A winter getaway to Anna Maria Island

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.

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.

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.

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 :)

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

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.

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.

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.

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 :)

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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