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Sun, Sand, & Savings: Affordable Caribbean Escapes

Sun, Sand, & Savings: Affordable Caribbean Escapes

Want to sink into a beach chair with an ice-cold piña colada in your hand… without worrying about how you’re going to pay off your credit card?

Welcome to travel in 2025. While more Americans are hitting the road than ever before, and while most Americans are more interested in experiences versus material goods, travel is expensive.

Luckily, as prices climb so do the number of tools that are designed to help you save while booking. Dollar Flight Club is one of those well-known tools. The platform lets you input your home airport along with your dream destinations and then sends you alerts when prices drop to your preferred range.

It’s a solid solution for those with tight budgets, and especially those who are dreaming of tropical destinations like the Caribbean Islands.

As one of the top spots for winter birds from America, the Caribbean is one of the most accessible and familiar places to escape the cold weather. But given its popularity, this region has some of the priciest resorts and hotels in the world.

Want to plan an affordable Caribbean getaway? Here’s where you need to go.

7 affordable Caribbean destinations

Aruba (Getty)

These selections are based on the cheapest flights and hotels in the area, along with the average price of highly rated tours, excursions, and cultural activities. All hotel rates are listed for mid-range options—meaning you can save even more at budget stays.

San Juan, Puerto Rico

  • Flights from Atlanta and Los Angeles are around $150
  • Mid-range hotels average around $150-200/night

Aruba

  • Flights from NYC are around $280
  • Mid-range hotels and resorts around $200-250

Cancun, Mexico

  • Flights from Denver are around $200
  • Mid-range hotels average around $100-150/night

The Bahamas

  • Flights from Miami are around $250
  • Mid-range hotels average around $150/night

Jamaica

  • Flights from Louisville are around $300
  • Mid-range hotels average around $210/night

St. Lucia

  • Flights from NYC are around $250
  • Mid-range hotels and resorts average around $200/night

Last affordable Caribbean destination: Dominican Republic

  • Flights from Miami are around $215
  • Mid-range hotels average around $160/night

What To Do If You Get Stranded at the Airport

Ah, being stranded at an airport—a perennial travel experience.

No matter how carefully we plan air travel, no matter how frequently we fly, and no matter how patient we are, hiccups happen. From missed connections to getting food poisoning, we’ve all been through a few unexpected surprises.

My most unexpected stranding happened when on a trip from Barcelona to Saint Louis, Missouri. I had a layover flight in Iceland, at which point the customs agent let me know that I had overstayed my Schengen visa.

That minor infraction delayed my time at the customs counter—causing me to miss my flight.

The catch? I had my chihuahua with me, and Iceland doesn’t allow pets to leave the airport to use the bathroom.

So, I had a nine-hour layover with a dog who was only allowed to pee in a concrete room in the basement airport. Also, I had to find an attendant to take us there every time my little bruiser needed to boo-boo.

Ultimately, that terrible experience was due to my own mistake in overstaying my welcome in Schengen. But many airport-based disasters are driven by bad luck, chance mistakes, and even karmic retribution… if you believe in that kind of thing.

Don’t worry—I’ve got solutions for you based on my own nine-hour hellscape of a layover and other expert tips. Want to know what to do if you get stranded in an airport? Here’s the rub.

What to do if you get stranded in an airport

Step 1: Give up hope (for a quick solution, at least)

Don’t hate me for this, but if you’re facing hours of delays, then your best bet at staying sane might be to give up hope.

Here’s what I mean: Many Americans are accustomed to finding a quick solution. We might even be willing to pay a lot of money for that solution, which is doubly true for those stranded at an airport with no way to make a connecting flight.

But all your worrying and fussing won’t sway the Airline Gods. Or the TSA. Or the ATC.

Why give up hope? Because these obstacles are far beyond your control. While you should advocate for yourself in the airport, I’ve found that relaxing is a more lasting and satisfying solution.

If you’re already feeling stressed out and exhausted, I suggest buckling in for the long haul instead of calling an airline, posting a bad review on social media, or even complaining at the airline counter. (Actually, your best bet at finding a solution is to use the airline’s app!)

Remember—you will get where you’re going, and keeping your head on straight can pay off in other ways.

Step 2: Get familiar with your rights

Every country and region has a different outlook on what an airline owes you.

Remember, while you aren’t in control, the delay probably wasn’t your fault. Knowing your rights helps you understand which actions to take—and when. (Most appeals are made much later on.)

In the US, we’re benefitting from a new era in flying thanks to the Fly Rights program. The concept is new and hit the ground running in 2024, meaning it needs a bit more time to mature in practice.

In Europe, by contrast, airlines owe passengers refunds when domestic flights are delayed by more than three hours and international flights by six. I’ve taken advantage of my rights in the EU multiple times thanks to FlightHelp, a company that charges a low fee to file your delayed flight to receive reimbursement.

Seriously—I’ve probably received close to $1,000 in reimbursements over the years.

If you’re stranded at the airport, you have time to look up your rights. Maybe making a plan of action will soothe your wearied soul.

Step 3: Make allies

If you’ve received a catastrophic delay at the airport, you’re probably not alone. Almost every time I’ve faced a hefty delay, I’ve chatted with other passengers to get the down-low.

Inevitably, we start sharing insights, ideas, and more.

For example, my flight from Milan to Barcelona was delayed back in August. I noticed another Spanish-speaking group closely watching the updates. I struck up a conversation and, later on when the new gate was posted, let my new friends know as I took off. They had powered down to rest and were grateful for my notification.

The same has happened in vice versa over the years. Remember—you aren’t alone, and you can always find help at the airport.

Step 4: Use lounges, hotel day rates, and prayer rooms

I’ve saved the best advice for last, my friends.

If you’re stranded at an airport all day, you can easily buy a day pass to a large airline lounge or even pay for a room for the day at a nearby hotel. The latter is known as a day rate—and dozens of hotel brands around the world are launching straightforward programs for their airport-adjacent hotels.

If you’re facing an overnighter at the airport, use sites like SleepingInAirports to find suitable spots to sleep. Some airports might even offer rentable sleeping chambers and similar experiences.

Lastly, the prayer room is the place to find ultimate peace. I had once assumed these rooms were for Muslims to use for Salah prayers, which are done five times a day. In reality, they’re multi-use.

While these rooms are geared toward quiet religious activities, let’s not forget that you don’t need to show a religious badge to get in. If praying isn’t your thing, a little meditation might do you right, too.

Winter Glamping Done Right: Best Cold-Weather Sites in the US

Glamping is on the map for travelers—even during winter.

In case you’ve missed out on the hype of glamorous camping, it’s slowly slid into the American purview for three main reasons. First, it gets exhausted city-slickers out into nature. Second, glamping removes the onus of buying equipment… and figuring out what you need to begin with. Third, it’s (usually) affordable.

That being said, the vast majority of glamping offers are summer and spring-centric. Many glamping grounds offer a range of amenities, from kayaks to restaurants to pools. Travelers get more out of their glamping experience during the warmer months, from April to October.

Or do they?

Let’s take a closer look at some of the best winter glamping grounds across the US that offer a quality, comfortable visit during the coldest months of the year.

Best winter glamping in the US

What makes a good glamping location during winter? Heating is (obviously) a major factor. I’m also prioritizing glamping grounds that offer indoor options for dining and hanging out, plus outdoor activities that showcase the region’s wintry wonders.

The last factor I’m focusing on is pure, beige canvas. It’s not a glamping site if there are cottages, tiny homes, and other lodgings made of wood. In my humble opinion, at least.

Under Canvas Grand Canyon AZ

Under Canvas is one of the largest US glamping enterprises. Its lodging and dining tents are massive, high-quality, and decorated with a charming rustic touch. At Under Canvas’s Grand Canyon location, you can soak up the southwestern views any time of year. There’s even a seasonal menu at the on-site restaurant that lets you sample seasonal winter ingredients.

Mendocino Grove CA

The small-and-chic Mendocino Grove glamping setup takes you to the coastal forests outside Mendocino. Every unit includes a fireplace and a shower with heated water—plenty to keep you warm in winter. There’s even Wi-Fi available.

Willow-Witt Ranch OR

This historic, off-the-grid ranch takes you into a fairytale-like forest. From friendly goats and ducks to roaming livestock, you’ll feel like you’ve stepped outside of time. The Willow-Witt Ranch offers multiple lodging options, including canvas tents and other unique choices like the Farm Stay Studio.

The Roost TN

Part treehouse, part glamping site, The Roost is ideal for anyone who wants to disappear rather than rub elbows with fellow glampers. With an outdoor fire pit and an electric fireplace inside the tent, you’ll be able to pass the time in comfort even when the temperatures drop. The only drawback might be the forest’s bare canopy once those leaves drop in autumn.

Terramor Outdoor Resort ME

This ultra-lux option is billed as an outdoor resort—and it doesn’t disappoint. From its gorgeously appointed suites to its unspoiled forest views, Terramor lets you escape the hustle without losing out on the finer things in life. From king beds to private fireplaces, its pure glamping extravagance.

*Given its location in Maine, Terramor is open from May through October instead of the whole winter. However, an October visit should still give you the chance to soak up those gorgeous, brisk fall days.

Klarhet MN

A regenerative food forest? Lakeside views? And eco-conscious domes? I might have failed on the canvas element here, but this bespoke and intentional glamping experience is too unique not to mention.

The owners at Klarhet are dedicated to restorative natural practices, letting you get wild without worrying about your carbon footprint. Also, every dome has a fireplace—nature is wonderful, but it gets cold in Minnesota.

Camp Long Creek MO

Want a more elevated glamping experience without the luxury tax? Camp Long Creek is part of the Big Cedar Lodge, a gold resort that’s well-known around the state. That means these large glamping tents are closer to five-star amenities than most others.

ULUM Moab UT

Similar to Under Canvas (mentioned above), ULUM is one of the US’s premier glamping brands—one that takes glamping luxury to new heights. Its Moab location is perfect for a visit any time of year thanks to its balance of pools and fire pit areas.

Clark Farm Silos MT

I’m offering an olive branch to anyone who is allergic to canvas. My last winter glamping recommendation is Clark Farm Silos in Montana. As the name suggests, these unique little homes are built into silos that offer mountain views. Sounds rustic, but these bad boys are absolutely gorgeous and larger than you think.

Flying Around the World? Save on Airfare with These 5 Tricks

The cold, hard truth of travel is that airfare ain’t cheap.

I’ve noticed major price spikes in the post-COVID era. The rise in airfare prices has been compounded by revenue loss in 2020, hiking fuel prices, added interest in travel, and more premium offerings from airlines.

From domestic flights to international long-haul flights, tickets are more expensive than ever before. More frustratingly, there’s more fine print involved and fewer liberties offered to travelers.

As someone who needs to cross the Atlantic to visit family, I’m painfully aware that my money doesn’t take me as far as it used to. On top of that, I’m more likely to face delays during connections. (If you’re looking for a silver lining, the US’s new Fly Rights might provide relief for flyers—but the program remains young and untested.)

As I adapt to this new era in air travel, one of my primary focuses is learning how to save on airfare when booking long-haul, international flights.

Let’s dig into the best advice out there, including tips based on my own experiences and advice from travel experts who focus on topics like finance and flying.

Looking for more than just how to save on airfare? Check out these resources.

  • How to book flights using Google Flights & Booking
  • Economy airlines with lie-flat beds (great for long-haul flights)
  • Best times to book holiday flights according to Google

How to save on airfare when booking international flights

Trick #1: Flexibility always has a positive impact

It’s really that simple: the more flexible you are with your travel dates, the more easily you can target cheaper flights. Rather than request time off of work to plan a trip, I suggest planning your international escape with flexibility in mind—and then asking off for the cheapest travel dates.

This isn’t the sexiest or freshest advice out there, but it’s tried-and-true. But keep in mind that I always suggest booking flights first thing in the morning to avoid the longer delays that come in the afternoon and evening.

So, stay flexible on the dates that you fly, but always target those early-morning flights to avoid delays.

Trick #2: Look into booking separate one-way flights

Some long-haul flights are best booked separately. Over the years, I haven’t been able to nail down when, where, or why one-way flights are cheaper than round-trip tickets. To be blunt, it feels a bit random to me.

But I’ve saved hundreds by booking separate one-way flights to and from international destinations. You can shop around for one-way flights using a deal platform like Booking or Kayak. The only times I’ve done this, I flew with different airlines, taking advantage of the cheapest fare from both.

It might not work if you have multiple layovers, but this trick should be viable if you’re flying between major hubs.

Trick #3: Bundle airfare with your hotel booking

If you plan on booking a hotel (instead of an Airbnb) at your destination, then look for bundled offers that include flights and hotels.

You can do this in a few ways, including shopping around for hotels directly on an airline’s website or by using a booking platform like Kayak and Booking.

While I’m not a fan or regular user of travel rewards, you should probably be taking full advantage when booking a long-haul international flight. Travel rewards members are usually the first to find great deals on both flights and hotels—just remember to read that fine print.

Trick #4: Bring a carry-on instead of checking a bag

My favorite money-saving tip is to skip out on checked bags—no matter if you’re heading out of town for a weekend trip or flying to Australia for the winter.

Checking bags has become exorbitant with many airlines, especially for international trips. It also makes traveling on public transportation more difficult.

That being said, I recognize that it’s sometimes necessary to bring a larger checked bag. If it’s unavoidable, then remember to pay for your checked bag when purchasing your ticket—not when rolling up to the airline’s counter before your flight.

Trick #5: For true savings, look for flash sales

Airlines don’t often offer sales—even during Black Friday and other sales-heavy periods. Thankfully, however, most launch flash sales throughout the year. They’re short, but they’re great times to book pricier international, long-haul flights.

The best way to keep your finger on the pulse for these types of events is to join an airline’s mailing list or set up an email alert.

Most airlines require you to sign up to receive these notifications, which I find a little annoying—that being said, signing up is free and non-committal.

(If you’re really flexible, you can also sign up for companies like Dollar Flight Club, which monitors your favorite destinations for price drops.)

Bonus trick to save on airfare: Loyalty pays for consistent travelers

I have one final trick for you: Consider becoming a loyal flyer.

Again, I’m not a big fan of travel rewards memberships because they involve tons of fine print, require you to spend to get those perks, and are always changing their rules.

At the same time, I think there are huge benefits when it comes to becoming a loyal member of an airline—even if you have no plans on seeking out rewards programs or other deals.

Booking directly through an airline as a loyal member gives you a few perks that will pay off in unique ways.

First, you get priority from the airline—from boarding early to upgrades. Second, the airline will be more willing to work with you in case of any emergencies or last-minute changes. Third, your miles will accrue over time and let you save big when booking, which is extremely helpful for frequent international flyers.

Winter Sun Escapes: Picture-Perfect Islands to Visit in Winter

I’m a huge fan of winter travel—a specific type of winter travel, that is.

From December through February, I’m prone to plan trips to places like Sweden, Poland, and Germany. Where I live in Barcelona, temperatures remain mild year-round before spiking in summer. At least once a year, I seek out a more traditional, bitterly cold winter escape. (I like darkness and snow, I like being cozy, and I love winter fashion.)

That being said, my outlook here is pretty unique—or outright bizarre if you’re someone who enjoys the sunshine. Most travelers seek out sunny, warm destinations during the depths of winter.

According to TripAdvisor, 57% of Americans plan to travel during winter—and most will favor mild, temperate destinations. Unsurprisingly, islands are a top choice thanks to their high temperatures, relaxing beaches, and laid-back atmosphere.

The only catch? Some islands see a huge influx of winter birds, which can create an overcrowded, opposite-of-relaxing kind of vibe. If you want sunny skies and mild breezes, along with a more remote and crowd-free vacation, then you need to look for islands that are a bit further off the beaten path.

Want to know where to find them?

Thanks to a data study from Discount Cruises on Instagram posts (the fewer, the better), I’m laying out some of the lesser-known and highly picturesque islands that will let you slip away from the cold grip of winter without any worries.

Islands to visit in winter with fewer crowds and gorgeous surroundings

Great Corn Island, Nicaragua (Getty)

Let me give you a fair warning: these islands really are farther off the beaten path. That’s not a problem for a more seasoned traveler like me—so let me give you a few pointers in case you’re interested in visiting one of the suggestions below.

First, stay flexible with your travel dates to find cheaper flights and hotels. Two, try to set aside more time to visit—the more transportation you need to take, the more likely it is that you’ll face delays. Three, pack your favorite meds and any other hard-to-find supplies—again, just in case.

Based on Instagram hashtags, these are some of the most popular yet under-the-radar islands to visit in winter:

  • Corn Islands, Nicaragua (11k tags)
  • Pemba Island, Tanzania (16k tags)
  • Taveuni, Fiji (24k tags)
  • Rodrigues Island, Mauritius (34k tags)
  • Guam, USA (95k tags)
  • Bequia, Saint Vincent and the Grenadines (96k tags)
  • Tioman Island, Malaysia (187k tags)
  • Isla Holbox, Mexico (266k tags)
  • Culebra, Puerto Rico (38k tags)
  • Koh Rong, Cambodia (406k tags)

What about the most popular islands to visit in winter?

Cala Salada, Ibiza (Getty)

Not everyone wants to avoid a crowd. In fact, some travelers might be even more excited by the prospect of vacationing with others.

For first-time international travelers, sticking with like-minded travelers lessens the intimidation factor of a new destination. For others, it’s all about having the chance to make lasting connections.

If you’re a social butterfly or simply aren’t interested in veering off the well-trod path, then head to these islands—you’ll find tropical vibes and new friends all around.

Most popular winter sun islands according to Instagram hashtag counts:

  • Bali, Indonesia (89 million tags)
  • Ibiza, Spain (22 million tags)
  • Sicily, Italy (19 million tags)
  • Mallorca, Spain (19 million tags)
  • Jamaica (16 million tags)
  • Maldives (16 million tags)
  • Okinawa, Japan (15 million tags)
  • Phuket, Thailand (14 million tags)
  • Cyprus (13 million tags)
  • Tenerife, Spain (12 million tags)

2025 Hotel Tips: Cheapest Seasons to Book Hotels in the US

In celebration of the New Year, I’m taking a fine-tooth comb to some of the best data-driven insights into booking hotels.

This time around, I’m relying on the great minds at Vio. This relatively new booking platform makes it easy for travelers to shop around for savings on hotels and more.

That also bodes well for data-driven reports that explore domestic and international hotel room rates.

According to the data, you’ll save big by booking hotels in the USA during these months and in these cities. Remember, while there’s usually plenty of information surrounding when to book international trips, it’s a little harder to nail down the domestic insights.

Let’s explore.

Cheapest times to book hotels in the US

Just like with international hotels, you can find better hotel rates in the US during Winter and Spring.

Summer and autumn, by contrast, cost about the same on average to book a hotel across the US—but keep in mind that the differences in price aren’t nearly as extreme as with international hotels.

Spring rates average at about $185, while winter rates average out at $195. In autumn, you’ll pay around $210 on average and in summer, that rises up to $211.

Cheapest cities to book hotels in the US during the off-season

Haven’t nailed down your destination? Consider focusing on one of the cities below if you want to really extend your winter and spring hotel rate savings. You won’t find a better deal in 2025.

The cheapest US cities to book rooms in winter are in Colorado Springs ($98/night), Columbus, Ohio ($107/night), Myrtle Beach, South Carolina ($109/night), Virginia Beach, Virginia ($113/night), and Arlington, Texas ($114/night).

The cheapest US cities to book hotels in spring are in Jacksonville, Florida ($115/night), Fort Worth, Texas ($120/night), Houston, Texas ($120/night), Colorado Springs, Colorado ($125/night), and Columbus, Ohio ($131/night).

Average hotel rates month by month for US hotels

If you stick to these cities during these seasons, you’re sure to find hefty savings on hotel rooms.

But if we dig a little bit deeper into the Vio study, some cities offer even steeper deals during specific months.

Winter

  • Hotels in Ocean City, Maryland offer savings up to 47%
  • Hotels in Portland, Oregon drop by up to 44%
  • Hotels in Colorado Springs, Colorado drop by 41%
  • Hotels in Virginia Beach, Virginia offer savings up to 40%
  • Hotels in Panama City Beach, Florida drop by up to 38%

Summer

  • Hotels in Austin, Texas drop by up to 37%

Autumn

  • Hotels in Panama City Beach, Florida offer savings up to 46%
  • Hotels in Ocean City, Maryland drop by 40%
  • Hotels in Virginia Beach, Virginia offer savings up to 40%


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