The Gilded Horizon

If you are craving an escape that blends luxury, natural beauty, world class dining, and unforgettable coastal scenery, Los Cabos should be at the top of your 2026 travel list.

Thinking about planning a big family trip? Take a deep breath. Multi-generational travel brings some of life’s most meaningful moments, but it is rarely as simple as picking a destination and going. Families come to me every week feeling stressed, unsure where to begin, and worried about making a mistake that affects everyone else.

Multigenerational travel isn’t just “pick a destination and go.” It’s multiple origin cities, mismatched flights, strollers and wheelchairs, and mountains of luggage.

Let’s be honest. Traveling with kids is less “rest and recharge” and more “snacks and strategy.” But that doesn’t mean it can’t be wonderful, memorable, and dare I say—fun. You just need the right plan.

Whether you’re craving a leaf-peeping escape, a spa weekend, wine tasting without the crowds, or a family trip that won’t leave you exhausted, here are eight unexpected but worthwhile picks.

Maui isn’t just a destination—it’s an experience. And if you’re seeking an unforgettable luxury vacation in Hawaii, Wailea is where you’ll find sun-drenched beaches, five-star pampering, and experiences that linger long after the tan fades. These three resorts define the best of Maui’s premium hospitality and are absolute standouts for travelers who want service, style, and serenity.

Experience the magic of Porto through the eyes of young travelers. This breathtaking view of the Duoro River from a charming Porto balcony captures the essence of family adventure—where vibrant city life meets serene river views. Perfect for families seeking unforgettable moments in Portugal, Porto offers both relaxation and exploration in every corner.

San Juan, Puerto Rico, is a destination that effortlessly blends history, culture, and tropical beauty. Whether you’re planning a romantic escape, a fun-filled girls’ getaway, or an unforgettable family vacation, this vibrant city offers something for everyone.

If you’re already overwhelmed by the idea of summer planning, relax—I’ve got you covered with five destinations that are perfect for a 10-day (or less!) escape with children or without them. The best part? You won’t need a car to explore them. Whether you prefer land, river, or sea, these spots are easy to navigate, family-friendly, and packed with adventure.