10 Most Expensive Vacation Destinations and the Cheapest Times to Visit Them

Editors' pick: Originally published Feb. 9.

There's always a cheaper time to visit a popular destination, even if that destination is one of the most expensive.

Rick Seaney, chief executive of travel advice and pricing site FareCompare.com, notes that we just passed a spot on the calendar between New Year's Day and Valentine's Day known as the travel season's "dark weeks." Folks who haven't managed to accrue enough vacation days early in the year or who are wiped out by holiday travel are steering clear of the airports, leaving a lot of empty seats and great fares in their absence until things pick up again around spring break.

Roughly 52 million passengers took trips aboard U.S. airlines last January, according to the Department of Transportation's Bureau of Transportation statistics. That's up almost 3 million passengers from January 2015, but still well below the 57.9 million passengers who caught holiday flights a month earlier in December and not close to the 66.1 million who fly during peak season in July. The only month when folks travel less is February, with a scant 51 million passengers putting up with foul weather and delays during that month.

The folks at travel site Hopper have been charting average airfares throughout the season and, despite dark weeks in early December, just before holiday travel, average airfare in the U.S. still hovered between $215 and $220. January is where the holiday travel price hikes comes to an end.

"The good news is that the best flight prices of the year are right around the corner," says Hopper data scientist Patrick Surry. "Historically, flight prices bottom just after the holidays in January at $211 round-trip."

There are spots like this all over the calendar. Prices also dip in early summer, just before schools let out, but rarely get better than what you see in late August and the September weeks following Labor Day. Seaney notes fall bargain travel season kicked off on August 23 last year and sent prices plummeting. With kids headed back to school, college freshmen weeks into their first semester and parents finally finished with back-to-school shopping, Seaney says demand for hotel rooms and flights dives on that first day, recovers somewhat for Labor Day and slides into deep autumn discounts.

"As for airfare prices, they can drop as much as a third or more over summer airfare," Seaney says. "For my money, autumn is the best time of the year for a vacation: it packs the one-two punch of great weather and great airfare prices."

Hopper noted that projected airfare peaked at an average of $252 in June, but steadily slid to $213 by October before perking back up around Thanksgiving. Hopper notes that the price of jet fuel, though more than 40% above its low point at the end of 2015, is still cheaper than it's been since 2009, giving airlines some room for discounts. Overall, prices are already down about 8% compared to the same time last year, and 15% compared to two years ago as airlines have played along.

The quality of off-season deals depends largely on the destination. With help from the folks at TripAdvisor Rentals, we flushed out some of the swankiest locations in the hemisphere and found ten that offer travelers steep discounts for arriving at unpopular times:

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10. Aspen, Colo.
10. Aspen, Colo.

Least-affordable dates: Mid-February

Weekly rate: $7,453

Most-affordable dates: Late April

Weekly rate: $4,917

Discount: 34%

Not surprisingly, a spot synonymous with both skiing and opulence is really popular and expensive at the height of ski season. After the X Games clear out and before the temperatures start climbing, Aspen is a renter's market. It isn't until there's absolutely no chance of spring skiing -- and a few months before the Aspen Music Festival reaches the meat of its lineup -- that there start to be some deals.

Read More: Can't take a trip? You should check out the the new Dodge Demon -- it will probably be the fastest Muscle car ever and take you where you want to go.

9. Newport Beach. Calif.
9. Newport Beach. Calif.

Least-affordable dates: First week in July

Weekly rate: $2,655

Most-affordable dates: Last week in October, first week in November

Weekly rate: $1,733

Discount: 35%

Surfing the Wedge, eating at The Crab Cooker, watching the yacht races in Newport Harbor, shopping the Dory Fish Market, exploring the Balboa Peninsula, taking the ferry to Catalina... it's all part of an idyllic Orange County summer, and it's all exactly how a lot of people want to spend their Fourth of July. It's all only somewhat less appealing in mid-fall, when temperatures dip into the mid-60s, but all the bars and restaurants on Newport Pier will still be open and there'll still be plenty of boats in the water to provide a lovely backdrop once you arrive.

8. Ka'anapali, Hawaii
8. Ka'anapali, Hawaii

Least-affordable dates: Last week in December

Weekly rate: $4,739

Most-affordable dates: First week in December

Weekly rate: $3,102

Discount: 35%

Best known for the beach of the same name (and the abundance of resorts and beach clubs lining it), Ka'anapali is the gem of Maui. But why are both its high season and low season in the same month? Because that first week in December acknowledges that it's in the center of Hawaii's rainy season, while the last week in December just happens to be when a whole lot of mainlanders and others arrive on the island for their Christmas and New Year's vacations.

7. Poipu, Hawaii
7. Poipu, Hawaii

Least-affordable dates: Last week in December

Weekly rate: $2,612

Most-affordable dates: First week in December

Weekly rate: $1,683

Discount: 36%

Located on the third-Westernmost island of Kaua'i, Poipu is a whole lot more quiet than tourist-heavy Ka'anapali or Waikiki and counts beaches and botanical gardens as its primary attractions. If you're not there to take in the flora, fauna and waves or stroll Māhāʻulepū Beach and Poʻipū Beach Park, you're likely on the wrong island. That said, the same rule applies here as it does on Maui: Get here just after Thanksgiving, leave before Christmas.

6. Wailea, Hawaii
6. Wailea, Hawaii

Least-affordable dates: Last week in December

Weekly rate: $4,412

Most-affordable dates: First week in May

Weekly rate: $2,714

Discount: 39%

If you really like Maui but would rather take in the southern, leeward part of the island... get in line. Wailea is by no means undiscovered country and is laden with golf courses, tennis courts, stores and resorts. Fairmont, Marriott, Four Seasons and Destination Hotels have all parked facilities here and all seem fairly aware of the lure of calm waters and clear skies. If you can get here in May, the temperatures should play along even if the vacation schedules don't.

5. Grand Cayman, Cayman Islands
5. Grand Cayman, Cayman Islands

Least-affordable dates: First week in March

Weekly rate: $2,883

Most-affordable dates: Mid-September, early October

Weekly rate: $1,773

Discount: 39%

Ask the locals, and they'll say that the off-season is in the middle of the summer when most tourists from the U.S. and other points north melt on Seven Mile Beach in 90-degree temperatures. However, if those same tourists can just wait until the kids go back to school in early fall, they'll not only have the turtle farm, Rum Point, Stingray City and the blowholes mostly to themselves, but they'll finally have temperatures that dip down into the mid-80s and air that's no longer humid enough to chew.

4. Kapolei, Hawaii
4. Kapolei, Hawaii

Least-affordable dates: Last week in December

Weekly rate: $3,941

Most-affordable dates: May

Weekly rate: $2,329

Discount: 41%

Nope, it's not Honolulu, it's the other city on Oahu. Founded only about 30 years ago after the land-owning heirs of industrialist James Campbell decided to build themselves a model city, it's now home to Disney's Aulani Resort, Marriott and Four Seasons resorts on Ko Olina and a whole lot of folks making traffic a general nightmare. Yes, people still want to be here for Christmas, but you're better off in that odd pre-summer catch period in May just before people start burning vacation days.

3. Saint James Parish, Barbados
3. Saint James Parish, Barbados

Least-affordable dates: February

Weekly rate: $3,946

Most-affordable dates: Late May through mid-July

Weekly rate: $2,222

Discount: 44%

Welcome to the Platinum Coast and all of the mansions, luxury hotels and pristine beaches that come with it. The Sandy Lane and Royal Westmoreland resorts have been drawing luminaries to this corner of the Lesser Antilles since the early 20th Century and have managed to lure no less than 18 billionaires into building homes along its six miles of beach. However, even somewhere this gorgeous and sought-after needs a little rain to fall, and it gets the majority of that rain during the monsoon season that occurs between the dates above. If you don't mind some drizzle, you can cut the price of your stay here almost in half.

2. Beaver Creek, Colo.
2. Beaver Creek, Colo.

Least-affordable dates: Last week in December

Weekly rate: $4,779

Most-affordable dates: First two weeks in October

Weekly rate: $2,061

Discount: 57%

Imagine if Aspen was somehow more exclusive, welcomed more heads of state (courtesy of the American Enterprise Institute's World Forum) and was actively kept as small a part of its surroundings as possible. That's Beaver Creek, which wanted to remain such a minimal portion of the surrounding White River National Forest that it lost the Winter Olympics to Innsbruck, Austria, in 1976 trying to do so. Not surprisingly, those lucky enough to own some property here generally want to be around for the winter holidays. However, if you can sneak in just before the ski season really gets under way, you can halve the cost of staying in such rarified company.

1. St. Barthelemy
1. St. Barthelemy

Least-affordable dates: Last two weeks in December

Weekly rate: $18,630

Most-affordable dates: Early May through early October

Weekly rate: $6,283

Discount: 66%

You aren't touching St. Bart's around the holidays unless you're of considerable means and global stature. Even then, you're less likely to book a room at Eden Rock, Cheval Blanc or Hotel Le Toiny than you are to simply drop your yacht's anchor off the coast. However, if you wait until after the St. Barth's Film Festival in April and hang out for Bastille Day and the religious feasts during the summer, you can stay at one of the few guest houses here for a third of the price that you'd pay to hobnob with the celebs. Though this French territory is still heavily French-influenced, its time as a Spanish, British and Swedish holding gives it a remarkably cosmopolitan flavor that's enjoyable year-round. If you can put up with the rainy season, you can live like a star while paying an assistant's prices.

Read More: Can't take a trip? You should check out the the new Dodge Demon -- it will probably be the fastest Muscle car ever and take you where you want to go.

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This article is commentary by an independent contributor. At the time of publication, the author held no positions in the stocks mentioned.