{Trip Report} Anna Maria Island

Well, the alarm sure came early this morning…but the good news is it’s already Tuesday! How do we lobby to make every weekend three days?! I’d vote for any crazy candidate that made mandatory three-day weekends part of their platform! 😉

We stayed home for the holiday weekend, but I’m still on a vacation-high from our trip to Anna Maria Island last month. We visited the quiet little island last Summer for the first time, and fell in love with the slow pace, sugar-white sand, and clear waters.

Several years ago, we moved our family vacation to the end of Summer, and it was such a great opportunity to reconnect before the crazy days of school schedules began again, so it’s become our new tradition. I also love having it to look forward to all Summer long!

Warning: This post is obnoxiously photo-heavy…so if you don’t like beaches or pictures of cute kids, you might want to skip it! 😉 #youvebeenwarned

We rented a little cottage nestled in the trees, just a few yards from the beach, so we could have our toes in the sand whenever the mood struck, and quickly fell into a lazy routine of beach, sleep, eat, and repeat. We met our dear friends there again this year (they stay in their own home a few miles away), and I think it’s safe to say a new annual tradition has been born!
Tee (2 for $16!) | Similar Shorts | Romper

Tank (2 for $16!) | Similar Shorts
Tee (2 for $16!) | Similar Shorts | Romper

{Where We Stayed}
You won’t find any big resorts or high-rise condos on AMI, but rather lots of rustic cottages, swanky homes, and small condos & townhouses for rent. Location is key for us, so we opt for beachfront, and this simple, little cottage fit us perfectly.
It’s located on Holmes Beach, the quietest area on the island, and close to restaurants and the one grocery store. There were a few beach items left behind by previous renters, but you can rent chairs & umbrellas from a local shop, or pick up inexpensive ones at CVS or Public. Everything else is provided.

Travel Tip: Tampa is the closest major airport, and an easy 1-hour drive away.

{Where We Ate}

For such a small island, there are a surprising number of yummy spots. Some are a little more upscale than others, but nothing requires more than a sundress & sandals.
One of only 11 restaurants in the U.S. to receive the top-score from Zagat. So basically it’s the Top 10 restaurant in the entire United States. Right in the middle of unassuming Anna Maria Island! We were never able to score a dinner reservation, but enjoyed late-night dessert & the place was pure magic. 
Little more than a road-side shack, but delicious burgers & cold beer. Plus, you can go in nothing more than a swimsuit.
All-natural & organic taco shop with made-to-order chips. Need I say more?!
Donuts worth waiting for, in tons of inventive flavors.
We didn’t enjoy the food or service, but it’s worth mentioning for the view. There are literally tables in the sand, directly overlooking the stunning sunsets. But it’s also the same sunset-view you can get from any point along the beach. #sotheresthat
Sign of the Mermaid
Excellent brunch, set in a cheery yellow house.
This marina-side spot is about as authentic Florida seafood as they come. Go for lunch & watch the fishing boats and seagulls parade by.

Travel Tip: There’s a free trolley that runs the length of the island, and many people rent bikes or golf carts to get around (the top speed limit is 30mph, so it’s safe!). We rented a car, but you could get by without one if you stay on-island.

No schedules or agendas, minimal bickering and nagging, and lots of laughing and relaxing…it’s our perfect retreat! I wish I could bottle that lifestyle…or at least the feeling of peace that comes with it…and keep it with us all year long. #sigh

Did your family get away this Summer? Have you figured out how to keep that slow pace and easy-going attitude during the school year?!

Obviously we packed light, and left hair tools and makeup behind! I’m fairly minimal when it comes to my hair and makeup routine at home, but it’s a whole other level of minimal while at the beach! You might want to check out my Tips for Staying Stylish at the Beach and my first Trip Report: Anna Maria Island, too.

{Shop My Beach Style}

{Shop the Kids Beach Style}

*This post created in collaboration with Nordstrom, but all clothes, ideas, and idyllic-island squatting is my own. Thank you for supporting Hi Sugarplum sponsors.*

Leave a Comment


  1. Anonymous wrote:

    We do a big Summer trip as well, but earlier in the season because High School sports doesn't allow for end of Summer get aways! Is the preseason schedule different in Texas?

    Posted 9.6.16 Reply
    • We got lucky with no conflicting schedules!

      Posted 9.6.16 Reply
  2. Beautiful! We love family time like that. I have to comment that your son seems like the sweetest big brother to your daughter. That's the way to raise a gentleman!

    Posted 9.6.16 Reply
    • Thank you so much!!! I pray he grows to be a kind and polite man and husband!! They of course, have their moments tho! 😉

      Posted 9.6.16 Reply
  3. We leave for longboat key this week! Enjoyed your dinning options (we feel the same way about the beach house) and I'm going to try to get a reservation at Beach Bistro. If you go again and make it in to longboat key or st armonds circle try lazy lobster, Dry Dock, Venezia or Crab and Finn

    Posted 9.6.16 Reply
    • Sounds divine!!! Have so much fun!!! #takemewithyou xoxo

      Posted 9.6.16 Reply
  4. Lilly wrote:

    love the relaxing feel and sounds like a perfect low key vacation! so, which airport to do you fly to? then take a boat to the island? so no car rental needed? even better!

    Posted 9.6.16 Reply
    • We fly into Tampa…then rent a car to drive about an hour to AMI. There are a few bridges that connect it to the main land. xo

      Posted 9.6.16 Reply
  5. Love all your photos! Your vacation style is on point! I'm saving some of your outfits for inspiration when I pack for a cruise later this year. 😉

    Posted 9.6.16 Reply
  6. Kristen wrote:

    Looks like such a fun family trip and beautiful location to visit!

    Posted 9.6.16 Reply
  7. That Striped dress is gorgeous ! http://www.brunna.co

    Posted 9.6.16 Reply
  8. Your vacation sounds perfectly relaxing and I love all the pictures!What airport do you fly into? Tampa? Do you then rent a car?

    Posted 9.6.16 Reply
    • Yes ma'am…we flew into Tampa and rented a car for the hour-drive to AMI. You could get a car service/shuttle, and then take the shuttle or rent bikes while on island though! xo

      Posted 9.6.16 Reply
  9. Beautiful! This place was on our list but we chose blue mountain beach for our annual florida trip. I saw reviews on how the water wasn't as pretty as the areas near destin. We may have to visit AMI now after seeing your blog! 🙂

    Posted 9.6.16 Reply
  10. Beautiful! This place was on our list but we chose blue mountain beach for our annual florida trip. I saw reviews on how the water wasn't as pretty as the areas near destin. We may have to visit AMI now after seeing your blog! 🙂

    Posted 9.6.16 Reply
  11. What a perfect vacation! The beach is always my favorite. Beautiful family girlie..love all the pictures.

    Posted 9.8.16 Reply
  12. Jana wrote:

    We too love AMI, I discovered it on a beach blog a few years ago. My 3 kids love it, we always rent a house with a pool and my husband and I feel it is great place to just totally relax. It is one of my favorite places too.

    Posted 8.1.17 Reply