Marc Bush

The Azores are one of those rare places that still feels undiscovered—a destination for travelers who value nature, authenticity, and a sense of quiet adventure. If you’re looking for something a little different—somewhere beautiful, active, and still largely under the radar—the Azores are well worth considering.

Jackson Hole is a wonderful year-round destination for families, offering outdoor adventure, wide-open spaces, and activities for all ages. In the summer, families can enjoy easy hikes, wildlife spotting, scenic gondola or tram rides, and time on the water, while winter brings excellent skiing, snowshoeing, sleigh rides, and other snow-based fun that works just as well for beginners as seasoned skiers. Grand Teton National Park is always close at hand—an awe-inspiring backdrop that’s surprisingly accessible, with guided tours and ranger programs that keep kids engaged. Both the town of Jackson and the slope-side village of Teton Village are welcoming and easy to navigate, with family-friendly hotels, restaurants, and shops that balance comfort, convenience, and classic Mountain West charm.

Guatemala is where some of the world’s finest beans are grown, and Antigua is a vibrant base from which to explore the culture, craft, and community behind every cup. The town is a charming colonial city set against a backdrop of volcanoes, and it's known for its cobblestone streets, colorful architecture, vibrant markets, and deep-rooted coffee culture and expertise. From here, immerse yourself in Guatemala’s coffee traditions and culture through hands-on experiences visiting coffee plantations, sampling local brews, and visiting vibrant cafés. It’s a journey and destination for casual coffee fans and aficionados.

Santa Ynez is one of California’s lesser-known gems. It’s a place where old-school cowboy grit meets new-school sophistication—home to ambitious winemakers, a thriving farm-to-table dining scene, and a generosity of spirit that always makes you feel welcome. The region offers all the charm, bounty, and beauty you’d expect from California wine country—without the pretense. It’s a place where the winemaker might pour your tasting, the chef might deliver your plate, and you’re welcomed like an old friend even on your first visit. If this sounds like your kind of escape—for a romantic weekend, a friends’ getaway, or a family trip—I’d love to help you plan a visit that blends the valley’s warmth, flavor, and charm into something unforgettable.

When it comes to family vacations, the Second City is second to none. Chicago has a wealth of parks, museums, restaurants, activities and hotels that will delight both children and adults. Below is a selection of my Chicago family picks. Be in touch for more recommendations or to plan a trip that everyone in your family will love!

Santa Fe is inseparable from its Native American heritage, which dates back thousands of years. The city sits at the heart of a region that has long been home to the Pueblo peoples, whose traditions, art, cuisine and spiritual sites continue to shape the area’s identity.

Within just a few hours of driving from Chicago, you can find yourself lounging on a quiet beach, exploring charming small towns or immersing yourself in outdoor adventures. This guide highlights three weekend driving getaways — each offering something unique. South Haven, Michigan, draws visitors with its Lake Michigan shoreline and charming downtown. Kohler, Wisconsin blends luxury, wellness and the outdoors in a sophisticated resort setting. And for those seeking a step back in time, Mackinac Island offers an unforgettable experience where horse-drawn carriages replace cars. For those not from Chicagoland, these destinations could be combined with a summer trip to the city to add on a couple of days and a different experience.