Generational Trips – Six Considerations

Generational trips can be amazing with the right planning. They are a great way to spend time with your loved ones near and far, share the responsibilities of childcare, and explore a new destination, but they can also be a little stressful if you’re not careful. While I can’t cover everything you need to know about successful extended-family trips in this post (one could easily write a book on the subject), I will cover what I consider the 6 most important considerations for planning a generational trip.

The greatest legacy we can leave our children is happy memories. – Og Mandino

6 Tips for Successful Generational Trips

1) Keep it simple:

• The smaller the group, the easier the planning and the more likely it is that you will get quality time with everyone. Also, the larger the group, the harder it is to get dinner reservations, the more complicated lodging becomes, and the less personal the gathering becomes (and the more likely you are to have conflict!).

2) Planning:

• When planning a group trip, you want everyone to have a say on the large decisions. This is especially important if you are asking everyone to contribute to the cost of the trip. People don’t want to spend money and vacation days on a location they have no interest in visiting.

• Not all family members have unlimited vacation time, and many individuals are trying to balance time with extended family, immediate family, and friends all within that limited vacation period. Allowing everyone a voice on the length and location of the trip makes it more likely your trip is one they want to sign on for.

• For the small decisions, keep options down to three or fewer. Also keep in mind that if every decision is a group decision you will never get anything booked! It’s a fine balancing act. Too many opinions can also be hard to sift through and waste valuable time, while potentially creating fog around the best answers.

• While everyone’s input is essential, it’s equally important that one person take charge of the actual planning so that the process is organized.

3) Location is everything: 

• Criteria to consider when deciding on location should include accessibility, proximity to a wide range of activities and restaurants, room situations to fit every member’s needs (you might not want a family with young kids right next to a family with tweens with very different sleep schedules).
  • Share the lodging layout and allocate rooms in advance.

4) Pick dates as soon as possible:

• With my in-laws, summer works best to get together. With my extended family, we plan a long weekend around my father’s birthday and just let my boys skip a day of school.  The biggest problem is often coordinating school, camp and work schedules.

5) A wide range of activities is crucial:

• The key to keeping everyone entertained and avoiding conflict is selecting a location with a wide range of activities. It’s also important to ensure that you include plenty of optional activities. The worst mistake you can make is trying to make every outing a group outing. Some family members will want a quiet activity, others might prefer more of a physically challenge, and others might want more unstructured free time.

• Meals: The one consistent gathering point for most families is meals, specifically lunch and dinner. I personally love watching cousins interact at the table!

• Share available activities with your group in advance. It will help sell the trip, allow everyone to pre-book their desired activities if necessary, and dictate the packing list.

• If I am training or desire a more challenging hike, I take advantage of the morning hours and go on my own. Once you take care of your own needs, it’s easier to make compromises for the group.

6) Back-up plan:

• A generational trip doesn’t always work for everyone. The solution: Skip-Gen Destinations! The idea of grandkids traveling with their grandparents—without their parents, thus skipping a generation—has taken off. There was a year where crazy schedules precluded a generational trip for our family, so we opted for the grandchildren to go on a trip with the grandparents without their parents.

• There are a lot of factors that go into this decision, such as the relationship the grandkids have with their grandparents, the age of everyone involved, budget, and the overall health and energy level of the grandparents. These trips vary from weekend getaways to international trips. As a parent, I loved the two domestic trips my kids went on with their grandparents. We also have friends that have had successful international skip-gen sailing and scuba diving trips.

• For inspiration, check out grandparent trips through Road Scholar Excursions and Kids Sea Camp. The advantage of outfitters like these is that grandparents are not responsible for entertaining their grandchild 24/7. You get experts who will help plan the itinerary and there will be other kids for the grandchildren to hang out with. If taking a cruise, small-ship expedition-style cruises work better than large ships.

• Lastly, remember to it is best to have a notarized letter of permission to travel with your grandchildren. Ideally, the letter should be signed by both parents. This detail is especially important if the parents are divorced.

Actually, the best gift you could have given her was a lifetime of adventures. ~ Lewis Carroll

In Summary:

Finally, here are a few destination recommendations for generational trips (criteria include flexible lodging, wide range of activities, and ample access to nature). Please share additional destinations or your own tips in the comments!

• The Broadmoor Hotel and Brownstone Rentals in Colorado Springs, CO (summer and early fall)
• Seaside or Rosemary Beach, Florida (all year long!)
• Sea Island Resort in Georgia
• Ski towns in the Rockies (summer or winter)
• Park City, Utah
• Zion (Utah)
• Cinnamon Shores in Port Aransas, TX
• Ashville, NC (early spring – late fall)
• Nantucket, MA House Rental (July and August)
• Big Island and/or Lanai, Hawaii
• Martha’s Vineyard, MA (July and August)
• Pelican Hill in Newport Beach, CA (all year long)
• Carmel Valley Ranch in Carmel-By-The-Sea, CA (all year long)
• Cabin rental in Gatlinburg, TN
• Cannon Beach, OR Home Rental (June – October)
• Florida Keys
• Iceland
• Sedona, AZ
• Bozeman, MT