Rio de Janeiro is a favorite. Here’s a cheat sheet.
I am a big Rio de Janeiro fan. I can’t sit on the sand endlessly, no matter how beautiful the setting, so a city on the beach like Rio is the perfect way for me to do the traditional holiday things plus a lot more. I love Hotel Arpoador and the Ipanema Inn if I am just doing a quick getaway. Hotel Arpoador is right on the beach at the border of Ipanema and Copacabana. I go every day for a quick lunch and catch up on work while sitting on their terrace.
Then the afternoons are for exploring. I find myself wanting to go back to even the obvious touristic places I’ve seen a dozen times: Christ the Redeemer, Jardim Botânico, Parque Lage. I always stop by Confeitaria Colombo in Centro for a coffee, have a pizza at Canastra, a big seafood meal at Satyricon, a drink at the Copacabana Palace, watch a horse race at the Jockey Club over a late lunch at Rubaiyat. The residential streets are beautiful, but they’re really quiet. I stay on the commercial streets, where things are open until 4 a.m. and no action is happening. I try to stay around people.
Find the cheapest way to travel to a secondary city long-haul.
If I am traveling for leisure and have a few days to spare, I always use Google Flights to find the city in Europe with the least expensive flights. Type in your home city and then for the destination you just type “Europe” and check the box for nonstop. It’s going to auto-populate direct flights to Barcelona, Milan, Prague or Berlin. Pick the best deal, and then you can connect to wherever on a discount airline, such as EasyJet or Wizz.
Every August I travel to Patmos in Greece, and lately I’ve avoided the overpriced and oversold New York-to-Athens route and have flown instead to Berlin, and then fly a discount airline to Kos, where I catch the ferry. It’s also a way to find cheaper business class: If you fly to a market that is mostly leisure tourism, for example, you can find better deals. On the way back, I use a website called Kiwi, where you can do the opposite, saying you’ll fly from anywhere in Europe to New York.
Ask local restaurant owners and diners to score the best recommendations.
I’ll go to a restaurant that someone has recommended to me and ask around. “I’m so happy that I found this place. It was amazing. Where should I go tomorrow?” And the locals will point you in the right direction. I know what my answer would be if somebody asked me that at my restaurant. I could tell them in two seconds where to go in New York. A lot of people in hospitality would welcome that question.