Tis the season to celebrate. The pandemic put a pall on the holidays last year. Many families had to settle for virtual gatherings via Zoom. It’s not surprising then, that now the desire to reconnect is feverish. Some are deciding that simply seeing each other is not enough and are ready to go next level with a family trip that includes kids, grandkids, parents and grandparents.

What better way to catch up in person than a getaway? No doubt the best gift is spending time with loved ones, especially if it’s in a locale that you all will love. It’s the warm and fuzzy stuff of a Hallmark holiday movie.
But that’s not to say the magical experience will happen without effort. Putting together a multi-generational trip takes work. Here’s what to keep in mind when planning.

What’s the goal?
Assess what everyone wants. “Is it to relax? Reconnect? Spend quality time? Travel has the ability to create impactful experiences that transform you but it’s important to understand what people need in order for those outcomes to occur,” says Sahara Rose De Vore, travel coach and the founder of The Travel Coach Network.
Set goals. What do the children, the parents, the grandparents want to do? “Try to build in everyone’s top priority,” says Cassie Shih, founder of the group travel site Tripsha.com.

Where to go?
Much depends on the size of the group, their finances, health concerns and their common interests. “Some families prefer a cruise or all-inclusive because it means less coordination and plenty of activities for everyone. Other families like the option of exploring various cities, national parks, cultural or heritage trails, rent a villa in Tuscany, take a safari in Africa, rent a house near a lake, or rent multiple RVs and explore the U.S. The options are endless,” says Elaine Lee, editor of “Go Girl: The Black Woman’s Book of Travel and Adventure.”
Ashley Nelson, founder of Tenth on Hudson, a luxury travel and lifestyle consultancy, says to come up with three or four destinations and narrow it down based on which one has the most activities (or votes) that work for everyone. “Make sure everyone has given feedback and feels their ideas were heard.”

The nitty gritty
This trip will be all about details. Discuss as a group how you want to handle logistics. Do you want to hire a travel advisor to take on the heavy lifting, or do you want to form a small committee of family members to manage the trip? When planning, a few things are key. “Consider budget, pace, and special needs of family members. Be flexible,” says Phyllis Stoller, president of The Women’s Travel Group.

Mistakes to avoid
You want this to be a memory that everyone cherishes instead of the trip from hell. Be mindful of missteps.
Acknowledge and accept differences. Everyone has different internal clocks, from young children energetic at 6 a.m., to night owl teenagers, to elderly parents who want to turn in at 9 p.m., keep this in mind when scheduling activities and consider that young kids may need nap time. Flexibility counts. Don’t over plan. Remember too, you aren’t joined at the hip. It’s okay to spend some time alone.
Now that you’re ready to move forward, a few destinations for a little inspiration.

Azul Beach Resort Negril, Jamaica
For the family craving sea, sand and sun, this is your spot. Situated on Negril’s legendary Seven Mile beach, Azul Beach Resort Negril is sure to get two thumbs up from the entire family. You can’t go wrong with this five-star all-inclusive resort, with Ocean View Family suites that can accommodate two adults, two children and a teenager, separate living room, balcony or terrace, and is convenient to the family pool and Azulitos Kids Club. Or go for a Family Loft Suite that can accommodate two adults and six children or three other adults. There’s a teen and kids’ club for when they want to do their own thing and an array of watersports to experience together. Parents and grandparents can wile away the day at the four pools, at the Vassa Spa, taking cooking, hat-making, or basket-weaving classes, playing beach cricket and basketball. Or go into town and hit hot spots like Rick’s Café to watch the cliff jumpers dive into the sea and enjoy cocktails and the DJ who will have grandma and grandpa dancing to booming dancehall reggae. Come mealtime, the family can gather at one of the six restaurants from Ackee, which serves up Caribbean cuisine to international fare at Mahogany.

Lisbon, Portugal
The Martinhal brand is all about families. It was founded by entrepreneur and developer Chitra Stern, a mother of four who saw a gap in the market when traveling with her children. Her goal was to create stress-free vacations for families. The Martinhal Chiado is luxury in the center of Lisbon. You and your family can stay in the boutique hotel that has studios and apartments with two spacious bedrooms (can accommodate two adults and four children) with a kitchen and living room. The kids’ club starts at 6 months to early teens, and even nighttime coverage is available. You all can enjoy Lisbon, be it sites like the Castelo de São Jorge, the botanical gardens, Oceanário or the Belem Tower. If you have time, you might want to take a short flight to Madeira, which is known for its over-the-top holiday festivities all of December ending with a big bang on New Year’s Eve with one of the largest fireworks displays in the world.

Beech Mountain Resort, North Carolina
For the family seeking a white Christmas, Beech Mountain is a good bet as it typically gets 80-plus inches of snow a year. Those mountain vistas set the stage for fantastic scenery, at more than 5,500 feet, and are the highest town in Eastern America. You know your family will have fun with skiing, snowboarding, tubing, snowshoeing, hiking (all levels) and ice skating. There are day camps for 3–14-year-olds and a Ski & Ride School. When the family is happily tired. A cup of cocoa and a fire await your return. Take your pick of accommodations, condos, chalets, private homes. The Beech Mountain Vacation Rentals/Pinnacle Inn has suites, as well as one and two-bedroom condos with full kitchens, living rooms and fireplace. Beech Mountain Chalet Rentals has small studios to 7-bedroom houses. No worries about the fussy eaters in the family, you’ll find a variety of restaurants, from barbecue, pizza, Mexican and more. If you’re not in the mood for cocoa at the end of the day, consider Beech Mountain Brewing Co. for a cold one.

Hotel Punta Islita, Guanacaste, Costa Rica
Is your family feeling adventurous? Guanacaste awaits you. There are national parks like Camaronal Wildlife Refuge and Monteverde Cloud Forest where you’re likely to spot jaguar, ocelot, monkeys, iguanas and more. You won’t be far from nature if you stay at Hotel Punta Islita. It’s in the rainforest on a hillside with forest and ocean coastline views. Choose among 2–3-bedroom villas and suites. As for what to do to keep your crew happy, there’s plenty for everybody, be it twilight ziplining, surf lessons, art classes, sea turtle watching, horseback riding and nature walks. Dine at the two sustainable restaurants and relax at the spa. Get into the holiday spirit with the hotel’s give-back activities that include beach cleaning and fruit harvesting on a farm built and funded by the hotel to create jobs for the community.

Terranea Resort, Rancho Palos Verdes, California
Okay, so you and the family can’t do the Amalfi coast, this is a bit of a teaser of what you can expect when you get there. Perched above coastal bluffs with to-die-for views of the Pacific Ocean, the Mediterranean-inspired Terranea sets the stage for good times. The 100+-acre estate is home to spacious casitas, with kitchens and living rooms, villas, with private outdoor hot tubs, and The Bungalows, a collection of guest accommodations featuring spa and wellness-focused amenities. You won’t have to settle come mealtime, with eight dining options, the whole family is bound to find a few favorites. The golfers in your group will be glad to tee off on the award-winning course. Others can splash in one of four pools. The kids have their club. Take advantage of a private lesson in the art of falconry, nature hikes, tide pooling, paddle boarding and kayaking. Anticipate seeing dolphins, sea lions and whales. The award-winning spa here is something special, 50,000 square-feet of indoor and outdoor oceanfront relaxation areas and views of the Pacific Ocean and the Palos Verdes coastline spectacular. From Thanksgiving to New Year’s Day there are holiday activity kits, and other seasonal specialties to add to the merriment.

Big Sky, Montana
With a name like Big Sky you know this is the choice for your family if you and your crew love the outdoors. Winter here is horse-drawn sleigh rides, dog sledding, ice skating, snowshoeing or snowmobiles to ramble through the white wilderness. Skiers will think they’ve died and gone to heaven with the abundance of trails. Big Sky is the third largest ski resort in North America and has the most consistent powder in the Rockies. For sure seeing Yellowstone National Park is a must. No worries you don’t have to drive, take a snow-coach or snow-mobile tour. For views of three states, two national parks, and wildlife, take a ride on Big Sky Resort’s tram to the top of Lone Peak, the highest scenic overlook in Montana. As for where to stay, take your pick of condos, cabins and homes. This place is for foodies too. You’ll get everything from a gourmet hotdog stand, sushi, street tacos, barbecue, to a slope-side dinner in a yurt, accessed by snowcat. Better still, for mom and dad or grandma and grandpa looking for a romantic evening, take a horse-drawn sleigh for a ride to an oil-lantern lit cabin for dinner.

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