{Trip Report} Anna Maria Island

Every August since moving back to Texas, we’ve taken a family beach vacation. Sometimes it’s fairly close to home, other times it’s a bit more exotic. People always question why we’d want to go to the beach during the hottest time of the year…but the answer is simple: if I’m going to sweat my face off anyway, I’d rather be doing it in a swimsuit with my feet in the sand!

Besides, any beach is going to be cooler than Texas in August!

We also choose mid-to-late August because the crowds have died down, prices are typically lower, and it gives us a chance to connect as a family before the rush of school begins again. This year’s spot came about kind of backwards, since I first stumbled on rock-bottom airfares to Tampa, Florida, then started looking for beach towns in that vicinity.

We’ve visited several Florida beaches in the past, including Sanibel and Siesta Key, but I wanted something a little rustic and rough-around-the-edges for this trip. My darling friend Jen knew just the spot, since it’s where she and her family have been going for years…and Anna Maria Island was just as charming, slow-paced, and beautiful as I’d hoped.

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

We spent our days swimming in the clear-blue waters, playing in the white sand, taking long beach walks, napping, watching movies, exploring the little town, eating big dinners on the deck, and staring at sunsets. Everyone kind of set their own schedule, and we enjoyed time together, and alone. With constant stimulation, it was a blessing for everyone to unplug and live a quieter, slower pace.

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
Swimsuit (similar)
Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
Swimsuit (similar)
Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

The icing on this perfect beach escape, was being able to spend part of it with Jen and her precious family! She and I have become close friends over the years #thanksinternet, and have wanted to get our families together for awhile, so I was thrilled we were able to make our schedules overlap!
Our kids are similar ages, and share so many common interests, so we knew they’d hit it off…but had no idea just how well! They had the best time together…freeing us up for some fun of our own. #bonus #popatop

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Our son enjoyed being around more guys, and her three boys loved having a ‘little sister’ for a change. Babygirl, of course, gobbled up all the extra attention!

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
Swimsuit (similar)
Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
Romper (similar)

I wonder how much longer I’ll be able to carry her? #gulp

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

This big guy tries to carry me now!

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
Favorite Racerback Dress in ‘Blue Spectrum’ | Straw Hat
Beaded Tassel Bracelets (use code SUGARPLUM & the set is only $20!)

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Mr. SP joined us for the last half of the week…one of the upsides of cheap, short-haul flights!

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Have you noticed hats are my saving grace secret weapons for casual trips like these? Not just for shielding my face from the sun, but saving me from fixing my hair! #nohairdryerzone 

Hi Sugarplum | Island Style
Dress (on sale!! Size up 1)Straw Hat | EarringsSunglasses

Honestly, I have no idea how I was blessed with these cuties. Being the mom of such kind and funny humans humbles me, and makes me immensely proud everyday. I’ll eat them up, I love them so! #namethatmovie

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
{Where We Stayed}
This was a quirky house, with eclectic decor, but was very comfortable.
You couldn’t beat the location on the island (a block from the only grocery store), not to mention,
it’s literally sitting in the sand with unobstructed Gulf views from every room.
The deck was a pretty perfect spot for morning coffee and sunset dinners, too!

Travel Tip: Anna Maria has a free, all-day trolley bus that runs the length of the intimate 7-mile island, so you could easily get by with no car!

Hi Sugarplum | Trip Report: Anna Maria Island, Florida
Hi Sugarplum | Trip Report: Anna Maria Island, Florida
{Where We Ate}
We utilized the fully-stocked kitchen and cooked most of our meals,
but ventured out a few times.
Excellent tacos & made-to-order chips. Need I say more?!
Handmade donuts, customized with your choice of topping and frosting!
Old-fashioned ice-cream shop/general store.

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

It’s exactly the laid-back, flip-flop, easy-going, no rules kind of place we were looking for, and we savored every second of the precious time together. Thank you, Jen, for sharing your special island with us (and for some of these awesome pics!). We can’t wait to do it all over again!

Hi Sugarplum | Trip Report: Anna Maria Island, Florida

Then it was back-to-school for this 4th and 9th grader! #doublegulp Gone are the flip-flops and swimsuits, and out came the school clothes and backpacks. In attempt to stay in our vacation frame-of-mind, they each chose a few new things to wear before we left, which were waiting for us when we arrived home! #thanksnordstrom #freeshippingforpresident Now that’s my kind of back-to-school shopping!

Hi Sugarplum | Back to School pics
On Her: Tee (similar) | Leggings | Tennies
On Him: Tee | Shorts | Shoes

Do you have a special beach or Summer spot that’s precious to your family? Do you prefer slick or bohemian beach towns? I hope you had an extraordinary Summer, chock full of memories, belly-laughs, and too much ice cream. Happy September, lovebugs!

*See more Travel posts & tips on my Travel Tab.

{Shop More Back-to-School Looks for Her}
{Shop More Back-to-School Looks for Him}






*This post was written in collaboration with Nordstrom, but all clothes, opinions, and frizzy beach hair are my own. Thank you for supporting Hi Sugarplum sponsors!



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