Sillin notes that the busy summer season can mean rising prices, but there are a few city-specific savings tactics that can take some of the strain off you budget.
First, look for insiders’ knowledge about the city you’re considering. Many major cities are covered by bloggers who focus on how to enjoy the city on the cheap. You could start your planning by researching online with the keywords "free or cheap" and the city's name. Some of the well-organized websites will even let you filter events by date, cost and your interests. Check the city's local newspaper sites for lists of free or cheap events. During the summer, many cities have free outdoor concerts and movie screenings; you can pack a picnic dinner and enjoy the warm weather and show.
Also, see if you can get around the city like a local. Sillin says that while it might make sense to take an occasional cab, especially in New York City, some cities have robust public transportation systems. Take a few minutes to study the city's layout before arriving and don't be afraid to ask locals for advice or directions.
If you're in town for more than a few days, consider time-based public transportation passes. For example, you can get a seven-day Unlimited Ride MetroCard for subway and bus rides in New York City for $32. (There's $1 new-card fee if you're not refilling an existing card.) You can even use it on the crosstown buses that can quickly get you from one side of Central Park to the other.
Explore new cuisine. One of Sillin’s favorite parts about visiting a city is trying the restaurants. Whether you save up and enjoy one of the city's finest eateries or find a hole-in-the-wall hidden gem, there's something for everyone. Luckily, many cities' must-try foods are on the inexpensive side. Chicago's hot dogs, Portland's doughnuts and Austin's tacos all often cost less than $5. You can also look for lists of cheap and delicious eats alongside the free-entertainment tips from frugal bloggers and local papers.
High-end restaurants will inevitably be pricey, but if it's on your "must-do" list, there could be ways to save. Some restaurants offer less expensive brunches or early evening tasting menus, or you might be able to grab a small bite and a drink at the bar rather than a full meal.
Sillin also suggests finding the “deals” if you’re going to shop. Some people see shopping as an intrinsic part of a vacation, and cities are often home to chains' flagship stores, boutiques and specialty shops. The wide variety of options could tempt you to overspend, but it also means there are plenty of opportunities to save.
If you're in the luxury market, look for sample sales where high-end brands might be charging (relatively) less for products formerly on runways or showroom floors. Trying to stick to a tight budget? Look for large retailers' clearance sales, particularly if you're visiting when stores are clearing seasonal items off their shelves.
Also, think outside the box when it comes to lodging. Most people know that hotels in the heart of tourist areas are often the most expensive, and many turn to home-sharing sites as cheaper alternatives. Another trick is to look for availability at hotels in the city's financial district. Holidays and weekends can bring vacancies at these properties, which may mean lower rates. Hotels right outside city centers, but accessible by public transportation, can also cost less.
Bottom line, according to Sillin, cities can be expensive, particularly during the busy summer, but there's a reason they're such popular vacation destinations. Whether you're interested in museums, shows, food, historic sites or all the above, there are ways to save and make the most out of your summer in the city.
Note: Sillin directs Visa's financial education programs. He can be reached at www.twitter.com/Practical Money.