Holidays & Festivals

Make it a celebration! Bring loved ones together for the Holidays on Anna Maria Island.

Anna Maria Island loves to celebrate. And we are so lucky to have a wonderful Chamber of Commerce and an awesome community, so much that the island plays host to a wonderful array of annual events with at least one celebration a month. So, it really is worth taking a look at the Events Calendar from the Anna Maria Island Chamber of Commerce to see what’s on while you’re here.

Parades, farmers markets, arts and crafts exhibitions as well as annual Festivals, there really is something for everyone to enjoy. Each year, visitors and locals come to the streets and beaches of our little island to experience a number of our annual events, including ‘Bayfest’, ‘Symphony on the Sand’, and the “Beach’N Food Truck & Music Festival’; awesome live music events, and classic car displays, with delicious local goodies to sample along with arts and crafts on exhibit or available for purchase.


Privateers Parades, St Patricks Day Parade, July 4th Fireworks, Easter Parade and Easter Egg hunt, Veterans Parade and Holiday Walkabouts in all 3 cities, are also some great events that we host to recognize and celebrate certain occasions.

And if you’re feeling brave and visiting over Halloween, you can even take a Ghost Tour and experience the history of the living dead on Bradenton Beach. These family friendly tours hosted by the Paranormal Society of Bradenton, give an insight into the rich history of their area, whilst sharing chilling ghost stories back on research, eyewitness accounts and factual and historical events. Starting on Bridge Street, these tours ake around 90 minutes!

Thanksgiving, Christmas, July 4th and Easter are great times to come visit, with families coming to enjoy the beautiful beaches and celebrate a special time with family and loved ones. Renting one of our Pineapplefish homes, or even 2 or 3 of them, being so close to each other, to accommodate all your guests, is a great way to get everyone together, often from different parts of the country and even from across the world. Our restaurants are set up at these times recognize the celebratory period; with decor, special menus and often fireworks. Always worth booking in advance though!

Or, for something truly personal, even for a wedding, anniversary, birthday or even just being together, a privately catered meal at your rental home can be very special. Our friends at TheLoft5, are one of the most exceptional caterers on the island, and have hosted many of our Pineapplefish guests celebrations. An exquisite menu can be developed with you, and will be cooked on site, using fresh, local, organic ingredients. TheLoft5 team, will set up the house and table, with as much or as little decoration as you would like, and will serve your meal, alongside specially chosen wine and a  musician can also be organized for that perfect ambience. A romantic meal for 2, a beautiful catered meal for 10, whichever your Pineapplefish rental home, the setting could not be anymore perfect!