Winter can be a tricky time to travel, what with holidays that bring insane fares, traffic-snarling snowstorms, and overhead bins stuffed fuller than a Christmas goose. But this winter is looking to be trickier than usual. Flights are fewer—which means deals will be tougher to find, planes will be full, and, should bad weather cause your flight to be canceled, it will be harder than ever to find seats on another plane. At the same time, pockets of value have cropped up in unexpected places, and new digital tools offer better solutions to age-old problems. Here’s how I’m planning to skate through winter:
1. Snag the Deals
Sneak away between Thanksgiving and Christmas.
December 3 through December 16 will be the best window for bargains at warm- weather resorts, which are relatively empty between the holidays. Think Arizona, the Caribbean, Florida, Hawaii, or Mexico. For early-season ski deals, look to the Canadian Rockies, which has relatively good snow in early December, or to places with world-class snowmaking, such as Vail.
Book Presidents' Day weekend, which is also Valentine's day weekend, in early December.
"Airlines won't start to lower their January and February 2014 fares until late November," says airfare expert Rick Seaney, founder of FareCompare.com, "so the perfect time to shop for Presidents' Day week- end airfares will be the first couple of weeks in December."
Escape to the sun in mid-January.
Unless you're going to a popular ski destination such as Aspen or Vail, "the cheapest time of year to fly within the Northern Hemisphere is the last three weeks of January and the first two weeks of February," says Seaney. Most airfares are 45 percent cheaper than peak summer rates. Go to Hawaii or Australia in late January and you'll pay well under half what you'd pay at Christmas."
2. Ace the Holidays
Hone your airfare searches.
The least expensive times to fly during the Christmas/New Year's window are, of course, Christmas Day and New Year's Day, as well as late afternoon and evening on Christmas Eve and New Year's Eve. Other dates for low fares differ from city to city, depending on when school lets out, and can vary wildly, from $1,000 one day to $400 the next. It can be tough to determine which days have the lowest fares to and from your destination, so do a one-way airfare search rather than a round-trip search. In other words, if you're trying to determine whether it's least expensive to fly on December 20, 21, or 22, a one-way search for each of those dates will tell you.
Try alternate airports.
If you can't find affordable fares to your Florida destination—say, Miami or Orlando—look at flights into Tampa or Fort Lauderdale, which are much less expensive over Christmas/New Year's. As for California, consider flying into Los Angeles—an almost always affordable hub—and driving to San Diego.
Use the right Web tools to find beach resorts that aren't sold out.
On a hotel company's site you should be able to see, at a glance, which resorts still have rooms available. Go first to the chain whose loyalty program you belong to or whose credit card you hold. Let's say it's Starwood: At SPG.com, under Quick Links, click on "Hotel Explorer," then click on the region and activities you want (for example,"Beach" or "Romance"), enter your dates, and you'll get a list of matching properties with availability. You can also find last-minute holiday deals at Travelzoo.com and TravelTicker.com.
Hit a fun city rather than the beach.
Instead of paying peak prices at a tropical resort, spend your money on restaurants, museums, and theater in a city—say, New York, Washington, D.C., or San Francisco— that loses its business travelers during the Christmas–New Year's window and thus has steep discounts.
Splurge on business class—or at least premium economy—to Europe. It should cost little more than coach did last summer.
It will be less expensive to fly to London, Copenhagen, Oslo, and Stockholm this winter than it has been for the past several years, says Seaney, and the lowest fares will be to Ireland, Germany, and Spain. Rome and Athens will be tough, notes business travel expert Joe Brancatelli of JoeSentMe.com, since there is no longer any airline that flies nonstop from the United States to those cities in winter. The good news, though, is steeply reduced business-class and premium-economy fares to Europe for the holidays, he says, since the business travelers who usually fill these seats aren't flying then. At press time, you could fly from New York to Paris for Thanksgiving on British Airways subsidiary OpenSkies, in its PremPlus cabin, for only $1,300; from New York to London for Thanksgiving in Virgin America's cushy Upper Class for $1,602; and from many U.S. gateways to many European destinations in Lufthansa's business-class lie-flat seats for less than $2,000. "The airlines are not promoting these deals," says Brancatelli— they're doing their savviest elite travelers a huge favor by not informing the masses—so uncover such fare drops through an e-mail alert system such as Kayak's price alerts.
3. Nip Problems in the Bud
Fly in the morning.
The earlier in the day you fly, the less likely it is that your flight will be delayed. Especially try to avoid landing between 7 and 10 p.m.—tarmac rush hour. And consider alternate airports; instead of flying into Chicago's O'Hare, for instance, which is notorious for winter hassles, choose Midway.
If you must book a connecting flight, choose a hub that is less likely to see bad weather or delays.
Stay away from the Northeast Corridor and Chicago. Opt for southerly cities such as Atlanta, Charlotte, Dallas, and Houston. European hubs that do well in bad weather, and are particularly pleasant and easy to connect in, are Copenhagen, Helsinki, and Munich.
Get a seat assignment at the time of booking.
Select the best possible seat using the airline maps on SeatGuru.com, which provide the pros and cons of each seat on the aircraft. If seat selection is not available at the time of booking, call the airline to get a seat assignment from a phone agent. Do not arrive at the airport without one, since this will significantly increase your chances of getting bumped if your flight is oversold (as is often the case during the holidays) or your aircraft is switched at the last minute.
Check in online 24 hours before your flight.
Checking in early reduces your chances of being bumped. It also increases your chances of getting a better seat—either an exit-row or bulkhead seat, or a better seat left empty by travelers with elite status who have just been upgraded from coach.
Traveling heavy? Ship your luggage, or get the right credit card.
If you're laden with ski gear or holiday gifts, consider getting a credit card that exempts you from baggage fees. The $95 fee for the Citi Platinum Select AAdvantage Visa Signature Card, the Delta SkyMiles American Express Card, or the United Mileage-Plus Explorer card is waived for the first year—which means you and at least one companion can check bags for free for the entire year. The cards also give you priority boarding, enabling you to get to your seat—and the overhead bin—sooner.
When bad weather is brewing, be the first to find out if your flight is canceled.
The sooner you know, the better your odds of getting rebooked on an alternate flight. Check your airline's Web site and Twitter feed for updates on airport closings and flight cancellations.
Have a Plan B.
If there are weather issues the day before your flight, delays may continue for days. So the night before your flight, go to FlightStats.com, open the drop-down menu under "Delays," and click on "Global Trends." At a glance you will see which airports and airlines are having the most cancellations and delays, and—just as important—which are not. Note which huge airports are having no weather or cancellation issues so that, if your flight gets canceled and there are no seats available on alternate flights to your destination, you can ask to be rerouted to a storm-free airport and from there to your destination. While you're at FlightStats.com, sign up for a status alert for your flight.
4. Solve Snafus Fast
Canceled flight? Head to Vegas.
Consider flying to a huge airport with clear weather, even if it's not in the linear path to your destination (see "Have a Plan B," above). If you're headed cross-country, Las Vegas is often a good option, since it's got plenty of flights out, as well as inexpensive hotels. In other words, instead of sitting around Boston for four days trying in vain to get on a flight to Seattle, fly to Vegas and from there to your destination the next day. If you're a family with kids and you cannot find seats together on the same plane, consider splitting up, with each parent taking one kid.
Know which alternate flight you want before you phone the airline.
Don't depend on an airline agent to find the best options for you—especially since there are better tools out there for digging up flight and seat availability than the agents' computer systems. You want to be able to tell the airline agent where to look for the departures and seats that you already know are available. So go to FlightStats.com, sign up for an account, click on the "Flights" drop-down menu, choose "Flight Availability," click on the "Advanced" search option (which allows you to specify the airline and connecting city—e.g., an American Airlines flight connecting through Las Vegas), and find the seats you need.
If an airline's phone lines are jammed, call one of its overseas reservations numbers.
Avoid long waits on hold by phoning the airline's reservations desk in the United Kingdom, Germany, or Australia. You can get those contact numbers on your airline's Web site. Use Skype so the call is cheap.
Stranded in an airport? Consider joining the airline's club for a day.
Not only can you escape the circus in the terminal, but you'll get access to agents who will likely do a better job of helping you get onto an alternate flight. The cost is typically $50 a day.
If all else fails, turn to Cranky Concierge.
When you're stranded and need urgent help getting on the first flight out, reach out to Brett Snyder of CrankyConcierge.com. For a $150 fee, he can work miracles for up to four people traveling on the same flights.
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