How to plan the perfect group trip

Jill
Travel in and around Silicon Valley
3 min readNov 9, 2015

Traveling with a group can be tricky. Whether you are negotiating shared rooms in a rental house or staging activities with former high school friends that you haven’t seen in ten years, organizing the group can be daunting. Even a simple weekend trip with some new neighbor friends can be filled with awkward moments if planned poorly. In all group trip scenarios, one thing is definite: everyone vacations differently. One group may want to prepare gourmet meals and plan expensive spa treatments while others may want to just have pizza delivered every night. Others may want to be super active and bike everywhere while some don’t want to do anything that involves wearing walking shoes. But don’t fret, here are some tips to help you navigate straight through those variables and plan the perfect itinerary.

  1. Don’t plan it all yourself. Solicit feedback from the group and get online using Google Docs or Travefy, which allow you to collaboratively build your itinerary with friends. If you are planning a trip with a group you don’t know much about create a short survey to get a feel for people’s availability, budgets and general lifestyle preferences. Once you have your data, create a shareable itinerary online that everyone can edit and comment on.
  2. Don’t overload the itinerary. Most people like down time on vacations and if they are very active, let them decide what to do between activities. Tight itineraries are stressful and who wants stress on vacation? Try to not plan anything before 11am or if you do, don’t be offended when they sleep right past your plans.
  3. Only book one or two things per day. People are generally comfortable with some structure and will likely be thankful that you’ve taken the thinking away from them. Have some suggestions of things for people to do during the off time like including a link to the operating hours of a nearby tourist attraction on the itinerary.
  4. Don’t be afraid of variety. Plan different types of activities and different types of meals. If you have a 4-day trip planned, don’t make every dinner a fancy affair. Switch it up, go to a different part of town or suggest casual hot spots in addition to fancy see-and-be-seen places. Use Yelp or tripadvisor for recommendations. You’re not going to please everyone, but trying to please one person once is worth it.
  5. Don’t stress about splitting tabs. Have everyone download the app Splitwise and let it do all of the thinking for you. Simply take turns paying for things and track them in the app. Once the trip is over settle up. Easy peasy!

Vacationing with a group is a great way to build deeper friendships and create new memories. Providing the outline for a great trip allows everyone to add in their own memories which is what vacationing is all about and they’ll have you to thank for it!

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Jill
Travel in and around Silicon Valley

Experience hoarder living in Silicon Valley trying to embrace the space between X and Y. Financial Analyst, travel writer and mother of 2 boys.