How To Survive Holiday Travel: Tips and Tricks from Savvy Travelers

How To Survive Holiday Travel: Techies Tips & Tricks
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With the leaves falling and the temperature dropping in New York City, there’s no denying that the holiday season is fully upon us. While one of the merriest times of year, I get the chills just thinking about traveling from Thanksgiving through New Year’s Day. Let me explain...

Two year ago, having booked last minute (and overpriced) flights home, I arrived at the airport excited, optimistic and, most importantly, armed with gifts for my two adorable nieces. I was more than ready for my 3,360-mile journey to Brussels to see my family. Or so I thought. After being delayed four hours, I realized I’d forgotten my noise canceling headphones in addition to my favorite FaceCradle travel pillow! After a seven-hour, turbulent and sleepless red-eye, I eagerly got off the plane—only to wait in line for another two hours at immigration. In my delirious and groggy state, I forgot my nieces’ gifts in the overhead compartment. I only put two and two together when I was already home, greeted by a pile of presents under the Christmas tree. Needless to say, it wasn’t a good start to my holiday!

Many of us have been in similar nightmarish travel situations, especially during the hectic hustle and bustle of the holidays. I’ve heard countless stories from colleagues and friends. For this reason, I’ve reached out to some of the savviest travelers and hustlers I know to help put together a list of the top six tips and tricks to better ensure smooth sailing this season:

1. Travel outside of the box

While many of us will be traveling to see friends and family, it’s also a great opportunity to go somewhere new and adventurous. For example, next on my dream bucket list is a trip to Finland to admire the Northern Lights from a glass igloo. Where have you been yearning to go?...Start dreaming. Better yet, start planning.

"Travel is the best time to push past limiting beliefs. On a recent trip with other entrepreneurs, we walked barefoot through the desert of Lençóis Maranhenses in Brazil, for eight hours straight. It was physically and emotionally terrifying but showed me that we are all capable of much more than we are comfortable with in day-to-day life."

-Lisa Winning, Founder & CEO of HeTexted

2. Avoid rookie booking mistakes

Make sure you get the best airfare deal you can for the right seats. Trust me, the dates you choose and your seat selection can make or break you on a long or overnight flight.

"When booking flights, I make sure to turn my website cookies off or open up an incognito window on my browser as to avoid travel websites from pricing me dynamically. It’s also helpful to book on the right days and times: FareCompare has found that the best time to book U.S. domestic flights is Tuesday at 3 p.m. Eastern."

-Amadeo Brenninkmeijer, Founder & Angel Investor

“I always load my phone ahead of time with helpful apps, such as Kayak (has a useful built-in flight tracker) and Hopper (tells you the best time to fly and buy). Once booked, I like to check out SeatGuru to help me decide which seats to choose for each specific flight. The website (also available as an app) provides you with a seating map and reviews for each airplane."

-Adrian Gradinaru, Founder & CEO of Sailo

3. Pack practicallyit’s both a science and an art

A well-packed suitcase can save you time, energy and headache! Set yourself up for sartorial success: choose your outfits in advance, pack your clothes methodologically and remember that less truly is more.

“At citizenM, we redefined luxury as being all about inspiration, comfort and convenience. When I travel I therefore like to eliminate any possible distraction or stress so I can enjoy exploring a new city to the max. For me this means planning an outfit for each day of the trip in advance, and packing them in that order, so that no ‘what do I wear today?!’ decisions need to be made. After I’ve worn the outfit it goes back into the suitcase, eliminating the need to pack my suitcase at the end of the trip. It helps me tremendously!’”

-Noreen Chadha, General Manager of CitizenM Times Square

"Pack light! Travel is meant to be adventurous and fun, so I take as little as possible. I only bring carry-on luggage with a couple black dresses (that you can wear to tech meetings and out at night), denim, and jewelry to dress things up. I firmly believe you can do everything from your smart phone and never bring a laptop."

-Lisa Winning, Founder & CEO of HeTexted

“The inter-fold technique. Wrap all items around a core (i.e. dopp kit). Helps to avoid creasing. Instead of having the dopp kit as a separate piece, you wrap all t-shirts, shirts and pants around it. I’m [also] a sunglasses fanatic! I put all my sunglasses inside my shoes — that way I save space and give my precious shades some extra protection.”

-Joshua Udashkin, Founder & CEO of Raden

4. *Don’t* dress to impress

Have you ever worn tight clothes on a six hour flight? So tight that it cuts off your circulation? Well, it’s simply a bad idea. While looking presentable counts, comfort is the way to go.

“I always make sure to wear comfortable long pants (usually joggers), light tee, cashmere sweater, and easily slip off flats onto the plane. In carry-on: eye mask, ear plugs, makeup remover wipes, headphones, chargers, moisturizer (bliss fabulous face lotion) and if a long flight, a facial mist.”

-Kamiu Lee, VP of Business Development & Finance at Bloglovin

5. Buckle up and chill

Because spending the holidays sick in bed is just no fun, especially after all the travel effort you made to arrive at your holiday destination. Don’t disregard your wellness on board. Remember to hydrate, hydrate, hydrate. Try an Airborne effervescent supplement with vitamin C to bolster your immune system. Make sure to get yourself situated before take-off so your mind and body can begin to quiet.

“Just like 25% of the population, I get anxious when getting on a plane. To deal with it, I found that a few things help keep me calm and relaxed. In addition, I bring either magazines or a really addictive book so that the ‘visual channel’ of my mind is fully occupied with something concrete. It keeps my imagination from gaining a foothold with every bump or movement. Sometimes I resort to meditation. Headspace, which is a fantastic meditation app, has a specific meditation focused on fear of flying.” Read more about how to beat flying anxiety here.

-Serena Oppenheim, Founder and CEO of Good Zing

“I'm on the go non-stop, so flying is the closest I get to a break. I religiously pack my Bose noise-cancelling headphones in my carry-on for peace and quiet...and to watch movies!”

-Mohammed Haouache, Founder & CEO of Storefront

6. Pick your digs wisely

If you’d rather not burden family members by staying at their home (or you prefer privacy), keep in mind that there are many other options for you to rest your jet-lagged self. With so many choices, you’re bound to find the right place to stay, from hotels to apartments, even tree-houses and boats.

"The travel industry has changed. Accommodations are no longer limited to just hotels. There are a ton of non-hotel options (Airbnb, Couchsurfing, vacation homes, hostels, etc.), so travelers may miss out on over 90% of the options that are available to them unless they use a site that aggregates all the rooms.”

-Joseph DiTomaso, Founder and CEO of AllTheRooms

“Choosing a hotel for the holidays is tricky because prices tend to be higher. The more central a hotel is, the higher the average rate will be. If you're looking to stay in a city and are price-conscious, consider booking a hotel on the outskirts of the city or away from any major landmark. If you're traveling with a large family or group, take advantage of group rates to get the best hotel deal for everyone.”

-Jason Shames, CEO and cofounder of Skipper

So there you have it. Best of luck with your holiday travel plans!

I’d love to hear about any of your tips or mishaps in the comments section.

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