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Dorothy Took a Detour

Dorothy Took a Detour

Well... Dorothy Travel's Instagram account lasted exactly one day. Twenty-four hours after it launched, Instagram shut it down because, apparently, our very first travel post looked suspiciously like adult content. I wish I were kidding. Somewhere, an algorithm looked at a story about travel and thought, "

Pricing for our Christmas market cruise

Pricing for our Christmas market cruise

You wanted pricing for the Christmas Market River Cruise? Well... I've got your pricing! Christmas on the Danube December 1–7, 2027 Grand Total: Approximately $13,789 per couple (about $6,895 per person) (Watch the video below. We're almost $5K cheaper than another cruise company!

Maybe the Map Knew Before I Did

Maybe the Map Knew Before I Did

There's a branch of astrology called astrocartography that claims your birth date, time, and location leave invisible lines stretching across the globe. The theory is that certain places amplify your energy while others seem determined to hand you a series of minor inconveniences and one terrible landlord. Do

Study It. Then Do It.

Study It. Then Do It.

Last week, I wrote that sometimes the best thing you can do is simply start... and be willing to be terrible at it. That's how we get better. Nobody skips the awkward stage. But I've realized something about myself. I'm not someone who jumps

The newest Dorothy Society Newsletter has arrived!

The newest Dorothy Society Newsletter has arrived!

This issue is filled with travel inspiration, permission to suck at something, my Favorite 5 things, stories from the road, and a closer look at our upcoming Christmas Market Cruise on the Danube. If you're dreaming about your next great adventure—or simply enjoy armchair travel with good

The Christmas Market Cruise I've Been Waiting to Host

The Christmas Market Cruise I've Been Waiting to Host

Experience Europe's most enchanting Christmas markets on a seven-day luxury Danube River cruise from Nuremberg to Vienna. Join Dorothy Travel for unforgettable holiday traditions, beautiful cities, exceptional cuisine, and the camaraderie of traveling with a welcoming group.

Go Ahead. Suck at Something.

Go Ahead. Suck at Something.

A friend and I recently started a podcast about travel and retreats. I went into it feeling pretty good about myself. I've been speaking in front of audiences for years. I've hosted hundreds of Zoom calls. I've taught classes. I've interviewed guests.

Five Things I'll Happily Spend Money On Every Time

Five Things I'll Happily Spend Money On Every Time

Everyone has something they're happy to spend money on. While social media often celebrates luxury splurges, my list is much simpler. These five everyday purchases, plus one bonus, quietly make life more comfortable, more colorful, and a lot more enjoyable. Today 9:37 AM • 496 Chars • 76 Words

The Best Souvenir I Ever Brought Home Wasn't Something I Bought

The Best Souvenir I Ever Brought Home Wasn't Something I Bought

What if the best souvenir from your travels never fit inside your suitcase? This personal essay explores how quiet moments, unexpected conversations, and new perspectives become the keepsakes that last far longer than anything you could buy.

Dorothy's Online Cocktail Party Is Coming Soon!

Dorothy's Online Cocktail Party Is Coming Soon!

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

What's the Most Challenging Travel Experience You've Had?

What's the Most Challenging Travel Experience You've Had?

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

What If Your Christmas Gift to Yourself Was a Circle of New Friends?

Solo Travel Featured

What If Your Christmas Gift to Yourself Was a Circle of New Friends?

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.

The Woman Who Refused to Be My Facebook Friend

The Woman Who Refused to Be My Facebook Friend

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.

The Price Tag You Never See

The Price Tag You Never See

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.

Reinventing Yourself Through Travel

Reinventing Yourself Through Travel

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

Mid-Chapter Rewrite: Small Acts of Courage

Reinvention & New Chapters

Mid-Chapter Rewrite: Small Acts of Courage

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 Isn’t the End of the Story

Starting Over Isn’t the End of the Story

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.

You Already Know Dorothy

You Already Know Dorothy

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.