Dorothy Presents a Culinary River Cruise Through France

Yes, It’s 2028. And Yes, I’m Telling You Now. You have plenty of time to plan. Delicious Decadence does not sail until July 18–25, 2028. So why am I telling you about it now? Because Avalon Waterways offers only one culinary cruise through France each year—and

The Only Gringo at the Table

I shared this post on another blog this morning, but I thought some of the "Dorothys" not on that blog would appreciate it. It is Saturday night, going on 9:00 p.m., and I have just returned home from a six-hour party here in Mexico. Six

Worth the Detour

Worth the Detour — a small-town museum that surprised us

Beyond a quiet door in the Marais waits a magnificent love letter to Paris. Come for the history, stay for the courtyard, and don’t miss the room that feels like a velvet-lined jewelry box.

Spend Well

Spend Well — Permission to Spend on Yourself

I was recently looking at a dog-earred ledger my mother kept, a meticulous record of every penny spent on milk and postage. It was a testament to a generation that saved for a rainy day and then, quite frankly, sat inside while it poured. We were raised by the

The Toast

The Toast — the art of going anyway

We spend far too much time preparing for rain and not nearly enough for champagne. Consider this permission to wear the velvet blazer, order dessert, and make a little more noise.

curiosity

11 Magical Things That Turn Grown Adults Into Delightful Children

Adulthood may come with bills, responsibilities, and increasingly opinionated knees, but wonder never disappears. These simple pleasures remind us that we’re never too old to play, explore, and become completely delighted by something wonderfully pointless.

Dear Dorothy

Dear Dorothy — What If Your Spouse Wants a Different Vacation?

Her husband dreams of hiking the Appalachian Trail. She dreams of linen, Burgundy, and a proper mattress. Dorothy explains why retirement doesn’t require couples to share the same definition of adventure.

Astrological Report

Astrological Report — the week ahead

August 30–September 5, 2026 Of course, this is presented for entertainment purposes only. Take what you find helpful and make it your own. The week begins in the emotional afterglow of the late-August Pisces lunar eclipse. Jupiter and Saturn form a constructive trine on Monday, while Tuesday brings

Happy Birthday, Dorothy Parker

Celebrating the woman who turned sharp observations, bad romances, and cocktails into an art form Dorothy Parker was born on August 22, 1893, in West End, New Jersey. She became a poet, short-story writer, theater critic, screenwriter, and one of the quickest wits of the twentieth century. She wrote

Maybe We’re Finally Entering Our Era

I read an article recently arguing that the digital economy is beginning to favor people over 50, and I haven't stopped thinking about it. The writer's point was largely about technology and business. Artificial intelligence now produces information, images, marketing copy, business plans, videos, and endless

The New Dorothy News Is Here.

Dorothy Podcast Episode 10:00/424.5333331× Hey, Dorothy! I was hoping to have a shiny new video podcast waiting for you today. Instead, I learned something important: I still suck at video podcasting. And strangely enough, that fits perfectly with today’s episode. This week, I’m talking about

Vienna Waited for Me

There are songs you love because they remind you of a particular time in your life, and then there are songs that seem to follow you for decades, quietly changing meaning as you change. For me, Billy Joel’s “Vienna” has always been one of those songs. I was in

You Need a Bigger World

I heard a story recently about a young man who came home from his restaurant job furious about ketchup. At the end of each shift, employees were supposed to combine half-empty bottles so everything was ready for the next day. One coworker routinely skipped the job. And it drove

Hats, Haircuts, and Tattoos

I heard a wonderful little analogy this morning about making decisions, and I haven’t stopped thinking about it. The idea is simple. Most decisions in life fall into one of three categories: hats, haircuts, and tattoos. A hat decision is easy to reverse. You put on a hat. You

I’ve Been Gatekeeping My Best Travel Laundry Secret

I have a confession. I’ve been gatekeeping one of my favorite travel tricks for years. If you’ve ever traveled with me and wondered why I pull a shirt out of my suitcase looking like I slept in it, disappear into my room, and emerge five minutes later looking

The People Who Are Missing From Your Life

A few months ago, I was standing in line at a small bookstore when the woman in front of me asked the bookseller an unusual question. "I'm looking for a novel," she said, "that will make me miss people I've never met."

conversations

Curiosity is the world's cheapest luxury

The most interesting woman I met recently hadn't climbed mountains or circled the globe. She'd simply wandered into the wrong aisle of a library. That encounter became a reminder that the richest lives aren't built by collecting achievements—they're built by collecting curiosity.

life after 50

The Fabulous Woman Who Taught Me to Stop Collecting People

About twelve years ago, I found myself at a cocktail party that was, if I'm being honest, fairly forgettable. Except for one woman. She was 84 years old and absolutely magnificent. She arrived dressed to the nines. Every movement seemed intentional. She held her cocktail glass like it

You Don't Need a New Life. You Might Just Need a New View

There's a funny thing that happens when we stay in one place too long. The coffee shop becomes invisible. The neighborhood park becomes something we drive past instead of through. Even the people we love can begin to feel like familiar wallpaper rather than remarkable human beings. Nothing

We're Not Collecting Stamps Anymore. We're Collecting Versions of Ourselves.

There was a time when travel was measured by how many countries you had visited. People proudly colored in maps, counted passport stamps, and raced through bucket lists as if there were some invisible finish line waiting at the end. That doesn't seem to be what people want

What if This Was the Year You Said Yes to Yourself?

It's easy to spend your life putting yourself at the bottom of the list. There will always be another bill to pay. Another project at work. Another family obligation. Another reason why "now isn't the right time." And somehow, before you know it, another

The Best Part Wasn't the Microphone

I had every intention of writing this article hours ago. It's Sunday. There are things to publish, emails to send, a blog to keep alive, and all of the ordinary work that quietly happens behind the scenes of building a travel company. Instead, I decided that today was

courage

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

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

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