ROOM KEY

U​​​nhurried time together is the ultimate luxury—so much so that it’s reshaping how families are choosing to travel. Enter Classic Vacations’ Luxury Family Collection, a curated portfolio of elevated, family-friendly stays—where generous space, intuitive service, and dynamic settings come together to create memorable, meaningful journeys. Here are three standout U.S. properties that set the scene.

SAN DIEGO, CALIFORNIA

The Stay: This boutique resort-within-a-resort sits in a gated, exclusive area on Coronado Island, just across the bay from San Diego. Spacious beach cottages and villas are designed as one, two, or three-bedrooms, along with full kitchens, living areas (each with a cozy fireplace), and a patio or balcony.

The Play: A personal family concierge helps plan activities, dining, and logistics, going above and beyond to make the entire experience effortless—delivering groceries or even a surfboard to your villa upon request. The pool is just steps from the beach, while the nearby boardwalk takes you almost all the way around the island—a perfect family stroll or bike ride.

Family Fun Fact: In the early 1900s, L. Frank Baum wrote several Wizard of Oz books from his winter home on Coronado Island—and is said to have modeled the Emerald City after the historic Hotel del Coronado. Today, the Coronado Public Library showcases a permanent Oz-based collection of art, books, and collectibles.

MAUI, HAWAI’I

The Stay: Set along Polo Beach—considered one of Maui’s more relaxed, family-friendly stretches of sand—the Fairmont Kea Lani stands out as the island’s only all-suite and villa luxury resort. Accommodations start at a generous 860 square feet, each with a separate living area, large lanai, and a kitchenette for added ease. For larger families or those seeking more privacy, expansive two- and three-bedroom villas create a residential-style retreat.

The Play: The resort features three pools to suit every pace: a family pool with a 140-foot waterslide connecting its upper and lower levels, a dedicated keiki (kids) pool for younger swimmers, and a separate adults-only pool for quieter downtime. Activities blend fun and culture, from lei making and ukulele lessons to hula and traditional outrigger canoe experiences. At the center of it all is Hale Kukuna, an open-air cultural hub dedicated to Hawaiian storytelling, art, and heritage.

Family Fun Fact: When designing the Fairmont Kea Lani, architect Jose Luis Ezquerra drew inspiration from Hawaiian architectural influences and the plumeria flower. In fact, Kea Lani translates to “heavenly white” in Hawaiian.

BIG SKY, MONTANA

The Stay: Just 45 minutes from Yellowstone National Park, Montage Big Sky brings together outdoor adventure, luxurious amenities, and family ease. Guestrooms, suites, and residences are designed with a warm, residential feel with fireplaces, heated floors, and large windows that look out to the surrounding Spanish Peaks. With ski-in/ski-out access to Big Sky Resort, rivers with world-class fly-fishing, a private 18-hole golf course, and the 10,000-square-foot Spa Montage, this is a place designed for four-season bliss.

The Play: A heated outdoor pool and hot tubs offer a year-round gathering spot, while Beartooth Pub & Rec is a playful restaurant with four bowling lanes, arcade games, and wood-fired pizzas. In warmer months, families can hike, ride horses, go fly fishing, river rafting, or take a day trip to Yellowstone National Park. In the evenings, a resident “marshmallowgist” hosts s’mores sessions around the fire pit.

Family Fun Fact: The concierge team is happy to create a custom in-room camping experience just for kids, turning the suite into a mini campsite with a tent, camping gear, toys, books, and a plush keepsake for each child. It’s all arranged before arrival, so the experience is waiting upon entry.