Coordinating a group vacation is rarely straightforward. Fixing the date is just the first hurdle; balancing competing preferences, navigating room hierarchies, and all manner of other demands add extra layers of complexity. To aid the process, Mark Ellwood taps into his most trusted travel experts to assemble thoughtful options for all types of group celebrations. Here’s what they recommend.
The wild family reunion
WHERE: Botswana, South Africa or Kenya
WHO: The entire family, aged eight months to 80
WHAT: The Big Five, cocktails, and connection
Why safari? Because it’s the ideal activity for an age-spanning group with a range of abilities and mobilities, as it can be calibrated and customized for every guest. Christopher Wilmot-Sitwell, owner of Cazenove & Loyd, recommends Botswana if you’re with under-fives, and consider the wet — or green — season, as the bush is alive with lush plants, heady smells and lots of babies, born when food is at its most plentiful (yes, it’ll be rainy, with torrential but typically brief showers).
The flooded Makgadikgadi salt pans will be alive with a flamboyance of pinktinged flamingos, and you’ll be able to take slower, near-silent safaris on canoes or mokoros, which offer an up-close perspective on the bush’s plants, insects and fishes. If the kids are older, stick with countries such as South Africa and Kenya, where the private reserves allow guests more flexibility beyond simply staying in the Jeep.
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“Teenagers need a variety of activities, like stalking a rhino with a Maasai tracker or horseback riding,” says Uncharted’s Sandy Cunningham. “It’s all about engagement, waking them up early and keeping them up late.” White lies about WiFi access being restricted to the main lodge often mean they won’t even try to log on with their devices anywhere else. She suggests Campi ya Kanzi or Ol Donyo in Kenya as ideal bases — both in the south of the country, with the plus that the former’s in a Maasai-owned sanctuary.
Cunningham and Wilmot-Sitwell agree that Cape Town is the ‘can’t fail’ starting point if you’re keen for the group to go beyond simple safari, staying perhaps at an exclusive-use property like Camissa House or Samara Karoo Reserve in the Eastern Cape. The winelands or urban adventures such as Table Mountain are easy add-ons. Wilmot-Sitwell often sends clients on a conservation-focused walk near Simon’s Town from Miller’s Point to the Cape Point section of Table Mountain National Park for what he says are “untamed beaches, fynbos-covered hills and spectacular ocean views” paired with a helicopter to whisk you off to Stellenberg Gardens, a private estate where the head gardener leads a tour before lunch amid the greenery.
Cunningham’s pick is beach time — Santorini Mozambique in Vilanculos is an easy flight from Cape Town. Horseback ride on the beach and snorkel in the reefs, but be sure to advise your travel advisor about phobias, says Wilmot-Sitwell. “We had a client who was scared of wild animals.” Might have been useful to know ahead of time…
Cookson Adventure’s Nick Davies says there’s so much to do in the bush. For a multi-gen group in Kenya, where the paterfamilias had grown up, they arranged for locals from his village to visit the safari lodge with area mementos. “He was able to go through photos with some of the people he knew as a kid and bring the destination to life for his family.” Davies suggests that the family gathering is a great time for an evening of reminiscing, with a twist. He offers a family dinner theater, with actors bringing family history to life for the guests with a loose script based on advance interviews with key figures from the group.
In Kenya, he’ll usually send clients to Nabiyotum Crater and Lake Turkana, a volcanic crater which looks particularly spectacular from a heli, and Reteti Elephant Sanctuary, the first community-owned elephant orphanage in Africa. Lunch at high-altitude Lake Alice, tucked in a deep crater which falls away into a plunging valley, is one of what he calls “our favorite spots.” Davies also recommends a dedicated kids’ host or guide, “a Big Brother type of personality.” He regularly rosters someone to take them out, say, to play soccer with the local rangers rather than take another four-hour game drive. Playing on a dirt field with goals made of deadwood in the middle of the African savanna makes for a wonderful story at the kids’ next game back home.
Ski getaways for group celebrations
WHERE: Colorado or Wyoming
WHO: 10 friends with snow boots at the ready
WHAT: Long weekend of ski (and après-ski)
When it comes to winter sports trips, all experts recommend adhering to the rule of K.I.S.S. — that’s Keep It Simple, Stupid. “Don’t worry about coming up with creative activities — it’s all about being the first to find fresh powder,” says Errington-Barnes. Most time-pressed friends convening on trips like this want an easy-in, easy-out domestic destination that’s readily reachable from across the country, like Jackson Hole, WY or Colorado’s Crested Butte and Aspen. They’re typically at higher altitudes than European counterparts, making snow levels more predictable for longer.
The ideal group size, says EXP Journeys’ Kevin Jackson, is roughly 10 people — the best lodges will have around five bedrooms. He recommends Oxbow Lodge in Jackson Hole with its large common area and a commercial kitchen; Jackson brought in recording engineer-turned-chef Shon Foster, an Aman alum, to handle all meals for a group there. He set up a helicopter flight to West Yellowstone as an extra activity. “Snowmobiles met the guests as they landed, transferring to the park to view Old Faithful.” Jackson Hole is ideal, too, if there are varying skills levels in the group, thanks to what Jackson calls “an amazing ski school” and the fact you can offer alternative activities, like snowskiing or snowmobiling, very easily. “Newbies don’t want to do it every day, as they’re working harder to get the same amount done,” he cautions.
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Vivienne Errington-Barnes says that top-tier chefs, even ones from Michelin-starred venues, are readily, affordably available in Aspen and the like (think $10,000 for an unforgettable meal). If you do opt to eat out, she suggests Bear Den — sit outside — and Betula, for its cocktail bar. Cloud Nine is a ski-in-only spot she says any of her clients can manage to reach; it’s not the toniest hideaway, but that access exclusivity keeps the vibe buzzy.
The Eleven Experience group, with more than a dozen turnkey lodges with transfers, guides and added extras built in, is another winner. Standout among them, per Sandy Cunningham: Scarp Ridge or even the brand new Sopris House next door (combine the two if you’re a larger group needing more bedrooms, as there are plenty of bunk beds in the former). “It’s an hour up the mountain to the top of their concession, with amazing bowls of untracked powder, and there’s a limo, with plush leather seating and movies on screens, to take you there,” she says, adding that the French onion soup at the mountaintop cabin is world-class.
The slopes around here, she adds, are the most impressive you can access without resorting to heli-skiing. Otherwise, consider a rental from LVH Global (think a highly exclusive Airbnb), which has a raft of spectacular private homes in most key ski destinations, often owned by boldfaced names who are both clients and hosts, such as Zynga founder Mark Pincus, for instance.
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The lesser-known European escape
WHERE: Greece, but not where your friends go
WHO: A more exclusive gang adventure
WHAT: Extended birthday revels in the sun
Forget the south of France or a Tuscan hillside hideaway — Greece is our experts’ go-to for a luxe group celebration. An assortment of accommodations combined with readily reachable, contrasting destinations means you can easily carve your time between a couple of places. How about taking a few of the villas at Amanzoe on the mainland, says Cari Gray. Do a day trip from there to Spetses, a shipbuilding hub turned weekend getaway of wealthy Athenians — the place to party, explains Ileana von Hirsch of Five Star Greece, with superb beach clubs: The buzziest are Kaiki Beach Club and Paradise Beach, or segue from day to night at the Bikini Top & Bottom bar (the view from upstairs, aka Top, is superb).
Alternatively, hire chef Elia Iliadi, an island native who now lives between the island and Athens, to cook for you. “She has fun stories about the food,” says von Hirsch, “And she is also an artist so her approach is really interesting.” One satisfied past client: Michael Jordan.
From Spetses, add an excursion to Dokos, a small, almost uninhabited island where the only resident is a woman and her herd of goats. There are no roads, boats or restaurants, but it’s beautiful for a quick walk or visit to the chapel. The other option for a day trip is Hydra, which is about an hour and a half by speedboat from the mainland. Art collector Pauline Karpidas, who recently sold some of her contemporary haul for a record-breaking €35.6m (approx. $41.3m), has made it her second home since the 1990s and attracted a slew of the arterati in her wake. There are no cars on the cobbled streets; look for the garbage-collection by donkey and book a long lunch at the contemporary Mediterranean Omilos with sensational views over the sea.
Pair that with some relaxing time in the Cyclades. Gray suggests a takeover of new resort Gundari on the small, chic island of Folegandros — the old town there is largely untroubled by modern development, making it a charming standout. Otherwise, opt for what she calls “more boho and originality” with a buyout of the rooms across the properties at Verina on Sifnos, which is the foodie hub — Greece’s answer to Julia Child, Nikos Tselementes, lived and worked on Sifnos, and dinner at the hotel’s Bostani restaurant is a must; manoura goat cheese and the slow-simmered garbanzo bean soup revythada are the dishes to ask for. There is a ferry service, but heli in to keep things much more exclusive, Gray notes.
Ileana von Hirsch agrees. Book chef Alberto Bourdeth for meals, the Athens-based cookingschool owner who works occasionally for events in Sifnos, she says, or buy out Cantina or Omega 3, contemporary-skewing restaurants on the island. Mix that with a casual lunch at a local taverna. The standout is Tsikali. “It’s a beloved family-run taverna right on the water. They serve their own meat and cheese, produced on their nearby farm.”
“Most people don’t want to fly, flop and drink,” she says, so program an opt-in activity every day — again an easy option in the Greek Islands, where rugged landscapes are ideal for e-bike rides, or you can charter a yacht to different destinations, depending on the day. The best resource for that, adds Gray, is Sofi Hatzivassiliou at Original Senses.
The best buy-outs for a big birthday
WHERE: Costa Rica or the BVIs
WHO: 40 or more of the principal’s closest pals
WHAT: Four days of celebrations
Dearly beloved, you’re going to Santa Teresa. The surf town in Costa Rica is the one location Shift + Alt’s Errington-Barnes recommends without reservation for briefs such as this. “It’s like the newer Tulum, with St Barths kind of vibes — it’s not teenagers doing Full Moon parties,” she says. Even better, the country’s pura vida mantra makes staff and vendors more welcoming and unflappable — not to mention less judgmental if you overindulge. “You’re still having fun, riding around on quad bikes — some of the roads have been paved, but a lot of them still haven’t. It has just enough infrastructure.”
She’ll commandeer the Anamaya Resort — the infinity pool is a knockout — or rent a private home, then organize a hike through the jungle to a cacao tasting-menu lunch served by the local artisan chocolatier Indigena. She’d bring in a security guard — not because you’re likely to need it, she says, but because it’s another thing you don’t need to worry about (and costs as little as $50 a day). And a pro photographer will accompany the group, keeping out of the way but immortalizing the essential ‘OMG’ moments you’ll be too busy to catch.
Ian Jordan from Black Tomato says that Richard Branson’s 74-acre Necker Island is another party-primed buyout spot in the BVIs. He’s facilitated sunset champagne toasts on private catamarans, or steel-pan concerts and rum-tasting master classes. His non-negotiable? A decent-sized yacht parked offshore to act as a VIP bar and late-night club, so the party animals don’t disturb the larks in the group.
It might be your party but don’t forget gifts, says Jason Squatriglia. He escorted a recent birthday trip where the principal spent $30,000 on goodie bags for attendees. “I had to pack two extra trunks just to haul the presents,” he says. If you’re bringing a disparate group together, Squatriglia suggests asking your travel specialist to prep a briefing doc — face pages, in other words — dressed up as part of a fun booklet given out to the group before the event with brief bios on everyone, as shortcut conversation starters. “Ask for their dog’s name, biggest career mistake, and where they have second or third homes,” he says.
A backup option for a shortcut to guaranteed good times, per EXP Journeys’ Kevin Jackson, is Over Yonder Cay in the Bahamas. The Exumas island spot features four villas with room for up to 30 guests, on a buyout basis. There’s even a ninehole golf course on-site.
Our expert panel
Nick Davies runs Cookson Adventures, an ultra-luxe specialist known for seven-figure expeditions such as a private, charter round-the-world trip.
Vivienne Errington-Barnes of Shift + Alt Events is one of Silicon Valley’s favorite vacation-wranglers.
Sweat-inducing, adrenaline-rushing action adventures are how Malibu-based Cari Gray of Gray & Co built her name.
Cazenove & Loyd’s Christopher Wilmot-Sitwell’s sweet spot sits at the nexus of luxury, adventure, and sustainability.
Former safari operator, Uncharted’s Sandy Cunningham is renowned for her know-how in all things Africa and adventure.
Your Favorite Travel Agent Jason Squatriglia is aptly named, with particular expertise as a fixer/concierge.
EXP Journeys’ Kevin Jackson combines outdoorsy experiences with cinematic scenarios for many of his clients.
Five Star Greece owner Ileana von Hirsch has unparalleled expertise in luxury rentals across the entire country.
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Ian Jordan is one of the team at Black Tomato, the British travel agency known for its bespoke itineraries.