How to Hold a Family Vacation Planning Retreat

You love your family. And you love to travel. Would you like to be more strategic and intentional with both? Hold a family planning retreat to involve all family members in planning and prioritizing travel. It’s a unifying and productive experience you’ll want to re-create every couple of years. Here’s the how-to in four steps, with free downloads to make it really simple.

family vacation planning retreat

1. Set date and location

Set a date for some time in the next 2-6 weeks. Make it happen as soon as reasonable, coordinating as needed if multiple generations are involved. One day is sufficient for the actual planning retreat, or you could spread it over two half-days if you prefer. You could set aside one day as part of a longer vacation.

Consider a nearby weekend getaway location or even day use of a resort. Focus on the session, not location. If you can’t get away soon, hold your planning retreat at home. But don’t let the distractions of home interfere. Make arrangements to clear calendars and focus for that day.

Regardless of when or where, make sure your family planning retreat is something everyone is anticipating with enthusiasm.

2. Prepare agenda and materials

Decide in advance what you want to accomplish in the planning retreat. Are you discussing travel destinations? What about timelines and dates? Come to agreement with your spouse about what will be on the agenda. Don’t include topics that are not open to group decision-making.

A family planning retreat allows you to be deliberate and intentional in spending time together. Use this opportunity to map out what you want to do with your children before they leave home, or to gather input from grown children and grandchildren about multi-generational travel. Based on your desired outcomes, develop an agenda. You can use ours available as a free download (skip the family visioning exercise if you just want to discuss travel).

In addition to the agenda, a long-range planning calendar is a useful tool. A calendar outline of the next ten years with known milestones marked, and space to sketch in travel opportunities and priorities, is helpful in visualizing how much time you have and what is already on the calendar. Mark high school graduations, major birthdays and anniversaries, etc., as they are great reasons to celebrate and travel. Download our free multi-year planning calendar and modify for your family situation.

Prepare copies of the agenda and the planning calendar for each participant old enough to read. Gather additional materials, including:

  • Flip charts
  • Masking tape
  • Sticky notes (post its)
  • Sticker dots in multiple colors (ideally one color per person)
  • Flip chart markers in multiple bright colors
  • Writing utensils for everyone
  • Food and drinks

If you’re at a hotel or retreat facility, check to see if they have these supplies. Otherwise, they can be found at office supply stores.

3. Hold the retreat

Act on your plans, while planning to be flexible. Recognize that your family planning retreat is an organic process; let it flow naturally, with guidance to ensure your priorities are accomplished. Take breaks when you see energy wane.

Consider group dynamics as you brainstorm travel destinations. You can do a traditional brainstorm where everyone calls out their ideas, or you can give each participant a pile of sticky notes. Each person writes one idea on each note, then places them up on large flip chart papers in the appropriate category.

With everyone’s ideas of “where” to go up on the flip charts, how do you translate that into travel plans? This simple prioritization exercise works wonders.

Give each participant six color-coded dots (Brother gets 6 blue ones, Dad 6 brown ones, etc.); each one can place their dots on the destinations to show personal priorities. The dots can be distributed however each person wishes- one on each of six destinations, all six on one destination, or any combination in between. In our family this was fun… and revealed an amazing unanimity. Five destinations received 21 of the 24 possible dots, giving us clear priority for planning.

4. Next steps

Develop a plan to act on priorities. Fill in the calendar or use another method to document decisions made in the planning retreat. You will revisit the plan and want it to evolve as your family does. For now, you’ve identified priorities, and hopefully had a uniting and validating experience in doing so.

Intentional time together as a family is never wasted. That was certainly evidenced for us in our family planning retreat. May you have the same positive experience in planning together for family travel, so that you enjoy the decision making as well as the destinations.

About Hilarie H. Robison

Hilarie RobisonHilarie H. Robison is a writer, facilitator and strategist who believes in leaving a legacy for loved ones. With a professional background in public policy and non-profits, she recently joined her husband in family entrepreneurship. Together they launched Legacy Tale, where they help families make and keep memories. Natives of Las Vegas, the Robisons love to travel with their two school-aged children. Follow Hilarie's adventures on Instagram and Facebook.

Click here to read Hilarie's articles

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