I Wish I Would Have Known….Traveling with Friends Changes Relationships

Show Me Your Trips · Jun 2, 2026 · 8m

Traveling with friends sounds amazing… until budgets clash, nobody agrees on dinner, and one person suddenly becomes a full-time vacation dictator.

In Episode 1 of the new “I Wish I Would Have Known…” series, Scott Showalter dives into the realities of group travel:

• Different travel personalities

• Budget battles

• Planning conflicts

• Room-sharing disasters

• And how to survive a trip without ruining friendshipsIf you’ve ever planned a group vacation, this episode will feel VERY familiar.Because sometimes the hardest part of vacation…

is the people you brought with you.

What to be a part…