A Relaxing Itinerary for Anna Maria Island
Florida is one of the ultimate getaway locations in the United States and it’s easy to see why with gorgeous ocean views and plethora of fun activities, especially in Anna Maria Island where you can relax and explore.
Since my first trip to Florida, I’ve always felt blown away at the number of places to visit within the sunshine state. But for this post, I want to focus on Anna Maria Island and the itinerary that helped make our stay relaxing yet fun.
Anna Maria Island has become a popular area for tourists over the past couple of years. Many people are seeking the perfect location for romantic getaways and retirement.
Anna Maria Island has everything that island lovers dream of.
Get ready to soak your toes in the blue water with this relaxing Itinerary for Anna Maria Island.
Day 1: Check into your Vacation Rental
The beautiful island in Florida is mostly filled with vacation rentals or beach houses, but you can also find some locally owned hotels. As someone who travels to Florida quite often, it is key to book a place well in advance.
Nothing like the disappointment of wanting to relax on Anna Maria Island only to find out there is nowhere left that is affordable. Here are some key things to look out for when booking your condo/vacation rental:
- Private pool
- Near Bridge St.
- Walking distance from Bradenton Beach
- Close to beach shops and restaurants
Spend A Day at Holmes Beach or Bradenton Beach
During Florida’s peak tourist season, it is generally more pleasant to head to Holmes beach early before everyone else.
It is also more convenient if you booked a place just across the street, so you don’t have to try and find a parking space because it can be a complete nightmare.
Anna Maria Island beaches are calmer than some of the other Florida beaches as if time has stopped. Even so, the calmness doesn’t keep people from planning their stay on Anna Maria Island well in advance.
Eat at a Local Seafood Restaurant
It’s not difficult to find authentic seafood on this stunning island. On every corner, there is a locally owned restaurant that gives us all the beach vibes and tequila to last the whole trip.
Some of the restaurants I recommend are Island Time Bar and Grill, The Beach House Waterfront Restaurant, and Anna Maria Island Beach Cafe.
Don’t miss out on these as some of them have live music and the best views of the turquoise water on the Gulf Coast.
Stroll Around Bridge St.
Visiting Bridge Street is a must on your Anna Maria Island trip. The popular area gives off the perfect island vibes. As you walk by, stop at the shops and aesthetic restaurants.
Bridge Street is often considered the place to hang out and cool down with a drink and music.
Shops at Bridge St.
- Bridge Street Bazaar
- Cove Gift Shop
- Beach Life AMI Boutique
- Back Alley Treasures (Coffee Shop and Gift Shop)
Day 2: Explore off the Island
Even though the island offers delicious food and cute boutiques, I wanted to see what other cool places that were within driving distance. I would say to choose wisely on the time to drive off the island during high tourist season as there can be heavy traffic.
Many of the shops and restaurants gave off less of an island feel and more of places you would find in Orlando.
However, if you need necessities that can’t be found on the island, making a trip is worth it. Although, there are a few restaurants off the island that I enjoyed such as the Asian restaurant, Stone Bowl.
Spend a day at the Pool
This was actually one of my favorite ways to relax on Anna Maria Island with the perfect private pool.
When the pool lights turned on at night, I couldn’t help but be entranced to swim under the stars. The vacation rental did have other guests but night swimming was exclusively ours for the days we were there.
Watch the Sunset on the Beach
Whenever we travel somewhere tropical, watching at least one sunset will always be a part of our plans.
I do have to say that Anna Maria Island has some of the most stunning sunsets. I would bring a blanket and admire the sun going down.
Day 3: Sleep in
Sometimes you have to take things slow and allow time to rest when you’re traveling. People would argue that sleeping in or taking a day off can be a waste, especially if you don’t plan on staying at a destination very long.
But if you’re like me, who needs a breather from constantly going, I encourage you to take that time for yourself.
Explore Anna Maria Island Like Bean Point
After sleeping in, I thought it was perfect to spend the majority of the day exploring more of the island that I haven’t seen before. We kind of had an excuse because our rental didn’t have a washer and dryer.
We stopped at a local laundromat in the downtown area of the island and explored till our clothes were ready.
Many people took the opportunity to rent golf carts instead of driving with their vehicles to see the sights.
There are also other beaches and places where you can catch fresh fish near the downtown area.
Places to See on Anna Maria Island
- Rod Reel Pier
- Bean Point
- Pine Avenue
Visit the most instagrammable places in Anna Maria Island for more photo-worthy locations for social media.
Take a Cruise
We always talk about taking more time to see the water and what better way to do that than to book a cruise?
We decided to go around sunset to not only capture Anna Maria Island’s gorgeous skies but also to see dolphins. But we ended up going on a windy day with not much of a sunset; however, the dolphins became the key highlight of the cruise.
There are different cruises you can take. I would recommend Go2seedolphins as you not only get to see dolphins but nice sunsets too on a good day.
We advise you to book a couple of days ahead of time, so you’re not scrambling last minute to find a slot.
I hope you found this Anna Maria Island itinerary to be helpful in your Florida travels.
It helps to have a little bit of a plan before embarking on a new adventure.
For more helpful itineraries and guides, visit these articles:
Sunsets and delicious good is what I’m looking forward to in Anna Maria Island. Hope to visit there soon! Thank you for sharing this helpful blog post, Alexis.
It’s such a beautiful place and you’re welcome! I wish to explore Anna Maria Island more soon!