Anna Maria Island, Florida — Vacation Recap!

Photo Apr 08, 12 31 48 AM

Happy Monday, friends! This morning, I’ve rounded up all my outfits from my vacation to Anna Maria Island last week. I’m still wishing I was there!

I’ll also be including activities that we did while we were there and restaurants we ate at. If you didn’t see my post from a couple weeks ago, I shared a few items that I was packing in my travel bag for this trip. For all of these outfits, you can either click the links  at the bottom of each photo, or screenshot the photos and use the LIKETOKNOW.IT app to find the links to all of the pieces I’m wearing.

Let’s get started!

Day One: Travel Day

Johnny and I woke up at about 2:15 in the morning (woof), to make it on time for our flight to Orlando, FL. The only reason I was semi-okay with the early flight was because we got the full day once we landed and we flew Southwest Airlines. 2 free bags for each of us! They are by far our favorite airline to travel with. We made the two hour drive to Anna Maria Island, and stayed on Holmes Beach.

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I was so excited about this trip because my entire family was coming! My dad found a huge beach house right on the ocean for all of us to stay in. We were celebrating my Nana and Papa’s 50th wedding anniversary. It was so special that we all were able to be together for vacation.

Plane Outfit

Photo Mar 31, 9 53 41 AM

Oh Hey Vacay Top| Distressed Jeans | Sunglasses | Sandals (old from Target, sorry!) |
Weekender Bag (sold out in cognac, but linked in black)

Beach Outfit

Photo Mar 31, 1 24 42 PM

Top | Jean Shorts | Sunglasses

Day 2

The second day of our trip was Easter! It’s one of Johnny and I’s favorite holidays, and our family celebrated by going to an early sunrise service on Manatee Beach. It was really cool to see people from the island and tourists all coming together to celebrate Jesus’ resurrection.

Photo Apr 01, 5 29 10 AM

My brothers Ashton and Aidan, and my parents Jerry and Jen!

Sunrise Service

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hahaha please don’t mind my awful photo shop skills in this picture–lol!
Aleesha’s Outfit: Dress (not available in black, burgundy in stock)| Earrings
Johnny’s Outfit: Patagonia Jacket | Dress Shirt | Shorts | Boat Shoes

While we spent a lot of time on the beach, we found time to make a big Easter dinner. It was the perfect sunny day. After every day on the beach, after getting a good tan, I made sure to put this tan extender on by California Tan. It lengthens the life of your tan, which I definitely need!

Criss-Cross Outfit

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Top | Jean Shorts | Earrings | Sunglasses

Day 3

My family keeps coming back to Anna Maria Island because we love how much there is to do. The downtown area is our favorite part, because there are fun shops to walk through and great restaurants to eat at. On this day, we ate at Annie’s Bait and Tackle Restaurant because they were offering all-you-can-eat fish and chips. This is a great place if you want to eat outside, and fish while you wait. When you have 13 people in your party, all-you-can-eat works for us!

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Thank the Lord for selfie sticks 🙂
Selfie Stick

Pier Outfit

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Top | Shorts (last season from Old Navy, sorry!)

We spent the rest of the day relaxing on the beach. I tell Johnny all the time that I can’t wait until we can retire on the beach! My mom, Nana, Aunt and I all played rummikub on the beach while we watched the boys fish. Such a great day!

Beach Babe

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Swimsuit Top | Swimsuit Bottom | Hat | Sunglasses | Cover Up

Day 4

Day 4 of this trip was spent out at sea. My whole family woke up early to go out with Cortez Deep Sea Fishing. We did the whole day trip, and walked away with four huge buckets of fish for us to keep! We had 2 fish fry’s later in the week. Johnny had so much fun fishing, and it was a great day to get some sun and spend time together.

Pre-Fishing Outfit

Photo Apr 03, 6 15 58 AM

Cover Up | Jean Shorts | Sunglasses | Tote

Later in the day, we met a good friend for dinner in North Point, FL at a fun Mexican restaurant. Here’s the outfit I wore below!

Mexican Restaurant Outfit

Photo Apr 03, 5 04 46 PM

Jumpsuit | Shoes

Day 5

In the morning, my mom, Aunt Vanessa, cousin Selah, and I went conch-ing! My family has been vacationing in this area for a long time, and we have found a few hidden gems in the area. We woke up early before the tide came in to find the best seashells. We found more than just seashells, hermit crabs too!

Photo Apr 04, 5 50 04 AM

This was such a fun memory to share together. Afterwards, we went to the local farmer’s market and walked around to look at the different shops.

I took this picture of my Nana and Papa while we were eating lunch. This was the day that we were celebrating their anniversary. I just thought they looked so cute!

Photo Apr 04, 9 14 21 AM

For dinner, we went to The Old Salty Dog on City Island. Half of my family loves seafood, and the other half does not, so this is the perfect place to go to make sure everyone is getting something they’ll enjoy. Johnny and I split the steamer pot!

Dinner Outfit

Photo Apr 04, 4 51 49 PM

Dress | Shoes

After dinner, we celebrated my grandparents with cake and ice cream! I can’t say it enough, I’m so happy we were all able to celebrate together!

Photo Apr 04, 8 17 55 PM

Day 6

We spent our entire day out on the beach and the boys went fishing. My uncle Brent, cousins Simon and Brent Jr, Ashton, Johnny and my Dad all caught so many cool fish!

My time was spent laying in the sun, and snapping this pic of my sun dress. 🙂

Perfect Sun Dress

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Dress | Shoes

Johnny and my brother Ashton rented kayaks to go out further in the ocean to fish. Johnny was excited that some of his “insta-husband” picture taking duties were handed off to my Mom, (so grateful for both of them, haha!). My mom is a hairdresser, and she bleached me back to blonde while we were on vacation. Because I live in Colorado, and she’s in Michigan, I don’t get my hair done as often as I use to. I will never let someone else touch my hair!

My family brought my Uncle’s golden doodle named Mac on the trip with us. He is just the cutest, so we had to get a picture together!

Sassy Dog Walking

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Top | Skirt | Shoes

Day 7

This was our last full day on the island. The best way to cope with that is by eating your weight in pancakes, right? At the Anna Maria Island Beach Cafe, you can get all you can eat pancakes every morning. This is a really fun tradition we like to do!

Pancake Lady

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Top | Jean Shorts | Earrings | Shoes

You guessed it–we spent the rest of the day on the beach (as you should on vacation!). My mom and I had fun playing in the sun and snapping this cute pic.

Let’s Flamingle

Photo Apr 06, 10 27 59 AM

Swimsuit Top | Swimsuit Bottom | Sunglasses | Flamingo Floatie

p.s. I love these swim bottoms, because they held in all of the junk food from the week (including the pancakes) perfectly. 🙂

The girls finished the night by grabbing ice cream and shopping at all of our favorite spots before leaving the island.

Day 8

Our last day of vacation was cleaning up the beach home and saying goodbye. The last day of vacation is the worst! Johnny and I had a later flight, so we still had time to look around the island and explore.

Travel Outfit

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Top | Jeans | Shoes

If you haven’t been to the Red Barn Flea Market in Florida, you’re seriously missing out. It’s one of our favorite stops. We get our oranges here to bring back home, and look at all of the other fun (and quirky!) shops. My dad, brothers, Johnny and I all ate the best tacos of our life here. Seriously, we’re still talking about it two days post vacation!

This trip to Florida was such an amazing trip. Johnny and I are still in shock that it’s all over. You can never beat time spent with family. I’m so grateful that we were able to travel to Florida together and relax and make memories together. We’re already planning our next trip back this year!

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Thanks for reading my Florida recap! Leave a comment below if you have any questions! Follow me on Instagram if you want to follow more of my travel adventures and daily outfits.

Always, Aleesha

One thought on “Anna Maria Island, Florida — Vacation Recap!

  1. Omg I loved reading thru this I felt like I was there with you guys!! You look amazing in all of your outfits. ♥️


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