A Traveling Mom’s Holiday Travel Tips and Deals

Kid crawls through playspace Ready to plan your winter family holiday getaway? Amie O’Shaughnessy, editor of family travel site Ciao Bambino! shares her top tips to make your family travels smoother, and rounds up some great holiday escapes.

Never again.

Those were the last words out of my mouth when I planned our last extended family Christmas vacation to Mexico two years ago.

At that point, airlines and hotels were asking for the usual holiday super-premium pricing for any travel between December 21 and January and I was banging my head against the wall trying to find something affordable and appealing for all tastes and ages.

In the end, we had a terrific getaway and I’d do the work over again in a heartbeat. After all, spending the holidays in a vacation destination can be much more relaxing and fun than staying at home.

The upside of the economic downturn for travelers is that there are unprecedented deals and specials, even during peak holiday travel dates in some destinations. However, due to decreased capacity, the flurry of inexpensive airfare are coming to a close—which means it’s time to jump on a good deal NOW. Moreover, many airlines are now charging additional fees for travel on peak days.

There are basic holiday travel tips that extend to everyone, kids or no kids. The issue for parents is that travel nightmares are extra painful with kids in tow.

Be diligent about the dates & logistics. By avoiding peak travel days, you are more likely to avoid crowds and this year’s airline surcharges—see Fare Compare’s List of Peak Travel Surcharge dates. Opt for alternate, smaller airports when possible and take non-stop flights.

Check out America’s Best Alternate Airports: New York City, Los Angeles, Miami, Chicago, San Francisco and find others in More of America’s Best Alternate Airports: Boston, Cincinnati, Dallas, Washington, DC

Normally, I’d say it is important to book seats at the time you purchase the flight, although I was shocked to read that some airlines are charging new fees for reserving seats over 24-hours in advance.

First flight out. Catching an early flight out increases your chance of an on-time departure. If a flight gets canceled, you have a better chance of getting on another one that day.

Check in online and arrive early. People carrying gifts and extra carry-on luggage dramatically slow up the security line. Avoid being stressed in long lines by arriving early with plenty of time for delays at one point or another in the check-in process.

Prepare for delays. Wise advice from Nancy Solomon, a mom with 4 kids under 10, “I plan for the worst and assume that we may get stuck or delayed and that our luggage may get lost. Included in my carry-on (usually a small rolling suitcase) is a change of clothes for everyone, food (mostly fruit so we can avoid carb-loading), medicines, and electronic chargers for the airport. Without the chargers, I become this crazy mother, rationing battery juice to ensure that the games, iPods, computer will last through the flight.”

For more, check out Nancy Solomon’s A Traveling Mom’s Tips for Visiting London With Kids.

Pre-ship luggage and gifts. Although shipping can be expensive, the new airline baggage fees reduce the cost difference. Logistics at the airport are much easier without piles of luggage. We’ve used FedEx for luggage and found that it is expensive but easy. The good old U.S. Post Office is more affordable and works fine, as long you ship at least seven days ahead of time.

Moderate sugar intake. Treats and sweets are everywhere over the holiday period. A welcome distraction in some instances, but it’s a nightmare if you need your kids to be calm and patient during a flight delay and they are on a sugar rush. Set expectations with your kids that sugary sweets will be limited in and around your travel days. Request that family and friends to minimize treat-related gifts.

Get creative with activities. At this point, it’s amusing how often I find myself not following my own family travel advice. On a recent four-hour road trip with my 6-year-old, I had no plan to entertain him on the way. Not surprisingly, we were all going nuts halfway through the drive. Given the likely travel delays over the holidays, meticulously plan entertainment options.

I love that babies are entertained with simple things like car keys and Starbucks coffee sleeves, however, entertaining toddlers and younger school age children is a different story. Check out Ciao Bambino’s long list of ideas to help keep kids entertained on planes –essential reading if you need new ideas and insight.

Or get more information on traveling with kids in our Family Travel section.

Leverage the Web. I like to have little structure when I’m on vacation and typically avoid making many reservations ahead of time. However, the holiday period is a different story. It’s worth taking the extra time to book restaurants, special events, and babysitters weeks before you leave.

The Internet is a phenomenal resource to research and book restaurants and activities for an upcoming vacation. Many concierge desks answer emails now too—you may not even have to pick up the phone to book all you need.

Select and book babysitters well ahead of time. If you know you want an adult-night out, do the legwork a few weeks in advance. For liability reasons, most hotels will not book a sitter on your behalf, but instead, will refer you to a local agency. The upside of an agency is that you can check references and get detailed information on available sitters. The downside of an agency is that they often charge steep fees for their services, and surprise, surprise—many will charge premium service fees over the holidays. We publish average starting rates for babysitters for all properties in the Ciao Bambino portfolio under Families Should Know.

I’m able to track general availability and price trends through the requests that go to our portfolio of properties. Although highly coveted beach destinations and properties seem to be at capacity over the peak holiday period, there is still availability and fantastic family-oriented specials running in appealing destinations for families. A few of the options that caught my eye include:

Kimpton’s oceanfront Vero Beach Hotel & Spa in Central Florida is running a hotel package for stays through December 30, including accommodations for two adults and two children, a goodie bag of pool toys, a two-hour bike rental for two adults and two children, an in-room movie, milk and cookies, and a donation to the Homeless Family Shelter equal to 5 percent of the room rate. Rates for a family of four start at $175 per night.

The ideally located Le Parker Meridien in New York City is offering a 20 percent discount off best available weekend rates from November 20-25 and December 20-27.

More travel ideas from Amie O’Shaughnessy: 7 Reasons to Choose a Family Ranch Vacation

The Resort at Paws Up in Greenough, Montana is offering an incredible Christmas package including a personal Santa for every family, Christmas Eve dinner and kid’s party, a tree in every guest room complete with a personal stash of decorations, a holiday horse-drawn sleigh and wagon ride, ice skating, holiday games, and a Christmas Day Brunch.

The starting rate for accommodations and breakfast, lunch, and dinner each day for a family of four is $9,543 for a five-night stay. Available from December 22-29.

On October 17, 2009, Peter was broadcasting from the Resort at Paws Up. Click here to check out guests from the show. Listen to the show online here:

Hour 1

Hour 2

Hour 3

And check out more destination information with our Ask the Locals Travel Guide: Greenough & Missoula, Montana.

Mammoth Lakes is known for early, fantastic snow conditions (typically, skiing is well underway by Thanksgiving) and now they have direct flights into the area from Los Angeles, San Jose and Reno (connections from Seattle and Portland). The Village Lodge at Mammoth has condo rooms that are ideal for families and there is holiday inventory available, although rates are not discounted, there’s a laundry activities in town in addition to this area’s phenomenal skiing including an outdoor ice rink, snow tubing, and dog sled tours. Rates for a family of four start at $254 over Thanksgiving and $569 over Christmas/New Years.

Get some Tips for Finding Family-Friendly Villa Rentals.

Hawaii is one of my favorite beach destinations for families, although flights there can be very expensive. One strategy to find more reasonable fares is to fly to Honolulu on Oahu where there is more flight traffic and options from which to choose.

Turtle Bay Resort on the North Shore is located far away from the bustle of Waikiki and the wide variety of oceanfront rooms, suites, and villas set this property apart from the other hotels in this quality category. They are running a Christmas/New Year promotion where the fifth, sixth, or seventh night is free and includes a complimentary room upgrade (based on availability). Rates for a family of four start at $289 per night.

By Amie O’Shaughnessy for PeterGreenberg.com. Amie O’Shaughnessy is the editor of Ciao Bambino!, a family travel resource offering tips and advice for travel with kids and comprehensive reviews of the best family-friendly accommodations.