One of my favorite ways to build community is through simple online gatherings. I already do this with a men’s coffee group every Friday morning. Anywhere from 60 to 100 guys show up. Sometimes we have a topic. Sometimes we check in, see how everyone is doing, and let
The past couple of weeks here in Mexico have been some of the most challenging I've faced while traveling. If you're curious what happened, watch the video below. More importantly, I want to hear your story. What's the hardest thing you've ever
Solo Travel
Join Dorothy Travel for a Christmas market river cruise from Nuremberg to Vienna aboard the Avalon Impression. This December 2027 journey pairs Europe’s holiday markets, river cruising, included excursions, and months of pre-trip connection so travelers arrive feeling like old friends.
conversations
A woman I met for only two hours shared a lesson I've carried ever since. Not every meaningful connection is meant to last a lifetime. Some people enter our lives for a single evening, leave us with a story or a piece of wisdom, and quietly continue on their own journey.
conversations
As I prepare to move to Mexico, I've been thinking differently about the things I own. Every possession once cost more than money. It cost time. That simple realization has changed how I decide what deserves a place in my life, and why travel remains one investment I rarely question.
conversations
Most conversations die before they ever begin. Discover three simple ways to move beyond awkward small talk, ask better questions, and create genuine connections with strangers—whether you're at a party, traveling solo, or meeting someone for the first time.
There is a moment, suitcase wheels complaining over cobblestones, when travel takes you gently by the elbow and says, Come along now, we’re going to meet her. Not the woman you were at nineteen, who could sleep on hostel bunks and flirt with fate. Not the woman you were
Reinvention & New Chapters
You don't need fireworks to change. This piece urges a mid-chapter rewrite: small, mundane acts — moving a chair, cancelling a committee, taking a class — that add up to real courage and a truer life. No parade; just pick up the pen and write now.
starting over
Starting over rarely looks glamorous. Inspired by Dorothy from The Golden Girls, this essay explores how travel helps people rebuild community, rediscover themselves, and find beauty, connection, and purpose after life changes.
Dorothy Travel is for people who want more than a vacation. Inspired by the curiosity of Dorothy Gale, the sophistication of Dorothy Parker, and the wit of Dorothy Zbornak, this is travel for thoughtful wanderers who care more about understanding a place than simply checking it off a list.
