The Do’s and Don’ts of Planning Group Travel

I am so excited about this post. Michael and I just got back from a fun getaway to Napa Valley with a great group of friends and family. We had an incredible time out there, but the idea for this post actually came to be while planning the trip. You see, the trip was a surprise for a family member. I had to check my ego and own plans while researching and planning. “This vacation is for the whole group, not just me” ran on a continuous loop in my mind everytime I sat down two make plans for Napa Valley.  Planning a group trip is a lesson in humility and flexibility.

Planning Group Travel

Traveling with friends and family can add fun to your trip and take away some of the financial burdens. It usually equates to a great experience, enhancing relationships and making memories with those you love the most. However, adding people – and their opinions, ideas and needs – to the mix when planning a trip can add stress and confusion if you don’t plan with care and kindness.

Here are some do’s and don’t’s for planning group travel.

Choose Wisely: Ernest Hemingway has a great quote that says “Never travel with someone you don’t love.” Keep this in mind when creating the guest list. Depending on your plans, you might be with these people every waking hour for multiple days in row. DO make sure the people you choose to travel with are close friends and/or family. You are bound to get into a few disagreements, but you (should) know how to best communicate with those that you know the best – which will help solve those disagreements quickly! DON’T forget to look at the group dynamic if inviting multiple couples or friends from different “circles”. Take into account the likes/dislikes of the majority of the party. For example, one of my very best friends loves to shop, eat a great restaurants and lay by the pool on vacation. She would be my first pick for a trip to The Bahamas, but my last choice for rappelling waterfalls in the jungles of Costa Rica or hiking sand dunes in Namibia! Your guest list matters.

Hiking Down Dune 45

Big Plans: A larger guest list means more opinions and ideas on what to do each day. Plan ahead to avoid frustration and boredom. DO have honest conversations about what all parties want/expect to see, experience and eat prior to arriving to your destination. However, DON’T be bummed if you can’t get to every wish list item.

Flexibility is Key: DO be flexible in your plans. With adequate planning you might be able to please almost everyone. But chances are, you might have to sacrifice eating at one of your preferred restaurants to check out that late night attraction that everyone else views as a must-see; majority rules. However, DON’T feel like you have to stick with your group like glue. Remember, those closest to you will likely be OK with the group dispersing from time to time.

Money Matters: This is where I see the majority of group trips (and even friendships) collapse! Figure out your financial plan prior to booking anything! Going back to your guest list, DO  think about only inviting those who you trust enough to pay you back for anything you book ahead of time (i.e. hotel rooms, group tours [if they cannot be booked separately], etc.). DON’T be afraid to ask for the money upfront and pester your friends and family for their financial share of the trip! It is smart to let everyone book as much as possible on their own, in order to avoid as many “I owe you” situations as possible! Lastly, be considerate of others’ financial capabilities. I would not plan on staying at a Five Star resort with your sister who is still paying her way through college; you feel me?

Dog Sledding with Friends in Breckenridge

Some of our best trips happened with friends and family. I’ve gone dogsledding in the American Rockies with high school friends, relaxed in Marco Island, Florida with old college roommates, sipped wine in Napa Valley with some of our favorite couples and had a classic New England Lobster Bake with family in Boston! Each trip strengthened the bonds we all share and added to the great memories travel affords everyone! Travel with friends is worth the added time and even headaches. Just keep an open heart, flexible mind and lots of optimism!

11 thoughts on “The Do’s and Don’ts of Planning Group Travel

  1. Bev MacDonald

    I love the tip about being flexible. It is an absolute when traveling with a group. Plus when everyone isn’t doing the same thing all day long, you have way more to talk about when you are together.

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