Ashley Whipple

There’s something special about building a weekend around a baseball game, especially when you’re traveling with friends and a crew of baseball-loving kids. Our Toronto Blue Jays getaway blended big-league energy with an incredibly walkable, family-friendly city. With a centrally located hotel, a lively day game and iconic attractions all within reach, Toronto proved to be an easy and rewarding destination for families. If you’re looking for a sports-centered weekend that offers far more than just nine innings, this one delivers.

Costa Rica had long been on our family’s list, and this stay at Andaz Peninsula Papagayo struck the perfect balance between tropical relaxation and meaningful adventure. With five nights on property, we were able to fully experience the resort’s thoughtful design, exceptional service, and family-friendly programming while still weaving in a taste of Costa Rica’s wild beauty. What makes this property special is its flexibility since it works beautifully for multi-generational families, couples, or groups who want equal parts downtime and activity without constantly changing hotels. It’s polished without feeling pretentious and immersive without feeling remote.

Nashville surprised us in the best way! Visiting friends who live locally gave our family a chance to experience the city beyond the usual tourist checklist, with a mix of classic Nashville sights and easy, everyday fun that worked well for our kids. It’s definitely a city that is easy to do with a loose itinerary. From wandering charming small towns just outside the city to sampling casual restaurants and coffee stops, this trip felt relaxed, approachable, and full of personality. It’s a destination we’d happily return to, especially in a different season, to explore even more.

My family spent a full week in Prague over the New Year holiday, using the city as our anchor while exploring some of Czechia’s most picturesque towns. Prague makes an incredible home base for a winter family trip due to its fairy-tale architecture, walkable Old Town, and lively Christmas markets. The city feels festive without being overwhelming, and once you add in easy day trips to Český Krumlov and Karlovy Vary, you have the perfect blend of culture, charm, and holiday magic. This itinerary is designed for families who want to soak up the Christmas atmosphere at a comfortable pace, with time to wander markets, warm up indoors, and enjoy the season together.

Cuyahoga Valley National Park was the fifth national park my family visited, and it turned out to be the perfect fall weekend escape. With its mix of boardwalks, waterfalls, wildlife, and easy trails, this park is incredibly accessible for families with young children. Whether you’re local to the Midwest or flying into Cleveland for a quick getaway, CVNP offers just the right amount of adventure without overwhelming little legs. In this guide, I’m sharing a full weekend itinerary that mirrors how we structured our own trip in October. It’s paced intentionally for families with slow mornings, realistic driving times, plenty of sensory-friendly nature experiences, and enough “wow” moments to get everyone excited for your next national park adventure.

Located on the shores of North Lake Tahoe in Incline Village, the Hyatt Regency Lake Tahoe Resort, Spa and Casino combines rustic alpine charm with modern resort amenities. It’s one of the area’s most well-known properties and although it is undergoing an extensive renovation to its beach area, I would not hesitate to recommend a visit to this property. My family spent a week at this property over the summer and we are already planning our trip back! For families planning a Lake Tahoe getaway, it’s worth understanding what’s available now and what exciting changes are on the horizon.

In my family, we started the tradition of celebrating our boys’ 10th birthdays with a special trip—just for them. For my oldest son, there was no question where he wanted to go: New York City, with a Yankees game at the heart of the adventure. It was his very first visit to NYC, so we set out to do all the quintessential “first-time” experiences, from the Empire State Building to strolling Central Park. What made it even more memorable was pairing the game with a Yankees Stadium tour, giving him a whole day of baseball magic before cheering on his team. Between iconic sights, unforgettable birthday moments, and a few sweet treats, this trip was the perfect blend of a milestone celebration and a classic New York adventure.

Scotland’s blend of history, dramatic landscapes, and welcoming towns makes it a wonderful family destination. For us, this was the second part of a larger Ireland and Scotland adventure, but it also works beautifully as a standalone trip. Families can follow this five-day loop through Edinburgh, St. Andrews, Aberdeen, and Inverness before returning to the capital, or expand it into a longer Scotland-focused itinerary. From castle ruins and legendary lochs to seaside villages, each stop brings something new—all at a pace that works with kids in tow. Trust me, our boys were 1 and 3 on this trip, so I get it! We found the Scottish Highlands to be pure magic and can’t wait to plan a return trip now that our boys are older.

Ireland is a country filled with history, natural beauty, and warm hospitality—and it makes for an unforgettable family trip. From ancient castles and dramatic cliffs to kayaking on quiet lakes, each day brings something new for parents and kids alike. My extended family and I took this trip when my boys were 1 and 3 years old, so this eight-day itinerary balances sightseeing, outdoor adventures, and cultural experiences. Following this itinerary will allow your family to explore Ireland at a comfortable pace.

Lake Tahoe is often known as a premier ski destination, but it shines just as bright in summer. Our family spent a week enjoying all that the lake and surrounding Sierra Nevada mountains have to offer: sparkling water adventures, kid-friendly hikes, and charming towns filled with history and good food. With its mix of relaxation and adventure, Tahoe makes the perfect family-friendly summer getaway.

This summer, my family embarked on a road trip through Northern California and Oregon to explore three of the West Coast’s most stunning national parks. Each stop brought something completely new—steaming geothermal features, ancient redwoods towering overhead, and the sapphire-blue depths of Crater Lake. Traveling with kids, we found the balance of shorter hikes, scenic drives, and playful downtime made the adventure not only doable but truly unforgettable. Whether you’re traveling with kids or just looking for a mix of outdoor beauty and family-friendly activities, this route is packed with variety and wonder.

This Utah road trip was my family’s introduction to the US National Parks out west. Once we experienced just how varied and amazing our landscape is in the United States, we were hooked and have now been to seven more parks! However, few places offer the wild magic and cinematic landscapes of Utah’s “Mighty Five”. For families looking to strike the perfect balance between adventure and ease, this thoughtfully paced 9-day itinerary stitches together the best of Utah’s treasures—from the red rock cathedrals of Zion to the whimsical hoodoos of Bryce Canyon and the gravity-defying arches of Moab, all capped with culture and comfort in Salt Lake City. Here’s how to turn Utah’s untamed beauty into the family road trip of a lifetime.

When I think of the trip that had my family feeling the most in tune with rugged, untouched nature and exciting wildlife encounters, there is only one place that comes to mind: the greater Yellowstone ecosystem. From steaming geysers and vast glacial lakes to wildlife encounters and starlit serenity, this eight-day journey through Bozeman, Yellowstone, and the Tetons is the ultimate family escape—crafted for curious young minds and parents who crave both discovery and downtime. If you want the perfect blend of gorgeous vistas, plentiful wildlife, geothermal activity, and exciting hikes, then look no further than Yellowstone and Grand Teton National Parks.

If you’re looking for family-friendly destinations without all the crowds that normally plague European capital cities, then look no further than Zagreb and Ljubljana. Don’t get me wrong, there’s a reason London, Paris, and Rome are perennial favorites for travelers around the world. However, my husband and I were searching for somewhere more under the radar, and Zagreb and Ljubljana delivered. We had such a pleasant experience while traveling throughout Croatia, Slovenia, and Italy with our then two- and four-year-old boys. I encourage you to think outside the box and consider Zagreb and Ljubljana for your next family trip!

After years of talking about visiting the Christmas markets in Europe, my family finally decided to make this trip a reality. We were a large family group of 15 people spanning the ages of six months all the way to 60 years, so we needed to prioritize budget and ease of travel. While we researched all the popular and more well-known markets in Germany, France, and beyond, we were on the hunt for a more budget-friendly and under-the-radar destination. We kept coming back to Poland and finally decided it was the perfect place for us. We had an amazing time exploring this often-overlooked country and we can’t wait to head back in other seasons to explore all that Poland has to offer.

When I was planning a beach trip for my large family group of 15 people, it was proving hard to please everyone — that’s where a cruise comes in! Cruising to sunny islands on the Freedom of the Seas means a ship full of endless activities with a bunch of different ports thrown in. This is the perfect solution when you have a large group of people traveling together. We didn’t have to worry about anyone being bored or not being able to find some way to entertain themselves. So if you have been thinking about a cruise for your family, read on and see how it can be the perfect solution for you too!

Colorado is a beautiful state that offers something for everyone in the family during all four seasons. My family loved our summer road trip through four different cities and I highly recommend adding Rocky Mountain National Park to your list of “must-see” places in the US. If you love outdoor activities, hiking, horseback riding, white-water rafting and adventure, this is the perfect itinerary for you!

An idyllic town nestled almost 9,600 feet high in the Rocky Mountains, Breckenridge boasts a long list of outdoor activities for every season. My family fell in love with Breck during our summer road trip through the Rockies but weren’t sure we’d ever go back in the winter since none of us ski. When presented with the opportunity to stay with some friends in Breckenridge over the winter break, we jumped at the chance to see what one of our favorite mountain towns could offer us as non-skiers. Spoiler alert: we were not disappointed!

A family trip to the Netherlands and Belgium will exceed all your expectations. From the array of colorful tulips to the multitude of museums to a chocolate-making class — there is something for everyone. You will be impressed by the rich cultural offerings, walkability of the cities and the diverse food offerings available throughout both countries. The activities we found to entertain our two young boys are experiences they still talk about today! Whether you're traveling with children like we were or as a solo, couple or group travelers, this eight-day itinerary is fully customizable to your unique tastes and needs.