Sanibel Island Family Vacation: Unforgettable Moments, Culinary Delights, and Hidden Gems

It’s hard to believe that nearly three weeks have already passed since our rejuvenating return from our recent family vacation to the enchanting Sanibel Island, Florida. The memories are still so vivid, and I’ve been eagerly awaiting the perfect moment to share some highlights and snapshots from our incredible time there. So, without further ado, let’s finally dive into the details of our latest Sanibel adventure!

This marked our third visit to this beautiful Gulf Coast paradise, and each time we’ve chosen a different accommodation, offering a fresh perspective on island living. However, I can confidently say that the condo we rented on this trip was, without a doubt, my absolute favorite. We secured a fantastic unit at Loggerhead Cay, a charming complex, through the popular vacation rental site, VRBO. To be perfectly honest, this particular unit turned out to be a complete gem, exceeding all our expectations. The owners clearly take immense pride in their property, maintaining it to an exceptionally high standard. We found it incredibly comfortable, impeccably clean, and thoughtfully stocked with every conceivable item one might need – from essential flashlights (which proved crucial during an unexpected evening storm) and tennis rackets for active fun, to an array of beach and pool toys for the kids. Evenings were filled with entertainment thanks to cabinets brimming with movies, books, and board games, alongside a very welcome, well-stocked wine rack for the adults. It truly felt like a home away from home, providing a relaxed and worry-free environment for our entire stay.

I just loved this…

The location of our Loggerhead Cay condo was simply fantastic, offering the best of both worlds. The complex itself is situated on a quieter, more peaceful side of Sanibel Island, allowing for a truly serene escape. Yet, it was perfectly positioned for exploration, close enough that we could easily ride our bikes to the iconic Sanibel Lighthouse, a variety of delightful restaurants, or even a quick trip to the local store for hot dog buns. Personally, I found immense joy in simply exploring the charming residential streets, admiring the unique island architecture. The unit also boasted an ideal placement within the complex, being just a short, leisurely walk to the pristine beach and offering picturesque views directly over the expansive pool. And speaking of the pool – it was truly impressive, enormous in size. I actually seized the opportunity on our very first morning to swim several laps in the refreshing water before it became bustling with other vacationers.

To balance our dining experiences, we planned to prepare most of our breakfasts and lunches in our well-equipped condo. We brought a selection of non-perishable food items from home, and supplemented these with a few trips to one of the island’s local grocery stores – Jerry’s Foods, one of only two main groceries on the island, if I recall correctly. We had fond memories of visiting Jerry’s during our previous trip with the kids, primarily for the tropical birds in large cages scattered throughout the shopping center. My son, Sammy, had a particularly memorable moment when one of the birds actually said “Hello” back to him, which was incredibly fun and a highlight for his young imagination. A key tip for budget-conscious travelers: while Jerry’s is convenient for fresh produce and last-minute needs, I highly recommend doing your major grocery shopping on the mainland before crossing the bridge onto Sanibel. Island prices, as one might expect, tend to be significantly higher. Stocking up at a Publix on the mainland can save you a considerable amount. However, Jerry’s remained an excellent spot for quickly grabbing sandwich fixings, fresh breads, beverages like beer and wine, and any other forgotten essentials.

For dinners, we were excited to explore a mix of familiar and new restaurants, sampling the diverse culinary landscape Sanibel has to offer.

Sanibel Island Dining Highlights

Lazy Flamingo – A visit to Lazy Flamingo has become a cherished tradition for us, marking our presence on the island each time. It’s best described as classic “pub grub” with a laid-back, rustic atmosphere featuring wooden tables and benches, a lively raw bar, an extensive beer selection, and a menu rich with fried delights and incredibly fresh fish. Without fail, I order the same delicious combination every time: a steaming pot of fresh oysters and a perfectly blackened grouper Caesar salad, while my husband opts for their renowned grouper sandwich. My absolute adoration for their salad knows no bounds – it’s a simple yet impeccably crisp Caesar, served with dressing on the side, accompanied by a delectable piece of garlic bread. Beyond the food, Lazy Flamingo is a wonderfully fun and family-friendly spot. The waitresses we encountered were among the kindest and most accommodating throughout our entire trip, taking excellent care of us and genuinely wonderful with our kids, which is always a huge plus for family dining. While the kids’ meals themselves were nothing extraordinary (the macaroni and cheese, in particular, was quite standard), they are served in a commemorative frisbee – a detail my children remembered from our previous visit, making the acquisition of another one a joyful event. Its proximity to our condo meant we could enjoy a lovely family bike ride to dinner. One evening, after sheltering from a big storm at the Dairy Queen next door, we rode home in a gentle rain, laughing all the way – a spontaneous memory I will undoubtedly cherish forever.

Gramma Dot’s – This charming establishment was a new discovery for us, highly recommended by a friend who, coincidentally, had stayed in the very same Loggerhead Cay condo just the week before us! Gramma Dot’s boasts an idyllic waterfront location within a bustling marina, offering delightful views of an array of impressive boats docked nearby. Despite it being dinnertime, we were pleasantly surprised to find we could order from the lunch menu, which provided the same generous portions (minus a side dish) for a more budget-friendly price. Every dish we sampled was superb. The kids happily devoured their fish fingers and chicken strips, while I savored a mesquite-grilled grouper sandwich. My husband indulged in a classic fried oyster po’ boy, and we all shared a delicious order of coconut shrimp. A standout feature were the homemade potato chips served with the sandwiches – I honestly believe I could eat them every single day; they were that good! We rounded off our meal with a slice of their famous key lime pie, which struck the perfect balance of tartness with just a hint of sweetness, an ideal island dessert.

The Island Cow – Another new addition to our Sanibel dining repertoire, but certainly not new to the island itself! The Island Cow is an incredibly well-known and beloved institution in the area, a fact evident by the consistent line of patrons always waiting eagerly to dine there. We loved it so much that we actually ate here twice – once for a lively dinner and again for a hearty breakfast. The menu is famously enormous, almost overwhelmingly extensive, ensuring there is truly something to satisfy every palate and craving. Our dinner wait was approximately 30 minutes, which flew by quickly on their vibrant back patio. We enjoyed a couple of refreshing drinks, observed a pair of parrots (or perhaps parakeets?), and were thoroughly entertained by a ring-on-a-string toss game that captivated the kids. I, meanwhile, happily sipped on a delicious Mango Sangria (YUM!) from a colorful Adirondack chair, meticulously studying the vast menu. Some of our absolute favorite culinary highlights from The Island Cow included the addictive fried pickles, crunchy grouper tacos, the satisfying crab cake and egg breakfast, the exquisite smoked salmon breakfast (as beautifully captured in the picture above), and the delightful complimentary muffins that accompanied our meals. It’s a vibrant, quirky spot perfect for families seeking a memorable meal.

A couple of other fantastic restaurants we were fortunate enough to visit:

The Bubble Room – The scenic drive to Captiva, where The Bubble Room is nestled, is an experience in itself – truly like none other, and one we always eagerly anticipate. A visit to this unique restaurant has firmly established itself as a cherished family tradition. The Bubble Room is renowned for its fascinating, eclectic, and wonderfully nostalgic decor, heavily themed around Christmas, which provides endless visual entertainment while you await your meal. My husband and I both opted for the “Eddie Fisherman,” a superb pecan-crusted grouper expertly cooked in parchment paper, delivering a truly delicious and moist dish. All meals are generously served with a robust salad (which, by this point in the trip, I was seriously craving after all the rich food!) and the glorious “Bubble Bread” – essentially garlic bread on steroids, so wonderfully indulgent it completely negates the health benefits of the salad! I was genuinely impressed with the kids’ meals here; both received generous portions of buttered bow tie noodles accompanied by sautéed carrots and tater tots on the side. It was, without a doubt, one of the best “kid’s menu” offerings I had encountered throughout our entire trip. After a few days of observing what my children were ordering at other eateries, this mom was starting to feel a little “nutso,” if you know what I mean, so The Bubble Room was a welcome relief!

Doc Ford’s Rum Bar & Grille – We chose Doc Ford’s for our final night on vacation, and it proved to be a thoroughly enjoyable experience. We savored a delicious meal, and I even went home with a captivating book – apparently, Doc Ford is a popular character in a compelling series of stories penned by Randy Wayne White, an author who actually resides on the island. My husband ordered the Half Roasted Chicken with Cuban Chimichurri Sauce, which was absolutely excellent, while I indulged in the Banana Leaf Snapper and loved every flavorful bite. We also shared an order of their famous Yucatan Shrimp, which was so deliciously spicy that I’ve been determined ever since to figure out how to recreate that incredible flavor profile in my own kitchen.

While we certainly enjoyed many culinary delights, there were still so many more intriguing restaurants we didn’t get a chance to try. Well, that just gives us another reason to return! After all this incredible eating, do you now understand precisely why I came home and promptly made this refreshing veggie cobb salad? It was a much-needed reset!

Engaging Activities and Island Exploration

Beyond the fantastic food, Sanibel Island offers a plethora of activities to keep families entertained and connected with nature:

• Bike Rentals from Billy’s Bikes & Rentals – Renting bikes is an absolute must on Sanibel. We rented four bikes for our family, and the convenience was unparalleled: Billy’s had them delivered directly to our condo, waiting for us even before our arrival. Dealing with Billy’s was a dream; their customer service was truly excellent, and they were incredibly accommodating when we had to make a last-minute switch for one of our bikes. Initially, my daughter and I planned a “tandem” style ride, but it quickly became apparent that it wasn’t quite working out for us! They effortlessly swapped it for a safe and comfortable training-wheel style bike for my daughter, and all was well. Sanibel is exceptionally bike-friendly, boasting miles upon miles of dedicated bike paths that make exploring the island’s natural beauty both easy and enjoyable.
• Bailey-Matthews National Shell Museum – Our last visit to Sanibel coincided with a hurricane, which necessitated finding engaging indoor activities. The Shell Museum proved to be a wonderful place to spend a few hours, perfect for a rainy afternoon or simply to escape the sun’s intense rays for a bit. Sanibel is world-renowned for its exquisite shells, and after my initial trip here years ago, I became utterly obsessed with discovering every possible kind of shell. The museum deepens that appreciation, showcasing the incredible diversity of marine life.
• Sanibel Lighthouse – The historic Sanibel Lighthouse was located just a few scenic miles from our condo, making it an ideal destination for a memorable family bike ride. We spent time exploring the charming area around the lighthouse and even lingered by the fishing pier, where we were treated to an incredible sight: a pair of playful dolphins swimming and leaping just 30-40 feet off the coast! It was also a fantastic spot for shelling, and we regretted not bringing our bathing suits to cool off in the calm waters after our invigorating ride.
• J.N. “Ding” Darling National Wildlife Refuge – We drove through this magnificent refuge during our previous trip a few years back. This time around, I had envisioned us cycling through it, as I’d heard that low tide offers the best opportunities to spot the diverse wildlife. However, it ultimately proved to be a bit too extensive a ride for our little ones’ legs. This adventure remains something exciting to look forward to for a future trip, perhaps when the kids are a bit older.

The Unforgettable Sanibel Vibe

Sanibel Island is, without question, a nature lover’s paradise, which is precisely why I feel an overwhelming sense of contentment and joy every single time I visit. Once you’re on the island, it truly doesn’t take long to completely unplug, unwind, and fully immerse yourself in the wonderfully laid-back vibe that permeates every corner. We have only ever visited during the off-season, which we adore for its peaceful tranquility. However, I’ve heard that during peak season, the island truly comes alive, bustling with activity and, honestly, becoming quite crowded (I’m definitely more of an “off-season” gal myself!). Regardless of the season, the sunsets are consistently spectacular and often celebrated by onlookers gathering on the beaches. Mornings on the beach are utterly blissful, filled with the fresh scent of salty air, the gentle sounds of birds feeding, and the fascinating sight of live shells and crabs scurrying their way back to the water as the tide recedes. In my humble opinion, it’s undeniably the perfect place for a family to truly “veg out” – lots of good eating, refreshing swimming, rejuvenating sleeping, and plenty of time for reading. Oh, yes!

My crew:

I will miss this breathtaking view more than words can express. Until next time, Sanibel, we’ll be dreaming of your tranquil shores and delicious treats.