How to Plan a Hassle-Free Holiday Vacation

Plan a low-stress holiday trip with these tips for flight and train reservations, road trips, keeping kids happy and more.

How To Plan a Hassle-Free Holiday Vacation - Mother and Daughter at the Airport

by NEA Member Benefits


“It’s the most wonderful time of the year,” or so the song goes. But everyone who travels knows that winter weather, heavy traffic and flight delays cause additional stress during the holiday season. Keep things calm by planning ahead and using a travel checklist.

Conquer seasonal travel-related hassles using our tips and strategies. Make your list, check it twice and get ready to bring cheer and smiles while saving time and money as we head into the holiday season.

Plane and train tips

  • Research and book flights early. Winter break is one of the year’s busiest periods for air travel, so book holiday airfare from September to November 25 to avoid rising fares. Although peak ticket buying for Thanksgiving is August and the first half of September, you might still be able to find some great rates. Use an online search tool such as Google Flights or Momondo to uncover the best rate and set fare alerts on apps such as Skyscanner, Hitlist and Hopper. Be sure to check out NEA Travel for airfare as well. You’ll receive $100 in NEA Travel Dollars when you complete your flight bought through NEA Travel. Regardless of what site you use, see a fare you like? Don’t delay booking it.
  • Travel early or late. Flying early in the morning or late in the day could mean lower rates and better on-time performance.
  • Score holiday savings. Check alternate airports, connecting flights rather than a nonstop and flying on Thanksgiving or Christmas Day to help save you money.
  • Track your flight. Download your airline’s app but also look for apps such as FlightAware that track flight status and delays. You can also visit the airport website, such as Baltimore-Washington Thurgood Marshall International Airport, for arrivals and departures information.
  • Reserve airport parking. Airport parking lots fill up fast during the holidays. Check out off-airport parking options such as The Parking Spot, where you can reserve a parking place ahead of time and take the lot's shuttle to the airport. You can also find coupons on their website.
  • Book holiday trains early. Thanksgiving is the busiest time for train travel, and some trains do sell out. In general, prices increase substantially closer to the travel date at any time of year. If you’re planning a train ride on Amtrak, for example, it’s recommended you buy tickets as soon as they are available (11 months before scheduled departure). Amtrak’s booking tool is handy, and you should look at the site’s Deals & Promotions section. 
  • Study car rentals. Book about six months to six weeks ahead to avoid a limited choice of vehicles during the holidays. To save money, use your NEA member discount through NEA Travel or check general travel sites as well as car-rental agencies. You can even call to ask about discounts. The number of days counts, too: It may be cheaper to pay for a weekly rate rather than rent for a few days.

Road trip strategies

  • Think safety first. Get your car checked (brakes, tires, oil, etc.) before you head out. Be sure to pack an emergency kit that includes a flashlight, blanket and small shovel.
  • Plan your route, but be flexible. Study driving options before you hit the road, and use an app such as Waze for real-time updates from other drivers to avoid traffic tie-ups.
  • Pack your trunk. Plan ahead for how you will transport holiday gifts and any winter sports gear.
  • Gas up. Start with a full tank to avoid lines and higher prices on the highway. GasBuddy is a valuable app that helps you find cheaper gas prices on the road.
  • Make smart stops. Save time and money on mid-travel stops by downloading iExit interstate highway guide to locate gas stations (with prices); it also has restaurants (with ratings) and ATMs.
  • Book city parking. An app such as ParkingPanda saves time and money on spaces in city lots. Parking on Thanksgiving Day or Christmas? Call the lot even if you have a reservation—to be sure it’s actually open.

Keeping the kids happy

  • Get kids involved. It’s always best to talk with your kids about your travel plans and what to expect well in advance. First-time fliers will benefit from a step-by-step rundown. Ask for kids’ vacation suggestions, and keep a countdown to the big day.
  • Take favorite stuff. A few toys and snacks are essential, and don’t forget the video game or tablet to keep kids occupied. Take earbuds and headphones. Books and audiobooks make great travel companions, too.
  • Consider childproofing. If you have small children, check with your hosts about specific concerns, or speak with your hotel. Take along any childproofing items (outlet covers, for example) as needed.

Gift guide for travelers

  • Keep gifts unwrapped. TSA rules mean gifts go through security screening, so plan to wrap items after you arrive at your destination. It’s a good idea even if gifts are in your checked luggage.
  • Consider shipping gifts. The holidays challenge the lightest packers, so check luggage weight restrictions. An extra checked bag may cost you $35 or $40; shipping can be more convenient.
  • Bring an extra bag. An easily foldable bag may be useful for gifts you want to carry home.

Ready, set, go: Advice for your travel day

  • Check in. Confirm your flight’s status; you can check in online up to 24 hours before you fly. Print your boarding pass or keep it on your phone.
  • Keep travel documents handy. Be sure any boarding passes, identification and other material are in a convenient place.
  • Leave early. Whether you’re driving or taking a plane or train, allowing plenty of extra time will keep everyone less stressed. If you’re parking at the airport, factor in time in for that.
  • Charge your devices. Be sure your phone is fully charged, and keep chargers handy during travel.

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