Anna Maria Island

The Trip That Taught Us How to Start

In June 2022, we flew to Anna Maria Island with a group of close friends.

There were eight adults, four babies under one and one older kid sharing a large house near Bean Point. Preston was a little over seven months old. It was his first flight, his first beach trip and one of our earliest chances to discover what leaving home with a baby would require from us.

At that stage, our instinct was to rebuild home wherever we went. We packed a Lotus travel crib, a SlumberPod, his sound machine, his infant car seat, the stroller it attached to and a significant supply of frozen breast milk. Looking back, we traveled with far more than we would carry now. At the time, though, we had not yet learned which parts of our routine mattered, which items made travel easier and which things we could live without.

The house gave us room to learn without the trip feeling fragile. Each family had private space. A fussing baby did not wake the entire group. The pool and beach were a few steps apart, and naps did not require anyone to end the day. We were all in the same new season of parenthood, figuring it out together.

We did not know how to travel lightly with a baby yet. We had to take the trip before we could learn.

Our Trip at a Glance

• DatesJune 4–11, 2022 — seven nights.
• Traveling WithMom, Dad and Preston, a little over seven months old; eight adults, four babies under one and one older kid in the full group.
• FlightsSouthwest from Columbus to Sarasota–Bradenton International Airport.
• Ground TransportationRental car from the airport; rental golf cart arranged through the home rental.
• Home BaseA large VRBO beachfront house near Bean Point on the northern end of Anna Maria Island.
• Trip RhythmPool, beach, naps at the house, home-cooked meals and a few casual outings.
• Food StopsThe Donut Experiment and The Ugly Grouper.
• Baby GearLotus travel crib, SlumberPod, Hatch sound machine, infant car seat, compatible stroller, one RTIC cooler and the Ceres Chill system.
• FirstsPreston’s first flight and first beach vacation.
• Would We Return?Absolutely — especially for another house-centered trip with both boys.

How We Arrived

We flew Southwest from Columbus into Sarasota–Bradenton, rented a car and stopped for groceries before reaching the house. That grocery stop shaped the week: once we unpacked, there was very little reason to leave. We used the car only occasionally, including to drive to The Ugly Grouper farther back down the island. The golf cart handled most of our local movement.

The House Was the Itinerary

Our rental was near the northern end of Anna Maria Island, close enough that we could walk to Bean Point for sunset. The back gate opened directly to the beach. With four babies under one, that access mattered more than almost any individual attraction could have. No one had to load the car, coordinate nap windows or carry a day’s worth of equipment simply to spend time near the water.

The house had approximately five or six bedrooms, and each bedroom had its own bathroom. Several additional half baths, an elevator, a workout room and multiple indoor and outdoor gathering areas made the property feel genuinely built for a large group. Outside, there was a private pool, a bar with a television, table games, exercise equipment, mini golf, a grill and an outdoor shower. Bikes, paddleboards and beach supplies were already there. Laundry made the week with infants easier.

We do not have a current link for the VRBO and cannot confirm that it is still listed. The useful recommendation is the setup rather than this exact property: direct beach access, a private pool, ensuite bedrooms, laundry and enough separation for each family to maintain its own rhythm.

What to Look for in a Group Rental

• Space to separatePrivate bedrooms and bathrooms kept one baby’s difficult moment from becoming everyone’s difficult moment.
• Two easy forms of waterThe pool was Preston’s favorite; the beach was available whenever the group wanted it without requiring a separate outing.
• A kitchen and grillCooking most lunches and dinners made a large-group week easier and kept the house at the center of the trip.
• Laundry and outdoor cleanupA washer, dryer and outdoor shower were practical amenities with babies, swimsuits and sand.

A Week With Very Little to Prove

This was not an itinerary-heavy trip. A typical day moved between the private pool, the beach and naps inside the house.

We cooked most lunches and dinners, sat outside and let the property do the work. With so many babies, staying close did not feel like missing the island. It was the reason the week remained manageable.

The Pool

Preston loved the pool. At seven months, it was the clearest success of the trip: controlled, close to the house and easy to revisit in short stretches. Pool time could end when he needed a nap and begin again without reorganizing the entire group.

The Beach

The beach was directly behind the rental, but Preston was more uncertain about the sand and Gulf water. He also developed a mild heat rash and did not adjust to the Florida heat particularly well. That experience taught us to pay attention to shade, temperature and the length of outdoor stretches rather than assuming every baby will love a beach simply because the adults do.

Bean Point at Sunset

One evening, we walked to Bean Point for sunset. It was one of the few moments that pulled the full group away from the house, but it still fit the trip’s unhurried rhythm: no complicated reservation, no long drive and no need to turn the day into more than it was.

Getting Around

The golf cart became our default transportation around the nearby part of the island. We had arranged the rental through the home-rental process. After the grocery run and arrival, the car mostly stayed parked.

A Few Stops, and a Kitchen Full of Friends

Most of our meals happened at the house. We had already bought groceries, the kitchen could support a large group and the grill made dinner an activity rather than another logistical task. Cooking together also meant that naps, feeding schedules and tired babies did not have to align before everyone could eat.

The Donut Experiment

The Donut Experiment was one of our casual outings. We remember it as part of the small rhythm beyond the house: a reason to take the golf cart, pick up something fun and return without turning breakfast into a full production.

The Ugly Grouper

The Ugly Grouper was a casual seafood restaurant known for its fun, laid-back outdoor atmosphere. Because it was farther back down the island, this was one of the few outings when we used the rental car rather than the golf cart. Unsurprisingly, given its name, Kyle really enjoyed the grouper here.

For a Similar Trip

• Buy groceries before check-inFor our group, one early stop reduced the number of decisions the week required.
• Choose a house worth staying inA good kitchen, outdoor dining and a grill matter more when most meals will happen at home. Having a pool and direct beach access was the single best amenity.
• Leave room for one or two easy outingsThe doughnut shop, the Ugly Grouper and Bean Point sunset were enough to give the week shape without crowding it.

What Our First Flight With a Baby Taught Us

Preston did well on the flight to Florida. The harder portion came on the return travel day, when the drive, airport transition and long series of expectations became too much for him. That distinction mattered: the airplane itself was not the only measure of whether a travel day would feel manageable. The cumulative time in a car seat, stroller, airport and plane mattered too.

We were also traveling with frozen breast milk. We packed it in one RTIC cooler and used the Ceres Chill system. Once we reached a full-size house with a kitchen, storage was straightforward. The larger challenge was simply the volume of equipment we believed we needed to reproduce home.

We would not judge our 2022 packing by the systems we use now. We were new parents taking a baby on his first flight. The extra gear gave us confidence before experience could. Over time, each trip helped us separate genuine needs from the things we carried because they made the unknown feel more controllable.

Our packing became lighter only after our experience became heavier.

What We Would Repeat — and What We Would Change

We would absolutely return to Anna Maria Island with both boys. For a U.S. beach destination, it remains one of the places highest on our list. We would again look for a home near the beach with a private pool, laundry, outdoor space and enough room for the trip to feel comfortable even when no one wanted to go anywhere.

We Would Repeat

• A house with direct beach access and a poolTwo easy forms of water within steps of the door made the week work with babies.
• Traveling with close friendsBeing in the same season of parenthood meant no one had to apologize for a nap, a meltdown or an early night.
• Cooking at homeFor a group this large, shared lunches and dinners were part of the vacation rather than a compromise.

We Would Change

• Pack lessLaundry, a stocked house and beach equipment already at the property meant we had more redundancy than we needed.
• Plan more deliberately for heatPreston’s mild heat rash and uncertain response to the beach would lead us to prioritize shade and shorter outdoor windows with a baby.
• Protect the return travel dayWe would reduce the number of transitions where possible and treat the drive back to the airport as part of the day’s total demand.

Anna Maria Island worked because the trip did not depend on doing very much. The house made room for naps, meals, pool time, beach time and the unpredictable rhythms of four babies. We left with good memories, but also with something that shaped every trip after it: a clearer sense that family travel is not a system you perfect before you begin. It is something you learn by going.