When it comes to long weekend getaways from northeast Ohio (and especially during the colder months), many of us love to flock south – and especially to the warm beaches of Florida. And one spot you can’t go wrong with in Florida is the Sarasota/Bradenton area in order to head to Anna Maria Island.
Despite many trips to Florida myself over the years, I actually had not visited Anna Maria Island (AMI) until this year! And I have to say: I’ve definitely been missing out.
AMI is the perfect laid-back beach getaway, whether you’re traveling as a couple, with friends, or with the whole family. The island on Florida’s Gulf coast has lots to do and has some of the very best beaches in the state. And, despite being affected by hurricanes in 2024, Anna Maria Island has bounced back beautifully and is fully open for business!
Why visit Anna Maria Island from Ohio?
So what makes Bradenton and Anna Maria Island such a good long weekend trip option from Cleveland?
A few reasons:
- There are direct, nonstop flights almost daily from northeast Ohio to the Sarasota Bradenton International Airport (SRQ). You can fly from Cleveland Hopkins (CLE) on Frontier (twice per week), and from Akron-Canton (CAK) on both Allegiant Air and Breeze Airways. The flights are roughly 2 hours one-way, and you can often find great flight deals!
- Anna Maria Island is big enough to offer plenty of restaurants and activities, but small enough to fully explore over one long weekend.
- Yes, you can just focus on the beach, but there’s more to do than just hang out on the sand, whether you’re into wildlife or water sports.
Read on for my perfect Anna Maria Island itinerary that you can feel free to use, too!
A long weekend itinerary for Anna Maria Island
If you’re planning a long weekend trip, I recommend flying to Bradenton/AMI on Friday morning and coming home on Monday afternoon to really maximize your time.
And here’s exactly how I would suggest planning your visit.
Note: This post is brought to you as part of a paid partnership with the Bradenton Area Convention & Visitors Bureau. As always, though, my opinions are my own and based 100% on my own experiences!
Day 1: Friday
Morning: Flight to Florida
You’ll book a morning flight on your preferred airline to the Sarasota Bradenton International Airport (SRQ). The flight time is right around 2 hours.
My husband Elliot and I did rent a car for this trip since we didn’t spend all our time on Anna Maria Island, but there *are* ways to get around without a car. If you’re going to rent one, you can pick it up right at the airport (SRQ is such a nice and small airport; you basically walk right out the door from baggage claim and are in the rental car lot).
Lunch in Bradenton
If you have a car, drive in to Bradenton straight from the airport. You won’t be able to check into your hotel yet anyway, so you may as well make a little detour!
We had lunch at O’bricks Irish Pub & Martini Bar, which has some incredible food (the grouper tacos were SO GOOD).
Afternoon: The Bishop
From lunch, it’s a short walk over to The Bishop Museum of Science and Nature, which is a cool little museum right near the Riverwalk in Bradenton.
This museum covers several subjects, from the history of this part of Florida to several science subjects. The real draw here, though, is the museum’s manatee rehab program.
The Bishop has been working with local Florida manatees since 1949, and act as the second stage of a manatee rehabilitation program where they help rescued manatees gain weight and learn skills that they need to be re-released back into the wild. (They don’t keep or breed manatees here; the goal is always to release them!)
When we visited, they were rehabbing 3 baby manatees, and I honestly could have watched them all day! If you want to see manatees while you’re in this part of Florida, this is a great place to visit.
Late afternoon: Hotel check-in
After your museum visit, it’s time to check into your hotel.
We stayed at the Compass Hotel Anna Maria Sound by Margaritaville, which is actually just across the main Anna Maria Island Bridge from the island itself. This hotel is newer, with bright and spacious rooms, a nice lobby area, and a pool that overlooks Anna Maria Sound.
It’s a great option, whether you’re traveling as a couple like we were, or as a family.
Early evening: Cocktail class
After some time relaxing at the hotel, it’s time to head over to Anna Maria Island itself! You *could* get a bike from The Compass and ride it across the Anna Maria Island Bridge, but this is where having a car comes in handy. (Many people visiting AMI rent golf carts, but unfortunately you aren’t allowed to drive a golf cart across the AMI Bridge!)
If this is a couples trip or friends trip, then a really fun and unique thing to do this afternoon/evening is to take a mixology class with Gulf Coast Bartender Co in the town of Holmes Beach. You’ll belly up to their very cute bar and be walked through making two unique cocktails.
While each cocktail class is themed and the drinks are set beforehand, you absolutely can opt to make mocktails instead of cocktails. I personally made one of each!
They usually offer classes on Friday evenings, but if you have a group of 4 or more, you can actually call about a private class if they don’t have one offered.
Evening: Beach dinner
For dinner tonight, I recommend the Anna Maria Island Beach Cafe right at Manatee Beach. It’s a counter service-style spot with a bar and attached ice cream shop – so very laid-back! They have live music every night of the week, and you can enjoy dinner and sunset with your feet in the soft white sand.
This is a great spot for people-watching on the beach, too, and is the perfect place to end your night.
Day 2: Saturday
Welcome to your first full day on Anna Maria Island! Today is mostly going to be a beach day, so be sure to pack a beach bag and wear your swimsuit this morning!
Morning: Breakfast
Breakfast is included at The Compass, so you could opt for a leisurely hotel breakfast this morning. But if you want to head straight to the island, we actually drove over in the morning (beating some of the worst traffic over the bridge) to have breakfast at a spot called The Cheesecake Cutie & Cafe, which offers up delicious breakfast sandwiches and bowls alongside coffee and mini cheesecakes.
You might want to get your breakfast to-go, and then head to the beach.
You could actually leave your car here at Cheesecake Cutie if you drove and use the free Anna Maria Island Trolley the rest of the day (more tips for this later in the post!). Since it was early-ish, we actually drove up to Anna Maria Island Beach and were still able to find parking before 10 a.m.
Morning: Beach day
For our visit, we were treated to a beach setup by My Beach Concierge, which is a business idea I had never even considered before – but it’s so smart! Basically My Beach Concierge will set up a tall canopy in the sand at a designated spot on the beach (you’re given the exact location before you arrive) that can serve as your beach spot for the day.
We got the “Couples Package,” which includes the canopy, two beach chairs, a table, and a bluetooth speaker set up for us at the northern end of Anna Maria Beach (it costs $115 for the day). They also have options for families, plus add-ons like coolers and beach toys. Your setup is reserved all day (10 a.m.-5 p.m. in our case), which is absolutely perfect for a spot like this.
We arrived at our beach setup, set out our towels, and immediately went for a swim. The water at Anna Maria Beach is generally calm and shallow, making it a great spot for families or anyone that doesn’t like deep water. There was even an ice cream boat coasting up and down the beach that you could swim up to!
Lunch: Sandbar
Our beach setup was at the end of Spring Ave, which is right next to Sandbar Seafood + Spirits. This beachfront restaurant has a fancier inside section (that is deliciously air-conditioned), but also a patio, some tables in the sand, plus a walk-up bar and walk-up food stand called Beachside Bites.
You could get some food to-go to enjoy at your beach setup, or you can sit out on the patio for lunch (you’ll just need to put on a beach cover-up for the restaurant).
Afternoon: Coconut delivery
Head back to the beach after lunch for some more sun and sand. And amp up your experience by ordering fresh coconuts to be delivered directly to you on the beach from AM I COCONUTS. This family-run business does have a physical shop on Pine Ave (which you can also visit), but they can also hand-deliver fresh coconut drinks anywhere on the island.
The coconut drinks (which are all non-alcoholic!) cost anywhere from $13-$20, and come in a full, fresh coconut with cute branding on the side. If you opt for delivery, you might want to order well in advance, as they can take an hour or more to get to you.
But talk about the perfect Instagram moment!
Afternoon: Pine Ave shopping
If you opt for a My Beach Concierge canopy setup, you’ll likely be placed not far from Pine Avenue, which is a nice little local shopping street. We left our beach setup in the mid-afternoon to explore Pine Ave a bit.
If you don’t want to deal with coconut delivery at the beach, stop by the AM I COCONUTS? shop on Pine Ave to get a fresh drink. You could also try a custom donut from The Donut Experiment, and stop by the Anna Maria Island Historical Society to snap a photo in the infamous Old City Jail, which was at one time an actual jail.
For shopping, the must-visit is Shiny Fish Emporium, which is just an explosion of beachy cute-ness. They also offer sand dollar painting here, which is something I’ve never seen before!
For $20, they’ll set you up with a sand dollar and paint, and you can design it however you want. They’ll seal it with a glittery clear coat, and you can come back and pick it up about 30 minutes later. This is SUCH a fun and unique souvenir!
Late afternoon: Free time
You *might* want to head back to your hotel after this to wash off all the salt water and change before any evening activities. (We were certainly craving some downtime in an air-conditioned room after being outside pretty much all day!)
Evening: Island dinner
Depending on what you’re feeling after a long day of sun and sand, you might want to keep it low-key tonight, or perhaps go somewhere a bit fancier.
Some options for dinner tonight include:
- The Ugly Grouper – A laid-back, mostly outdoor spot for seafood and live music. (It can be quite busy on weekends, though, so go early and expect to wait for a table.)
- Duffy’s Tavern – Recommended for good burgers.
- Pizza Social – Good pizza spot on Pine Avenue.
- The Porch – This place has elevated beachy vibes, and serves really good food. Ron the bartender is also a hoot!
Day 3: Sunday
Have breakfast at your hotel today!
Morning: Kayaking tour
If you want to get a little physical activity in during your weekend, an excellent option is to book a clear kayak tour with Get Up and Go Kayaking in Robinson Preserve in Bradenton. These relaxed, eco-focused tours get you out in the calm water of a nature preserve where you can look for wildlife like birds, turtles, rays, and even manatees if you’re lucky.
You’ll stop to climb a lookout tower, too, and no kayaking experience is necessary. (They also accept kids as young as 3, so this is absolutely something just about everyone can do.)
Afternoon: Pool or beach time
If you’re staying at The Compass, head back to the hotel for lunch at Floridays Woodfire Grill & Bar, and then spend some time enjoying the pool. We found sun loungers in a shaded cabana area, which was the perfect spot to relax for a bit.
If you’re staying elsewhere, you can either hang out at that hotel this afternoon, or maybe check out another AMI beach.
Elliot and I also went up to Bean Point Beach on the northern tip of Anna Maria Island, which is a much quieter beach – though the water isn’t as good for swimming as there can be strong currents and even rip tides up here.
We were traveling during peak sea turtle nesting season, too, so we saw several roped off turtle egg nests at Bean Point. If you encounter any of these, leave them alone and definitely don’t disturb them! Turtle nesting season is generally May-October, with turtles hatching usually August-October. Learn more at AMI Turtle Watch.
Early dinner on AMI
I would grab dinner early tonight on the island. A relaxed spot like the Ugly Grouper or Duffy’s would be good if you didn’t already hit one of them up on Saturday.
Evening: Sunset dolphin tour
This evening, it’s time to get back out on the water! We went on a sunset dolphin cruise with Anna Maria Island Dolphin Tours, which takes you out into Anna Maria Sound to look for resident bottlenose dolphins.
We went on the public tour on a larger boat, but met up with the company’s smaller private tour boat once we found a few dolphins. The smaller boat offered the dolphins a wake to “ride,” and they did! That was fun to watch, and then we headed to the northern end of AMI to watch the sun set.
Our sunset dolphin cruise (in July) was at 7 p.m., and we were back to the marina just before 9 p.m.
Nightcap: The Chateau
AMI Dolphin Tours leaves from the Waterline Villas Marina, which is also home to a really nice restaurant called The Chateau Anna Maria. Stop in for drinks or perhaps dessert after your cruise!
Day 4: Monday
Have breakfast at your hotel, re-pack those bags, and head back to the Sarasota Bradenton airport for your flight home this morning or afternoon.
We took a lunchtime flight home to Cleveland, and were back well before dinnertime.
Anna Maria Island travel FAQs
And now for a few more things it’s good to know before a trip to Anna Maria Island.
When to visit Anna Maria Island
So when is the best time to visit Anna Maria Island? Honestly you can take a trip to AMI year-round. The island is busiest basically when kids are off school (which includes around the holidays, during spring break, and in the summer), but people visit all year.
The summer months (June-August) are the hottest on Anna Maria Island, which might be ideal if you want to spend all your time at the beach. Summer also brings with it wetter weather, however, as well as the risk of hurricanes from June-November.
Winter on Anna Maria Island is cooler, so perhaps not as ideal for beach days. (Though we know that the winter months are when people from Ohio need the escape!)
How to get around on Anna Maria Island
Having a car is going to be ideal for the itinerary I’ve suggested, but there are several ways to get around on AMI:
- By car – Like I said before, you absolutely can drive a car on Anna Maria Island. Parking can sometimes be tough, however, especially on busy weekends. You need to pay close attention to parking signs, which make it clear where you can and cannot park. A lot of parking on AMI is free, though there are a handful of paid parking areas now, too.
- By golf cart – You can also rent gold carts on Anna Maria Island, which are sometimes easier to park. There are several places on the island to rent from.
- By bike – Some hotels offer bicycles for guest use, or you can also rent bikes on the island. This is great if you don’t plan to travel too far, but isn’t super practical if you need to get from one island to the other, as it is about 7 miles long.
- By trolley – There’s a FREE trolley that runs a set route all through Anna Maria Island. The great part is that it’s free, and there are clearly marked trolley stops. The downside is that the trolley only stops every 20-30 minutes, so using it exclusively does mean you have to time your day right.
- By Monkey Bus – The Monkey Bus is another great local option. You can call these small buses and they will take you anywhere on Anna Maria Island, Cortez and the Palma Sola Causeway for $5 per person.
- By ferry – If you’re staying in Bradenton, another great way to get to AMI is by using the Gulf Islands Ferry, which travels between The Bradenton Riverwalk and The Historic Bridge Street Pier on Anna Maria Island. You also get nice views this way!
Where to stay on Anna Maria Island
I know I’ve already suggested staying at the Compass Hotel Anna Maria Sound, but if you’d prefer to stay ON Anna Maria Island, there are plenty of other options, too! Many of the accommodation options on the island are vacation rentals (i.e. apartments or condos), but there are a handful of hotels/resorts, too. A few more to consider include:
- Silver Surf Gulf Beach Resort – This family-friendly hotel is at the south end of AMI, and even has private beach access for guests.
- Waterline Villas & Marina – An Autograph Collection hotel on AMI where all the rooms are multi-room villa-condos.
- Mello on the Beach – Mid-century-inspired motel-like vacation rentals on Manatee Beach with very cute design elements.
- Anna Maria Vacations – Vacation rentals of all sorts (small, large, with pools, dog-friendly, etc) across the island.
Is AMI worth visiting from Cleveland?
If you’ve read this far, you can probably already guess my answer: yes! I think Anna Maria Island is a great beach getaway, and it’s very easy to get to from northeast Ohio!
If you go, be sure to let me know what your favorite thing to do was!
Who’s ready to plan a long weekend trip to Anna Maria Island?
Amanda was born and raised in northeast Ohio, and has always been a fangirl of her home state. Now, she’s sharing her love of the Cleveland area, highlighting all the best things to do, see, and eat in the CLE. She’s been running Cleveland Traveler since January 2019.