As a strategic finance advisor, my days are often filled with data, reporting, and a focus on results. While I love the work I do, I’ve found that one of the best strategies for long-term success is knowing when to step back and recharge. For me, that means traveling.
About 99% of the time, I travel with my wife—and sometimes with the kids, depending on the location. Over the years, we’ve discovered a few spots that we return to for their unique ability to help us unwind, explore, and create lasting memories.
Each destination serves a different purpose in our travel rotation, from pure relaxation to cultural connection to urban excitement. Here are three of my absolute favorites.
Cancún, Mexico
When I think of a true getaway, I often use “Cancún” as a catch-all for the entire Riviera Maya region. This is our go-to for a classic tropical vacation: blue skies, beautiful pools, and pristine beaches (I don’t actually love going in the water, but I love having the option to).
What truly differentiates Cancun for me is the quality of service. It’s surprisingly, consistently excellent. The people working at the resorts are incredible and make the entire experience seamless.
For a Couples’ Getaway: We love UNICO 20°87° Hotel in Riviera Maya. It’s an adults-only, all-inclusive resort that’s a bit smaller than the mega-resorts, which makes for a more intimate and relaxing setting.
For a Family Trip: We’ve also taken the kids to Club Med Cancún. It was a fantastic resort, but it offered a learning experience: it was heavily geared towards French-speaking Europeans. While a wonderful place, it was a bit tough for our kids to connect and play with the other children. It’s a small detail that can make a big difference on a family vacation.
Related article: We stayed in Cabo San Lucas, Mexico for a family vacation. Click here to read the full story.
Montego Bay, Jamaica
While Mexico delivers on relaxation, Jamaica offers something completely different—a vibrant cultural experience that feels like coming home. As someone from the Caribbean, being around more Black and Caribbean people is a wonderful experience that adds a deeper layer to our travels.
Jamaica’s vibe is fantastic, and the food is a major highlight. You can’t go wrong with oxtail, curry goat, and rice and peas. My wife loves seafood, and she always enjoys the fresh crab and lobster.
The service style here differs from Mexico’s ultra-polished approach—I’d say it’s like a nice restaurant compared to Mexico’s “really, really nice restaurant” level of service. However, the upside is that English is widely spoken, making it easy to explore beyond the resort.
What sets Jamaica apart is how family-friendly and adventure-packed it is. We’ve gone zip-lining and ridden ATVs, and there are always opportunities for unique experiences like playing with dolphins. For our 10-year anniversary, my wife and I stayed at the Iberostar in Montego Bay, which was another incredible, adults-only experience.
New York City, USA
This last destination might sound completely different from the first two tropical paradises, but New York City serves an entirely different purpose in our travel repertoire. While some people are overwhelmed by the city’s intensity, I actually thrive on the energy—the hustle and bustle is part of the appeal.
The best time to visit, in my opinion, is fall or winter. The weather is cooler but not too cold, and the way the city transforms with all the lights is really special. Unlike our beach destinations where the focus is on slowing down, NYC is about ramping up and experiencing everything the city has to offer.
The appeal isn’t just about the food (though it’s amazing), but the endless activities. We love seeing Broadway shows—we’ve seen Memphis and Hamilton, and my in-laws even took the kids to see Frozen, which they still talk about. Wicked is next on my list.
My wife’s best advice for anyone visiting is to explore beyond the usual tourist spots in Manhattan. We love spending time in Brooklyn. It’s more manageable, and walking across the Brooklyn Bridge is an experience in itself. Seeing the city, the water, and the park on the other side turns a simple walk into a destination.
Conclusion
Finding the right destination is about matching the place to your needs and what you’re hoping to get out of your time away. For me, these three spots work together to cover every base, from pure relaxation to cultural connection to high-energy exploration.
- Cancún/Riviera Maya: For unparalleled service and a truly relaxing, all-inclusive beach experience. It’s my top choice for a stress-free couples’ getaway where the biggest decision is which pool to visit.
- Montego Bay, Jamaica: For a vibrant dose of culture, adventure, and amazing food. It’s perfect for family-friendly excursions and reconnecting with Caribbean roots while still enjoying resort amenities.
- New York City: For an injection of pure energy, world-class entertainment, and the unique thrill of urban exploration. There’s always something new to see, especially on Broadway.
Taking the time to explore and experience new things—whether that’s unwinding on a beach, exploring your heritage, or diving into city culture—is one of the most valuable investments you can make.