Travel Tips for the Holidays

I know, it's not even Halloween yet and people are already thinking about the winter holidays. In this Bankrate.com piece by Dana Dratch ("9 Ways to Manage Holiday Spending"), I shared some tried-and-true travel advice.

My biggest tip would be to cough up the extra money to fly nonstop. Blizzards have a funny way of occurring the busiest travel season of the year, and you don't want to deal with the extra stress of missed connections.

As for being flexible on travel dates, I've flown on Thanksgiving Day, when the airports were empty and the TSA agents were super-friendly. Upon seeing my slice of chocolate bourbon pecan pie that I was going to hand-carry onto the plane, the TSA agent joked, "No mashed potatoes?" A jovial TSA agent, imagine that.

Photo Caption: Last year's Snowtober, when it snowed in New York City a few days before Halloween
Photo by Amy Chen

Post-Labor Day Travel Savings

When Kelli Grant of SmartMoney.com asked me for destinations that cost less after Labor Day but still feel like summer, I felt a slight tinge of regret for blowing several vacation days earlier this summer. If I waited just a few months, I could've saved hundreds of dollars.

Read the article here on SmartMoney.com.

My first money-saving suggestion was Cape Cod. A few summers ago, I visited in August and sat in bumper-to-bumper traffic on Saturday. After chatting with the bartender at the Bramble Inn in Brewster, I learned that Saturday is the absolute worst day to travel for a weekend getaway since many weekly rentals "change over" on Saturday. Lesson learned.

My other suggestion was Hilton Head Island, which apparently has a lower risk of being affected by hurricanes than, say, the Outer Banks. As much as I love the idea of traveling to the Mexico or Caribbean during hurricane season (cheap hotels!), sometimes the uncertainty cancels out the relaxation. For example, just this week, Tropical Storm/Hurricane Ernesto swept through coastal Mexico and many tourists at Cancun resorts were evacuated, according to this Associated Press article.

Depending on your flexibility or travel needs, I probably would try to pick a vacation destination with slightly less risk. Then again, I was in Seattle last weekend and my return flight was oversold (thanks, United!). I ended up at the airport Holiday Inn eating some pretty terrible food, showering in my flip-flops, and taking the first flight out, which meant waking up at 4:45 a.m. Monday and heading straight from SFO to the office. When is it worth adding something like the potential of a hurricane to your travel stress? Only you can decide.

By the way, I second the suggestion of Hawaii, which was recommended by Courtney Scott of Travelocity. A few years ago, I spent Labor Day weekend on the Big Island with my mom. We tacked on a few days after the holiday weekend (the long weekend typically overlaps with my birthday, yet another perfect excuse to travel).

Photo Caption: A small beach facing one of the ponds in Cape Cod
Photo by Amy Chen

Up in the Air? Try on the Ground

If this is what holiday travel is going to look like, good luck to us all.

I've just returned from a quick weekend trip to San Francisco. It's been a while since I've experienced such a horrible breakdown in the system, but my return flight was, in a word, hellish. I spent four long hours at SFO before boarding the plane at 1:30 a.m. PST. The flight itself, thanks to strong tailwinds, was a miraculous 4.5-hour jaunt — so my cross-country trip basically took as long as the time I spent at the airport. Call me crazy, but that's just unacceptable.

While waiting for the plane to show up, I asked for–and was given—an upgrade to a seat with extra legroom (a $40 value). As the hours ticked by, I repeatedly asked the gate agent what other compensation could be given. The airline employees were firm in saying that due to weather delays, it was out of JetBlue's control. By this time, it was after midnight. I asked for water and restaurant vouchers. An employee fetched a case of bottled water, but said that all the airport restaurants were closed so any vouchers they could offer wouldn't help. I was then told that there was a ground delay at JFK so the incoming flight had sat on the tarmac for two hours. Somehow that information didn't comfort me much. If the weather on the East Coast was truly that atrocious, I wonder why JetBlue's flight to Boston took off on time. Note: I've contacted JetBlue, the FAA, and JFK airport to double-check that there was in fact a ground delay at JFK airport. No one has confirmed that yet.

I think my breaking point came when the JetBlue gate agent told me that she has worked for the airline for 5 years. "If you're flying to New York in the winter, you should expect delays," she said. Maybe she was trying to commiserate but somehow that response seems inadequate, especially since it hasn't even snowed yet. Does that mean that airlines should only operate seasonal service in the summer?

As for my next trip, I think I might pack an old bed sheet or something so at least I'll have something clean to spread on the floor as I join other stranded travelers on the ground.

Photo: Amy Chen