THE BASICS
Name: Michael Dorf
Title: Founder and CEO
Company, city: City Winery; New York City
First job: Founder of Knitting Factory
Where to next: I’m heading to Nashville for some real estate work, then to St. Louis to host a 40th‑anniversary college reunion at our location there. I’ll also attend wine meetings in Northern California.
© Michael Dorf
A LITTLE BIT MORE
What actor or actress would play you in a movie of your life? David Constable — we share certain traits like facial hair and a playful, goofy energy. I try to bring levity and good humor to my work, even during tough conversations, and I think he captures that well.
What would you be doing professionally if you weren’t in your current industry? Commercial real estate development. City Winery’s expansion is driven by the spaces we choose and develop. As an operator you stay involved, but as a pure developer you move on to new projects — and likely would have earned more.
What is your favorite book, movie or television show? One Hundred Years of Solitude by Gabriel García Márquez resonated deeply with me and left a lasting impression.
What historical figure, dead or alive, would you love to have dinner with? Abraham Lincoln — his perspective and leadership would make for an extraordinary conversation.
THE BUSINESS
What is your most recent project, and what was the inspiration behind it? Our most ambitious adaptive reuse project is the Milk Factory in New York’s Hudson Valley. We’re transforming the 150‑year‑old ruins of a condensed milk factory into a 60‑room boutique hotel. The property will include a hotel, winery component, restaurant and spa, answering a local demand for a luxury, urban‑style destination.
What is your favorite aspect of the job? I love adaptive reuse of historic buildings. Chicago City Winery — set across a 130‑year‑old complex — exemplifies that approach. Entering the new structure that connects to older buildings highlights how spaces with history can be reinvented for modern use and set a standard for future locations.
What’s the biggest business risk you’ve ever taken? Launching the City Winery concept was my biggest risk — and one that defined our path.
Who is someone you admire professionally in the travel industry? Richard Branson. He’s a successful entrepreneur who follows his instincts across varied businesses rather than relying solely on data, and he’s executed that vision remarkably well.
AS A TRAVELER
Tell us about a travel nightmare: In 1984, while traveling on a Eurail pass, I fell asleep on an overnight train and accidentally got off in East Berlin. The army stopped me, checked my passport and escorted me to Checkpoint Charlie. Walking through East Berlin showed a stark contrast with the West — the disrepair made a lasting impression.
Share a comical travel experience: On an Acela from Washington, D.C., to New York I happened to be seated near Wolf Blitzer. He was on the phone wishing people “Shabbat shalom” as we approached Penn Station. I greeted him the same way, and we ended up talking and walking off the train together — a small, memorable moment.
What is your preferred method of travel — planes, trains, automobiles, cruise ships — and why? Trains. They feel soothing and meditative, are more scenic and often more relaxing. For routes like New York to Boston or D.C., trains make better use of time and are more environmentally friendly.
What has been the best example of customer service you’ve experienced during your travels? As a Concierge Key member with American Airlines, I once received private‑car transfer between gates in Dallas, rushing me from jet bridge to jet bridge — an excellent example of attentive, high‑level service.