Caryl and I live in Manhattan; our friends, a couple we've known forever, live in Bethesda, Md. So far we've rendezvoused in Philadelphia, Baltimore and Chicago with Montreal in our sights. What's made the trips so much fun, aside from the warmth of our friendship, has been staff work — literally, long-distance planning.
Here's how we go about it:
- The date for our trips is chosen several months in advance, and we allow nothing short of catastrophe to change it. That gives us a deadline and gets us researching.
- We immediately make airline reservations because we travel on mileage. If nothing is available, it is a catastrophe and we have to choose another date.
- As soon as the airfares are lined up, we start emailing everyone we know, asking whether they have ever spent time in our target city and, if so, what hotels, restaurants and entertainments they recommend — and why.
- We compare those results with information we gather online and from the city's tourist office. We focus on suggestions that rate highly with all three sources. Tourist offices tend to shy away from specific hotel or restaurant advice, but we look for exceptions. We try to engage someone in the tourist office in conversation so we have someone to call back with unanswered questions.
- Aside from the standard travel Internet sites such as Expedia, Travelocity and Priceline, we check the city out on Wikipedia and follow its links to the various places of interest.
- We troll for free days at museums, special price deals for seniors, AARP discounts at hotels, prix fixe specials at restaurants. If we're going to a show or a museum, we call there to ask for suggestions for nearby restaurants.