Guide to Traveling During the Holidays

We know that traveling during the holidays can be overwhelming, but we’ve thought out all the details to make your trip one less thing to think about. We put together a list of must have carry-on essentials, what layers to wear to and from your destination that are comfortable, yet stylish, and our top locations followed by some extraordinary holiday festivities you should consider for a magical winter seasonal getaway.

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Carry-on Essentials

With the surprise of the unknown you can never know who may end up sitting next to you on the plane. Regardless, headphones are a great way to escape into your dream vacation before arriving to the real thing.

A great book or magazine can keep you entertained throughout the small or long hours of a flight. With great reads it can make your dreaded flight into one you may never want to leave! 

No one likes the feeling of being jet lagged so make sure you bring a water bottle with you to keep hydrated. If you have an international flight, make sure to bring 1Above Anti Jet Lag Flight Drink Tablets for prevention and relief from travel fatigue. We are huge fans of these tablets!

An RFID travel wallet is key on your journey abroad, which will keep your credit cards and passport free of electronic thieves from scanning your personal information from you through your pocket.  

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Eliminate the stress of a low battery phone by always carrying your charger. Just in case there is no plug around, a portable charger is inevitably your best bet. Or we highly recommend smart luggage, Away, which has a built in charger to their carry-on suitcase. Never scour the airport again for a plug. 

Whether your flight is 12 hours or 2 make sure to always pack a healthy snack and some breath mints to remove any lingering traces. 

Taking a snooze on the plane is always a great way to arrive to your destination feeling rejuvenated. An easier way to make sure your getting in some shut eye is by bringing an eye mask to block out any light that may come in your direction. Check out our favorite silk eye sleepmask ever!

Airport Style

Be an expert in airport style this year. You can never go wrong by wearing a combination of these pieces while on the go. Keeping it simple with multiple layers will ensure you the most comfort and style during those long plane rides and climate changes.

Unless you're planning on tending to aching feet while traveling, we recommend leaving the heels at home. A good pair of athletic shoes, flats or boots will be much more kind to your feet during your travels. Don't forget a pair of cute socks to protect your feet from those nasty airport floors during security. 

As far as bottoms go, we suggest something with an elastic waistband such as a stretchy pair of denim, faux leather leggings, or even a stylish track suit to help maximize your comfort on crammed airplanes.

A simple tee under a button up is perfect for layering up or down for any weather changes during your journey. What better way to pull together an outfit than with the perfect casual jacket or comfy sweater. It's hard to go wrong here and it's up to you how you want to look when you arrive at your destination. Considering the hassles of airport security and getting through it quickly, our best advice would be to keep it simple on the accessories, a light scarf, dainty necklace, small cross body purse, and small stud earrings. Regardless, your journey to your destination should be just as simple as the destination itself.

We would absolutely LOVE to help take care of the rest of your travel wardrobe. Tell us more information about your personal style and travel details here! Rent up to 4 items. We will send you options to approve before your trip and those approved items will be waiting at your hotel destination. Once the trip is over, you leave your items in a pre-paid shipping envelope with the front desk to ship back. Take all the hassle out of packing and planning your wardrobe and discover a new way to travel and experience fashion!

Holiday Luxury Hotel Destinations

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The Plaza Hotel, New York 

New York City is a magical place to spend the holidays, especially if you choose to experience the 25th anniversary of Home Alone 2: Lost in New York. The Plaza is excited to give film fans the opportunity to ‘Live Like Kevin.’

Staying at The Plaza Hotel, you're just ten minutes away from the Wollman Rink and Rockefeller Christmas Tree. If you're looking for something else, the Union Square Holiday Market is just a fifteen minutes train ride away from this luxury hotel. For something style related, check out the Volez, Vogez, Voyagez – Louis Vuitton exhibition, open through January 7th at the former American Stock Exchange building. 


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The Conrad Chicago Hotel

The Conrad Chicago Hotel is the perfect stay to get your holiday shopping done. It’s only a short walk away from the Magnificent Mile where you can shop for holiday gifts from top fashion brands. There are also many spectacular holiday events to visit that are less than ten minutes away. Between the zoo lights at Lincoln Park, the Christkindlmarket, caroling at Cloud Gate, ice skating at Millennium Park, or visiting the Navy Pier Winter Wonderfest, there is no doubt that you’ll spend every moment in joy here in Chicago this holiday season.


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Faena Hotel, Miami Beach

Miami, Florida might not be your typical go-to holiday trip, but we’re confident that’ll change once you check out these fun festivities! The Faena Hotel is the perfect luxury stay with amazing ocean views this holiday season. With Santa’s Enchanted Forest and Gulfstream’s Park Symphony of Lights just thirty minutes away, this trip will surely turn into the perfect holiday getaway. If that isn’t enough, their Miami sea aquarium holds an annual Christmas Gala that’s filled with unlimited cocktails, salsa performances, and not to mention their project to help children in need called ‘A Toy for Every Child’. If beer is more your style then make sure to check out the Bousa Brewing Company with their Ultimate Holiday movie series. Christmas giving, lights, cocktails, beer, and holiday movies, who would want to miss out on this cheery holiday celebration?


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Loews Regency, San Francisco

San Francisco’s Loews Regency Hotel is a great stay with breathtaking views of the city and is decked with traditional Christmas decor! A holiday favorite, Tchaikovsky's Nutcracker is a classical ballet that brings fantasy to life and is a must see! Bring your family and friends to A Christmas Carol and check the "humbugs" at the door! The Great Dicken’s Christmas Fair is only thirty minutes away and is a holiday favorite. Stroll by and see the spectacle of sparkle of Ghirardelli Square any night of the week. You can stroll the Embarcadero and warm your hands (and tummy) with a bowl of clam chowder. San Fran will sweep you off your feet alongside it’s quaint charm of the city.


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Montage Laguna Beach

Montage Laguna Beach is an excellent couples retreat that is set on an oceanfront bluff with sweeping panoramas of the Pacific Ocean. It’s only thirty minutes away from the Christmas boat parade and only less than five minutes from the annual Sawdust Art Festival Winter Fantasy. At the hotel join in on amazing dining experiences, taking in the custom designed Gingerbread Village and Hanukkah Menorah Lighting during the eight nights of Hanukkah.  They even have fantastic New Year's Eve celebration options at different parts of the hotel. This romantic getaway is the ideal holiday treat that couples need for a little R and R this time of year.



Grace Bay Club, Turks and Caicos

An unexpected, but worthwhile holiday destination overseas this season is awaiting you at the Grace Bay Club in Turks and Caicos for some of the finest villa experiences in the Caribbean. Join their Christmas festivities early December with their beach barbecues, holiday crafts, and Maskanoo parade celebrated the day after Christmas along Grace Bay. This trip will satisfy your perfect Caribbean craving, adding some warmth to your winter, while adding a twist to your typical holiday celebrations.

To book these wonderful luxury accommodations, please contact our travel partner, Travel Hub 365. They offer Worry-Free, Expert Planning,  Unforgettable Luxury Experiences and Exclusive Perks and Upgrades to travelers across the globe. Email and use code TRVLPORTER for 50% off your booking fee!  


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