I’ve never gone a summer without visiting Anna Maria for at least one week. My grandfather began the tradition of taking my dad and uncle here in 1972, and my family hasn’t stopped going since. My fiancé has been going to the island about as long as I have, and it’s often our getaway spot for long weekends or a quick summer day trip. Here are my recommendations for the best of Anna Maria Island in a three-day weekend.
Day 1 — Friday
Leave work early, and go for lunch at the City Pier Restaurant. Browse the handmade jewelry for sale by the hostess stand while you wait, and try to get a seat near the back window to people watch. Order the fried grouper nuggets if they’re available or the blackened mahi sandwich and fries. After lunch, walk down the dock to Two Scoops for ice cream or to do some island shopping on Pine Avenue. My favorite boutiques are The Island Cabana, Pink & Navy and Bella by the Sea. Run in to Ginny & Jane E’s at the corner of Pine Avenue and Gulf Drive for to-die-for baked goods and artsy home accessories.
By now it’s time to check in at one of the two-bedroom, two-bathroom LaCosta Condominiums on Bradenton Beach, where my family has rented every summer for 15 years. Take a quick shower and change for dinner. The drive back to the north tip of the island is worth it for a meal and the view at The Waterfront. If you prefer to eat right in the sand, the Sandbar has an excellent sunset view. For a little island nightlife, go to the Kokonut Hut, a beachfront tiki bar. They have live music and a great drink list, and it’s just a short walk from LaCosta.
Day 2 — Saturday
You can walk from LaCosta to Gulf Drive Café in less than 10 minutes. Order their Belgian waffles for breakfast like I did all the time when I was tiny. They’ll most likely seat you outside, where you’ll have another great view of the gulf. Catch some early morning rays after breakfast on LaCosta’s private beach. They offer free lounge chairs, so all you’ll need is a towel and sunscreen.
Once the summer sun starts to get hot, it’s time for lunch. The free trolley is worth riding at least once, so hop on at the stop across the street from LaCosta and head up to the city of Anna Maria. For a great burger on the island, my pick is Duffy’s Tavern. Their hours are very random, especially in the summer, so I’d recommend taking the trolley here first. You’ll know when they’re open because there won’t be a single parking space available. My order is typically the Tex Burger with Lay’s Classic Potato Chips and a Blue Moon. If Duffy’s is closed, take the trolley to Tortilla Bay for some modern Tex-Mex. With chips and guac, burritos and tacos to rival Chipotle & Moe’s, one dish is sure to fill you up. Now you’re ready to get more sun, and no time is better than late afternoon for water sports. I love renting paddleboards or Jet Skis at Coastal Watersports, just a short walk south from LaCosta beachside. For a little more risk, go parasailing with YOLO Adventures. I’ve seen sharks, stingrays and manatees from 50 feet above the water.
For dinner, try Old Hamburg Schnitzelhaus, an unassuming little restaurant tucked away in a shopping plaza on Holmes Beach. As soon as you walk through the door, the décor, music and food will transport you directly to Germany. Gary, the German owner, is a perfect host and personally oversees each table; he even welcomes and bids farewell to every party that enters his restaurant. I highly recommend any schnitzel dish and Warsteiner Pilsner for dinner and espresso with Black Forest cake for dessert. A typical night in Anna Maria ends with an after-dinner walk on the beach to watch the sunset – something you must do at least once while you’re here.
Day 3 — Sunday
Wake up early and pack up your belongings – check out for LaCosta is 10 a.m. My family cannot leave Anna Maria without stopping to eat breakfast at Peach’s. I recommend any of their egg dishes with black coffee to perk you up for one last carefree day on the island. After eating, visit historic Bridge Street for a little last minute shopping and relaxation. They have cute boutiques, cafes and touristy shops to browse around in.
My 5 Favorite Things
1. The plethora of ice cream shops on the island
2. Boat-accessible water hangouts like Egmont Key or Jewfish Key
3. The cool breeze off the gulf in the morning
4. The Anna Maria Island Publix, for necessities you forgot or food for your fridge
5. Night walks on the beach
