The Perfect 3-Day Anna Maria Island Itinerary
If you’re planning a visit and wondering how to spend your time on Anna Maria Island, this easygoing three-day itinerary captures the charm, flavor, and laid-back island lifestyle that makes AMI so special. Stay in one of our Anna Maria Island vacation rentals and experience Florida’s best-kept secret.
Anna Maria Island Day 1 – Arrival Day
🏡 Check Into Your Anna Maria Island Rental
You’ve survived the hectic travel day and have finally made it to beautiful Anna Maria Island. Before you dive into your vacation, you’ll likely want to grab some snacks, beverages, and things to cook for meals at home. Fortunately, there are several grocery stores on Anna Maria Island, so you won’t have to go far to grab the necessities. Publix is the largest grocery store on the island and is located in Holmes Beach. You’ll also find an AMI General Store, Island Fresh Market, and Time Saver Food Store on the island.
Now that the not-so-fun stuff is out of the way, it’s time to settle into your Anna Maria vacation rental. Once you’re done unloading your suitcases and other beach goodies, order pizza for delivery or pick up for an easy dinner option. Pizza Social is a popular pizza joint offering handcrafted pizzas and salads. Try one of their specialties like the Social or AMI, or build-your-own and create a pie to your liking.
Once you’ve filled up on good eats, it’s time to rest up for day two’s packed adventure.
Anna Maria Island Day 2 – Beach Day
🍳 Breakfast at Anna Maria Island Beach Cafe
Wake up bright and early and head to Anna Maria Island Beach Cafe for breakfast and coffee. This beachfront cafe is the perfect way to start your day. Imagine spectacular views of the water, good eats, and great company. The breakfast menu includes just about every classic breakfast item, including waffles, pancakes, omelets, and biscuits. The cafe does not accept reservations, so try to arrive early to avoid the long wait lines.
🐚 Beach Time
There are several beaches on Anna Maria Island, so depending on your interests or if you’re looking to be closer to your vacation home, you’ll have several options to choose from. For a family-friendly setting, many prefer Manatee Beach in Holmes Beach. The wide beach and calm waters make it ideal for swimming, and if you’re coming from Anna Maria Island Beach Cafe, you only have to walk a few steps to get to Holmes. There are restrooms, a playground, and beach volleyball courts.
Coquina Beach is also considered one of the best beaches on Anna Maria Island. With access to plenty of concessions and the largest stretch of sand on AMI, you’re sure to find plenty of space to unwind.
🐟 Lunch at The Ugly Grouper
After a few hours of swimming, bronzing, and building sandcastles, we’re sure you’ve worked up an appetite. Head to The Ugly Grouper for some of the best grouper you’ll find on the island. The menu features several Grouper dishes as well as soups, salads, sandwiches, and seafood. Live entertainment is provided daily, so sit back, relax, and enjoy an Anna Maria Island favorite.
🐬 Sunset Cruise with Anna Maria Dolphin Tours
End the day watching the sun descend over the glistening waters of the Gulf Coast. The two-hour tour with Anna Maria Dolphin Tours takes you out onto the waters of the Gulf and back bay, cruising alongside dolphins and other marine life as the sky turns into incredible colorful hues. Private tours are available as well for a more intimate experience for your family and friends.
Anna Maria Island Day 3 – Explore Anna Maria Island
🥞 Breakfast at Ginny’s and Jane E’s Cafe
Begin your day with a hearty breakfast at Ginny’s & Jane E’s Café, a local favorite nestled inside a quirky, art-filled shop. From giant cinnamon rolls to freshly brewed coffee and beachy vibes, this café is as much a cultural experience as it is a morning meal.
🏖️ Explore AMI’s Beach Towns
After breakfast, hop on the free Anna Maria Island trolley to explore each of the island’s charming beach towns—Anna Maria, Holmes Beach, and Bradenton Beach. Each has its own unique personality, from the quaint residential feel of Anna Maria to the livelier, shop-lined streets of Bradenton Beach. The trolley is not only convenient but also gives you a chance to take in the island’s tropical beauty without worrying about parking.
🦪 Lunch at Anna Maria Oyster Bar
When it’s time to break for lunch, head to Anna Maria Oyster Bar for a bite. Known for its fresh seafood and laid-back atmosphere, this local gem serves up everything from oysters on the half shell to fish tacos and Key lime pie. It’s the perfect mid-day stop to relax, sip a cold drink, and enjoy island flavors.
🛍️ Shop at Local Businesses
Post-lunch, take time to explore the island’s many local shops and boutiques. Whether strolling Pine Avenue or poking around smaller shops near Bridge Street, shopping local here feels more like a treasure hunt than a chore.
🥗 Dinner at Sandbar Seafood
As the sun begins to set, make your way to The Sandbar Seafood & Spirits for a beachfront dinner. With toes in the sand and a view of the Gulf, enjoy fresh catches like grouper or shrimp and grits while the sky transforms into a watercolor masterpiece. It’s the perfect finale to a day well spent on Anna Maria Island.
From sunrise coffee to sunset dinners, every moment on Anna Maria Island feels like a peaceful escape. This itinerary lets you experience the best of AMI in just three days, but if you need help planning a longer Anna Maria Island stay, contact our team at Island Dreams Realty. As locals, we know all of AMI’s hidden gems
