A senior trip with mom? A Destin-area beach vacation is a good option (2024)

SANTA ROSA BEACH, FLORIDA — I started hearing about these vacations about five years ago: Moms going on senior trips with their sons. My first reaction was to deride the moms for their helicoptering ways and to feel sorry for the kids who had to share this first taste of freedom with their parents.

But as it’s become increasingly hard to find a hotel rental in Florida for those under 21 and with both house and car rentals often requiring renters to be 25, I started to understand.

And then I did it. I went on a senior trip with three of my closest friends, and their sons, all 17 years old and graduating high school this year. Suddenly it made some sense. We all became friends when our kids were 6 years old and started playing hockey. They stayed friends, we stayed friends, and why wouldn’t I want to spend a week at a beach near Destin (specifically Santa Rosa Beach, along South Walton’s famed 30A) with some of my favorite people. Turns out, the kids thought their moms were pretty cool, too.

First, a place to stay

Before going on the trip, be sure to discuss plans with everyone involved. Who is paying for what? What rules will you have for the kids? What are the house rules?

Next, find a house rental where everyone can spread out and where there is something else to do. For example, ours had a swimming pool. Some have hot tubs, billiards, bikes. Rental sites such as Vrbo and Airbnb are good places to start, but for such a large vacation investment, I prefer to go to the source: the company that manages the house. This was my second time using Newman-Dailey (destinvacation.com), and it did not disappoint. The folks there helped me find the perfect house and were available any time if I had an issue (I did not though).

And oh, was this house perfect. At Your Leisure Luxury Vacation home, which rents for about $1,000 a night in the offseason (April is offseason) was a perfect location. Just a block from the beach, it was also within walking distance of five restaurants and bars. None of them was directly on the beach though; you have to go farther west toward Destin for those.

Each of the four moms had her own bedroom and bathroom. The boys shared two bedrooms and a bathroom. The kitchen was huge, the dining table seated 12, and I’m pretty sure the giant sectional would have, too.

Newman-Dailey also has a Be Rewarded Program, which offers one free adult pass daily to a variety of activities and attractions, including dolphin cruises, parasailing, golf, Big Kahunas Waterpark, the Gulfarium Marine Adventure Park and more. In addition, most rentals include complimentary seasonal beach service with two chairs and an umbrella set up on the beach each day of your stay.

The small back yard had a small pool, which we paid to heat, and that turned it into a hot tub on chilly April nights. With a couch, a high top, a TV, a grill and some fun pool lights, we turned it into a mini party.

The first night of our stay, after a couple of hours on the beach, we decided to stay in. We had ordered groceries online and had them delivered. The house, which is three levels, has an elevator. We sent the groceries from the bottom floor to the kitchen on the second floor in the elevator. We grilled burgers, made a little charcuterie board and brownies. Then we played card games and board games. It was a fun way to connect as a group before we went our separate ways.

Give the kids their own activities

Our boys love to golf, so we arranged for them to go on two golf outings without us. Because they couldn’t drive the rental car, we dropped them off and picked them up each time.

Regatta Bay (about $125), inside a gated home community, was as gorgeous as you’d expect from a course designed by Arnold Palmer. A cart offering drinks makes the rounds for golfers. The boys declared it a challenging but fun course.

Emerald Bay (also about $125) was also in a gated community. This championship level course is often on Northwest Florida’s best-of lists. And a couple of holes along the back nine are beside the water, making for the kind of views you can’t get in Missouri.

The boys also had one request: jet skis. We found a deal online out farther west at Power Up Watersports. After signing waivers and forking over $120 each, the boys got a quick briefing and were off on a one-hour adventure in the Choctawhatchee Bay. The moms headed to the Gulf, a restaurant built out of shipping containers, where you order drinks from a center bar, get food from a window and sit along the water with a view of the bay. We spotted our jet skiers going through the no-wake zone on their way back.

The boys also needed their own beach time. We brought along Frisbees and footballs so they could head down the coast from us and play on the sand and in the water away from our watchful eyes.

Give the adults their own activities

While the kids played golf, the moms did their own things. One day we dropped the kids at Regatta Bay and then headed about 20 minutes west to the Gulfarium Marine Adventure Park ($34.95 at gulfarium.com). Sure, it was a place we could have taken the kids, but it was nice to explore the sea lions, penguins and alligators at our own pace. With the Gulf of Mexico in the background, it was unlike any such place I’d been. A sea lion show was hilarious and left you marveling at these creatures (much like you do at our zoo). A dolphin show in the new Dolphin Oasis was nothing short of spectacular. After the show, we headed next door to Al’s Beach Club, right on the beach. A sand volleyball tournament provided our entertainment as we sipped drinks and ate the best tuna burger I’ve had: a seared tuna steak topped with pickled veggies, cilantro and a sweet chili soy sauce.

On the boys’ other golf day, the moms started with breakfast at a cute cafe, Raw and Juicy, formerly Hibiscus in Grayton Beach. There, we took our waffles, breakfast sandwiches and bowls to the back yard shrouded by live oaks and magnolias. Next, we set out for a short hike at Grayton Beach State Park. There, four miles of trails wind through pine flatwoods and around freshwater ponds (always be on the lookout for alligators, though we saw none). This trail even takes you through the dunes that are otherwise off limits.

We spent the rest of the afternoon back at Santa Rosa Beach before picking up the boys from golf. It’s been written about countless times, but it bears repeating. This area is called the Emerald Coast for a reason. The water is a gorgeous turquoise, and the sand is white, fine and without shells and seaweed.

Do a few things together

Moms and teenage boys sometimes love the same things. One afternoon, we found an online deal and rented a pontoon boat with a captain to take us out to Crab Island (about $600).

Sitting just off Destin Harbor at the entrance to Choctowhatchee Bay, Crab Island isn’t really an island at all (though it used to be) but an underwater sandbar where the water is about waist deep and crystal clear (though winds on our visit muddied them up a bit). The guys got a kick out of food boats (like food trucks) that come by to serve drinks, ice cream and Chick-fil-A.

We anchored right in the middle of it. It was a Wednesday in late April, but there were still several dozen boats with partying people around us. We cranked up the music on our pontoon, and our captain, Diego, rolled out the floating lily pad. I climbed on, grabbed a drink and relaxed.

We dined as a group every evening. My favorite meal was just down the road from our house rental at Stinky’s Fish Camp, which serves a sampler trio of shrimp and grits, crawfish pie and catfish meuniere.

But my favorite memory was a slightly chilly night, sitting outside, with the gulf in the distance at Shunk Gulley Oyster Bar at Santa Rosa Beach. It features classic coastal cuisine as well as live music. The oysters, both cooked and raw, provided much discussion, but the duck fat fries, crab bisque and grouper were also a hit. And sitting at the picnic-style table, with some of my favorite people, is a memory I will have forever — of some moms and kids celebrating 10+ years of friendship and high school graduation. Maybe we’ll do it again when they graduate college.