A small miracle in my life has changed my travel patterns. Her name is Layla, and we already planned our first grandma, grandpa, mum, dad and baby taste grand trip 2 months in.
My son and his wife were aiming for a beach vacation in December to St. Pete Beach when Layla would be 6 months old and sunscreen eligible. Avid travelers that we are, we couldn’t wait to take her on the road and booked her first mini-vacation to Stuart Beach, a lesser-known beach getaway on Florida’s east coast, at four months old. After that, we immediately began mapping out future destinations with great accommodations to house the five of us near family attractions.
Note: I have hosted all three resorts covered, but opinions and recommendations are my own.
1. Stuart Beach
Aaron, his dad and I fondly remember the trips to Martin County that started when Aaron was a tote and continued through his teenage years as a surfer. Indian River Plantation, once a single sprawling beach and golf resort, was firmly embedded in our happy memories, so that’s where we cast the first arrow.
Now a collection of accommodations that includes a Marriott resort and short-term vacation rentals through Water Pointe Realty Group, Indian River Plantation’s inventory offers diverse options. We stayed in a two-bedroom beachfront apartment with a full kitchen and living room facilities. The elevated (third floor) view of Stuart’s Atlantic-washed tawny sand meant we could enjoy the beach all day without exposing Layla’s porcelain skin to the sun’s rays.
But of course we could hardly take her on her first beach trip without a proper baptism in the sea. The ritual dipping of the feet took place on the first morning under cloudy skies. Layla, dressed in her flamingo-flecked swimsuit and corrective ocean-themed baby helmet, looks skeptical in all the photos and videos, but only bordered on a pout at one point. Mom and Dad picked up shells to decorate a picture frame they would later make to preserve the moment.
Aaron had the rest of the day planned. After all, he has been traveling with his travel writer mother for 32 years, and even collaborated with me on travel articles for teenagers. First stop after breakfast in Stuart was the Children’s Museum of the Treasure Coast in neighboring Jensen Beach. We climbed aboard a pirate ship and played with a model railway. The highlight was Layla catching a tarpon in the fishing and boating show — with the help of mom and grampy who landed the cloth fish with a magnet in its mouth. More pictures.
Lunch was grown up at Ocean Republic Brewery in Stuart, family (and dog) friendly with indoor and outdoor seating. For dinner, we went back to Conchy Joe’s Seafood in Jensen Beach, where Aaron once ordered “dinosaur bones” from the kids’ menu. There are still kid-friendly items (but no dinosaur bones) on a coloring/puzzle menu and an Old Island Keys vibe that Layla slept through but families around us enjoyed.
The next day we followed breakfast at the Seaside Café, a tiki at Stuart Beach public access, with a visit to the Elliott Museum before heading back home. Elliott has matured a lot since our last visit with a sophisticated showcase of nearly 100 vintage cars, a 1931 Ford Model-A school bus for kids to board, and scavenger hunts to keep them engaged as well.
2. St. Pete Beach
Layla’s proper sand diving, however, awaited her six-month celebration at TradeWinds Island Resorts on St. Pete Beach, Florida’s ultimate family vacation destination. With its patented brand of soft, sugary, white sand, it’s the perfect sandbox experience. It was pure joy to watch my granddaughter discover the texture and pleasant flow of a puddle of sand, which inevitably ended up in her mouth.
Our two-bedroom villa with kitchenette adapted to our plan with naps and snacks. We briefly considered getting out to explore the wealth of family attractions in the Tampa Bay area—from historic old-school Sunken Gardens to bucket-list Busch Gardens—but found so much to do at the 40-acre resort. We got in the car just for lunch one day at Sea Dog Brewing Co. on Treasure Island 10 minutes away. In case you haven’t discovered, craft breweries are largely designed for family entertainment. This open-air room has a games table and a full food menu with children’s items.
At the resort we had our choice of half a dozen places to eat, plus bars, a Pizza Hut and an ice cream shop on the Island Grand section of the resort where we stayed. TradeWinds also includes the adjacent RumFish Beach Resort campus with a few more restaurants and bars, including RumFish Grille with three saltwater fish tanks. In the largest, at 33,500 litres, guests can snorkel with local fish. There is also the Zing Ray Zipline for adventurers at the RumFish resort.
Back at the Island Grand, the three-story inflatable High Tide Water Slide on the beach is the top children’s attraction. Families also love pedaling a paddle boat through the inland waterways around Pirate Island, complete with a pirate ship on the beach and ducks bobbing alongside.
The family activities are practically endless with a full range of water sports from kayaks and Aquabanas to a floating water park. Poolside crafts, duck feeding, a touch tank experience, bonfires with s’mores, magic shows, pool parties, cornhole tournaments…the list of organized pastimes goes on and on.
Then there is the beautiful, wide beach overlooking the child-friendly waters of the Gulf of Mexico. Included in the resort fee, you get one day’s cabin use. It was perfect for Layla’s first extended beach session. She could stay mostly in the shade, take her 11:30 bottle and a nap afterward, and get her feet in the sand. Like the rest of the family, she returns to the beach again and again, now a true beach baby.
Pro tip: Our go-to for breakfast quickly became Skidder’s, a short and pleasant two-block walk away. Greek in heritage, the breakfast menu offers all our family favorites perfectly executed – cheese flashes, eggs benedict, pancakes, huevos rancheros and the most delicious home-baked potatoes. Plus, it’s much more budget-friendly than the resort breakfast options.
3. Key West
Based on my Florida travels over the years, I now dream of places I would like to return to with my grandson. Key West isn’t the first place that comes to mind when planning a multigenerational vacation, but Parrot Key Hotel & Villas tweaked that image to bring family more into focus.
Away from the famous craziness of Duval Street and Old Town, it creates its own, quieter mini-version of Key West on the island’s edge. This version has all the white picket fences, gingerbread-trimmed rooftops, balconies and Victorian hues you’ll find in Old Town and even a great bar with fun craft cocktails.
The best news is that it has its own beach on the property, hidden by mangroves and hammocks. Sunset Pier juts out into the Gulf of Mexico for a private, upscale version of what everyone flocks to Mallory Square and Pier for at the end of the day. However, the legendary sunset celebration may require at least one visit, and Parrot Key makes it easy with a free shuttle to Old Town or Smather’s Beach on the other side of the island, where the beach scene is also legendary.
For older children, the Old Town has its appeal. Aaron, as a young age, loved the quirky Key West Cemetery and the ghost tours. One of my favorite family attractions is free: the Florida Key Eco-Discovery Center. The center allows you to explore the exquisite coral reef system that lies completely dry offshore with hands-on experiences (and in the case of a virtual stand-up paddleboard exhibit, on your feet).
Other nature-related favorites include the Key West Aquarium and the Key West Butterfly & Nature Conservatory. The wannabe pirates in the family shouldn’t miss the Key West Shipwreck Treasure Museum. Take a nutritional break along the water’s edge. Half Shell Raw Bar in the Historic Seaport has the right salty air and casual feel for kids.
You can also stay right on the property at Parrot’s Key for breakfast, lunch and dinner at The Grove Kitchen & Bar, set among the resort’s four swimming pools surrounded by jungle-like vegetation. Dig into pizza or go bold with a Key West specialty like local pink shrimp or conch fritters. Many other family friendly restaurants plus a supermarket are within walking distance.
The villas on Parrot Key have up to three bedrooms and are designed for families of eight. Clean and spacious in design, they perfectly suit the simple, airy, Keys-y lifestyle. The Villa Stay and Play package includes family outings on the crystal clear waters the Keys are known for. The three-night holiday is based on a dolphin tour, scavenger hunt and other family games.
Pro tip: The shuttle bus to the old town runs until 16.40 and brings you close to the Conch Tour train station. The train is fun for kids and an easy way to get around to Old Town attractions with a historical overview of the fascinating destination.
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