Last Minute Spontaneous Getaway to Anna Maria Island, FL
Escape for a long weekend getaway to Anna Maria Island, Florida! We’re sharing our 3-day travel itinerary featuring boutique beachfront resorts, the best local restaurants, beach adventures and unforgettable sunsets.
Why Anna Maria Island?
Sometimes the best trips are the ones that happen on a whim. Our spontaneous long weekend getaway to Anna Maria Island, Florida turned into one of our favorite escapes this year. A blend of white-sand beaches, turquoise water, coastal charm and incredible food.
If you’re looking for a laid-back Florida beach destination that feels like paradise, this barrier island on the Gulf Coast might just steal your heart like it did ours.
Here’s our full Anna Maria Island itinerary, where we stayed, what we ate, and all the wonderful moments in between!
Where to Stay on Anna Maria Island
Let’s start by letting you know there are 3 cities of the Island: Anna Maria, Holmes Beach and Bradenton Beach. The island is relatively small, so all 3 cities are very close to one another.
- Bradenton Beach: Located at the Southern part of the island.
- Holmes Beach: Centrally located with great shops and restaurants.
- Anna Maria: Located at the Northern part of the island. We love this area – great shops along Pine Avenue and one of the best beaches. (Bean Point Beach)
Where We Have Personally Stayed:
- Compass Hotel by Margaritaville: We spent our first night here – it’s right before the bridge that takes you into Anna Maria Island, but still a very short drive to AMI. We really enjoyed our stay here. It’s a bright, coastal-inspired property overlooking the marina. The tropical pool area is perfect for unwinding after traveling. Rooms are airy and modern, with great views of the marina. 📍Ideal for: Travelers who want resort-style comfort near Anna Maria Island for a great price.
- Bali Hai Beach Resort: We spent 3 nights here – it’s a lovely boutique hotel located on Holmes Beach. The property blends tropical serenity with modern design. The pool and on-site spa make it easy to slip into full vacation mode. 📍Ideal for: Beach lovers and couples seeking a true beachfront experience.
More AMI Recommendation:
You can check out our full list of Anna Maria Island recommended properties here.
Day 1: Travel Day – From Take off to Tiki Time
Our adventure began with a nonstop Avelo Airlines flight to Tampa International Airport (TPA)…quick, easy and super affordable! After landing, we picked up our rental car from Sixt Rental Car right at the airport and started the one-hour drive to Anna Maria Island.
Tip: If you can, fly into Sarasota-Bradenton International Airport (SRQ) because it’s a lot closer to Anna Maria Island (approx. 30 minutes). Since we booked this trip on a whim, we were unable to find flights for our dates, so we chose the second best choice which is Tampa.
For our first night, we checked into the Compass Hotel by Margaritaville, a relaxed coastal-style hotel overlooking a beautiful marina. The pool area is a true highlight with palm trees, adirondack chairs and a tropical ambiance that instantly puts you in vacation mode.
After hanging by the pool for a bit, we freshened up and headed into Anna Maria Island for dinner at Beach House Waterfront Restaurant. This spot sits right on the sand of Bradenton Beach. We dug into crispy, golden fish and chips that were absolutely delicious. Great atmosphere, food and unbelievable views – the perfect first meal on the island.
We ended the night with tropical drinks (Pain Killers) back at our hotel, relaxing by the water.
Day 2: – Check-In at Bali Hai Beach Resort
The next morning, we checked into Bali Hai Beachfront Resort & Spa, where we stayed for the remainder of our trip. This boutique beachfront resort is a tropical dream – newly renovated, beautifully designed and perfectly located steps from the sand. Our 1-bedroom Beach Side King Suite was spacious and modern, with a coastal chic decor and resort views that made it hard to leave. The Living room/kitchen had a sleeper sofa, tv, dining table, mini refrigerator and freezer, coffee pot, dishes and utensils.
To explore the island in style, we rented a Moke from Beach’N Rides in Bradenton. The process was seamless. They delivered it right to our resort and picked it up at the end of our rental term. Cruising around in a colorful open-air Moke was one of the most fun parts of our trip!
Our first stop was The Donut Experiment, a local favorite famous for its made-to-order donuts. You choose your base, icing and toppings, and then they make them fresh – warm, fluffy and delicious! Our favorite was Chocolate Icing with reese pieces and peanut butter drizzle…OMG!
We spent the afternoon relaxing and playing games like cornhole and giant connect-four in the Bali Hai’s pool area. The afternoon was filled with alternating between the sun beds and dips in the Gulf, which is only a 100′ walk from Bali Hai Resort!
For a late lunch/early dinner, we hopped in the Moke and drove down to Sandbar Restaurant, another beachfront gem known for fresh seafood and incredible beach views. We shared the blackened chicken nachos and shrimp tacos…both were amazing!
As the day came to an end, we returned to Holmes Beach at our resort to watch one of Anna Maria Island’s signature sunsets. Picture cotton candy skies reflecting off the water in shades of gold and coral…absolutely stunning!
Day 3: Biking, Beach & Horseback Riding
Our third day began with a quick stop at Ginny’s & Jane E’s Cafe for a delicious breakfast sandwich. We ordered a bacon, egg and cheese on a croissant to share. This cafe gets crowded, so expect to wait 25-30 minutes for a breakfast sandwich. And oh, if you are a lover of cinnamon rolls, this is a must stop for you as they are known for their homemade cinnamon rolls!
After breakfast, we borrowed the complimentary bikes from our resort and spent the morning riding down streets lined with pastel beach houses and swaying palm trees.
Later that morning, we jumped in our Moke and drove down to Bean Point Beach. This is our favorite beach on Anna Maria Island. The turquoise water and soft white sand create the perfect setting for a relaxing beach day.
Travel Tip: There’s no public parking lot at Bean Point Beach, but you’ll find limited parking on Fern Street, Gladiolus Street and Jacaranda Road, each with access paths to the beach. Arrive early if you hope to get one of these limited free spots. You can also take the free island trolly or walk if you’re nearby.
That afternoon, we headed 15 minutes off-island for a one-of-a-kind experience…Horseback riding in the Palma Sola Bay with Florida Beach Horses. We booked the “Cruise Ride” which is approximately 1.5 hrs and $155 per person. Our guides took us through calm coastal waters where we even learned to swim with our horses. It was one of the most memorable adventures I’ve ever had in Florida.
We capped off our trip with an amazing dinner at Dry Dock Waterfront Restaurant in Longboat Key, just a short drive from Anna Maria. Joe picked this restaurant and I would honestly rate it a 10/10!
Our favorite dishes:
- (Sharon) Lobster Pasta – tender lobster meat and a Maine Lobster tail in a creamy Tuscan sauce…sooo freaking good!
- (Joe) Citrus Grouper – lightly breaded and sautéed, served with a refreshing citrus cream sauce…it was outstanding!
It was the perfect ending to a perfect weekend.
Travel Tip: Make a sunset reservation and request outdoor seating – the views are breathtaking!https://drydockwaterfrontgrill.com/
What to Pack
Anna Maria Island has an “Old Florida Charm” feel to it. It’s not real fancy and you can dress super casual. We did pack a few resort style outfits for dinner. Nothing too fancy (casual sundresses for me and polo shirt and shorts for Joe). Majority of the time we were in swimsuits and coverups. Here’s some of my favorites from Amazon.
Final Thoughts of Anna Maria Island (AMI)
Our AMI weekend getaway was everything we needed – relaxing, rejuvenating and full of coastal charm. Between luxury boutique resorts, ocean front dining and unique island adventures, Anna Maria Island captures that rare small-town beach magic for a perfect mini vacation.