Family Travels: Anna Maria Island, Florida

Our family recently returned from a dreamy two night staycation on Anna Maria Island. We totally fell in love with the little gem of an island. Anna Maria is only 45 minutes north of Sarasota and easily accessible from most cities in Florida.

While Covid has put a damper on international and other big travel plans, I’ve appreciated the opportunity to discover so much beauty so close to home.

Here’s a recap of our stay and some ideas for your own AMI family getaway.

Stay

Anna Maria Island has no shortage of places to stay. There were vacation rental signs on homes all over the place along with some hotels. We opted to stay at a hotel, The Waterline Resort and Marina and it was perfect.

I tend to prefer hotels over vacation rental homes because I like the consistency of hotels. With vacation rentals, it has been my experience that there is often an element of “you just never know what you’re going to get.”

On the flip side, rental homes are often more practical for us because we are a family of five so having access to multiple bedrooms, separate living space, a kitchen and laundry room is ideal.

The Waterline Resort was the perfect combination of both. It is a Marriott Bonvoy hotel property (as a Platinum Elite member, I’m a loyal fan!) so it came with all the things I’ve come to expect from a Bonvoy hotel (great service, toiletries, an endless supply of towels, etc.) but the entire hotel is villa/condo style, meaning all of the rooms are two bedroom, two bathroom suites with full, well stocked kitchens, a separate living room, a washer and dryer and a balcony.

The hotel opened in 2017 so everything still feels fresh, clean, and BRIGHT!

Our condo was lovely and featured a nice view of the marina, making it easy to keep an eye on our boat throughout our stay (my husband drove it up from Sarasota!). The master bedroom was bright and had a king bed with an en-suite bathroom. The bathroom was great. The shower floor was river rock, which felt great on our feet and it featured two shower heads; a handheld and a rain shower head.

There was a door separating the toilet room, double sinks and a small storage closet that housed a vacuum cleaner and ironing board. The toiletries were not name brand but they were good. There was a very generous supply of towels.

The other room had two queen beds and a smaller bathroom with a shower/tub combo. It was more than enough space for our three kids. In fact, one of the nights I ended up in bed with my two boys (#momlife) and I slept surprisingly comfortably despite having three of us in one bed!

We took advantage of the amenities on site too, enjoying lots of time at the pool, trying our hand at ping pong and playing JENGA and corn hole. We could have enjoyed a bike ride using the hotel’s bikes but we ran out of time!

As a result of Covid, the restaurant is currently closed and will reopen in the next couple of months but we knew to expect that as it was notated on their homepage. They also suspended housekeeping as a precaution and masks were required any time we were in common indoor areas (the lobby).

The marina had plenty of slips and we enjoyed watching boats go in and out throughout the day from our balcony.

We loved our stay at The Waterline Resort and Marina and plan to go back often!

Eat

The food at Anna Maria was so wonderful! Most of places the places we visited were crowded and had waits, despite it being the middle of the week. Masks were strictly enforced throughout the island.

We brought food for our kiddos and took full advantage of the kitchen in our condo for breakfast (since my husband and I fast) and for snacks but also made sure to sample all of the flavors of the island!

While we had several great meals during our trip, the winner was dinner at The Waterfront Restaurant. We had to wait more than 30 minutes for a table but it was worth it. The shoreline is across the street so our kids were entertained while we waited (they text you when your table is ready, so there’s no need to stay super close!).

I had their special, which was a pumpkin seed crusted mahi over a thin layer of butternut squash with green beans. It was a top 5 meal of my life for me. So. Good. I also had a spicy margarita that came with giant leaves of basil and I just don’t know if I can ever have a margarita without basil again!

The kids had grilled fish with vegetables and I appreciated that there was a healthy option for them!

After dinner we walked a very short distance to Two Scoops for ice cream. It was delicious. By the time we finished our cones, the line was out the door to get in (for good reason!).

We also had lunch at The Rod and Reel Pier. We had beached our boat on the gulf side of Anna Maria and were collecting seashells when we realized we were nearing lunchtime. Hungry kids are not exactly happy kids so we searched for the nearest restaurant with available boat docks and found Rod and Reel.

The restaurant is tiny (the whole restaurant is basically in the picture above) and very old Florida (built in 1947!) but it had a lot of charm! It’s at the end of a long pier and there were a lot of people fishing on either side. The restaurant is up a flight of stairs and there was a short wait for a table. The food was good (not great) but the views were worth the visit. I loved looking out to the Skyway Bridge as we enjoyed our lunch!

On our last night, we had dinner at The Sandbar Restaurant and that was excellent as well! We sat outside, on the sand, so the kids were able to play while we sat. If you have kids, you understand when I say: #winning. It was hot but the sun was low in the sky and it made for that dreamy golden hour lighting (please say you know what I mean?).

I had fish tacos and they were some of the best I’ve had in a while. The atmosphere was light and our server was great. The highlight though was being right on the beach.

On our last morning there, the kids woke up offensively early, before most places were open. Luckily, we found The Donut Experiment which opened at 7am, so off we went!

At The Donut Experiment, you get to design your own cake donut. I didn’t get one but the kids enjoyed picking their glaze and their toppings. Cute concept. Outdoor seating only.

After donuts and some exploring, we made a stop at a fabulous place, Northshore Cafe. This place was great, an absolute can’t miss! I had a magnificent avocado toast dusted with red chili flakes and a squeeze of lemon.

My three kids split an acai bowl. I had a bite and it was delicious. I also had a blackberry jasmine tea infused champagne and it was just as amazing as it sounds. Ok, now I want to go back right now!

Shop

There were several shops all within walking or biking distance from the hotel. Admittedly, I didn’t make it to the shops on Pine Avenue, so I can’t speak to the ones there but the ones I visited were worth the stop.

My favorite shop was howluckyami. The first thing that stood out was the happy greeting from the girl at the cash register. The store features local, handmade and unique items. I spent a fair amount of time admiring all the lovely things in there and ended up buying some cheery bracelets and a ring dish.

I also made a stop for souvenirs for the kids at Island Trader. The store was large and there were lots of affordable options. I picked up some shell collection mesh bags and rubber sea animals for my kiddos and a Christmas ornament for our tree.

I also made stops at Azure and their sister store, Beach Vintage. They might be worth a quick pop in but howluckyami was my can’t miss.

In Summary

Anna Maria was a great place to get away for a few days with family but I could absolutely also go back for a romantic weekend without kids or for a girls getaway (who’s ready?!).

My top recommendations are to stay at The Waterline Resort and Marina, have dinner and a margarita at The Waterfront, enjoy breakfast or a snack at Northshore Cafe, shop at howluckyami and bask in the beauty of the beaches and the sunsets!

Have you been to Anna Maria Island? What are your favorite stops there? Taking notes for my next trip!