Image: Napa Valley vineyard
Charles O'rear  /  CORBIS
If you want to avoid the Napa Valley crowds, traffic and high prices, forget the summer. Instead, come in early spring. That's when the mustard flowers are blooming and the hotels offer gentler rates than they have in summer. If you want to pay even less, visit in winter. If you can handle some wet and foggy weather, you'll find the cheapest rates of the year.
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updated 9/8/2009 11:00:40 AM ET 2009-09-08T15:00:40

If you want to visit such hot getaways as Hawaii, Aspen, New York City, Paris, or Napa, you can bring a large billfold. Or you can time your visit to the periods during the year when these places are at their most affordable.

When is the best time to visit to get the most bang for your buck? It varies from destination to destination. That can mean shoulder season or even off season, or finding that window in high season when rates take a dip, if only for a couple of weeks. And it's worth the effort, because the savings can be anywhere from 20 to 50 percent off high season prices. They may not be truly "cheap" at that point, but they often become affordable.

Take London, which provide sticker shock regardless of how low the pound has fallen. Both airfares and hotels fall between October 15 and March 31, with the exception being the Christmas and New Year's holiday period.

The caveats are weather and daylight. Wet, rainy and cold weather is not uncommon, and the lack of daylight is, um, profound. In mid winter, the sun sets in London at 3:45 p.m. But if you accept that museums, the theater, and restaurants are where you'll spend the lion's share of your waking hours, you probably won't mind it so much.

Then there's Hawaii. How do you deal with a place where room rates seem uniformly high throughout the year? You go now, since the recession has left thousands of empty hotel rooms throughout the state. And to make sure the rate is even lower, plan on traveling between September and early December, which has long been the low season for travel to the Aloha State. A company like Pleasant Holidays (www.pleasant holidays.com) has long been the loss leader for air/hotel packages. But an increasing number of properties are discounting directly.

As for the Caribbean, the merry month of May represents the sweet spot for Caribbean travel. Prices have dropped as much as 50 percent from winter highs, the weather is still terrific, and the spring break crowds are gone. The weather gets warmer in June, but it can still be a terrific time to go. While July and August are quite hot, they might still be preferable to the weather in the U.S. at the same time. September through November represent the quietest time in the islands.

Image: New York City
flickr.com/idletype, Troy McCullough
The recession has forced many New York City hoteliers to trim their rates but the best hotels are still expensive. So plan a visit between January and March, when you can pretty much guarantee getting a great deal at virtually every hotel in the city. If there's a drawback, it's those chill winds off the Hudson. But there are plenty of upsides as well. It's the easiest time of the year to score Broadway tickets and a coveted restaurant reservation.
Of course, there is one caution in the Caribbean and that's hurricane season, which extends from June through November. You should have travel insurance and stay at a hotel that has a hurricane policy (with refunds clearly spelled out). It's worth noting that hurricanes rarely, if ever, strike the southernmost islands in the Caribbean, such as Aruba, Barbados and Trinidad.

Then there's New York City. While the recession has cut the average hotel rate in the Big Apple, you still need all the help you can get. January through March represent the best time to get a deal in New York City. But dress warmly—those winds off the Hudson mean business

Image: Sant'Angelo Bridge over Tiber River
Dennis Degnan  /  CORBIS
The primo time to visit Rome is from April to June or from late September through October. You avoid the heat, the tourists and the highest prices at these times. Winter is an option, but be prepared for the inevitable museum closings and renovations, as well as shorter hours. But if all you need is a fix of “la dolce vita” and maybe a plate of spaghetti carbonara, then a quick trip in January and February will be easiest on the wallet.
Want to go skiing in a tony Western resort like Aspen without dipping into your kids' college fund? Then go in early December. Rates at such luxury hotels as the Limelight Lodge are a mere $159 a night for a mid-December stay. In February, that same room jumps to $409 per night. Other dates worth look at are the entire month of January, excepting Martin Luther King Jr. Weekend, and dates after March 20.

Balmy breezes and empty beaches are why Martha's Vineyard and Nantucket are best during May and June. Before the private jet set—and the likes of President Obama—arrive for a little R&R on these storied and pricey islands every summer and fall, most hotels offer weekend deals to entice mainlanders all of stripes. You'll especially see a lot of midweek deals. You can stroll on these island beaches during May and June, but swimming is only for those with iron constitutions. These waters don't really begin to warm up until July.               

Of course, some places are not governed by season, like Moscow and Tokyo, and their high rates are pretty much stuck in the stratosphere. But if you pay close attention the calendar, you'll see that most places will give you a break.           

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