Girls Trip to Anna Maria Island

When planning our girls trip, we were advised to visit Anna Maria Island during the last week of August to avoid the crowds, traffic and long lines. I am so thankful we took that advice! We found a cozy three bedroom, two bath house with a small pool on VRBO, located near the northern end of the island that was within walking distance to the beach. This trip was inspired by the need for crystal clear blue water, white sand and some incredible food. I am thrilled to say we checked all the boxes!

First Stop…South Pasadena

Our first night we stayed with Anna, who lives on the bay in South Pasadena, and the views outside the condo were breathtaking! We saw a dolphin, blue herron and lots of fish right outside her window.

It wasn’t raining so we decided to head to Treasure Island Beach to get a little sun. Anna shared her floaties with us and it was perfect! We celebrated Amy’s birthday with dinner at Park Shore Grill. I couldn’t stop eating Anna’s Truffle salt fries. We sat next two different couples: one couple was celebrating a birthday and the other couple was celebrating winning the lottery!

Happy Hour, Beach and Pizza

We arrived on the island mid afternoon and met with friends at the Bridge Street Bistro. The second floor view overlooking the beach was incredible! While enjoying the view, an older gentlemen from New York sat at the bar and shared great restaurant recommendations.

It was time to check-in to the house so we headed north, got settled and immediately headed to the beach. The walk wasn’t far and the view was amazing! It’s turtle hatch season so there were turtle nests all up and down the shore. After grabbing a few pictures, we headed back and enjoyed the pool. Staying in for dinner sounded like a good idea so we ordered pizza and salad from Pizza Social.

Cinnamon Rolls, The Pier, Bean Point Beach, and The Waterfront

In the morning, coffee is always the first thing on my mind so we headed to Ginny’s and Jane E’s Café. We were instructed to get their famous cinnamon roll. Since the cinnamon rolls are huge, we told the cashier we wanted to share one. She smiled and explained that they actually have 2 smaller cinnamon rolls as buy one, get one free. We laughed and explained that we both didn’t need a cinnamon roll and when she opened the container we laughed even more because the 2 “smaller” cinnamon rolls were HUGE! We left with two cinnamon rolls -probably one of the best cinnamon rolls I’ve ever had!

The pier was recently remodeled so we headed to the edge to check out the view of the skyway bridge. While waiting, an older man walked by and asked if we were there to watch the launch. Apparently NASA was scheduled to launch an empty rocket headed to the moon but the launch was delayed. We spent the next hour in great conversation with him and learned a lot about the local area.

We drove to Rod & Reel and decided to walk to Bean Point Beach. This beach is where two bodies of water merge on the northern end of the island. The clouds were so dramatic as storms began to roll through.

The destination for lunch was a last minute change and I am so glad we went with our gut. Tide Tables is a hole in the wall right on the water. While waiting in line, we met a couple from Clearwater who frequents this place and offered great menu suggestions. They even shared their pitcher of beer with us: Calusa Zote IPA. The blackened Grouper with beans and grilled veggies hit the spot and we topped it off with their famous key lime pie!

Dinner at the Waterfront was one of our favorite places! It’s not uncommon to wait 2+ hours for a table but we walked right in and were seated. Our waitress was extremely helpful. We shared a grilled romaine salad. I ordered scallops and pork belly. Amy had shrimp and grits and she said it was great! We were stuffed and couldn’t finish the meal but overall, this meal stands out as one of the best.

A storm was about to roll in but we decided to chance it and walked to the beach to catch the sunset. It was perfect. Dad called me while standing on the beach and I was able to share my view with him. His words: “That’s beautiful”. We also saw the most amazing rainbow form where the clouds collided.

Donuts, Kayaking & Burgers

The following day, breakfast was at the Donut Experiment. This is a place where you make your own donut. Honestly, it’s a cool concept that quickly can become overwhelming. We devoured our donuts and got ready for our Kayaking adventure with AMI Paddle Boarding.

We arrived to AMI Paddle Board a little early and Andrew, the owner, greeted us. This was Amy’s first time to Kayak so we used the additional time for him to show her the ropes and get her feet wet.

A family from Boston joined us and we all had such a great time! While Andrew was giving us instructions, a duck joined us. Andrew said, “That’s George. He comes with us on all our tours”. In total, there were three ducks: Elle, Bill and George. The ducks followed paddlers to the mangroves and then reunited once the group heads back. While we paddled, the ducks bobbed up and out of the water for fish brushed-up against our paddles multiple times. It was about an 1.5 hour trip and I loved it! The mangroves were beautiful.

Lunch was at Skinny’s Place. We each ordered a burger with tater tots. We decided that ice cream sounded good so we headed to Two Scoops and enjoyed the view of the pier. We have friends in West Bradenton and met them for Thai dinner.

Sunrise, Beach, Cocktails and Dinner at Euphemia Haye

The next morning, we were up early to make sure we could catch the sunrise. We stood on the pier and watched as the sun began to show it’s face. Incredible! We headed back to Ginny’s for breakfast and enjoyed a savory meal.

After breakfast, we enjoyed the beach for 2.5 hours and couldn’t believe how empty the beach was. There was literally no one there. After the beach, we headed into town and hit up Scotts Deli for lunch. So good!

Pre-dinner festivities were at the Doctor’s Office where we enjoyed a cocktail and Mediterranean platter.  The service was great and the drinks were fancy.

Dinner was further south in Longboat at Euphemia Haye where we enjoyed ceasar salad, peppercorn steak, brussel sprouts and truffle mashed potatoes. For dessert, we devoured a banana cream pie with and incredible crust! We were stuffed and practically had to be rolled out of the restaurant. As we left, we couldn’t help but laugh at the 7+ raccoons going after the food scraps near the trash outside. Smart raccoons.

Coffee & Avocado Toast

On the final morning of our trip, we woke up and packed our suitcases. Outside the house, we met a really nice woman from Pennsylvania who was walking her dogs. We then headed to The North Shore Café for coffee and breakfast. The Avocado Toast was the best EVER: sourdough, cream cheese and guacamole with everything bagel seasoning!

Overall, the trip was just what we needed and we will be back!

Add these restaurants / things to do on your list:

  • Waterfront
  • North Shore Café
  • Tide Tables
  • Duffy’s Tavern
  • Scotts Deli
  • The Doctors Office
  • Pizza Social
  • The Feast
  • Ginny’s & Jane E’s Café
  • AMI Paddle board
  • The AMI Pier
  • Euphemia Haye (get the red snapper & visit the dessert room)
  • Monkey Bus