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How to plan a group trip – 10 tips for the best time of your life


A few months ago, I celebrated my 40th anniversary in Paris. On my return, even if I had some restaurant recommendation requests, which most people really wanted to know was, “How did you organize a trip for so many people? !“Because you all, I organized a Parisian party with my 11 closest friends. So if you’re wondering how to plan a group trip, I’ve got answers.

To be clear, this is not hyperbole. I hold these people close to my heart, and there is no one I would rather celebrate such an important anniversary with. And while I have a knack for planning and getting the right group of people together, I was a little surprised at how well this trip turned out.

Image selected by michelle nash.

Imagician by michelle nash

If you followed Priya Parker as long as I have, then you know how crucial it is to understand what she calls “the art of picking”. Priya has been a huge inspiration in both the approach to planning this trip and the telling of the story I reflect on here.

If you have a big party coming up, here are my top 10 tips for planning a group trip. Of course, even though the experience was smooth and which I will never forget, no trip goes without a few surprises. I’ll preface it here: The only consistency among all of this advice is flexibility.

Because while planning and preparation are key, timing changes are inevitable. The key is to embrace them.

Picture by Melissa Gidney for Jenni Kayne

10 tips for planning a group trip you’ll remember for years

Consider personality types

Who do you want to celebrate with? Sounds like an easy question, but when planning your group trip, it’s crucial to think about it. For this one, I wanted him to be easy-going, fun, easy-going, spontaneous, silly, and full of energy (a long list, I know).

I had to consider who would work well in a space together, who is excited and cool to be around new people, and who can spark a conversation with anyone. When I tell you this band clicked so well immediately and had the best time, I think. Literally: there was no moment of frustration, annoyance or attitude. In fact, it was quite the opposite.

There were more laughs than I thought possible. (The name of our group text thread has changed no less than 25 times – the inside jokes keep pouring in.) Take some time to reflect and think about who you’re gathering. Do you want to manage your egos along the journey or sit back and watch beautiful friendships form?

Size Matters

Depending on where you are traveling, keep in mind that the more people you have, the harder it can be to make reservations, book the same train tickets, or get in anywhere in a large group. Fortunately, during my trip to Paris, we were able to make two separate tables, dividing the couples into a men’s table and a women’s table. Be sure to plan ahead, as larger groups are more difficult to accommodate.

Picture by michelle nash

Keep the route open

With the exception of a day trip to Reims (located in French Champagne for champagne tasting) and my 40e birthday dinner, I kept the itinerary open and loose for everyone to choose their own adventure. I shared a few things I would love to see in Paris, but knowing that I had five couples joining the trip who may not have traveled or spent time away from their children in recent years, I wanted to leave it open so they could have their own Parisian experience too. This freedom allowed everyone to have their own solo time and to come together as a group.

Picture by Mikola Accuardi

Communication is key

I quickly put the group on a thread via email and text, not only to keep everyone informed of updates, but also to allow everyone to start getting acquainted and building relationships before our meeting in Paris. It’s amazing how quickly inside jokes can materialize over text and email!

Ask for advanced needs

Just as you would approach any type of gathering, asking your friends if they have specific needs (dietary restrictions, no drinking, ADA-compliant rooms, etc.) will help put them at ease. . Plus, this advance planning will show your guests how much you care about them when booking reservations or experiences. It can also serve as an open invitation for a friend to share what’s going on in their world so you can be aware of when they may need some rest, space, or anything else that will help them settle down. feel supported.

Let your guests decide

From where to stay to what they want to do, let your guests structure their experience. The one event I wanted everyone to attend was my birthday dinner. Beyond that, the whole trip was free play. Some of my guests came for different parts of the week and some stayed the whole time. Remember: we all operate on different timelines, with different budgets and from different backgrounds. I always want to come from a place of gratitude. Keep in mind that your guests have chosen to spend time with them and celebrate you.

Find out what excites them

What do your guests want to see? What do they want to do? Chances are the answers to these two questions are pretty much the same, which makes the task of planning a day that much easier. (Bonus: it gives you more opportunities to connect!)

Lots of people in our group wanted to see the same museums and first timers were adamant about catching the Eiffel Tower or stopping at the same falafel spot (hint: this was the big winner!). Thanks to this, we were able to connect for a few fortuitous moments.

Imagician by michelle nash

Discuss money in advance

Larger groups likely mean you’ll be sharing meals and owing people money at some point. Before you dive into these conversations, know this: talking about money doesn’t have to be awkward.

Several applications (like Splitswiseor, of course, Venmo) can be used for large groups. We made the Venmo decision on the spot after meals when someone entered the bill. Don’t forget to include the exchange rate, ensuring that whoever pays will be fully reimbursed.

Set aside one-on-one time for everyone

As much as possible, be sure to spend some intimate time with everyone who has taken time out of their busy lives to celebrate you or join you on the journey. Change the person you sit next to at meals, on trains or on walks. Ask them how they are. Be sure to check it out and show that you care. This will make them feel seen and you will quickly know if you need to make any changes to the schedule.

Ask someone to plan one of the days

I like to welcome and bring people together. It is one of my greatest joys and pleasures. But it can be somewhat exhausting to make sure everyone is having a good time and that I’m intentionally spending time with each person. Looking back, I would have liked one day to “be the guest” of the party and not have to think about anything. So if you’re following the steps for planning a group trip, consider gifting someone else a day and asking if you can take a back seat.

If you are planning a specific trip to Paris

Camille’s Parisian guide served as an *amazing* starting point. But, of course, I wandered around and found a few favorites on my trip that I can’t help but recommend.

  • Day trip to Reims for champagne tasting. Our favorite house was Taittinger.
  • Shop at The Good Marketone of the most iconic Barney’s (RIP) indoor malls in the United States
  • Eat at French Nile Street. They don’t take reservations so get them early!
  • Take oysters at Régis Huiterie.
  • Late night drinks at The counter. Don’t miss this famous spot where they bring you a full plate of butter and bread while sipping on an amazing selection of wines.
  • If you like jam you must visit The Jam Room. My favorite thing is to take a jar, a baguette, a few cheese and charcuterie (plus a good wine!) and sit on the Seine to people watch.
  • Last but not least: it’s not a trip to Paris without having dinner at the The Fountain of Mars.





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