A GT TRAVEL STUDIO NEWSLETTER

Hey First name / friend,

 

Multi-generational family trips make up a large share of the inquiries that cross my desk. They're beefy and complex, with a lot of moving parts. 

 

I LOVE them. 

 

Finding thoughtful solutions for families who want to spend time together is one of the things that gets me excited to work each day. They often go like this: three generations want one warm week somewhere everyone can reach easily, with plenty to keep everyone happy.

 

That request calls for a villa, and sourcing villas is where I earn my keep. 

 

A privately owned, privately managed house is only as good as its owner and whoever they hired to run it, so I proceed with caution on those. 

 

But that's why I've loved watching hotels add villas and residences to their offering over the last several years. You get the square footage, the communal space, the full kitchen, and the private pool, plus a front desk, a housekeeping team, every resort amenity, and someone who answers the phone at 11pm.

 

Multi-gen trips tend to land on peak weeks like the festive season, Presidents' week, and spring break, because that's when everyone's calendars line up and for that reason, it can be pricey. 

 

Round Hill Hotel and Villas sits on a private peninsula west of Montego Bay, and it has been Jamaica's most storied address for decades. JFK and Jackie were guests, and Ralph Lauren owns a villa here and designed the hotel's interiors. The 27 villas are privately owned and run by the hotel, so each one carries its owner's art and personality.

 

What's included. A housekeeper, cook, breakfast cooked in the villa every morning, and a plethora of activities, including group wellness classes, water and racquet sports, and afternoon tea. Groceries and meals beyond breakfast come on top.

 

Getting there. About 25 minutes from Sangster International Airport in Montego Bay.

 

At peak. About $7,400 a night, or around $52,000 for the week for a 4-bd / family of eight.

 

Best for. Families who love a classy tradition, tennis, laid-back vibes, and deep rooted hospitality. Guys wear long pants to dinner, the team knows everyone by name, and the grandparents are ready to return as soon as they leave. Note: Teenagers may get bored here after three or four days, but littles will be happy as long as they're there.

 

Oil Nut Bay sits on a private peninsula at the eastern tip of Virgin Gorda, created with a deep ethos in innovation, sustainable architecture, and nature. It's a community of privately owned villas run by a resort team, with a marina, the Sundara overwater spa, a Beach Club with three pools, tennis and pickleball courts, and a Nature Center with an animal rescue barn. 

 

What's included. Daily breakfast, the golf cart, and full use of the resort, from the Beach Club pools to the Nut House kids' club and the Nature Center. Lunch, dinner, a private chef or butler, and grocery stocking.

 

Getting there. A private boat transfer from Tortola's Beef Island airport, or a helicopter to the resort's helipad.

 

At peak. $9,500 a night, or $67,000 for the week for a 4-bd / family of eight.

 

Best for. Families who want a to feel like they're at their second home a world away. The little ones split their days between the Nut House and the animal rescue barn, the teens take out the paddleboards and sailboats, and the parents book the overwater spa. Bonus is the resident doctor on site and private helipad for any emergencies (for those  that are nervous being far away from civilization but love the idea of being remote).

 

Jumby Bay is a 300-acre private island two miles off Antigua, run by the Oetker Collection, which also runs Eden Rock in St Barths. The island has no cars. Everyone gets around by bike and golf cart, and hawksbill turtles nest on the beaches. A four-bedroom villa comes with a private pool, a golf cart, and butler service.

 

What's included. Everything but the spa. That covers every meal at the resort restaurants, cocktails and house wine, a villa bar restocked daily, snorkel trips, non-motorized watersports, the sunset cocktail cruise, tennis, bikes, and turtle hatchling releases for the kids. The spa and motorized watersports are extra.

 

Getting there. A short drive from V.C. Bird International Airport to the resort's private dock, then a six-minute boat ride.

 

At peak. About $15,300 a night, or around $107,000 for the week for a 4-bd / family of eight.

 

Best for. Families with kids old enough to want to roam. The kids bike to the beach on their own, the grandparents settle into the Estate House for dinner, every meal and drink is already covered, and the parents get a week off from running everyone's schedule.

 

Every family I plan for arrives with its own mix of needs. There's the grandparent who needs the ground-floor bedroom, the parent up at 6am with the baby, the teenager hunting for a tennis partner, the youngest who released baby turtles and greeted by a baby turtle stuffy on their bed later that day, and the dad who only wants a book and a lounger by the pool.

 

Getting those details right is how a week in a villa becomes the week your family talks about for years.

 

Multi-generational family trips take the most lead time of anything I book. The right villa for a group, on the one week everyone can make it, books early. 

 

If your family has been talking about it, or you know it'll come up around the holiday table this year, let's move it out of the what-ifs and into a we're-on-it conversation.

 

I can't wait to plan this for you and your loved ones. 🖤

P.S. The Caribbean is one answer for a family week. If your family is open to a longer flight, or multi-legs, the options open up considerably. Inquire above to find your family's next gathering place.