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The Best Tips for a Successful Multi-Generational Family Vacation

Expert traveler Sarika Chawla shares her top tips for traveling with the WHOLE family. 


"Um, yeah, he's just going through this phase right now."

CreditParental Guidance (movie)

Multi-generational travel is all the rage these days. Preferred Hotel Group, a collection of luxury hotels, estimates that more than 20.8 million household/travelers in the U.S. have taken a trip with parents, grandparents and grandchildren in the previous 12 months. So if you're considering rallying everyone together for a big family vacation, here are a few wise tips from travel expert/mom Sarika Chawla. Have any questions about planning a multi-generational vacation? Let us know! 

They say if you want to get to know someone, travel. That's where true characters emerge under the stresses of flight delays, cramped spaces, and endless debates about what to do that day. Now add in the emotional conflicts of being a parent, a spouse, a child, and a sibling at all once in an unfamiliar location. 

On the surface, multi-generational travel — in our case mom (me), dad and kid, plus grandparents and uncle—  is the ideal way for family to celebrate milestones and spend time together in neutral territory. But like any gathering, it requires strategy to make it work. After four family vacations in as many years, each one in a different destination, I've collected a handful of lessons learned on my multi-generational vacations.

Age: 6 Months; Setting: Cruise

You can't please everyone. My husband's blood pressure rises every time we get near an airport, and both he and my brother dislike humidity. My mother and I overlooked both of these things when we picked a Caribbean cruise on Celebrity Cruises. We booked the trip to start immediately after my son turned 6 months old, the minimum age on most cruises for babies to travel. 

For a multi-generational trip, cruises can be pretty great: There's space for everyone to do their own thing, roomy cabins are affordable as long as you control your a la carte spending, and it's easy to find quiet spots for breastfeeding. I was most charmed when the waiters created a menu of preferred baby foods and each night asked whether sir would enjoy the pureed apples, peas or carrots. (Although on our last night he “enjoyed” all three, resulting in a multi-colored diaper on the flight home.) 

The drawbacks: It's a long process to get from home to relaxing in your cabin, between flights, the embarkation process and mandatory muster drills. Shore excursions can be a challenge with small ones in tow and it's hard to anticipate your surroundings. On Grand Cayman, getting from the port meant hopping in a crowded, overheated van with zero space for a car seat to each an even more packed, blazing-hot beach. In Jamaica, our ship unexpectedly docked in a different port due to weather, meaning our excursion took six hours instead of the expected three. Although this time the baby was safely on the ship with my parents, I fretted most of the day and ended up hand-expressing breast milk in a bathroom stall. Also, during the trip I developed an irrational fear of him plummeting over the side of a ship that remains to this day. 

Age: 1 year; Setting: All-Inclusive Mexican Resort

We agreed on a location more convenient to Los Angeles, where I live, and have the non-baby-toting grandparents and uncle fly cross country. I also employed a new strategy: I put my mother and husband, both natural planners, in direct contact instead of being the go-between. Together, they researched all-inclusive resorts in Mexico, and ultimately landed on Villa del Palmar in Los Cabos. The harmony set a good tone before leaving.

There are many benefits of an all-inclusive resort for families. Food: not world-class, but in abundance. Pools and fire pits galore. Other kids to play with. Also, the alcohol. There's something oddly freeing about being able to drink unlimited Miami Vice cocktails (a joyous layering of pina colada and strawberry daiquiri) without your parents side-eyeing the bill. 

The drawbacks: After a couple of days of lounging, the all-inclusive experience can get repetitive, which then brings up the inevitable “So what are we doing today?” conversation. In Los Cabos, there are two main areas to explore outside of the resorts: high-energy Cabo San Lucas, where I gave up trying to navigate the stroller after an hour, leaving the men to drink tequila shots at Cabo Wabo; and charming Cabo de San Jose, where we easily strolled into art galleries and enjoyed margaritas in the sunshine, but got bored rather quickly. Also, the water on the shores of Los Cabos is treacherous; Although we were in what is touted as a“swimmable” beach, both my toddler and 71-year-old father were knocked down by waves, at which point we skidaddled back to the safety of the pools. 

Age: 2; Setting: Lake Las Vegas

By now we had everyone's preferences in check and sought something non-beachy and still full of family-friendly activities, and Las Vegas was a natural fit.

Booking multiple hotel rooms in a cavernous casino seemed counterintuitive, so we Googled vacation rentals, which brought us to Lake Las Vegas. If you haven't heard of it, this is a replica of an Italian village built around a man-made lake in Henderson. Star-studding openings of luxe resorts once promised a four-star desert retreat, which quickly gave way to financial disrepair. As a result, our vacation took place in a little faux village that belonged almost entirely to us. And it was glorious.

Our vast, three-bedroom condo inside the Aston Montelago Village Resort was dirt cheap, we ran around wide-open cobblestone streets, dined in our own kitchen or at the walkable pub, wine bar and Mexican restaurant, and paddleboated on the lake. Within driving distance were grocery stores for supplies, non-glitzy casinos for the grownups, and the Hoover Dam. The Las Vegas Strip is only 20 miles away where my then-2-year-old got a huge kick out of the “aminals” at Siegfried & Roy's Secret Garden and Dolphin Habitat.

The drawbacks: Lake Las Vegas is a ghost town of a fake village set on an artificial lake, which is a strange setting for a vacation. There's no sense of local life, a distinct lack of other families to socialize with, and no nearby pool or ocean. 

Age: 3; Setting: Mission Beach, California

At this point, we started to get a little ridiculous with making things convenient for the Los Angeles branch, but the East Coasters were craving sunshine. So an hour and a half drive later, we arrived in Mission Beach with a car-load of snacks and gear and entered our four-bedroom house on the water.

Mission Beach is an old-school California beach town on the border of Tijuana, attracting a low-key crowd. Life moves at a slower pace here, with not much more than a handful of surf shops and restaurants, and a sole pier where locals fish off the side. (That's all set to change soon with the coming addition of luxury resorts that will attract a different kind of crowd.) Walks to the ice cream shop became a daily event and the weekly farmers market was a pleasure to stroll around. Grocery stores and other amenities are within driving distance and San Diego and the zoo are less than 10 miles away.

The drawback: While staying within a two-hour drive from home was convenient with a child, it didn't satisfy my wanderlust. A short plane ride at least feel like you're “going” on vacation. Other than that, there was little to complain about and we may have hit upon our magic combination for our successful multi-generational family vacation: a rental house in an uncrowded beach with mild, breezy weather, low-pressure days with activities in walking distance, and a major city and amenities within easy reach.    

Parting thoughts: 

  • Only involve those who want to into the planning process. Some family members want to know what's happening in the big picture, while others want their voices heard in the day to day discussions. Don't forget to include the kids in those conversations.
  • Accept that there will be conflict: The first couple of days, everyone is excited to be together and busy exploring the new setting. By day three, the bickering sets in. 
  • Everyone falls into their old patterns. Sibling rivalry flares up, your parents will inevitably push your buttons. You'll also be on hyper-alert for any negative behavior from your spouse or child. If you see it coming, grab a cocktail and go look at the scenery.
  • There's some pressure to spend every moment together because it's all compressed into a short time and dangit, you paid for this opportunity. It's perfectly OK to go your separate ways and regroup later, choose a nap over a group activity, and plan a date night while the grandparents babysit. You are on vacation, after all. 

Have your own tips for multi-generational travel? Share them in comments below!

[PHOTOS: Parental Guidance; Celebrity Cruises; Villa del Palmar; Aston Montelago Village and Flickr]


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