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You Need to go to Anna Maria Island This Winter


I am just over halfway through my month stay in Anna Maria, Florida and there is only one thing I have to say: everyone should spend some time here. Anna Maria is the picture-perfect beach town we always think about in daydreams - local restaurants, sandy beaches in walking distance, and warm weather (well, warm compared to cold NJ winters) all year long.


I arrived in Anna Maria two and a half weeks ago to spend some time in the warm weather while I work and see my extended family and grandparents for a socially distanced Thanksgiving. I am joining my uncle and cousin for 3.5 weeks of their month-long stay. The rest of our families visited for just over a week before returning home. We rented a gorgeous house on the canal with the rental company Once Upon a Beach. Can I just say, so far, so GREAT!! We all work during the week and try new activities and walks in the evenings and weekends. Each one of us has our own balcony/area of the house to work and take calls undisturbed.


We've only had one day of rain and one day of weather below 65 degrees - I'd call that a success. Typically it is chilly in the early morning before the sun really comes out and shines. Then, throughout the afternoon, it is hot and sunny until the sun disappears again and night falls. At night, you may want a light sweater depending on the wind that night it can get chilly. Generally, it's shorts and a tee-shirt kind of weather. As is typical, the ocean gets colder the further into winter you get - the manatees even migrate inland for warmer waters - so beware that you might not be going for a full swim in the ocean (unless you're really brave).


Tourist season in Florida is typically from mid-December to April. This is why you should travel to Anna Maria in mid-November through mid-December, just before tourist season. Yet, if you cannot make it in time, you should still visit Anna Maria. It lacks the hustle and bustle of hot spot tourism while maintaining the relaxation and exploration your vacation deserves. The Island is relatively quiet because many of the houses are empty rentals but, there are enough locals here to keep the restaurants and shops open. It's nowhere near deserted, just quiet. Given that I came during COVID, we cooked at home for 97% of our meals. There is a small local outdoor City Farmer's Market each Tuesday, where we picked up some vegetables for the weeks to come! We ordered take out twice and ate outside at a secluded table at the Waterfront. I enjoyed both take out options, Pizza Social and Ocean Island Sushi (which took forever but had delicious dumplings). We also walked own of the two ice cream shops, Two Scoops or Dips, nearly every other night. I personally preferred grabbing some Two Scoops and walking along the pier.

Local vendors at the City Pier Farmer's Market every Tuesday morning!
Some shots of City Pier and the two ice cream spots in AMI.

Anna Maria is a bike-friendly town. On numerous occasions, we biked around the Island, either to the beaches for sunset or just for leisurely exploration. The flat terrain made biking easy after over a year of not riding. It is impossible to go out and not pass walkers, bikers, and runners. If you get tired of laid back people-filled bike rides or are looking for some nature biking, drive or ride your bike over to Robinson Preserve and bike the paths. Another common mode of transportation is the golf cart. Golf Carts can be rented at a few different shops throughout Anna Maria. You cannot pass them on the road, so if you get stuck behind one, prepare for a slow drive! They are pretty popular on the island.


Looking for somewhere to walk to? Pine Street has lots of shops to pop into. It is also home to most of the restaurants in Anna Maria. The street takes about 10-15 minutes to walk from one side to the other. Each side ends at the beach/the pier, spanning the width of the island. Some of my favorite places to stop were Pink & Navy, the Doughnut Emporium, and the olive oil shop! Pine street is also where you will find most of the rental agencies in the area (and there are a lot). All the businesses are located in brightly painted home style buildings that bring out the fun, local, beach vibe of the island.



Bean Point beach is the major beach in Anna Maria, wrapping around the tip of the island. The whole island is wrapped by beaches. You cannot walk more than 10 minutes without passing one. That said, Bean Point is my favorite and one not to miss. The sand is unbelievably soft, and the sunset views are picture-perfect. Bean Point started by the Rod and Reel and continues on past the Sandbar.

There are also many places to visit within a short driving or sailing distance from Anna Maria. Looking for some walks through nature? Drive or bike to Perico Preserve or Robinson Preserve. Take a boat out to Egmont Key to wander the deserted island once used as a fort or sail the opposite way toward Jewfish Key to find warm, clear waters and a sandbar to hang out and swim. We also took day trips to Fort De Soto and Shell Key, as well as to Captiva and Sanibel, for some outdoor adventures, including shell hunting and kayaking.

Biking and Walking in Robinson Preserve
Walking the Perico Preserve
Rented a sailboat from Bimini Bay Sailing to explore!

If you are looking for a quiet getaway, look no further than Anna Maria Island! It has everything you could possibly want while allowing you to relax and stay close to your vacation home.

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