Go Away With ... Kendra Cunningham
A. I still think of Boston as home, even though I've been in New York City for over a decade. Chicago reminded me a lot of Boston. Boston is a pretty contained city. You can walk to a lot of different areas and not get bored.
Q. Where is the most romantic destination?
A. Mykonos. But I was with my mom and my sister, so I have to go back with a man.
Q. If you've ever gone away for the holidays, which was the best trip?
A. One year, my mom, my sister and I went to Playa del Carmen for Thanksgiving. It was such a great way to spend the holiday. We went for five days. We went to Tulum, held monkeys, rode a donkey, played tennis. ... It was the most action-packed five days. We did not have turkey, but we didn't care. We befriended a handsome tennis pro who came to dinner with us on Thanksgiving. Every year since, I advocate for travel on the holidays.
Q. What are your favorite hotels?
A. I'm a big fan of the Kimpton Hotels. Now it seems like there are more and more boutique hotels popping up. I remember reading an article about Bill Kimpton and how hard it was for him to convince people that his vision for boutique hotels would work. Underdog story.
Q. What are your five favorite cities?
A. Boston, New York, Milan, Amsterdam, Kilkenny.
Q. Where would you like to go that you haven't traveled to yet?