Top Picks for Mom and Son Vacations: Creating Lasting Memories

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Ever since my son was just a little guy navigating the big world of elementary school, we’ve embarked on what’s become our annual tradition – mom and son vacations. Picture this: just the two of us, hitting the open road, ready to dive into whatever adventure awaits, from the scream-worthy roller coasters of Orlando to the laid-back, leafy retreats in the heart of the Midwest.

But here’s the thing – not every destination hits the sweet spot for these special getaways. It’s got to have the right mix of fun, food, and comfy places to crash at the end of the day. Finding that perfect spot? That’s the challenge.

These trips are way more than just a break from our everyday lives; they’re our golden ticket to building a treasure chest of memories. It’s our time to bond, to laugh, to explore – and yes, to feast on some seriously good eats (thankfully, my son’s a foodie just like me).

So, after years of weekend getaways together, I’ve nailed down a list of places that really cater to the mom-and-son vacation vibe. Each spot we’ve chosen offers that perfect backdrop for creating those unforgettable stories and strengthening our bond.

From the thrill-a-minute parks of Orlando to the serene landscapes that define the Midwest, and every hidden gem in between, I’m excited to share these destinations with you. They’re the ones that have passed our test for fun, food, and coziness, making each trip a chapter in our ongoing adventure together. Get ready to discover places where you and your son can make your own set of memories, just like we have.

go karting in Pigeon Forge Tennessee

1. Pigeon Forge, Tennessee

Heading to Pigeon Forge, Tennessee, with my son has always been a blast. This place is like a magnet for fun, especially if you’re into go-karts, miniature golf, and heaps of outdoor adventures (as most teenage boys I know are!). And if your son likes to hike, it’s a fantastic location!

First up, go-karts. Pigeon Forge is packed with tracks, each one offering a different thrill level. My son and I like to challenge each other to see who could lap the other first, turning each race into a mini-competition. Let’s just say, it’s still up for debate who holds the title of ‘Go-Kart Champion.’ (I claim it’s me!)

Miniature golf is another hit in Pigeon Forge. With courses themed from pirate adventures to rustic gardens, it’s an easy and fun evening activity. As we are competitive by nature, we play to win and keep score every game – he does usually beat me at this one.

And then there’s The Island. This place is a terrific way to spend a few hours, with rides, shops, and places to eat. It’s a place we always visit on our trips to Pigeon Fore, hopping from one attraction to the next, and ending our day watching the fountain show, which, by the way, is pretty cool with all the lights and music.

🌟 Is your son really adventurous? Try this highly-rated zipline tour – I guarantee it’s an experience you’ll talk about for years!

Boy painting a Figment mural at Epcot.

2. Orlando, Florida

Orlando is like hitting the jackpot for mom and son trips. This city is the ultimate playground with its world-famous theme parks and endless sunshine. We never get tired of visiting and have enjoyed several long weekends there together.

The theme parks are obviously the big draw. From the magic of Disney World to the thrills of Universal Studios, there’s something for every kind of adventurer. My son and I have visited Disney World just the two of us numerous times and always have a blast eating delicious food in Epcot, riding the rides at the Magic Kingdom and Hollywood Studios, and checking out the animals at Animal Kingdom.

But Orlando isn’t just about the parks. We’ve discovered some gems off the beaten path too, like checking out Winter Park, finding new, local restaurants in Orlando and even just chilling at the pool.

🌟If you decide to go to Disney or Universal, I’ve always had good luck buying my tickets from Undercover Tourist, so check them out!

St. Louis Arch

3. St. Louis, Missouri

St. Louis is an underrated gem for mom and son getaways. It’s got this cool mix of history, sports, and outdoor fun that can make any trip memorable. Every time we visit has been a new adventure for us, packed with moments that still pop up in our dinner table conversations.

The City Museum is an absolute must. It’s not your typical museum; it’s more like a giant playground built out of reclaimed architectural and industrial objects. Climbing through airplane fuselages, sliding down enormous slides, and exploring caves together was as much a blast for me as it was for my son. It’s like being in a giant jungle gym, where even the moms can’t help but let their inner kid out.

Then there’s the Gateway Arch, which you just can’t skip. Riding to the top gives you this incredible view of the Mississippi River and the city, making it a perfect selfie spot for us. It’s also pretty cool to stand under it and feel just how massive it is.

Outdoor activities are plentiful in Forest Park, bigger than Central Park in NYC, believe it or not. You can rent a paddleboat, cruise around the Grand Basin, or just take a leisurely walk, soaking in the beauty of the park. And if you’re into science like we are, the St. Louis Science Center is another hit, with its planetarium and interactive exhibits.

🌟If you aren’t familiar with St. Louis, the first thing I’d suggest doing is this trolley tour – it’s a great way to get your bearings and learn a little bit about the city.

son and mom in front of the Bellagio fountains in Las Vegas

4. Las Vegas, Nevada

Las Vegas might not be the first place that comes to mind for a mom and son trip, but trust me, it’s full of surprises beyond the neon lights. The city has plenty of cool stuff to do that doesn’t involve setting foot in a casino, although it was nice letting him see some of the places we’ve talked about as we take a “grown-up” trip to Vegas every year.

First up, the adventure experiences are top-notch. We hit the High Roller Observation Wheel, and let me tell you, seeing Vegas from 550 feet in the air is something else. It’s a great way to kick off the trip, giving you a bird’s-eye view of everything you’ll want to explore on the ground.

And you can’t visit Vegas without catching at least one show. We opted for Michael Jackson One, and it was mind-blowing. The dancing, the music, the storytelling—all of it was on another level. It’s the kind of entertainment that keeps you talking long after the curtain falls.

Las Vegas also serves up some great outdoor adventures not too far from the city. You can take a day trip to Red Rock Canyon for some hiking. It is a welcome break from the buzz of the Strip and a chance to enjoy some quality time together in nature.

🌟 My favorite place to stay in Las Vegas with kids is Park MGM. The pools are fantastic and the entire building is non-smoking!

Chihuly glass at the Indianapolis Children's Museum

5. Indianapolis, Indiana

I’d be remiss if I didn’t include my family’s hometown of Indianapolis. It is a treasure trove of activities for moms and sons looking for a memorable getaway. This city combines the charm of small-town vibes with the excitement of a bustling metropolis, making it an ideal spot for families looking to explore and have fun together. And, you can’t beat the focus on sports – if your son is a sports fanatic we have a team for you to cheer on!

If your son is in about sixth grade or younger, a trip to Indy wouldn’t be complete without a visit to the Children’s Museum of Indianapolis, the largest children’s museum in the world. With exhibits ranging from dinosaur fossils in Dinosphere to interactive traveling exhibits, it’s a place where my son and I can easily spend the whole day. In fact, we were members for years and spent many happy Saturdays exploring and playing.

For sports-loving duos, the Indianapolis Motor Speedway Museum is a hit. Even if you’re not a racing fan, the history and the thrill of the Indy 500 are contagious. We took a tour of the track, and feeling the vastness of the Speedway was something we both won’t forget. It’s a unique experience that gives you a real sense of the racing world.

The city’s outdoor spaces are another highlight. Walking along the Canal and White River State Park, we found the perfect blend of relaxation and activities. Renting a pedal boat gave us a different perspective of the city and a bit of exercise, too. Plus, the park’s proximity to other attractions, like the Indianapolis Zoo, made it easy to hop from one adventure to the next.

🚂Indianapolis is super affordable, and a fun place to stay with kids is at the Crowne Plaza downtown – you can book an actual train car converted into a hotel room!

mom and son in Ybor City, Tampa

6. Tampa/Sarasota, Florida

After several years of soccer tournaments in the Lakewood Ranch area, we’ve discovered what a fantastic spot Tampa and Sarasota are for mom-son vacations. It’s a nice direct flight for us to fly into Tampa from Indy, and from there you can visit Sarasota, Siesta Key, and plenty of other fun places quite easily.

One of our most memorable experiences (we still talk about how fun it was) was taking a food tour in Ybor City, Tampa’s historic neighborhood known for its Cuban and Spanish roots. Wandering through the old streets, we savored everything from authentic Cuban sandwiches to decadent coffee con leche, learning about the area’s rich history along the way. It was a perfect experience for both of us – my son loved the food and I loved the history!

Siesta Key, a short drive from Sarasota, became our go-to beach destination. The powdery white sand and crystal-clear waters offered the perfect backdrop for our days in the sun. Building sandcastles, chasing waves, or just lounging around, Siesta Key provided us with those quintessential beach moments and has quickly become one of my favorite beaches in Florida.

And let’s not forget the seafood. Our trips to this area are never complete without indulging in the delicious seafood that the Gulf Coast is famous for. Whether it’s dining on fresh grouper sandwiches by the beach or enjoying a seafood feast at one of Sarasota’s fine eateries, we always search out the local restaurants.

🌴The first year we visited we stayed in Lakewood Ranch near the soccer fields, but last year we based our stay on Siesta Key at the fantastic Sarasota Beach & Racquet Club – it allowed us to enjoy Siesta Key and Sarasota equally!

Cincinnati Ball Park entrance

7. Cincinnati, Ohio

We’ve been heading to Cincinnati for weekend getaways for years thanks to soccer tournaments which we combine with all the fun and educational experiences the city offers. Plus, it’s close to Indy – we can get there in less than two hours. Our very first soccer weekend out of town many years ago was in Cincinnati and my son and I still talk about that weekend as it was also our first mom and son getaway.

One of the places we love to visit if the weather is nice is the Cincinnati Zoo & Botanical Garden, one of the oldest zoos in the United States. Another fun experience was a Cincinnati Reds/ Chicago Cubs baseball game – the Reds stadium is right downtown and it was my son’s first time to watch a full game. Plus, you can visit the Cincinnati Reds Hall of Fame & Museum too which is a treat for any baseball fan.

Finally, we love the great restaurants, shopping, and neighborhoods in the Cincinnati area. For the dozens of times we’ve visited, we’ve never run out of things to do and never been bored!

🌟Want a nice overview of Cincinnati? Check out this highly-rated top sites and food of Cincinnati tour!

Fun Illusions museum in Arizona. I'm "holding" my son off a balcony

8. Peoria, Arizona

Another location we found thanks to a soccer tournament is Peoria, Arizona. It’s a short drive from Phoenix and a fantastic place for a mom and son vacation as there are plenty of terrific “kid-approved” things to do! Although it might not be the first place that pops into your mind when you think of a mom and son trip, it’s a hidden gem waiting to be explored.

Our adventure in Peoria was filled with unexpected discoveries, starting with the Lake Pleasant Regional Park. This vast reservoir is a playground for water enthusiasts, offering everything from boating and fishing to kayaking. It was a little cold on our trip for kayaking, but I would absolutely try it on our next visit if it’s warmer.

One of the fun things we DID do was rent electric bikes and explore the trails around the city. It was so much fun and a wonderful activity for a teenage boy to do with his parents – let’s face it, by the teen years, it’s a bit harder to find experiences you both love doing together.

🌵If you visit Peoria, I highly recommend staying at the Cibola Resort. It is gorgeous and we both loved our accommodations!

Cloud Gate in Chicago (aka the "Bean")

9. Chicago, Illinois

One of my favorite mom and son vacations near me is Chicago, Illinois. With its towering skyscrapers and bustling streets, the city offers a dynamic setting for a mom and son weekend getaway that’s both educational and thrilling. Only three hours from Indy, it’s a place we enjoy regularly.

Our trips to the Windy City aren’t complete without a visit to one of the wonderful museums like the Museum of Science and Industry. This museum is a place where science comes alive through hands-on exhibits and captivating displays. From stepping inside a real submarine to experiencing a simulated tornado, it’s a day filled with awe-inspiring discoveries.

Another highlight is Millennium Park, where you can see the famous Cloud Gate sculpture, affectionately known as “The Bean.” Taking silly selfies reflected in its shiny, bean-shaped surface is fun and I love looking back on these pictures to see how my son has grown through the years.

And as foodies, we find Chicago’s food scene to be an adventure all its own. From deep-dish pizza to gourmet hot dogs, every meal is an opportunity to explore the city’s culinary delights. My son, ever the adventurous eater, is always all in on trying everything, making each dining experience a fun exploration of flavors.

🌟If this is your first visit to Chicago (or just want to experience the city in a new way), consider a Hop On Hop Off bus tour – you’ll get your bearings and it will help you decide what you want to do during your trip!

View of Pixar Pier in Disneyland at night

10. Disneyland/Anaheim, California

As a Disney fanatic, I have to add Disneyland to my list of fantastic places for a mother-son trip idea in the United States. Although we typically go to Disney World, if you are closer to Disneyland (or just want a change of pace), give it a try.

From the moment we set foot in the park, we were swept up in the magic, greeting beloved characters, and embarking on legendary rides. It was super fun to experience the difference between classics like Pirates of the Caribbean and Space Mountain, as well as try new rides like the ones we encountered in California Adventure.

Disneyland is also a really easy vacation for a mom-and-son trip. You can stay within walking distance of the park, and you never have to worry about what you’ll do together or where you’ll go. And in our family, we consider any Disney vacation “guaranteed fun.”

Anaheim is also home to Knotts Berry Farm if your son prefers roller coasters. I took my daughter there on a mother-daughter trip because she’s a roller coaster fan, but my son would have enjoyed it on one of our trips too (maybe the next one!).

🌟Get your Disneyland tickets before you go so you don’t have to waste time waiting in line. I purchased ours from Undercover Tourist and it was simple and quick!

Going up the magic carpet at Boyne Mountain Michigan

11. Boyne Mountain, Michigan


Boyne Mountain in Michigan is one of our go-to’s when we are looking for a mix of outdoor adventure and relaxation. During the winter months, Boyne Mountain transforms into a snowy paradise, perfect for hitting the slopes. Whether you’re a seasoned skier or a first-timer, the resort has trails for all levels. We started my son on skis when he was three, and we’ve had years of fun ski vacations ever since.

But we love Boyne Mountain in the summer too. As the snow melts and the landscape blooms, the resort offers a plethora of different activities. We’ve found ourselves exploring hiking trails, enjoying scenic chairlift rides, and even trying our hand at ziplining, which is an absolute blast. The chance to experience the natural beauty of Michigan from the treetops was unforgettable, offering both adrenaline-pumping fun and moments of awe at the panoramic views.

One of the things I love about Boyne Mountain is how accessible everything is. We usually stay at the lodge and with a range of activities and restaurants on-site (the first night is always the Trophy Room), sometimes we spend an entire weekend without leaving the resort!

🌟Find your perfect room at the Grand Mountain Lodge here!

playing soccer in Orlando on a vacation

Tips for Planning Your Mom-Son Trip

Planning a mom-and-son trip can be an exciting opportunity to bond and create unforgettable memories, but it also requires a bit of planning to ensure a smooth and enjoyable experience. Here are some general tips to help you plan a successful vacation:

Involvement is key

Start by involving your son in the planning process. This not only makes him feel valued and excited about the trip but also ensures that the activities you choose are interesting to both of you. Sit down together and discuss potential destinations, activities, and things you both want to see and do. I usually do a little research and then present him with some ideas and let him lead the way from there.

Packing the essentials

When it comes to packing, make a list of essentials together. Depending on your destination, this might include weather-appropriate clothing, comfortable shoes for exploring, sunscreen, hats, and any necessary gear for planned activities (like swimwear for the beach or warm layers for skiing). Don’t forget to pack any favorite snacks, games, or books to keep entertained during travel times. This is also a great opportunity to teach your son about planning and responsibility by having him pack his own bag with supervision.

Be flexible!

While having a plan is important, the beauty of a mom and son trip often lies in the spontaneous adventures that arise. Create an itinerary that includes your must-do activities but leaves room for unexpected discoveries. Maybe you’ll stumble upon a local festival, a hidden beach, or a recommended diner that wasn’t on your radar. These unplanned moments are often the highlights of our trips, so be open to deviating from the plan.

Balance activities

This is a good tip for ANY family travel, but I always try to strive for a balance between activities that are fun and those that are relaxing or educational. For instance, after a day at an amusement park, consider a quieter day exploring a natural park or visiting a museum. I’ve found my son is much more receptive to a museum or landmark if we’ve spent the day before doing something fun and active.

Document your journey

Finally, encourage your son to document the trip in his own way, whether through photos, a journal, or collecting souvenirs. This not only enhances the experience but also gives him something personal to look back on. And I love looking back at our years of trips and seeing how he’s grown.

On the skyliner in Disney World

FAQs: Vacations for Mom and Son

Why should I plan and mom and son vacation?

It’s a great way to strengthen the bond and create lasting memories.

How do I ensure my son wants to go on vacation with me?

Pick a location with fun things to do, and get him involved in the planning.

Where are some great places to go on a mom and son vacation?

Really any location with things you can do together is a great choice.

How old should my son be for a mom and son vacation?

Any age, although elementary school on up will make for easier travel.

son and mom wearing sunglasses

Conclusion: Mom and Son Vacations

I can’t help but feel a sense of gratitude for all the roads traveled and the memories made with my son. From our very first getaway, when he was just a tiny guy stepping wide-eyed into the grand world of elementary school adventures, to the more recent escapades that have seen us exploring every nook and cranny from Pigeon Forge to Peoria, each trip has been a wonderful experience and now memory.

Reflecting on these destinations, from the adrenaline-pumping theme parks of Orlando to the serene beaches of Siesta Key, it’s clear that the essence of these mom and son vacations isn’t just about the places we’ve been. It’s about the laughter shared over missed turns (or trying to find someplace when both our phones were dead!), the excitement of discovering new foods., and the in-depth conversations I don’t think we would have had at home.

These travels have taught us both so much more than just how to pack efficiently or navigate airport security. They’ve shown us the value of stepping out of our daily routines to embrace the joy of discovery, the importance of adapting when plans go awry, and the beauty of the world around us. More than anything, they’ve underscored the irreplaceable bond that forms when you share the road with someone you love.

So, as you contemplate your next mom and son getaway, remember that the perfect destination is any place where you can explore, laugh, and grow together. Whether it’s the bustling streets of Chicago, the historic charm of Cincinnati, or the magical realms of Disneyland, there are so many fantastic choices out there.

And remember, the journey is as much about the moments of connection as it is about the destinations themselves. So pack your bags, set off on that road less traveled, and discover the endless adventures that await you and your son. My final bit of advice. Take that trip – you won’t regret it!

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Memorable mom and son vacation ideas