Throughout the year, my family enjoys sneaking away from Sarasota for a weekend staycation. It’s as if we’ve left the area. Anna Maria Island boasts wide, white sandy beaches & towering lifeguard stands overlooking this gorgeous blue-green Gulf of Mexico.

One of our favorite beachfront cafes for breakfast is this very Coquina Cafe. Can you imagine yourselves in this photo, enjoying your breakfast with Gulf waves lapping the shore as beachgoers meander from the shaded parking lot to the water’s edge?

At nearby Historic Bridge Street, my wife & kids just had to browse every shop on our stroll to lunch at the oyster bar. I should’ve known better that my wife wouldn’t be able to resist the shopping temptation. As they shopped, I relaxed outfront, appreciating this historic area’s vintage vibe from the roundabout, the Bridge Street Bistro & Island Time Bar & Grill, the Island Time Inn, quaint shops, clock tower, fishing pier, and the iconic dockside bar…that’s irresistible.

Life music fills the air at the nearby dockside bar, nestled among oaks that offer shade and this view of the Bay. You can stroll the pier beyond the clock tower to the very end. Grab a bench & enjoy the view…the fishing…the seafood aroma from the Oyster Bar. Hopefully, this isn’t your boat that’s going to need a little super glue and tender loving care.

It’s true, snowmobiles are not allowed at the iconic Bridge Street Inn’s dockside bar. After dinner, my wife & I grabbed an adult beverage and sodas for the kids. At a nearby park bench, we huddled facing the Bay while enjoying a live rendition of Player’s “Baby Come Back,” a hit 70s/80s band. Great music. Great “island time” beach vibes. Great company. What more could you want out of a wonderful family moment?

Once upon a time, The Freckled Fin hung its iconic Irish shingle in Bradenton Beach near the gateway to Anna Maria Island. Since, it’s relocated down the road to Holmes Beach. On St Patrick’s Day, I can’t think of a better place to go to enjoy a delicous meal & friendly vibe.

Dining options abound along Historic Bridge Street. The Bridge Tender Inn and Dockside Bar is a favorite of locals and visitors from around the world. They serve fresh seafood and mouth-watering appetizers, an appealing menu that interests even my picky daughter and wife who don’t like seafood. GASP! The Bridge Tender Inn provides three full service bars on the water and live entertainment daily. You can arrive by boat, foot, car or trolley.

For many of us, this is 5-star ambiance. We seek and appreciate the simple pleasures in life. Kick back, discover new friends while enjoying your favorite drink. On island time, locals aren’t in a hurry. You already know those type “A” tourists from cities in the North are desperately trying to relax. They want to taste what locals enjoy throughout the year…they want to bottle the feeling and take it on the plane for safe keeping until their next visit.

Simple shops and boutiques along Bridge Street remind visitors of the kind of Main Street they recall from their youth. You don’t have to buy when browsing. Go ahead, poke your nose in these shops. This isn’t just shopping. It’s stepping back in town to a classic beach community, taking time to admire the work of myriad local artisans. Enjoy the moment.

Can a classic hotel define vintage more than BridgeWalk on Historic Bridge Street? You can check in & hop the trolley that runs north on AMI to Bean Point.

My wife says no, but I say yes. I want to hop onto a catamaran and sail across the Gulf. The last time my family enjoyed AMI, we rented jet skis instead. For a few hours, I forgot about the urge to sail. Can you hear Christopher Cross’s immortal song lyrics from “Sailing” wafting across the Gulf?

On the Gulfside, this is the type of vacation rental you can expect. We don’t destroy the beach vibe with towering condos typical of the East Coast of Florida. The West Coast still exudes a low-key vintage beach vibe.

At The Beach House Restaurant, you will discover fine dining & a relaxing beach vibe. Dinner on the veranda may never be the same if you’re lucky enough to witness a fiery sunset over the Gulf.

Hurricane Irma wasn’t kind to the original City Pier, built in 1911. The newly rebuilt City Pier, when it re-opens, will hopefully maintain its classic look and feel, building better onto something that’s grown beyond a classic. At the end of the pier, you’ll rediscover a bait shop and seafood restaurant. Before or after lunch/dinner, you should grab a fishing pole and kick back. It’s OK to relax.

My wife, daughter, and I plopped down on the bench staring out onto the Sunshine Skyway in the distance. My son, on the other hand, enjoyed chatting with these oldtimers about fishing. Unfortunately for my son, my wife politely stepped in to decline (on my son’s behalf) the beer these gents offered him as a consolation prize for solving the world’s problems one beer at a time. You know it’s always the people who make these landmarks the memories they are.

At the northern end of the Island, you can’t miss the brightly painted Beach Bums for bike, kayak, paddle board, and beach rentals. On this stretch of AMI, you’ll want to explore it including AMI Outfitters, Libby’s Island Jewelry, Shady Mango, and Hometown Desserts.

Take Gulf Drive north to Palm Avenue where eclectic meets curious. Of course, I dare you to keep your foot on the gas as you approach Slim’s, Harry’s, Ginny’s and Jane E’s or even The Sandbar. I double dog dare you. I have such fond memories of this part of AMI. It represents the growth of my own kids and the moments these iconic places have contributed to memories. Once you [eventually] round the corner onto Palm, you will enjoy the moment…meandering to the City Pier.

I remember when my wife & I first took our kids to The Sandbar restaurant. They couldn’t focus on lunch with that alluring white sand & big, blue-green “swimming pool” staring at them. At the time, it was frustrating. Looking back, I smile. Lunch could wait. The call of the ocean was too great to resist. Anna Maria Island is known for exquisite waterfront dining and tiki bars..a different vibe indeed.

Tucked away at the lesser-known northern tip of AMI is this vintage jewel, the Rod&Reel Pier and restaurant. Off a roughly hewn wood plank pier, boasting 100s of names, hundreds (maybe thousands) stroll to and from this local icon. To walk out into Sarasota Bay, surrounded by blue-green water as old grizzled locals hold statuesque positions, fishing line bobbing in the lapping waves. This is quinessential and unapologetic “Old Florida” vibes.