long weekend destination. After spending a few winter vacations in cold destinations, I was looking to escape to some sunshine so over President’s Day weekend, we took the opportunity to finally visit Anna Maria Island.
Anna Maria Island is a barrier island off of Florida’s Gulf Coast and has three towns to explore in its seven miles – Anna Maria at the north, Holmes Beach in the middle, and Bradenton Beach at the south. There is tons to do on this small island with the entire west coast covered in perfect beaches and picture perfect sunsets every night. While cars are permitted, the island is also known for non-car alternatives for getting around including golf carts and bikes as well as a free public trolley. And you won’t find high rise condos, fast-food restaurants, or chain shopping here – it is truly a local vibe with old Florida charm.
Here is our complete itinerary!
| Activity | ||
| Day 0 | Evening | Flight to Tampa Drive to Anna Maria Island |
| Day 1 | Morning | Ginny’s & Jane E’s Cafe and Gift Store Walked Pine Street – The Donut Experiment – Shiny Fish Emporium – Olive Oil Outpost Historical Park / City Jail Dips Ice Cream at Anna Maria General Store Anna Maria City Pier |
| Afternoon | Red Reef Pier Walk to Bean Point and Bean Point Beach Lunch at North Shore Cafe Relax on Anna Maria Island Beach | |
| Evening | Dinner at The Porch Restaurant Sunset at Anna Maria Island Beach | |
| Day 2 | Morning | Breakfast at Anna Maria Island Coffee Shack Robinson Preserve |
| Afternoon | Lunch at Ugly Grouper Relax at Holmes Beach Happy hour at The Porch | |
| Evening | Bradenton Beach Walked Bridge Street – Fudge Factory – The Fish Hole Mini Golf – Back Alley Treasures Bridge Street Pier Dinner at Pane e Amore Italian Cafe Gelato-go Anna Maria Island Sunset at Bridge Street Pier and Bradenton Beach | |
| Day 3 | Morning | Breakfast at Blueberries Cafe and North Shore Cafe Day on the Anna Maria Island Beach |
| Afternoon | Day on the Anna Maria Island Beach Lunch at Sandbar Seafood + Spirits | |
| Evening | Two Scoops Ice Cream Anna Maria City Pier Dinner at The Doctor’s Office | |
| Day 4 | Morning | Flight home |
Read all the details of our trip – here!
See all blog posts for visiting Anna Maria Island – here!
Planning your trip? Check out the Perfect Itinerary for Anna Maria Island here!
Discover more from DESKRIB
Subscribe to get the latest posts sent to your email.
