Cheapskate’s Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots

Post originally Published January 2, 2024 || Last Updated January 2, 2024

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Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Ski Resorts Slash Prices Post-Season


Cheapskate’s Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots

Hitting the slopes can put a major dent in your wallet, with lift tickets, gear rentals, and lodging eating up a huge chunk of any ski vacation budget. But the good news for powder hounds on a budget is that ski resorts slash prices drastically in the weeks and months after peak ski season.

Lift tickets that cost over $100 a day during Christmas, President's Day and Spring Break drop to as low as $20-50 in late March and April at major resorts like Vail, Aspen, and Whistler Blackcomb. Accommodations also see major markdowns of 40-60% during the spring shoulder season. For example, a slopeside hotel room at Beaver Creek that went for $300+ a night during peak times can now be booked for $100-150.
The key is timing your ski trip to chase the snow. While March and April are generally too late for the East Coast, Colorado and the Pacific Northwest still get plenty of snowfall through April. I scored a last minute deal at Snowbird Utah for $45 lift tickets in mid-April a few years back and enjoyed nearly empty slopes and tons of fresh powder.

Just be sure to check snowfall reports and trail openings closely in the spring – lower elevations will start slushing up in the afternoons even if new snow is falling up high. Focus your late season trip on resorts with plenty of above-treeline terrain and North facing slopes that hold snow better. Places like Aspen, Jackson Hole, and Whistler are prime spring ski spots.

What else is in this post?

  1. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Ski Resorts Slash Prices Post-Season
  2. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Island Getaways Offer Low Rates During Rainy Spells
  3. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Europe's Shoulder Seasons Mean Affordable Airfare and Accommodations
  4. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Off-Peak Visits to Asia's Hot Spots Offer Big Savings
  5. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - South America's Winter Temps Bring Chile Deals
  6. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - safari Savings Abound During Low Wildlife Viewing Months
  7. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Skip the Crowds and Costs at U.S. National Parks in Fall
  8. Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Score Budget Caribbean Trips Before Hurricane Season

Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Island Getaways Offer Low Rates During Rainy Spells


Escaping to a tropical island sounds like the ultimate dream vacation. But peak season prices at posh resorts in Hawaii, the Caribbean, and other island hotspots can turn that dream into a budget nightmare quicker than you can say "mahalo." Luckily for bargain beach bums, visiting an island destination during its rainy season can slash hotel rates by 40% or more.
Sure you'll risk a few afternoon cloudbursts and occasional storms by opting for low season savings. But creative travelers can easily find ways to relax under cover or even enjoy getting caught in the warm rain when the sun peaks back through. As a bonus, rainy seasons also tend to be less crowded so you'll have those palm-fringed beaches more to yourself.
Hawaii sees major hotel discounts from November to March, which coincides with the northern hemisphere's winter and thus Hawaii's rainy season. But temperatures stay balmy year round, rain showers are usually brief and isolated, and whale watching thrives during the wet months. Heading to the Caribbean or Mexico during the late summer/early fall hurricane season also scores major savings, with resort rates slashed 40% or more compared to winter highs. Keep an eye on storm forecasts and consider travel insurance for full protection. Then get ready to have some of the region's most beautiful beaches virtually to yourself.

Southeast Asia also offers tempting island getaway bargains from May to October during its annual monsoon rains. Places like Koh Samui in Thailand, Bali in Indonesia, and the Philippine islands of Boracay and Palawan can see daily downpours. But rains tend to follow patterns you can easily work around - an hour of morning drizzle then clearing skies or a drenching late afternoon storm before an idyllic sunset. Creative travelers can save big and still enjoy island bliss in between the raindrops.

Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Europe's Shoulder Seasons Mean Affordable Airfare and Accommodations


Escaping to Europe in the peak summer travel months might be every wanderluster's dream, but sky-high airfares and packed tourist hordes can quickly turn that dream into a budget and crowd averse traveler’s nightmare. Luckily Europe's extensive shoulder seasons from March to May and September to early November offer the tantalizing trifecta of affordable airfare, discounted hotels, and fewer fellow travelers battling for selfie space at all the top sights.

Focus your trip around the April to June or September to October shoulder seasons and airfares from most U.S. cities to Europe can be hundreds of dollars cheaper compared to summer rates. I always aim to depart for Europe in late April/early May if possible. Roundtrip flights from the West Coast to Paris or Amsterdam that would cost $1200 or more in July/August can readily be found for $700-800 during spring shoulder season. East Coast travelers enjoy similar airfare savings. Hotel rates also see major discounts of 20-40% compared to peak summer. A centrally located 3-star property that goes for $200+ a night in August can be booked for $120-140 in May or September.
The big draw of shoulder season travel though is not just the savings but the sanity that comes from having Europe's top museums, attractions, restaurants, and sights way less crowded than summer. In peak months lines for the Eiffel Tower, Anne Frank House or Sagrada Familia can waste hours you'll never get back. But visit in shoulder season and you can practically waltz right in many places. The experience becomes so much more enjoyable when you don't have to battle endless rows of umbrellas and selfie sticks.

Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Off-Peak Visits to Asia's Hot Spots Offer Big Savings


Asia dazzles travelers with its diversity of landscapes, cultures, cuisines, and sights. But experiencing the best of this dynamic region often comes with a big price tag, especially when visiting popular hubs like Tokyo, Singapore, and Hong Kong. Luckily for budget-minded wanderlusters, traveling during off-peak periods can slash costs for flights, hotels, and even entrance fees at top attractions.

Peak tourism in much of Asia aligns with the northern hemisphere's summer break and major holidays like Chinese New Year. Hotel rates in Asian cities easily triple during peak times while flights get snapped up months in advance. But visit during Asia's off-season of late winter and early spring and you'll unlock huge savings. I flew from Los Angeles to Tokyo for just $450 roundtrip in late February this year, compared to $900+ during cherry blossom season just two months later. Tokyo hotels were also about 40% cheaper than their high season rates.
Singapore celebrates its iconic Formula 1 night race in September which can send hotel prices soaring. But visit in June or July during the Southeast Asian summer monsoon season and you can stay in the heart of the city for half the price. The rain typically follows reliable patterns, allowing you to plan indoor activities during the afternoon showers and enjoy evening walking tours once the storms pass.
In Bali, peak season runs May through August drawing partiers, surfers and sun seekers alike. But visit in the quieter months of late February and early March before the crowds descend and enjoy 50%+ discounts on airfare and hotels. The weather is still ideal, with warm, sunny days and intermittent rainfall mostly at night. You'll be sharing those famous beaches and hip hangouts with way fewer people. And entrance fees to temples and other sites offer reduced rates in low season.

Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - South America's Winter Temps Bring Chile Deals


Escaping to South America sounds exotic and adventuresome but can also come with a hefty price tag, especially when visiting popular tourist draws like Machu Picchu, Iguazu Falls, Rio de Janeiro, and Patagonia. However, clever travelers can unlock significant savings by timing their trip during South America’s winter months of May through August. While Peru, Brazil, and Argentina remain balmy if not downright steamy year-round, Chile and Patagonia offer a prime opportunity for chilly weather discounts.
Santiago and central Chile don’t get super cold in their June to August winter, with daily highs still reaching the 50s. But that’s cool enough compared to the hot 70s and 80s the rest of the year that hotel rates and airfares take a big dip. I checked flights from LA to Santiago on Google Flights for June vs January this year and found savings of over $300 roundtrip flying during Chile’s winter months. Hotels in the heart of Santiago were also about 40% cheaper compared to peak season rates.

Even bigger savings await in Chilean Patagonia's chilly winter. Popular hiking and nature destinations like Torres Del Paine, Punta Arenas, and Puerto Natales see far fewer visitors when temperatures dip below freezing and snow starts blanketing the mountains and glaciers. But for adventurous types who bundle up, winter is arguably the best time to visit Patagonia on a budget.

I camped at Torres Del Paine in late August a few years back and enjoyed having the park nearly to myself for long days of hiking among the granite spires. Campsites that go for $50+ a night in peak season were now only $10-15. Refugios and hotels also offered rates 50-60% lower than their summer peaks. If you can handle frozen mornings giving way to sunny 40 degree afternoons, winter is an amazing time to experience Patagonia’s majestic landscapes on the cheap. Just be ready for fierce winds that can shutter some hiking trails on blustery days.

Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - safari Savings Abound During Low Wildlife Viewing Months


For wildlife lovers, an African safari is the ultimate bucket list trip. Getting up close and personal with lions, elephants, giraffes, and more exotic species in their natural habitat is a peak life experience. But safaris also carry notoriously high price tags, especially if you want to stay in one of Africa’s top luxury tented camps or lodges. However, deal seeking safari-goers can unlock major savings by visiting during the region’s low season months.
In East African safari destinations like Kenya’s Maasai Mara and Tanzania’s Serengeti National Park, the prime wildlife viewing months are during the Great Migration from July through October. Over a million wildebeest and other ungulates migrate in a giant loop chasing rains and pasture. Predators follow in kind, with lion, cheetah, and hyena sightings peaking. Unsurprisingly, savvy safari operators charge top dollar for visits during these peak months. But come in the low season months of November through February and rates for safari lodges and guided tours can be slashed 40% or more.

I went on a Tanzania safari last February and enjoyed 50% savings on our lodge compared to August high season rates. The winter months deliver far fewer safari vehicles crowding sight lines as well. Our guide said these low season months were his favorite time to spot predators, like sleepy lion prides lounging under acacias. We had some of the Serengeti’s most stunning leopard sightings all to ourselves.
The tradeoff is fewer large herds migrating through the parks and woodlands during the low season. But the payoff is having a more intimate safari experience unhurried by other vehicles, lower prices, and lush landscapes following the rainy season. February falls in the “green season,” leaving the Serengeti blanketed in emerald grasses and acacias popping with pink blooms. Just bring plenty of layers for chilly early morning game drives.

Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Skip the Crowds and Costs at U.S. National Parks in Fall


America's national parks are epic bucket list destinations, with soaring mountains, carved canyons, cascading waterfalls, and wild coastlines that capture the diverse beauty of the U.S. landscape. But enjoying these natural treasures alongside hordes of fellow travelers during the peak summer months can quickly put a dent in your vacation serenity and budget.

Lodging outside the parks skyrockets in rates during summer, with bare bones motels by theGrand Canyon going for $250+ a night. Inside park lodges like Yosemite's Majestic Ahwanee charge $600 or more per night for a basic room. And good luck if you want to snag a last minute wilderness permit to hike Half Dome or camp at backcountry sites like Havasupai Falls. permits sell out 6 months in advance thanks to overwhelming summer crowds. I tried to get walk up tickets to take the shuttle bus into Zion Canyon last July 4th weekend. After waiting in line for over an hour at 8am, they had already given out all the tickets for the day!

Luckily, fall brings delightfully thinner crowds and tempting discounts on lodging and activities at even the most popular national parks like Yellowstone, Yosemite and Glacier. With kids back in school come September, crowds thin considerably during the fall shoulder season. I visited Arches National Park in mid October and enjoyed having spectacular sights like Delicate Arch and the Windows Section nearly to myself during golden hour. In summer, you're lucky to get even a few seconds of unobstructed views.

Accommodations both in and around the parks offer major rate drops starting in September that continue into October. I got a modern cabin just outside Glacier National Park for $110 a night in early October this year, compared to peak summer rates over $300. The weather can still be amazing in the fall too, with pleasant days in the 60s or 70s at parks like Rocky Mountain and Tetons. Just bring layers for cool nights.

Cheapskate's Calendar: The Best Months for Budget Travel to 50+ Global Hot Spots - Score Budget Caribbean Trips Before Hurricane Season


The sapphire waves lapping sugar sand shores. Palm trees swaying in the balmy breeze. And those legendary sunsets that burn bright tangerine before the moonrise. It’s no wonder a Caribbean escape ranks at the top of so many travelers’ bucket lists. But peak season prices at luxury beach resorts and hotels can quickly turn a dream Caribbean getaway into a budget nightmare.

Luckily for sun chasers on a budget, visiting the Caribbean during the late spring and early summer shoulder season means deep discounts on hotel rates and airfare before hurricane season arrives. Most travelers flock to the Caribbean from mid-December through April when temperatures reliably hover in the 80s. Resort rates skyrocket, flights fill up fast, and good luck finding an empty chaise lounge on the most iconic beaches.

But come May, the mercury starts to rise along with humidity. And many fair weather travelers turn their sights back north, leaving resorts eager to fill all those empty rooms and flights with empty seats. This presents the perfect opportunity for budget-savvy wanderlusters to take advantage of shoulder season savings.

I scored roundtrip flights from Los Angeles to Jamaica for only $280 in late May this year, compared to $600+ during the winter high. Rates at beautiful boutique hotels and all-inclusive resorts also saw discounts of 30-50%. One traveler I spoke with paid only $150/night for an oceanview room at a luxury adults-only resort in Montego Bay that goes for $400+ a night over Christmas.
The weather is already steamy with lows in the 70s and highs around 90. But ocean breezes keep it tolerable and rains are still infrequent. Hurricane season doesn’t truly ramp up until late August. Just be ready for brief passing showers and monitor storm forecasts using an app like Windy to adjust your plans if needed.
The biggest perk though is having those talcum soft beaches, colorful coral reefs, and lush rainforests way less crowded. You might have to share with a few giant iguanas but otherwise some of the Caribbean’s most beautiful and secluded beaches are practically deserted.

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