Multi-Generational Travel: How to Plan a Trip That Works for Your Whole Family

Multi-generational travel has its perks—like plenty of sitters and cousins for your kids to play with—but will it drive you nuts? Travel experts help you land on a vacation that suits everyone.
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Vacation Rental

Good for Long Weekends and Smaller Budgets

Why It Works: “You can easily go somewhere within driving distance for three nights, so your time and financial commitment isn’t that big,” says Eileen Ogintz, founder of TakingTheKids.com. That’s what Nate Whitson, of Olivet, Michigan, does every winter when his wife, four kids, her parents and siblings and their families (about 20 people in all) share an eight- to ten-bedroom house instead of exchanging Christmas presents. “We cook meals, play games, sit around and do nothing, and end the time together with skits or karaoke or show-and-tell.” 

Money Matters: A three-bedroom rental averages $213 per night while four- and five-bedroom homes are around $300, according to HomeAway, one of the largest rental sites. Figure on $100 per night for your portion of the lodging and another $100 a day for your cost of food and activities. “It’s best for all families to pay their share up front and designate a person to make reservations and shop for groceries,” says Ogintz.

Great Deals: If you plan to stay a week or more, ask for a lower nightly rate or to have the cleaning fee waived. Even on large vacation-home sites, such as Airbnb, owners may be willing to negotiate the price. Also take a look at Tripping.com, which is like a Kayak for vacation rentals, pulling home prices from all the popular rental sites. And we brokered a deal for you with Vacasa, a vacation rental management company with more than 5,000 properties from coast-to-coast: Book a rental through September 30 at vacasa.com/deals/ParentsMag and get 10 percent off the rate before taxes and fees. 

Trip Ideas That Are Trending:

  1. Gulf Shores and Orange Beach, Alabama. More than 80 percent of the lodging is rental condos or beach houses— and, because of the volume, you’re likely to get a good deal. Bring your bikes to ride on the trail that connects the two towns.
  2. Destin, Florida. On the Gulf of Mexico, this beach town is nicknamed “the world’s luckiest fishing village.” Let Grandpa teach the kids how to reel ’em in. Later, take a wildlife-watching cruise; the waters are teeming with dolphins, stingrays, and loggerhead sea turtles. Get your cameras ready! 
  3. Greater Palm Springs, California. It’s filled with unique activities for everyone, like taking the aerial tramway up Mount San Jacinto, exploring the air museum, or going on an easy bike tour (all downhill through the San Andreas Fault).

All-Inclusive Resort 

Good for Active Families

Why It Works: Tennis, biking, and golf are usually on-site and the kids’ programs typically cover toddlers to teens, says Gabe Saglie, a senior editor at Travelzoo, which offers all-inclusive deals. “You just need to decide what type of resort you’d like—one on a beach with a lot of water sports, a mountain resort, or even a dude ranch,” suggests Saglie. Lynn Ferry-Nelson, of Longview, Texas, travels with her aunt and uncle and their kids and grandkids to an all-inclusive Caribbean resort every summer. “We break up into little pockets throughout the day—some golf, some go on tours, some do water sports, some just hang at the beach—but everybody’s happy,” says Ferry-Nelson, who has an 8-year-old daughter. “We all talk about our day at each night’s mandatory family dinner.”

Money Matters: Discuss each family’s max budget for the trip so you can choose a resort that will work for everyone. “If you know some family members won’t participate in water sports or upscale dining, look for one that offers these options à la carte rather than as part of the base price,” says Ogintz. (Note: If ten or more of you are flying from the same airport, check with the airline about a group rate.) But once you’re there, money won’t be an issue. “No one will be worried about ordering wine and who is going to pay for it,” says Ferry-Nelson.

Great Deals: Among the popular all-inclusive destinations, the Dominican Republic and Mexico tend to be the least expensive places to visit. Rates are lowest in the summer, but consider trip insurance in case of a hurricane. “We’ve been to seven resorts, and Dreams Los Cabos Suites Golf Resort & Spa is my favorite because the rooms tend to be updated and large for the price,” says Ferry-Nelson.

Trip Ideas That Are Trending:

  1. Generations Riviera Maya in Mexico. With its “Grandparents Stay Free” promo during 2017, you get a free one-bedroom suite when you book a two-bedroom suite.
  2. Beaches Turks & Caicos. The resort offers villas that sleep 12 and can arrange private beach barbecues, bonfires, and snorkel trips for your clan. 
  3. Woodloch Pines. This charming resort in Pennsylvania’s Pocono Mountains has dozens of activities daily, from beanbag bingo to bumper cars. 

Cruising 

Good for Families With Different Interests

Why It Works: Your group only has to agree on three things—the destination, date, and cruise line. “Once you’re on board the ship, family members can be as active or as relaxed as they wish, stay together, or go off independently,” says Claudia M. Laroye, founding editor of The Travelling Mom blog. Plus, your parents or in-laws can easily get one-on-one time with their grandkids without a logistics hassle. Amy Heimbach, of Centreville, Virginia, appreciated that her dad took her daughters, ages 8 and 11, to The British Invasion show on a Princess Cruise to Alaska while she, her husband, and her mom went to the comedy club. On a recent Disney cruise, Lisa Bourke’s mother-in-law slipped away with her older daughter for a movie while the rest of the gang was at the pool. “My in-laws also put the kids, ages 3 and 6, to bed one night while my husband and I had dinner in the ship’s adults-only restaurant,” says Bourke, of Hartford, Connecticut. “We were right there if anything went wrong, but it felt like we were a world away.”

Money Matters: Since most of the cost is paid in advance, no one has to deal with the awkwardness of who’s picking up the check for every meal or activity. Plus, segments of your group can choose the category of stateroom that best fits their budget and still be near each other. 

Great Deals: “Most of the major cruise lines typically have a big sale in January to March, so book at that point if you already know your summer 2018 dates,” suggests Colleen McDaniel, senior executive editor of CruiseCritic.com. To find a good deal sooner, check out Cruisecompete.com, which offers comparisons from multiple travel agencies and posts a list of weekly cruise specials on its home page. Travelzoo also posts cruise deals for sailing in the U.S., Caribbean, and Europe.

Trip Ideas That Are Trending:

  1. MSC Cruises. Kids age 12 and under always sail free on this European-owned line, which departs from Miami to the Caribbean. The MSC Seaside, with new Lego programming for kids, debuts in December. 
  2. Adventures by Disney, Rhine River Cruise. Designed for different generations traveling together, these 2018 weeklong cruises will stop in Switzerland, France, Germany, and the Netherlands, highlighting where the live-action version of Beauty and the Beast was filmed. 
  3. Princess Cruises. With new Camp Discovery programs on the fleet for toddlers to teens, this line is a fantastic way to see Alaska. You can depart from Los Angeles, San Francisco, or Seattle, and most trips stop at Glacier Bay National Park. 
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