February 2025
Our Long Weekend on 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 award winning white sanded beaches touching clear blue water – I knew this would be a great long weekend destination.
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.
Unfortunately during the 2024 hurricane season, Anna Maria and the surrounding areas were hit but back to back hurricanes and suffered significant damage. I had checked in prior to booking to ensure the island was welcoming visitors and luckily many spots were reopening before the new year and eager to return to normal operations.
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. We flew into Tampa after work on Friday, rented a car, and drove an hour to reach our Airbnb. We stayed in Bradenton just five minutes from Anna Maria Island as it had a significant discount and we had the car to get around the area easily. We loved our Airbnb both for the location and comforts it provided. We even had access to a full complement of beach essentials – chairs, umbrella, blankets, and more – so we could enjoy a beach day easily. We arrived super late so we went straight to bed excited to get started with the weekend getaway.
Day 1
Since we got in so late, we allowed ourselves some sleep in time before heading out for the day. Where we were staying in Bradenton was an easy five minute drive to reach Anna Maria Island. Over our three days, I wanted to visit each of the three sections of the island – Anna Maria, Holmes Beach, and Bradenton Beach. On today’s agenda, we would explore Anna Maria – the northern most part of the island.
Despite the fact that many people on the island use the free public trolley, rent or own golf carts, or ride bikes, cars are still abundant and parking is limited so keep this in mind if you are renting a car. Our choice to sleep in may have impacted our ability to find free parking – the paid lots were wildly expensive – but we found a small parking lot by City Hall that ended up being a gold mine. We confirmed with a local the parking was legit and indeed this small lot that maybe fit thirty cars is a block off the beach and right in the middle of the action. If you can find a spot here when visiting the northern part of the island, you are set.
Our first priority was breakfast and the most popular spot in town is Ginny’s & Jane E’s Cafe and Gift Store. And boy did we pay for sleeping in – the line was a bit crazy but leaned into the chill island vibe and waited with the crowd. After all, we were in no rush – this was vacation! Kevin walked through the store and they have quite the collection of souvenirs, beach essentials, home decor, and more. I overheard people in line discussing the cinnamon buns but by the time we got a visual of the bakery counter, it was cleared out so keep that in mind if your heart is set on these. About a half hour later, we made it to the front register where we ordered and grabbed a table. You can also select take out from here but the wait for the food is most likely going to be the same. There is an impressive coffee bar that definitely excited Kevin’s morning brew. I ordered the avocado toast and Kevin ordered the two egg platter with bacon, biscuits, and hashbrown casserole. No matter what you order here, get the hashbrown casserole – what a brilliant breakfast invention.
Fueled for the day, we turned down Pine Street for the main attractions of Anna Maria. Even though we just ate breakfast, we immediately came upon the Donut Experiment and we could not pass the opportunity to try probably the most popular spot in Anna Maria. We must have missed the morning rush as there was no one in line. We grabbed a form to customize our donuts. I think that is why the wait here can be insane since everything is choose your own adventure and each donut is freshly hand made. We each ordered a donut and were impressed by how delightful these were – being made fresh is certainly something you can’t beat. It is easy to see who this is a staple for vacation mornings on Anna Maria Island.
We continued our walk down Pine Street and browsed stores like the Shiny Fish Emporium and Olive Oil Outpost before passing the hilarious Old City Jail. Now a photo op, this jail built in the 20s was used to drunk folks who needed a time-out from the tavern dance hall that was located down the street. A fire in the 40’s rendered it to its current form. Also, the number of golf cart rental companies are numerous so if you are staying on the island for a long period of time, definitely consider renting a golf cart – they come in all sizes and premiums.
More dessert? Yes please. Ice cream has a good game on the island and I wanted to try them all. The first of which was on Pine Street at the Anna Maria General Store – Dips Ice Cream. We ordered a cone to split since I did not anticipate this much deliciousness on Pine Street and we both really enjoyed the flavor – well made ice cream! I was relieved to be starting the ice cream journey on a positive one.
Piers around the island still show the damage from the back to back hurricanes. The first Pier we came across was the Anna Maria City Pier and it only became really clear when we ventured to the side to get a good view of just how much damage there was. The building all the way out there was a restaurant! We continued walking north and passed Red Reef Pier which had similar damage. I know repairs are still ongoing but I wonder what the future of all these piers will be.
I was hoping to take the trolley north to Bean Point but I did not realize the trolley does not run on the Bay side in this part of the island. So we walked to Bean Point and while it was not that far, the rather hot sun and no shade made this walk a bit uncomfortable. Though it was fun to see all the houses, many of which were so gorgeous, others still under construction from damages. By the time we made it to Bean Point Beach, we were in no mood to sit in the sun on the beach. So we circled back by heading south on the Gulf side at a rather slow pace. As a reward for this long walk, when we arrived at North Shore Cafe, we indulged! We grabbed lemonade and an acai bowl which really hit the spot. There is also a great shop for souvenirs – high quality clothes and more – where Kevin grabbed a t-shirt. This cafe is amazing so definitely add it to your list.
We grabbed the beach stuff from the car and made our way to Anna Maria Island Beach for a little slice of heaven. This beach is perfect – the water is stunning and the beach is pristine with the softest white sand. We enjoyed several hours of lounging and relaxing here which honestly, I loved for this vacation and could not wait to do more of. We sat near My Beach Concierge tents which is a fantastic idea for anyone that does not want to bother with hauling beach accessories, getting up early to get a spot during peak season, or any other reason. They have several packages you can choose from but I had not seen this concept before and thought it was very neat.
After several hours, we packed up our beach set up and headed to dinner. Nearby, I made reservations at The Porch Restaurant which was one of the first places I knew we had to try when researching restaurants so I was very excited to give this a try.
Read our dining review for The Porch Restaurant here!
On our way to the car, we caught a glimpse of the beach and saw the sun had just set so we headed back to the beach to enjoy the colors in the sky. Sunset every night on Anna Maria Island is definitely nothing to complain about – absolutely beautiful and the perfect end to our first day.
Day 2
After a perfect first day on Anna Maria Island, we were up early and ready for day two. Our first stop was breakfast at Anna Maria Island Coffee Shack. We could tell this is a popular spot on the island for a quick and simple breakfast which included a large menu of beverages and customized bagel breakfast sandwiches. Kevin ordered his coffee and we enjoyed a bagel breakfast sandwich which was a solid way to start the day. I definitely recommend Anna Maria Island Coffee Shack for no fuss and delicious breakfast, especially if you are on the go.
One of the aspects that attracted us to this area was the opportunity for bird watching and wildlife. The Bradenton area is home to a wide variety of wildlife – from sea turtles to manatees, bald eagles and alligators. Depending on what you want to see will drive which activity you should choose. Kayaking and boat tours are great for manatees and dolphins where as hiking the numerous nature preserves will give you a great opportunity to bird watch. We opted for the bird watching option and ventured to Robinson Preserve for the morning.
Read about our morning through Robinson Preserve here!
After a lovely morning stroll, we returned to Anna Maria Island for lunch at The Ugly Grouper. This spot is recommended on every traveling planning guide so while it is definitely a spot the tourists frequent, the locals stop by as well. We ordered frozen beverages before diving into lunch – I got coconut shrimp and Kevin ordered the Grouper Tacos which is what The Ugly Grouper is known for. These tacos have a cheese shell with blackened grouper and they really were great – everything we had was great.
Ready to relax, we decided to try a different beach for a few hours. Holmes Beach is in the middle of the island and the big benefit here is the large free parking lot and public facilities so this beach is definitely popular. We set up shop until it started to rain but we still enjoyed our time here. I think in comparing to yesterday’s beach, we like Anna Maria Beach better cause it was had a less rowdy crowd.
Since our beach time was cut short from the weather, we returned to The Porch for their happy hour before making the journey to the southern part of the island – Bradenton Beach. The parking here was most challenging but after several laps on Bridge Street, a spot eventually opened and we ventured out. Bridge Street is full of delights including shops, cafes, and more. I wanted to try the mini golf but the weather was uncooperative – the course does look fun if this interests you.
I knew our dinner spot was going to be a hidden gem on this trip – Pane e Amore Italian Cafe. With a perfect five star rating on Google but no one really talking about it – this was going to be a great dinner.
Read our dining review for Pane e Amore Italian Cafe here!
Around the corner from dinner was Gelato-go Anna Maria Island and while we already had dessert, second dessert was an easy sell – this was vacation after all. This ice cream / gelato was pretty underwhelming so I would skip in favor of the other ice cream spots we found on the trip. We then walked off dinner along Bridge Street Pier where the bay is located before heading back to the Airbnb. But not before spotting a once again beautiful sunset – we pulled over and soaked it in before continuing on an ending our second day.
Day 3
Our third and final full day on Anna Maria Island! I showed Kevin a few breakfast spots and he selected Blueberries Cafe which I almost tried to persuade him away from – I am always skeptical of acai joints as most places make them way too sweet. But he doubled down and I did offer it as an option so we headed over for opening. I ordered the Acai Bowl (Acai, pineapple, and coconut water base topped with strawberries, banana, blueberries, granola, hemp, almond butter and shredded coconut) and Kevin went with the Peanut Butter Bowl (banana, oat, peanut butter and almond milk topped with strawberries, banana, granola, and chia). I have to say, my acai bowl was amazing – the base was not sweetened and the toppings were plentiful – this is probably the best acai bowl I have had in awhile outside of me making it at home.
I had kayaking on the activity list for today but we both enjoyed our beach time so much that we decided to turn the entire day into a beach day. We headed back to Anna Maria Beach and luckily found parking in the same spot we did on day one. One of the birds we enjoyed observing all weekend was the osprey and when we parked we were lucky enough to spot one enjoying breakfast.
Kevin needed his morning coffee so we walked around the corner to North Shore Cafe. This spot was much more crowded than the first time we visited which was later in the day so this is definitely a popular spot for breakfast and everyone’s caffeine fix.
And then we spent the rest of the day at the Anna Maria Beach which was shockingly empty upon our arrival. We enjoyed the day soaking up the sun and completely relaxing. I can easily see us returning here, renting a house with some friends, and spending time being beach bums.
With little motivation to move, we luckily positioned ourselves where Sandbar Seafood + Spirits was just a few steps away. This beach front restaurant is another popular spot and what is great is you can order take out. We grabbed drinks and lunch – we both ordered coconut shrimp – and continued relaxing literally up until we had to leave for our dinner reservation.
But not before trying one more ice cream spot! Two Scoops located on Pine Street was one more I wanted to try and they did not disappoint. Ice cream on Anna Maria Island overall has been very impressive so I am happy to report from our small sampling, ice cream here is solid. Another place to highlight is Pizza Social – we did not get to eat here but I would add to my list for a return trip.
Our final dinner of the trip – I had a hard time choosing but ultimately when with a classic and fan favorite, The Doctor’s Office. Specializing is cocktails and other beverages, The Doctor’s Office additionally showcases quite an impressive food menu for the complete package.
Read our dinning review for The Doctor’s Office here!
And with that, our final day exploring Anna Maria Island came to an end. We went to bed and had an insanely early flight out of Tampa which meant with the hour drive and dropping off the car rental we were up and out at 3AM – still worth it for this perfect weekend getaway.
I honestly cannot wait to visit again. This is a perfect spot to rent a house on the beach with a bunch of friends and relax for a vacation. The vibe on the island is unmatched and I cannot believe this is so accessible – it feels like you are on an island somewhere far away. There are also so many surrounding areas to visit for an extended trip including Tampa, Clearwater, St Petersburg, Sarasota, and more. I hope you add Anna Maria Island to your travel list!