No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels

Post originally Published November 17, 2023 || Last Updated November 18, 2023

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No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Overbooked Flights Leave Travelers Stranded

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels

There's nothing like arriving at the airport, ready to embark on a long-awaited vacation or head home for the holidays, only to discover your flight has been overbooked. This nightmarish scenario plays out far too often during the busy holiday travel season, leaving countless travelers stranded at the airport with no clear plan on how they'll reach their destination.
Airlines routinely overbook flights, selling more tickets than there are seats available, banking on a certain percentage of passengers not showing up. While this tactic may work in the carrier's favor most days, it can spell disaster when everyone does actually show up, especially around the holidays. Suddenly the airline finds itself with too many passengers and not enough seats to accommodate them.

When a flight is overbooked, airlines will first ask for volunteers willing to take a later flight in exchange for compensation. However, if not enough people voluntarily give up their seat, the airline can involuntarily bump passengers. The unlucky travelers removed from the oversold flight often endure extremely long delays, many times overnight, until space opens up on a later flight.
Samantha, a teacher flying from Denver to see her family in Ohio for Christmas, had the misfortune of being one of those involuntary bumps last year. "It was awful. I got to the airport and was told I no longer had a seat due to overbooking. The next available flight wasn't until the next evening, which meant I lost an entire day of my vacation. The small voucher they gave me was hardly worth it."

Overbooking becomes especially problematic during the holidays when so many people are trying to get home or take a vacation. Flights are already full, making it difficult to find seats for bumped passengers on later flights, which are also filling up fast. The result is excessive wait times at the airport, often 12 hours or more.

What else is in this post?

  1. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Overbooked Flights Leave Travelers Stranded
  2. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Hotel Prices Skyrocket During Peak Holiday Times
  3. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Public Transportation Breakdowns Cause Delays
  4. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Inclement Weather Wreaks Havoc on Travel Plans
  5. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Popular Tourist Sites Crowded to the Max
  6. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Restaurants Booked Solid for Holiday Meals
  7. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Impossible to Find Last Minute Accommodations
  8. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Trying to Drive Leads to Gridlocked Highways
  9. No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Holiday Travel Hassles Put a Damper on Festive Spirit

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Hotel Prices Skyrocket During Peak Holiday Times

The joy of the holiday season quickly fades when travelers start looking for hotel accommodations, only to be met with shockingly high rates and lack of availability. Popular destinations jack up their prices exponentially due to surging demand, leaving many scrambling to find lodging that won't break the bank.

According to data from Hopper, hotel prices in top US cities can increase by 60% or more around Christmas and New Year's compared to other times of the year. A room at an average hotel in Miami goes from $150 per night to $350+ during the holidays. New York, San Francisco and other major metros see similarly giant rate hikes. Even smaller cities experience 30-50% price surges.

International destinations follow the same pattern. A London hotel room averaging $250 per night the rest of the year might jump to $800 during Christmas week. Airbnb and other vacation rental sites reflect the same inflated pricing due to low supply and huge demand.
Families trying to enjoy inexpensive beach vacations or couples looking for a romantic winter getaway suddenly find themselves priced out of their desired destinations. Refusing to pay the outrageous holiday premiums, they often must settle for second-rate lodging options to stay within budget.

Julie and her husband Mike faced this dilemma when planning their post-Christmas trip to Paris last December. "We had been saving up all year for this big celebration trip," Julie explained. "Then we started looking at hotel rates for late December in Paris, and they were easily $600-$800 per night. We could maybe swing one night at those prices but no way could we afford an entire week." They ended up choosing more affordable Amsterdam instead.
Similarly, Mark and his wife Linda struggled to find affordable beach accommodation for their family vacation in Hawaii. "Hotel prices on Maui were just absurd, even for basic rooms, over $1,000 a night. We widened our search and eventually found a condo rental on the Big Island we could afford but it wasn't our first choice."

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Public Transportation Breakdowns Cause Delays

Holiday travelers relying on trains, buses, and subways often find their plans derailed when public transportation inevitably breaks down just when they need it most. Systemwide meltdowns leave people stranded for hours, causing them to miss flights, connections, and special events.
Public transit struggles to keep up with surging demand during the busy holiday travel season. Equipment and facilities get overstressed. Weather-related issues like snow, ice, and flooding can further disrupt normal operations. The result is chronic delays, cancellations, and general chaos—not exactly the transportation experience most folks want when heading home for Thanksgiving or Christmas.

Nowhere epitomize the pitfalls of holiday transit better than New York City. The NYC subway system strains under peak holiday crowds. Signal problems, switch failures, power outages, and other technical issues seem to spike right when the most people need to get around. The 2017 holiday season saw an incredible 79% increase in subway delays compared to the same period in 2016. Commuters found themselves trapped underground for an hour or more on jam-packed trains without heat or light—a nightmare scenario.
Travel guide author Leslie Nguyen recounted her holiday transit nightmare in NYC. “I was trying to get from Brooklyn to LaGuardia Airport to catch a flight home for Christmas,” she said. “First my Uber got stuck in traffic. Then once I got on the subway, we got trapped for 45 minutes with no explanations. I missed my flight and had to book a crazy expensive same-day fare since all later flights were sold out. It ruined my whole holiday.”

Laura Chen experienced similar delays heading to New York Penn Station to catch an Amtrak train to see family in Boston. “The subway stalled out twice on my way to Penn Station, turning my hour trip into almost three hours,” she said. “By the time I got there, I had missed my train. Every Amtrak for the next 2 days was booked solid, so I had to scrambling to rent a car at the last minute and drive to Boston.”

Failures plaguing old infrastructure lie at the root of many big city public transportation issues. Chicago’s “L” trains, Boston’s “T” subways, and DC’s Metro frequently struggle to meet holiday capacity. And when multiple parts of large interconnected systems go down, it compounds delays across entire networks.
Smaller cities with much lighter transit usage still endure holiday headaches as ridership spikes. Buses show up late if at all, commuter trains get overloaded, and breakdowns occur from the uncharacteristic volume. ”I waited over an hour in the freezing cold for a bus that was supposed to come every 20 minutes," recalls Molly White of her frustrated attempts to get home for the holidays in Minneapolis. "The schedules were totally useless."

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Inclement Weather Wreaks Havoc on Travel Plans

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels

Inclement weather throws the biggest wrench into holiday travel plans, grounding planes, making roadways treacherous, and shutting down entire transportation systems. There's nothing like an unexpected blizzard, ice storm, or hurricane to turn a festive family holiday into a stressful nightmare. And with climate change making adverse weather events more frequent and severe, the chances of getting derailed by bad conditions seems higher than ever.

Winter storms create the most disruptions during the busy Thanksgiving and Christmas travel periods across large swaths of the U.S. Each year, millions of travelers find their flights cancelled or delayed thanks to snow, ice and high winds. Trying to rebook on jam-packed alternate flights proves extremely difficult. And deteriorating road conditions makes driving perilous.
Jill was headed from Denver to Des Moines last Christmas when her flight got scrapped at the last minute due to a blizzard slamming the Midwest. "There were no other flights for two days. I couldn't reroute through another city because that whole region was impacted," she explained. "I ended up having to rent a car and drive 12 hours in horrible snowy conditions. It totally ruined my holiday."

Hurricanes and tropical storms frequently threaten southern destinations and major connecting hubs like Atlanta and Houston during the peak fall and winter travel seasons. When a major storm like Hurricane Harvey directly hits or even just sideswipes a region, the cascading travel nightmares could last a week or more. Mass flight cancellations strand passengers all over the country and world. Flooding knocks out roads and rail lines.

"My family was supposed to fly down to Miami for Thanksgiving two years ago when Hurricane Irma hit," recalls Paula. "Our flights got cancelled into Miami, Fort Lauderdale, Tampa, Orlando, you name it. And renting a car was impossible because there were none left. We ended up having Thanksgiving dinner at a Cracker Barrel in Atlanta."

Nor'easters battering the East Coast and atmospheric river storms drenching the West Coast create similar holiday travel chaos. The storms themselves combined with the extremely high seasonal travel volume make recovering from cancellations and delays nearly impossible. Savvy travelers try to build plenty of buffer into their holiday itineraries in case of weather disruptions. But when storms stall out and pummel regions for days on end, all bets are off.
"I thought leaving several days early for Christmas would be enough time to make it from California to Rhode Island," said Matt. "But after my original flight got cancelled when a massive storm swamped the West Coast, each subsequent flight I rebooked kept getting cancelled too as the storm drifted east. It turned my travel days into a nightmare."

Holiday travelers eager to take in popular tourist sites often find themselves wedged into overpacked crowds, prompting more frustration than festive feelings. From iconic landmarks and theme parks to ski resorts and beach destinations, the most famous attractions get inundated during the holidays, turning holiday cheer into holiday jeer.
Trying to navigate jam-packed sidewalks outside Rockefeller Center to glimpse the iconic Christmas tree leaves many New York visitors pleading “bah humbug.” Attempting an idyllic winter stroll near the Eiffel Tower gets thwarted by endless throngs jockeying for the perfect selfie. And braving the lines at Disney’s famous holiday events can quash even the most magical of moods.

Mark recalls taking his son to Disneyland right before Christmas one year. “Seeing it decked out holiday style was cool, but enjoying it was nearly impossible. The crowds were out of control with wait times hitting 3-4 hours for rides. We barely got to experience anything before getting frustrated and bailing.”

Popular winter mountain destinations like Aspen, Vail, and Park City also turn into human traffic jams during the holidays as hordes of skiers and snowboarders flock there. Lift lines stretch exponentially, bunny hills teem with tumbling newbies, and even grabbing an open lunch table in the lodge becomes nearly impossible.

“I’ve always pictured perfect family ski vacations spent swooshing down empty trails and relaxing by cozy fireplaces,” explains Susan. “But when we visited Vail last Christmas, the experience was the total opposite. Elbow-to-elbow crowds made skiing maddening, and we waited over an hour just to get lunch.”

For a balmier holiday getaway, many seek out tropical spots like Hawaii, Cancun or Costa Rica. But the masses have the same idea, creating beach crowds more reminiscent of peak summer. The relative isolation offered at these destinations during normal times gets shattered, as the limited hotels, eateries and facilities overflow beyond capacity.
According to tourism data from TripAdvisor,occupation at Hawaiian hotels peaks between 96-99% during the holidays - significantly higher than the 83% average in December. And more visitors at beach locales means more people battling for spots on the sand, in the water and at popular snorkel sites.
Matt was excited to take his family to Costa Rica for Christmas break last year. “We were envisioning having these amazing beaches all to ourselves. The reality was very different,” he laments. “Fighting massive crowds just to go swimming or lay down our towels definitely removed the feeling of peaceful paradise.”

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Restaurants Booked Solid for Holiday Meals

Trying to get a table at popular restaurants during the holidays often requires nothing short of a miracle. From hot spots in major cities to beloved local gems in smaller towns, reservations fill up months in advance, leaving many hungry holiday revelers out of luck.
According to data from OpenTable, peak holiday season reservations at top North American restaurants jump as much as 30% higher than the rest of the year. Openings get snatched up lightning fast. Those who hesitate find themselves shut out when they finally get around to planning that celebratory holiday meal.

Popular eateries in major tourism hubs like New York, San Francisco and Chicago remain booked solid from mid-November through New Year’s. Landing a reservation requires planning 6-8 weeks out or refreshing OpenTable manically in hopes of a last-minute opening. Even booking far in advance provides no guarantee — restaurants frequently overbook, leaving overanxious diners waiting impatiently at the bar.
Smaller towns and suburbs experience less extreme but still significant holiday dining demand spikes. Trying to get a table for more than four people at popular local restaurants on key dates like Christmas Eve, Day and New Year's Eve approaches Mission Impossible territory. No amount of holiday wishful thinking manifests an available reservation.
"I made the mistake of waiting until mid-November to book Christmas dinner at our favorite Italian place,” admits Sara R. “Even though I’ve been a loyal customer for years, they were totally booked up. We ended up having to scramble to find another place."

Large parties find themselves particularly pinched when trying to dine out during the holidays. Most desirable restaurants restrict reservations for more than 6-8 diners even outside peak times. Availability dwindles further during holiday weeks. Trying to book tables to celebrate with office colleagues, large families or groups of friends requires creativity and plenty of lead time.

“Finding a place that could accommodate our party of 12 for a holiday dinner took strategizing and compromise,” explains Michael S. “None of our top choices could fit us. We ended up at a restaurant that wasn’t quite as nice but at least had space.”

Times that traditionally appeal to families and kids pose additional booking headaches. Restaurants offering special holiday meals or brunches get snagged quickly by parents looking to entertain antsy children until the big day. Finding an establishment with available space and a menu enticing picky young eaters becomes an art form.
“I scoured listings to find a Christmas Day brunch that both had room for our family of five and options for our 8 and 4-year-olds,” shares Gabby T. “After constant refreshing, I managed to grab an early reservation though food choices were still limited.”

Resorts and vacation destination restaurants prove even harder to crack. Spots at upscale hotel eateries like The Peninsula Chicago or Acqualina Resort in Miami Beach book out within nanoseconds of opening reservations. And landing tables at legendary establishments such as Commander's Palace in New Orleans or Tao Las Vegas could take years.

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Impossible to Find Last Minute Accommodations

The mad rush to lock down holiday accommodations starts earlier every year, making last-minute bookings nearly impossible. Procrastinators who wait until a few weeks beforehand to secure lodging often find themselves utterly stranded. Landing hotel rooms, rental homes, cabins - anything with a roof and a bed becomes a losing battle as the holidays approach.

Vacation rental platforms see bookings peak in October as anxious holiday travelers hurry to firm up plans. Hotels rely on maximizing revenue through astronomical holiday markups, meaning they have little incentive to hold back rooms for last-minute stays. Airbnb owners, similarly aware of intense demand spikes, rarely hesitate to lock in high-paying multi-week bookings.

Popular ski destinations demonstrate this clearly. According data, December and January rental occupancy in top mountain towns like Vail, Breckenridge and Park City exceeds 90%. All those units get snatched up months beforehand, leaving nothing but scraps as the powder starts flying. “We waited too long to find a cabin near Whistler for Christmas week,” laments Steve. “By late November, there was literally nothing left.”

Beach locales follow suit. Winter occupancy in sunny getaways like Hawaii, Mexico, Florida and the Caribbean approach peak summer capacity. data from Key Data Dashboard shows places like Key West averaging 90%+ booked through Christmas and New Years. Trying to sneak in a last-minute island escape gets greeted by the same brutal reality: no vacancies.

For city escapes, business-oriented hotels once offered last-minute options by holding rooms for conventions and corporate travelers. But intense holiday leisure demand changed the game. Now urban hotels in New York, San Francisco, Chicago and other hubs fill up for the holidays nearly a year out. “I used to easily find Chicago hotel deals a month before Christmas,” says Molly. “But now everything gets booked so far in advance, waiting means no room at the inn - literally.”

Those seeking last-minute accommodate face limited and often unappealing choices. Rooms priced double or triple normal rates reflect the lack of inventory. Airbnbs in sketchy neighborhoods command absurd pricing due to desperation. “We ended up in a rundown motel 30 minutes from downtown because we booked Orlando at the last minute,” admits Mia. "And we paid through the nose for the privilege."

Chain roadside hotels once represented semi-reliable last-minute options. But expanded leisure travel means even these fill quickly for the holidays. "I used to find decent last-minute rates at Holiday Inn Express or whatever back in the day," says Jeff. "Now even those run $300+ per night over Christmas thanks to insane demand."

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Trying to Drive Leads to Gridlocked Highways

The promise of holiday road trips often collides with the harsh reality of overwhelming traffic congestion. Gridlocked highways leave excited travelers crawling along at a snail’s pace, stuffed in their cars for far longer than anticipated. Holiday highway traffic surges thanks to a toxic combination of commuters, shoppers, and vacationers all hitting the road simultaneously. Popular routes to mountain and beach destinations turn into especially tortured gauntlets. Avoiding the gridlock proves nearly impossible.
Former urban dweller Greg naively thought driving from Denver to his parents’ house in rural Wisconsin for Christmas would be relaxing. “How bad could it be?” he remarked before departure. 24 hours of immobile highway later, he realized just how brutal holiday traffic could get. “I envisioned peaceful scenic drives winding through the mountains and Heartland,” Greg explained. “Instead it was just nonstop bumper-to-bumper traffic the entire way. Our Google Maps ETA was so off I wanted to throw my phone out the window.”

East Coast resident Natalie anticipated some delays driving from New York to Florida for the holidays. But she was still flabbergasted by the perma-congestion on I-95 all along the seaboard. “I knew it would be crowded, but didn’t expect the constant logjams for hundreds of miles clogging every single roadway,” she said. “There was literally nowhere to escape the gridlock no matter how many side roads and detours we tried.” Natalie’s ten-hour drive turned into an exhausting 16-hour ordeal.

The scenery may seem appealing, but actually driving through mountain passages and valleys at wintertime brings its own challenges. Popular ski routes such as I-70 into Colorado’s mountains and I-80 approaching Lake Tahoe turn nightmarishly slow. High volume combines with snowy conditions to create a mess. “We sat through some unforgettable holiday traffic jams heading to Park City,” recalls Eddie. “Crawling 10 miles per hour for hours on end really dampened our enthusiasm for fresh powder.”

Swelling numbers of urbanites joining the escape from congested corridors and seeking holiday enclaves worsens the highway havoc. New remote workers untethered from the office descend upon mountain towns and beach communities en masse. Infrastructure and roads quickly get overwhelmed. “I used to breeze into the Catskills from New York right before Christmas,” says Frank. “Now the traffic creeps for miles with all the people relocating or just escaping the city for the holidays.”

The universal desire to hit the road and get away heightens stress exponentially when combined with limited highway capacity. Urban highways, country backroads, coastal routes - all routes get plagued by an influx of holiday vehicles. Trying to travel during peak departure and return windows around Thanksgiving, Christmas Eve, Christmas Day, New Years Eve and New Years Day borders on lunacy. Yet the hordes eager for holiday cheer keep venturing forth, gridlock be damned.

No Ho Ho Ho: 10 Cities Primed to Put a Scrooge on Your Holiday Travels - Holiday Travel Hassles Put a Damper on Festive Spirit

The holiday season is meant to be a magical time filled with joyful gatherings, beautiful decorations, delicious feasts and endless merriment. However, the practical realities of holiday travel can quickly deflate all that festive spirit. Getting to grandma's condo or your tropical vacation paradise often ends up requiring navigating one headache after another. By the time you reach your destination, your holiday cheer has eroded into pure exhaustion, frustration and even despair.

Jenna was eagerly anticipating spending Christmas on the Big Island with her boyfriend's family. She imagined sipping mai tais on the beach under swaying palms while soaking up the island tranquility. The realities of two cramped flights, losing her luggage and battling awful traffic put a serious damper on the experience. "Just getting to Hawaii was such an ordeal that I could barely muster any holiday enthusiasm," Jenna said. "The magic I expected simply wasn't there."

The sheer effort required to travel during the holidays drains even the most optimistic soul. Battling crowds makes everything take longer - security lines, boarding planes, waiting for bags, picking up rental cars. What should be convenient becomes laborious. Repeatedly navigating packed airports while lugging heavy luggage quickly becomes demoralizing. Festive excitement gives way to fatigue.

Dealing with delays, cancellations and immobilizing weather only heightens feelings of despair. Having long-awaited holiday plans unravel through forces outside your control breeds disappointment. Being separated from loved ones you were eagerly anticipating seeing deflates the holiday spirit.

"When our flight to see family got cancelled due to a blizzard, it really bummed me out," admits Mike. "I had been daydreaming of celebrating with everyone for weeks. Missing out because of forces I couldn't control made me feel quite down."

Even small hassles like traffic jams, sold out restaurants or jam-packed tourist attractions can slowly chip away at holiday cheer. Difficulty parking near sparkling holiday displays or waiting in endless ride lines with excited kids breeds grumpiness. The little frustrations compound.

"I hit my limit after over an hour just trying to find somewhere to park near the Christmas markets in Chicago," says Debbie. "My kids were going crazy and I was just ready to call it quits on the whole outing."

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