Is it worth taking your kids back to a vacation destination you've already visited? In this episode, I share why repeat family trips are often the smarter move, especially for multigenerational travel, plus the honest downsides and how to make a return trip to Costa Rica, Hawaii, Italy, Alaska, Puerto Rico, or Amsterdam feel brand new.

Every family trip we have planned for the next six months is a repeat destination: Miami, New York, Costa Rica, a mystery state, and Amsterdam and Paris. In this episode, I explain why that's not a rut. Going back lets you scout logistics for a big group, explore new regions, see a place through older kids' eyes, and travel with a lot less planning stress.

In this episode:

  • Why I scout destinations with just the four of us before planning winter break for our extended family of about 13
  • Lessons from Riviera Maya, Hawaii, and Costa Rica: group transportation, restaurant reservations, accessible hotels, pacing, drive times, and car-sickness routes
  • Going deeper on a return visit: Rome versus the Dolomites in Italy, three very different Alaska trips, and two Puerto Rico trips that felt like different destinations
  • Amsterdam with a newborn and a toddler versus Amsterdam with two teens
  • How familiarity makes family travel easier, including knowing where to find Celiac-safe, gluten-free food
  • The downsides of repeat vacations: less novelty, limited school breaks, changed expectations, and why Celiac would make a return trip to Japan harder
  • Questions to ask before choosing a new destination or a return trip
  • Simple ways to make a repeat trip feel fresh

Timestamps

  • 00:00 — Every trip is a repeat
  • 02:00 — Why go back?
  • 02:36 — Scouting for big groups
  • 07:48 — Going deeper
  • 11:56 — Same place, older kids
  • 14:44 — The comfort of familiarity
  • 16:47 — The downsides
  • 21:02 — New or return?
  • 21:55 — Making it feel fresh
  • 23:59 — Wrap-up

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Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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