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  • Writer's pictureNancy McAleer

My Favourite Anna Maria Island Festival

Food and Wine on Pine Logo

Anna Maria Island

Food and Wine on Pine Festival


Sadly, as of 2017 the organizers have decided to cancel this event. But you can find great wine tastings at local vendors on Anna Maria Island throughout the year. Like the Olive Oil Outpost on Pine Ave., The Waterfront Restaurant and more...

I'm letting the cat out of the bag and letting you in on an Insider's Secret.... my favourite festival on the island is the 'Food and Wine on Pine' Festival.

Not just because I REALLY, REALLY, REALLY, love wine, but because it happens during the off season on Anna Maria Island, Florida. It's nice and warm and the accommodation rates are low on the island.

It's easy to get to, by hopping on the Free Island Trolley, and parking at the Crosspoint Fellowship Church on Gulf Drive, Anna Maria.

This is a culinary event where the entire Pine Avenue street is closed to traffic and opened up to people who love to sample food, wine and beer samplings. Not only showcasing food and wine, the festival also has arts and craft booths, and great music playing all along the street. It's a great way to enjoy a day meandering down the Greenest Main Street in America, while enjoying all that the local vendors have to offer. Beautiful and hot weather in a Key West style village, what more can you ask for?

Crab legs and wine

The Beachhouse Restaurant

Here are all the details you need to enjoy a fun and delicious day at the Food and Wine on Pine in 2016.


  • Saturday, May 7th 2016

  • 11:30 am to 6:30 pm

  • (rain date Sunday, May 8th, 2016)


  • Pine Avenue, at the northern end of Anna Maria Island, in the village of Anna Maria.


  • $5 admission fee - cash only - ATM access available

  • Includes complimentary wine glass and buffet tray

  • Tickets for food and beverages - $1.00 each

  • Wines and craft or specialty beers are available for tastings or by the glass. 1 Ticket a Tasting

  • Wines and beers are also available by the glass. Wines are 5 tickets a glass (6 oz)

  • Beer is 3-5 tickets a glass (12 oz)

  • Food and beverage items are priced between 2-10 tickets each

  • ID required for alcohol purchase


This year they are offering over 30 different types of wine from the major distributors in our area. Representing nearly every continent that produces wine. You will find Pinot Noir, Chardonnay, Riesling, Sauvignon Blanc, Rose's, Pinot Grigio. Yummy!

Beer For the beer livers, J.J. Taylor is the event sponsor. They will offer a variety of beers, both regular brands as well as some craft beers to try. You can taste a sample of these before you commit to a full glass. Cheers!

  • Wines and craft or specialty beers are available for tastings that are 1 Ticket each

  • If you prefer a full glass of wine or beer, you can purchase them both for 5 tickets. Wine will be in a 6 oz glass, beer in a 12 oz glass.

Fish Tacos


  • Delicious and unique food from over 20 of the area's finest restaurants

  • At least 30 upscale wines

  • Craft and domestic beers

  • 25 juried artists

  • More than 30 musical acts

  • Actors depicting characters from Anna Maria's history

  • Art Demonstrations

  • A Children's Art and Activity Area and the annual 'sliming" of CrossPointe Fellowship Pastor, Ed Moss, located across from Roser's Church on Pine Avenue

  • A Children's Artist Tent

I highly suggest trying out the following vendor's culinary delights. They are my favourite restaurants to eat at on Anna Maria Island!

Want to Visit and Stay during the Food and Wine on Pine Festival?

We have accommodations available for minimum one week stays at our waterfront vacation rentals during the Food and Wine event. Contact us for information on our fantastic last minute deal at Sirenia Cove!

All within walking distance from Pine Avenue and the Beaches!

Sirenia Cove - Last Minute Deal

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