‘Practice the fine art of shuttle diplomacy. Don’t bicker over breakfast. Include a wildcard. Aperitivo is Italian for bottomless brunch. Drop the intermittent fasting. And do not, for heaven’s sake, Splitwise.’ 

Hello lovely readers; why am I inspired by such sage advice from the vacation guru – David Prior? (A man known for org

anising groups of strangers to have the time of their lives) Because dear reader, I’ve been invited to join a group holiday, and excited though I am, we need to talk about the rules of engagement.

When my dear friends invited us to join them and a dozen or so of their nearest and dearest to celebrate a milestone birthday aboard a Yacht cruising along the Croatian coast, I squealed, ‘hell yeah!’ The silver fox, with face aghast, exclaimed, ‘hell no!! 

If you’re nodding at my man’s declaration, yet the agenda sounds too exciting to pass up, fear not. It can be an absolute blast if the right mutually decided rules are established, agreed upon and adhered to. When done well, a seamless mix of fun, relaxation, and exotic locales can be fun. Sunset cocktails overlooking the Mediterranean with a rocking soundtrack, locally sourced dishes and animated bruise comparisons after a day banging around that yacht’s deck, anyone? 

Sounds fabulous. But what about the things no one likes to discuss, such as money, habits, expectations, familiarity, group v solo time, room size, agendas etc.? Is there a secret to ensuring all that fabulousness? Yes there is!

EXPECTATIONS

‘Diplomacy, yes; however, the first rule of group travel is: This is not a democracy. There isalways a ringleader with a clear idea of where the group should go. Before committing to anything, think about where you are in your life. Are you coming off a super stressful work time and want to be blissed out with tropical waters and nothing but mellow? (In this case, French Polynesia, Sardinia, or Antigua might be the go) Or are you looking for activity and action? (Perhaps Croatia, Iceland or Costa Rica). Does the chosen agenda match your headspace?  

FAMILIARITY

Old friendships can mean a lot of history, but intimacy can breed conflict. After all, the whole point of going on holidays with others is to avoid the kind of breakfast table drama that can blow up a family vacation. “There can be so much gossip and showing off with groups of friends,” says George Scott, who owns the Andalusian guesthouse Trasierra with his sister Gioconda and organises group horse rides with stays in old farmhouses.

What does that history look like? Will too much familiarity be an issue?  Possible to put diplomacy front and centre?

MONEY

The trickiest issue is how much everyone will spend, say, on a villa in Bali or Santorini for a week. “One of the things that can make a group vacation weird or tense is money because people have different capabilities and levels of comfort around it,” says Ezra Woods, who co-owns the L.A.-based showroom Pretend By Appointment (this man goes on many group trips with an eclectic mix of folk and associated budgets). How will the monetary side be addressed?

Ezra has found a few successful formulas: “Everyone splits accommodation equally, and then it’s nice if friends take turns hosting meals or activities.” (His inspiration for that was The Real Housewives.) “This way, someone can host a dinner for 10 people one night or pick up the tickets to an archaeological site or massages at the villa for everyone. Maybe another friend with more resources could rent a boat for the day.” He recommends cutting it off at one or two items on the itinerary daily. This isn’t a sightseeing bus tour or a class trip. “It’s grating when you feel obligated to participate in everything. 

SCHEDULE

If someone is overscheduling, set expectations from the outset. Say, ‘I’m so excited, but I sense that I’m not going to be interested in doing every group activity,” says Christopher Golden, a yoga teacher in New York who plans retreats (Provence! St. Lucia! Oaxaca!) and goes on his fair share of trips with friends. “If I’m in Cape Cod with a crew, and everyone wants to go to the beach, but I don’t, it’s nice to say no, and suddenly I have this huge house to myself. That’s when I really feel like I’m on vacation.” Comfortable setting your own pace?

PRIVACY

Private space is essential, whether that means having a room to yourself or not staying together. Travelling as a group for adults does not have to be a slumber party. Golden went to Paris with friends one spring, and part of what made it successful was that five people stayed at a mix of hotels and rented apartments. Some would pilgrimage to Dries Van Noten together, others to the Pompidou, but there was no pressure to do any of it. Every night they came together for long dinners that started with seafood towers and steak frites and ended with cheese courses and pavlovas, and they talked about their days. A room of one’s own can also avert disaster: everyone getting sick of one particular person, whether the reason is the person is high-strung or won’t stop talking or is a chronic complainer. What level of privacy will you need?

PREFERENCES

This brings up another important though often unspoken rule: It’s wise to have a shared level of hedonism. Some folk like to work out every day on holidays, while others don’t. Some want to maintain their Gwyneth Paltrow–esque intermittent fasting regime no matter what. Some want to dance till dawn at a club and then continue partying back at the digs. Some would rather die than part with their phones for an hour (or, worse still, lose service altogether). There are no correct answers. To travel well together, you don’t need cohesion, but you do need to be able to coexist happily. Looking at your fellow travellers, feel you can coexist?

CHEMISTRY

Ultimately, the perfect group to vacation together is like the ideal blend of dinner party guests. It’s about chemistry, but also some wildcards and surprises. Up for it?

So am I going? I would love to, however having enjoyed that same journey pre-Covid, albeit on a slightly bigger boat (you can read about that here: Sailing the Adriatic) my travel lust is begging for new territory – Sweden, Denmark, Norway, Finland – or maybe southern Italy and Turkey, or possibly boarding the newly opened Orient Express from Paris to Opatija – so much to see, so little time! Followed by finding my ‘post cruise’ beloved friends and celebrating that birthday. 

I hope you all have a lovely holiday in mind and why not drop a line and tell us about your best or worst group travel experience?

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