Jennifer Klingner

Boston holds a profound place in my heart because it brought the very history I taught for years to vibrant life. After spending so much time teaching 5th-grade Social Studies and the Birth of a Nation, walking those historic cobblestone streets felt like stepping directly into the pages of a textbook, evoking a powerful sense of resilience and discovery. Every neighborhood tells a story of overcoming monumental obstacles, beautifully connecting the strength our country was built upon with the personal milestones of my own journey. Getting to share this with the most important women in my life made Boston a place where we shared unforgettable memories, great stories, and many, many laughs.

If you’ve ever dreamed of stepping into a city where cobblestone streets, live oaks, and centuries of history meet coastal beauty, Charleston, South Carolina delivers it all—and then some.

I recently spent six incredible days exploring this Lowcountry gem while staying at the Francis Marion Hotel, and it was the perfect balance of history, romance, and coastal charm. Here’s how it all unfolded—and how you can recreate the magic for your own Charleston escape.

Las Vegas has this magical way of letting you be whoever you want to be for a few days—adventurous, indulgent, carefree, or completely relaxed. I love Vegas because it’s a place where luxury meets fun. One day I can be sipping cocktails at a serene adults-only pool, and the next I’m zip-lining above the neon glow of Fremont Street or getting lost in the Bellagio Conservatory’s seasonal displays. Having been to Vegas many times, I love that each trip is unique. Each time we go, we are doing new things. It is rare to find a destination with that level of variety.

Playa del Carmen was the perfect blend of relaxation and adventure for our family trip with two teenagers. We stayed at Generations Riviera Maya, and the first thing that stole my heart was our swim-out suite. Each morning, I’d step out onto the patio, coffee in hand, sink into a lounge chair, and watch the early light dance across the pool. Those moments alone made the trip worth it.

Lahaina, Maui, is a place where adventure, relaxation, and island culture come together beautifully.

Hilton Head is more than just a place for the beach and golf. We “accidentally” stumbled upon Beaufort, which was a hidden gem. The town’s role in early efforts toward racial equality after the Civil War was a powerful and moving experience.

Puerto Vallarta, on Mexico’s Pacific coast, perfectly blends culture, nature, adventure, and relaxation. It’s a safe, vibrant city full of things to do, whether you’re after adventure, authentic cuisine, or stunning beaches. Organizing a 9-day trip for six adults and four teens from four households with different interests was no easy feat. With multiple flights, various transportation modes, and a variety of preferences, we found just one activity that appealed to everyone besides dining!

Celebrating a 16th birthday in New York City was a memorable experience filled with Broadway shows, sightseeing, and a comfortable stay at the Paramount Hotel. The staff was incredibly kind and accommodating when I called ahead about the service dog accompanying my clients. As a pet-friendly property, they provided helpful information about nearby pet relief areas and even included water bowls in the room. Their thoughtful service made the entire stay smooth and enjoyable for both the guests and the service animal.

Hollywood Studios was the top park for my teens. They loved the vibe, the rides, and the themes. Thankfully, we had Park Hopper passes. This helped as we ended up at the park for six out of the eight days we were traveling.

The Columbia River Gorge offers an array of experiences to suit every taste. From outdoor adventures to leisurely wine tasting in picturesque vineyards, and geological history that dates back centuries, the gorge caters to a diverse range of interests. With its breathtaking natural beauty serving as a backdrop, visitors can indulge in activities such as hiking, windsurfing and kayaking, immersing themselves in the stunning landscape. Additionally, opportunities for pampering and relaxation abound, with spas and wellness retreats providing the perfect escape from the hustle and bustle of everyday life.