Unexpected family summer getaways that became instant favorites — and why they’re special

One family vacation spot from our summer that surprised everyone with its immediate appeal is Madeira, Portugal. We had expected Madeira to be nice, but were not aware how perfectly suited it would be for a great day on shore with our kids.

It was the mix of activities that allowed each member of our family to choose what they wanted to do without overloading them. That day we rode the tramway over the city of Funchal and then walked through the colors of the marketplace, sampled local pastry and also wandered along the waterfront before returning to the ship. Families will appreciate this type of flexibility because many destinations are so big, or require so much travel and/or advance planning; if your kids tire easily while traveling, Madeira provided enough activity, culture, food and scenery to keep everyone happy, all within a short distance from where we docked.

My biggest surprise was how much my children enjoyed their visit to the Island. The children really liked seeing the steep cliff faces, all the flowers and feeling like they were in a new country that was still easy to experience with their family. This experience reminds me that some of the most memorable family vacations occur when there is at least a little bit of space left in your plans to allow the destination to surprise you.

Isabela Island wasn’t even our first choice, but it turned out perfect. We snorkeled with sea turtles that brushed against us and watched marine iguanas stroll down the sandy road outside our little beach hotel. My son just stood there, mouth open. For a family that loves animals but needs some quiet, it was exactly the right mix of wild and calm.

Spent a long weekend last summer riding the back roads around Newbury Park with the family following in a truck—stumbled onto Figueroa Mountain in Santa Barbara County. Zero cell service, a dirt road that winds through oak groves and wildflowers, and a view that honestly stopped everyone mid-conversation.

What made it hit different was the shared discomfort. The road got rough, the truck had a close call on a switchback, and everyone had to problem-solve together. That’s the same thing I see happen with riders in our training—when you put people in a low-stakes challenging environment, real connection happens fast.

My law enforcement background taught me that people reveal who they are under mild pressure. Family trips that include some friction—wrong turns, unexpected terrain, improvised meals—build more trust than any resort weekend ever will.

If you’re near Southern California, Figueroa Mountain Road off Highway 154 is criminally underrated. Take something capable, bring enough food, and leave the itinerary loose.

Vis is a Croatian Island in the middle of the Adriatic Sea, and is actually one of my favorite islands. It is good for people who want to explore a quieter and more authentic place. I also appreciate how slower the pace of life is and how it’s kind of away from the big crowds. My family and I often hang out in fishing villages and take a dip in the waters. The island has this traditional character to it that gives it uniqueness and at the same time privacy.

One thing I really love about this place is how we can easily explore history and nature. There is less noise and we can focus more on relaxing and enjoying its natural beauty. In fact, one of the activities we love to do as a family is exploring hidden spots. We used to go to hidden beaches that not many people knew about – we enjoyed both the water and the privacy. While we were there, we got the chance to encounter many locals. We had long meals – eating seafood with them. Overall, I think it was a beautiful experience having to watch the sunset and there were no tourist crowds around us.

Now that I work in luxury travel, I often see people having the most memorable experiences. Usually, the ones which are more memorable are the ones which are not known yet to people. I think it’s all about choosing a unique path that could lead you to the right place where you can have all of these experiences with the local life.

If you want to spend a good time with your family, then you need to choose a less popular destination. An example of that would be Vis. It has been our top choice since it offers true relaxation and connection with nature.

This summer I took my family to a tiny lighthouse lodge in the Chilean fjords. We got there by Zodiac, then watched storms roll in from a warm kitchen. It felt adventurous but safe. Being cut off like that, we just played games for hours and talked. Honestly, those remote spots are the ones you remember most. Don’t skip them.

This past summer, the unexpected favorite was Tainan, in southern Taiwan. We’d planned to spend most of our trip in Taipei, but a friend insisted we head south for a few days. So we did — my wife, our one-year-old son, and far too much luggage for someone so small.

Tainan surprised us. It’s older, slower, and quieter than Taipei, full of temples tucked between noodle shops and night markets that come alive after dark. One evening, we wandered into a tiny family-run spot for danzai noodles. The owner, a grandmother in her seventies, took one look at our son and forgot about us entirely. She didn’t speak English. My Mandarin is functional at best. But she pulled up a chair, bounced him on her knee, and spent twenty minutes teaching him sounds and clapping every time he babbled back. We barely ordered. We didn’t need to.

After two decades living across Asia and Europe, I’ve learned that the richest parts of travel almost never come from the itinerary. They come from these small, unscripted exchanges — the ones that only happen when you can meet people in their own language, even imperfectly. Our son won’t remember that night, but my wife and I always will.

Here’s what struck me afterward: connection rarely waits for you to be fluent or prepared. It shows up in the gaps, when you’re willing to be a little awkward and a lot open. The places that become instant favorites aren’t the ones with the best views. They’re the ones where a stranger decides to treat you like family — and you let them.

We walked into a bookbinder’s workshop in Basel’s old town, and it became the most talked-about stop of our entire summer.

Nobody planned it. We were walking through a narrow street and I noticed a ground-floor workshop with the window open. Inside, someone was hand-stitching a leather binding. I knocked. She waved us in.

Nobody in our group had seen anything like it. Not the bookbinding specifically, but watching someone genuinely skilled at something work without performing for an audience. No tour script. No guide translating everything into digestible chunks. Just actual work happening in real time, and everyone asking questions because they actually wanted to know the answers. She spent thirty minutes showing us how to fold and stitch a single page. We left with small handmade notebooks and a story we’ve retold more than once since.

Speaking of that, most families walk past a hundred interesting things every summer because stopping feels like losing time. But that hour in a backstreet workshop nobody had on their itinerary is the one we still talk about. Planned attractions deliver a managed version of an experience. Walking through an open door put us somewhere with none of that structure, and that absence of preparation was exactly what made it work.

We ended up taking the kids out to this little lake in East Texas that a friend mentioned. I’d never been there before, and honestly, it wasn’t on our radar. No big attractions, no water parks with slides. Just a quiet spot with a pier, some kayaks you could rent, and a tiny pavilion area.

What got me was watching my kids actually put their phones down. They were catching tadpoles, building sandcastles, asking a million questions about the fish. My youngest, who’s usually glued to a screen, spent three hours just exploring the shoreline. That doesn’t happen very often in our house.

The special part came when we rented those kayaks. My oldest took the lead, and we paddled out to this little cove where the water was perfectly still. We just floated there for a bit, no agenda, no rushing to the next thing. As someone who runs a company where every day is about making sure events run on time and everyone’s happy, that kind of stillness hits different.

It reminded me why I started this business in the first place. I want families to have moments like that. Not crazy expensive experiences, just real ones where people disconnect and actually enjoy each other.

We’re already planning to go back next summer.

The most unexpected “place” we discovered this summer wasn’t a destination at all, it was our own backyard right here in San Benito, transformed into something magical for the kids in our care.

Working at Sunny Glen Children’s Home, I get to witness moments that travel brochures could never capture. This summer, what became an instant favorite was a simple evening tradition we started under the big trees on our campus grounds. We pulled out blankets, strung up lights, and turned an ordinary patch of grass into a gathering spot where kids could just be kids, roasting marshmallows, telling stories, laughing without a worry in the world.

What made it special had nothing to do with the location and everything to do with belonging. For children who’ve experienced abuse, neglect, or being forgotten, the most powerful place you can offer them is one where they feel safe and seen. That backyard became a place where trust got rebuilt one conversation at a time, where a child who arrived guarded finally let their guard down.

We’ve been doing this work since 1936, serving the Rio Grande Valley, and if there’s one thing 90 years has taught us, it’s this: kids don’t remember how far you traveled or how much you spent. They remember who showed up and made them feel like they mattered.

So my honest take? The most unforgettable summer spots aren’t the ones with admission tickets. They’re the ones where someone made you feel at home. Whether you’re a parent, a big family, or just someone with a backyard and an evening to give, you already have access to the best destination there is.

This summer reminded us why we do what we do, because every child deserves a place that feels like home, even if that place is right where you already are.

One unexpected place I took my family this summer that became an instant favorite was a small local airport observation area. It was not a big attraction, and that was part of the charm. We were looking for something simple to do in the evening that did not involve a screen, a long drive, or a crowded event, and someone mentioned that you could park near the fence and watch small planes take off and land.

I did not expect much from it. I thought we might stay for 20 minutes, let the kids see a plane or two, and then head home. Instead, it turned into one of those surprisingly peaceful family outings that everyone wanted to repeat.

What made it special was the mix of excitement and calm. Every time a plane started moving, the kids stopped whatever they were doing and watched closely. They asked where it was going, how pilots learn, why some planes sounded different, and whether the people inside could see us waving. Between takeoffs, we sat on a blanket, ate snacks, and watched the sky change as the sun went down.

It felt different from a planned family activity because there was no pressure to make it amazing. We were not waiting in a line, keeping track of tickets, buying overpriced food, or trying to fit everything into a schedule. The entertainment was simple, real, and just unpredictable enough to keep everyone interested.

The best part was that it gave the kids room to wonder. A small plane lifting off can turn into a conversation about travel, weather, maps, engineering, or dreams about where they want to go someday. It reminded me that children do not always need a huge experience to be fully engaged. Sometimes they just need a front-row seat to something ordinary that still feels a little magical.

By the time we left, everyone was already asking when we could go back. That is usually my sign that something worked. It was inexpensive, low-stress, easy to repeat, and memorable in a way I did not see coming. For us, that little airport viewing spot became a summer favorite because it gave the whole family a shared sense of curiosity without requiring much more than time, snacks, and a clear evening sky.

We ended up spending an afternoon at this tiny roadside fruit farm about an hour outside the city, mostly because traffic was terrible and we needed somewhere to stop. It wasn’t a planned family outing at all. There was no polished experience waiting for us — just a small stand, a few picnic tables, animals wandering around, and a handwritten sign advertising homemade peach ice cream.

The funny part is my kids still talk about it more than the expensive trips we actually budgeted for. I think it’s because nobody had expectations. We weren’t trying to maximize the day or turn it into content. Everyone was sweaty, slightly annoyed from being in the car too long, and then suddenly we were sitting under these huge trees eating fruit that had probably been picked that morning.

As a founder, I spend a lot of time optimizing things. Vacations can accidentally start feeling the same way — overplanned, overresearched, scheduled within an inch of their life. That stop reminded me that families usually remember how a place felt, not whether it was impressive. The places that become instant favorites are often the ones that catch everyone off guard a little.

We took our family, which always includes my dog Auggie, to an unexpected hidden gem this summer: a converted old growth forest park in the Pacific Northwest. Normally, when you think of a dog park, you picture a flat, dusty field with a chain-link fence. This spot was completely different. It’s a fully fenced, towering canopy of pines with winding bark-dust trails, natural log obstacles, and fresh running spring water for the dogs. It felt like a true wilderness hike, but with the safety of a secure off-leash area.

It became an instant favorite because it solved the ultimate tradeoff we often talk about with dog owners: adventure versus safety. As the team behind Doggie Park Near Me, a directory of over 6,300 dog parks across all 50 states, we’ve seen every layout imaginable. We research these spots extensively to build trust through clear communication about amenities like fencing and water access. Finding a spot that combined rugged nature with secure double-gated entry and designated areas for different sized dogs was a revelation. It proved that dog parks don’t have to look like concrete pens to be safe.

Auggie spent hours navigating the natural terrain while we enjoyed the shade. We loved it so much we immediately added its unique features to our database so other families could experience the same magic. That trip reminded us why we prioritize verifying these specific amenities. Dog owners want more than just a patch of grass; they want an experience where their pets can be dogs safely. If you want to surprise your family, look beyond the standard municipal square and seek out these wooded, natural play areas. They turn a simple afternoon walk into a memorable summer adventure.

Our spur-of-the-moment discovery of Mineral Wells Fossil Park treasure hunt has become our favorite family activity. We didn’t expect to stay long but spent nearly four hours hiking through piles of loose shale looking for microscopic marine fossils. Each kid discovered 20+ treasures to bring home AND spent hours outdoors with no electronics or activities being “scheduled” for them. It also didn’t feel like we were at a tourist attraction whatsoever because the grounds are so rugged and “free-range.” All four of us were filthy, tired, and comparing fossils in the parking lot before departing.

The children loved that they could roam freely. Since there really aren’t designated paths telling you where to hunt, they could choose their own digging spots and learn patience while digging through rock after rock with no success. Once they unearthed that first teeny fossil after searching for 15 minutes, they felt such a sense of pride that I don’t think many expensive ‘attractions’ can beat. For less money than we would have spent eating dinner at home, we walked away with cherished memories bonded to physical treasures the kids excavated on their own. That piece of ownership is what transformed our whim-in-the-moment trip to one they talked about for months.

As a former NCAA football player and trainer balancing a busy business, our family vacations have to match our high-energy lifestyle. We took an unexpected road trip from Orlando up to Pisgah National Forest in North Carolina.

We ended up tackling the steep, grueling trail up to Looking Glass Rock, which pushed our conditioning and was the perfect challenge for our active husky. The rugged elevation and crisp mountain air were a phenomenal contrast to our usual Florida training environment.

What made it an instant favorite was watching my teenage daughters power through the physical grind without a single complaint about cell service. If you want to genuinely connect with your family, swap passive sightseeing for a shared, high-effort physical adventure.

Our original plan was for us to go to Lake Michigan for the 4th of July, but every halfway decent rental close to Lansing was either already booked or way out of our price range. On Thursday evening, before our trip, my wife found Indiana Dunes National Park and just like that, we were on our way Friday morning en route to I-94. Having driven past the signs for the park hundreds of times, I feel somewhat silly that I never stopped to visit the park.

I did not have high expectations going into it if I have to be honest. I imagined there was just going to be some sand dunes and a beach. That was it. What we ended up discovering was that there were 15 miles of Lake Michigan shoreline, sand dunes reaching heights of over 200 feet and trails through forests, wetlands and open beach, all within a day. My kids spent three hours climbing Mount Baldy (one of the largest dunes in the park) and at no time did anyone want to leave or get bored.

Aside from the trails & the water, what really made this place special to me was how non-touristy it was. There were no expensive boardwalks, no long lines for photos, and no overall impression that the park was just going to take your money. It felt like a hidden gem for many Midwestern families and I liked the way that made the experience feel like a find as opposed to just another summer activity.

Monhegan Island in Maine was the last place I expected my whole family to fall in love with this summer. My partner found it in her search for something other than the typical Cape Cod vacation and I was skeptical. An island with no cars, only 60 year-round residents and a one-hour ferry from Port Clyde didn’t sound like something everyone would enjoy. But I was totally wrong.

There was nothing to do except be present and that’s because Monhegan genuinely offers no alternative. The island has only one general store, two restaurants and dirt paths instead of roads. Cell service is very limited after the ferry has departed. When your children can’t pull up YouTube and you can’t check work emails, everyone does the same thing: be wherever you are. My children who normally use up a beach day in two hours, spent an entire afternoon on the Cliff Trail, which hugs the eastern side of the island with nothing between you and a 160-foot plunge to the Atlantic. We dined that evening at the Monhegan House, and saw the lobster boats unloading at the dock and were at our inn before 8pm. Nobody complained once.

This past summer, my family and I stumbled upon an unexpected treasure during our travels: a designated Dark Sky Park nestled deep within a remote desert landscape. We had initially planned a quick stopover, thinking it would be merely a scenic point of interest, but it quickly became an instant favorite. Far removed from the incessant hum and bright lights of urban life, the sheer clarity of the night sky was absolutely breathtaking. My children, usually captivated by their digital devices, were utterly mesmerized by the vibrant tapestry of the Milky Way stretching across the heavens. We spent hours identifying constellations, sharing ancient myths, and simply absorbing the vastness above us. It was a profoundly humbling experience, fostering a deep sense of wonder and connection, not just to the universe, but more importantly, to one another. This trip powerfully reminded me that the most enriching and cherished family experiences often emerge from stepping outside our routine, embracing the simplicity, and finding grandeur in unexpected places. These unique, shared moments are invaluable for truly strengthening our family bonds.

One unexpected favorite this summer? A raw, undeveloped acreage tract right here in South Texas, Starr County, specifically. I know that sounds funny coming from someone in land development, but hear me out. We loaded up the family on a Saturday, drove out past Falfurrias, and just walked a piece of land we had listed. No playground, no pool, no admission ticket. Just open Texas sky.

What made it special was watching my kids react to space they’d never had in town. They chased grasshoppers, found a hawk’s nest, and asked a hundred questions about what you could build out there. My youngest decided she wanted a barn. My son wanted a fishing pond. Suddenly we weren’t looking at dirt, we were sketching out a future.

That’s actually the same thing I see when families tour lots with us. People walk onto a piece of land and start dreaming out loud. It’s the most honest moment in this whole business. There’s no sales pitch that beats a kid pointing at a spot saying “my room goes here.”

So my unexpected favorite wasn’t a theme park or a beach. It was a quiet patch of acreage that turned into an afternoon of imagining. It cost us nothing but gas and time, and it gave my family more conversation than any resort would have.

My advice to anyone reading this: the best summer memories aren’t always the ones you pay top dollar for. Sometimes you just need open ground and the people you love standing on it.

We run roofing crews across Southern Oklahoma and North Texas, so our summers are usually consumed by storm season. This past summer though, we carved out a long weekend and drove the family out to the Wichita Mountains Wildlife Refuge near Lawton, Oklahoma — completely on a whim, just an hour and a half from our home base in Ardmore.

What made it hit different was how genuinely wild it felt. Bison walking alongside the road, granite boulders the kids could actually climb, and almost no cell service — which meant everyone was actually present for once.

The unexpected part was how much it reframed my own headspace. I spend my days reading roofs in Carter County and Collin County, watching what wind and hail do to structures over time. Being out there in that landscape, seeing the actual weather systems that roll across this region, made me appreciate why we take Oklahoma storms as seriously as we do — but also why it’s worth living here.

If you’re anywhere in Southern Oklahoma and haven’t been, go. It’s underrated in a way that won’t last forever.

I took my family to the middle of France, the Puy-de-Dome department in Auvergne, and it became our instant favourite because it is quite empty, not many tourists and not even many French people. It has a beautiful nature, old volcanoes, enjoyable spas, excellent cheese and of course wine from closer regions. It was also quite cheap and perfect for a trip for hiking, enjoying the nature and visit farms for cute animals.

We also tried Velorail (rail bike) on an old train route which crosses Viaduc des Fades. Construction finished in 1909. It is over 92 m in height and it is one of the tallest bridge piers ever built in traditional masonry. It was spectacular to see it. Lastly, Clermont-Ferrand was a cute city near old Volcano. While this area might not be the most popular one like Burgundy, Normandy or Paris, it is really worth to visit. It takes 3-4 hours from Paris to drive.

One unexpected place that became an instant family favorite was a local botanical garden with a small outdoor sculpture trail. It was not a big-ticket summer destination, which is exactly why it worked so well. There was room to wander, no rigid schedule, and enough variety to keep everyone engaged without that overstimulated feeling you sometimes get at more commercial attractions.

What made it special was how easy it was for different age groups to enjoy it in their own way. Kids could treat it like a scavenger hunt, adults could slow down and actually talk, and the setting naturally encouraged curiosity. A simple walk turned into spotting unusual plants, taking photos near the art pieces, and finding shaded corners where nobody felt rushed. Those are often the outings families remember most because they leave space for small surprises.

As a founder, I spend a lot of time thinking about experiences that reduce friction and create genuine engagement, and family outings are not that different. The best ones are often not the most expensive or most hyped. They are the places with just enough structure to feel interesting, but enough freedom for everyone to make the day their own.

I have noticed that “unexpected favorites” usually share three traits: they are easy to navigate, they give kids something to discover, and they let adults relax instead of managing logistics every minute. In that sense, a botanical garden or similar low-pressure local destination can outperform bigger summer plans because the memory comes from how the family felt there, not just where they went.

This summer I took my family geocaching, and it quickly became an instant favorite. Geocaching is an app-guided treasure hunt where you locate small caches that contain a logbook and trinkets. My children loved the hunt so much that weekend outings took us to parts of our city we had lived near for years but never explored. Even our youngest kept a notebook of finds, and everyone joined in, and the outings were low cost and left the kids happily tired by bedtime.

One surprising place that our family discovered this summer and fell in love with is an almost unknown place called Tongue River Reservoir in Dayton. We always saw the turn-off road many times and thought it was just one more dusty boat ramp, but finally we decided to stop there out of curiosity. The thing that made it unique is the perfect combination of all factors: warm shallow water where kids could play in, huge rock cliffs for kids’ climbing, and no one else around. We rented a cheap pontoon boat, caught our family first fish together, and saw amazing sunset above the Bighorn Mountains. They better expect us to always frequent it!

Meersburg on Germany’s Lake Constance is my dark horse pick to become a top family destination soon. When families are looking for serene summer getaways, I think places like Meersburg will shine. You can walk from Meersburg’s medieval town, along the lake, catch a ferry, and visit some beaches all within a leisurely 2 kilometer radius. Visit the castle in the morning, take a 20 minute ferry for lunch, and end the day with a relaxing lakeside stroll. Just enough to break up your day without packing too much in.

Overall, I think the best family destinations have 3 elements: minimal dead space between attractions, engaging variety, and yes, dead space. Kids will remember feeding bread to ducks by the lake, sprinting up and down ancient staircases, and arguing over gelato flavors to get after a ferry ride long after they remember stopping at 10 places in one afternoon. Meersburg hits all the marks because there isn’t a ton to do, which leaves you with lots of down time to relax and wander at your leisure. The time in between becomes the memory.