A winter getaway to Anna Maria Island

22 February 2018

Here is something you should know about my husband: he strongly dislikes cold weather. Like, gets a very mild case of SAD in the winter. (Hence our daughter’s name, in part!) For years he has dreamed about taking a warm-weather vacation in the depths of January or February, but the opportunity always snuck up on us after the holidays.

Anna Maria Pier

That is, until this year. After a tough 2017, where, among other things, our surprise 30th birthday/fifth wedding anniversary trips fell through, we decided on a whim to finally make a snowbird getaway happen. The deciding factor was a fall Southwest Airlines sale, where we snapped up tickets to Tampa. With a destination in hand, John began researching where, exactly, we wanted to go once we landed. The criteria: warm (obviously), clear water, somewhere within driving distance of the Tampa airport, somewhere with an “Old Florida” feel, somewhere with a relaxed and laid-back vibe, and somewhere we could walk most places. Anna Maria Island checked all of those boxes and then some.

beach vacation

Anna Maria is a tiny, white-sand sliver of a barrier island known for its beautiful beaches and quaint vibe. There are no high-rise condos or obnoxious chains. The island-wide speed limit is 35 MPH :) We stayed at the even quieter north end of the island (the Anna Maria section), and it’s so narrow that you can see the Gulf at one end of the street and turn around to see Tampa Bay at the other. We stayed at the Sunrise Garden Resort, which is really the only “hotel” at that end – it’s surrounded by colorful houses (many of them rentals), cute shops, and restaurants. We were very happy there and would absolutely recommend it over the more commercial south end of the island.

Sunrise Garden Resort

fancy beach house

Here’s how we really knew this was the perfect destination for us: I could probably count on two hands the number of people we saw under 40. Ha! That’s a little bit of an exaggeration, but if a place is good enough for retirees, it’s good enough for us! Those people know how to relax, I tell you what :)

colorful beach houses

This vacation was quite possibly the least-planned out adventure we have ever had. We didn’t make any reservations or an itinerary in advance, and that worked out fine! We arrived Wednesday afternoon and left Saturday afternoon, and here were a few highlights:

Ginny’s and Jane E’s for breakfast sandwiches and smoothies
The Waterfront Restaurant for dinner (twice!)
— Bean Point, the beach on the north tip of the island, for long walks, shell collecting, and nature sightings
— Renting chairs from Beach Bums and reading on the Tampa Bay-side beach
— Browsing the many adorable shops on Pine Street
The General Store for yummy deli sandwiches, salads, and ice cream (twice!)
Poppo’s Taqueria for burrito bowls and quesadillas
The Donut Experiment for a design-your-own morning treat

Poppo's Tacos

We walked to all of these spots from our hotel easily, which was so nice! We also enjoyed watching the Olympics from bed in the evenings and lounging by (and taking a dip in) Sunrise’s heated pool.

Sunrise Garden pool

The only real off-island adventure we had was kayaking in Robinson Preserve, launching from nearby Bradenton — the perfect active counterpoint to our generally lazy schedule. We rented a tandem from Kayak Jacks for a two hour or so self-guided paddle (through a mangrove tunnel and out to a sandbar!) and it was a seamless experience.

mangrove tunnel

sand dollar

My favorite part? Aside from the flights themselves, which felt absurdly luxurious without wrangling a two-year-old, my favorite part of the trip was our last morning. After checking out of our hotel, we brought our beach chairs back to the water’s edge and chatted through the famous 36 Questions That Lead to Love. We had never done them before, and though of course we knew many of each other’s answers, it was such a treat to just sit there, enjoy each other’s company, and be reminded of all the ways we are similar and all the reasons we are a perfect match for each other.

beach reading

Which really, was the whole point. I’m not the first one to say it, but time away together is a joy and a priority if you have kids. Yes, we generally like to prioritize trips that include the whole family (and love traveling together dearly!), but John and I plan to be best friends long after kiddos are off to college, and best friends need love and attention and special memories all along the way, not just after the kids have officially turned out alright. We’re grateful we got to to take this trip (our first multi-night stay away) and especially thankful to my Mom for watching June! They had a great time, too :)

beach vacation photos

Anna Maria was the perfectly relaxing winter getaway we were hoping for, and we couldn’t recommend it more!!

I’d love to hear: Do y’all have a favorite winter getaway? And, if you have kids, have you gotten away yet with just your spouse?

P.S. Clearly I am a big fan of this hat – perfect for such a sunny location!

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February 22, 2018 8:28 am

This really makes me want to get away for Sam for one night sans toddler (one of my 18 for 2018 goals). My birthday is in November, by which point he will be nearly two (we are born two days apart on the calendar year) so maybe, just maybe a grandparent sleepover will work then! xx

February 22, 2018 9:18 am

What a fun, relaxing trip! Texas is pretty reliably warmer than NC so we often have that “break” if we go for Christmas…even though it’s not usually that cold here yet. We haven’t done any other winter escapes but I am a big fan of the idea! We are planning our first vacation without Charlie in September after the CPA and I have my fingers crossed for Palmetto Bluff :)

February 22, 2018 10:32 am

What a wonderful trip! We did a spring break getaway with a large group of friends during my senior year of college down to Bradenton to stay at a girlfriend’s house. It was absolutely a winter getaway as it was snowing on the trip down from Ohio! We have a 5 year anniversary/turning 30 trip to Italy planned for the fall. Besides a couple of one night staycations, we haven’t done a trip without our kiddos yet!

February 22, 2018 2:56 pm

The best most magical place! We have two, potentially three, trips lined up to Florida this year. I never thought I’d fall in love with the sunshine state. Also, tell John I too suffer from SAD. Except my SAD is more sad probably given that I live in Michigan hahaha

Kelly Strawberry
February 22, 2018 3:15 pm

I’m a big fan of the Florida Keys, mostly because we have a free place to stay at my in-laws beach house. They also have a house in Palm Beach, so pretty much anytime we go on vacation, we’re headed to Florida. I guess that is both good and bad at times. It limits where we go, but you can’t beat that price.

With my parents nearby, I’m lucky that they keep my son overnight often (about once/week!). They have been keeping him overnight since he was 3 months old. I love the relationship they have with him. They are more like his second set of parents! Growing up, all of my extended family lived out of state, so it’s very different than what I experienced as a child. I feel so fortunate to have parents that are relatively young and in close proximity. I never knew how much of a game-changer that would be until I had a baby.

ps – I’m loving the book All Joy, No Fun.

February 22, 2018 3:27 pm

What an amazing trip! Sounds lovely and relaxing and quiet :) Would you reco getting a rental cal to get from Tampa airport to the island? Not sure if you’d really need the car once on the island – sounds very walkable! Thanks!

February 22, 2018 4:41 pm

These photos are so beautiful, Em! Really happy you guys were able to sneak away for a bit together, too!

February 26, 2018 10:51 pm

LOL at the number of people under 40. Are you guys team #oldsouls like we are? Most of the people we get along with best are older than our parents, haha. Looks like a beautiful trip. <3

March 3, 2018 10:59 pm

All that fun you had and I got to have lunch with your mother!