Weekend Getaways for Families

Believe it or not, we’ve planned bucket-list trips in exotic locations around the world for clients who have just a few days to spare for travel. That said, generally we encourage families to choose destinations with convenient airport connections or a few hours’ drive from home to maximize their family weekend getaway.

Lodging choice is key. For weekend trips in a big city, a well-located urban hotel that makes sightseeing a breeze is essential so families don’t waste precious time getting around. We know the best properties with walk-out access to all the fun activities like horseback riding and outdoor pools. For families seeking total relaxation and simple travel logistics, a full-service resort in a gorgeous setting means there’s no need to leave the property. Our favorite resorts cater to families in meaningful ways, like kids’ clubs and sports lessons. Or perhaps you’d prefer an amazing home or villa rental that allows your family to spend a few days reconnecting in a more private setting. We work with suppliers in top markets who vet all their accommodation rentals firsthand so our clients can be assured of quality.

Florida

There’s a reason Florida is a perennial favorite among family vacation destinations. Easy, affordable airline routes combine with beautiful beaches, kid-friendly resorts and endless activity options like theme parks and zoos. Our planners can get you off the beaten path and arrange some really unique experiences, like deep sea-fishing charters, art tours or swimming with manatees.

Quebec City

A taste of Europe just across the Canadian border, this charming city is perfect for a weekend getaway, as you can easily cover all the highlights in just a few days. Summer weather is delightful with cool breezes coming off the St. Lawrence River. And winter means fun festivals to keep everyone warm. Quebec City’s spectacular hotels have plenty to impress families as well.

Arizona

You’ll never have to worry about what to pack for a trip to Arizona: The desert ecosystem around Phoenix, where most families fly in, means you’re just about guaranteed sunny, warm weather for all the outdoor activities offered here, like legendary golf courses and scenic hiking trails. Our favorite resorts are incredibly luxurious with some of the best spas in the world. Or consider a few days exploring the Grand Canyon instead.

California

The question isn’t whether California works for a quick family getaway, it’s where to go. The variety of this beautiful state is boundless. Choose between the kid-friendly attractions of San Diego, a few days enjoying Disneyland, cultural immersion in San Francisco, laid-back fun in wine country or a national park like Yosemite … and that’s just for starters.

New York City

Is there any destination quite as exciting as the Big Apple? We can help with needs that range from booking the best seats at a Broadway show to ensuring you don’t waste time in line for popular attractions like the Top of the Rock. And our planning service really shines here, as we’ve identified New York City’s most kid-friendly accommodations and can snag your family special perks when you book your stay through us.

Caribbean

In the Caribbean, kids will love immersing themselves in the most spectacular of tropical paradises, even if they only have a few days to enjoy it. Weekend getaways are ideal for those islands where direct flights are plentiful, like Jamaica, Puerto Rico and the Dominican Republic. Once you arrive, the family fun is effortless.

Ski Trips

Winter can be a tricky time for travel, especially for families who have limited school breaks or prefer not to leave home at the holidays. Fortunately, a weekend is just enough time to hit the slopes and ski or snowboard at one of our favorite family-friendly North American ski resorts. And if you don’t ski, consider a weekend getaway in Colorado, Idaho, Utah, Montana or Western Canada in the summer, when the mountains morph into gorgeous outdoorsy playgrounds.

New England

Does your family seek big-city fun? Consider a weekend exploring Boston’s phenomenal history and vibrant neighborhoods. Or if you’d rather slow the pace a bit, go leaf peeping in the fall throughout Vermont and New Hampshire, or wander the picturesque beaches of Maine and Cape Cod. Don’t forget to sample the homemade ice cream! Regardless of what your perfect weekend looks like, New England is bound to have it.

Chicago

Spend a few days in Chicago, and you’ll join Frank Sinatra in singing the familiar tune that it’s “my kind of town,” too. Indulgent, kid-friendly dining options like deep-dish pizza and hot dogs with all the fixings; world-renowned museums; afternoons at the ballpark and more will make you long to book another weekend in the Windy City.

Mexico

Resorts with tons of amenities dominate Mexico’s beach scene, whether in Cabo San Lucas or the Yucatan Peninsula. These hot spots make ideal destinations for weekend relaxation. Or consider a cultural experience in Mexico City or San Miguel de Allende, where we can arrange walking tours that explore the interesting history and heritage.

Philadelphia

A trip to Philadelphia is a chance to walk in the footsteps of some of our nation’s most important historical figures, like Ben Franklin and Betsy Ross. Admire the sites your children have read about in history books, such as the Liberty Bell and Independence Hall, and then top off the weekend with a Philly cheesesteak showdown.

Bermuda

Only a 90-minute direct flight from East Coast airports, this island works incredibly well for a weekend getaway. Families with younger kids enjoy the relative safety of the calm waters in Bermuda’s harbors, while older children love the fantastic scuba diving opportunities and activities like golf, kayaking and spelunking.

With only a few days to play, families shouldn’t spend hours and hours poring over online hotel reviews or mapping out a sightseeing schedule — it’s just not a good return on investment. Let us do the heavy lifting and plan a fabulous weekend getaway that may be short on time, but full of incredible memories.