The Important Conversation You Must Have

If you want to stay friends, it’s critical that you are transparent and honest about your expectations for this trip. As the group leader, people will be looking to you for the outline of the trip.

How much time do you want to spend together each day?


Is the expectation that everyone will do everything together? Will people go their own way during the day and then meet up for dinner each night? Is there one event you’d like everyone to attend?

Does everyone need to come for the whole time?

If it’s a cruise, yes. If not, then you’ll have some flexibility, if you want it, for which dates a person can join your vacation.

Do any of the travelers have special needs?

If the expectation is that everyone will attend a group activity together, it’s important to understand if there are any physical limitations or allergies that would impact what type of activity is chosen. For example,

-          If you want a group dinner and someone in the group has a food allergy, it’s important we know so we can make sure the restaurant has safe menu options.

-          If your dream is for everyone to hike the Coba ruins in Mexico, but someone can’t stand or walk for longer than 15 minutes, we will need to make special accomodations.

-          If your bucket list is to scuba dive at the Great Barrier Reef, what are the families will little kids going to do while you are finding Nemo?



Who is allowed to join the trip?

Is your vision that this is an adults only trip? A Girls’ Only Getaway? Families are welcome?

How will you pay for things not included in your vacation package?

A cruise or all-inclusive resort make things easier because all your meals are included. If you are renting a house or visiting a regular hotel, you’ll want to have a conversation about how buying food, drinks or sharing a rental car will work. Are you splitting all food expenses evenly? Do you have to make sure that restaurant you visit will take separate checks? Are you going to make everyone buy matching t-shirts to wear each day?


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