12 unexpected winter vacation ideas for a warm getaway


If you crave the sensation of winter sun on your skin amid the slowly dropping temperatures in the United States, a few obvious holiday destinations may spring to mind.

Mexico, Florida, the Maldives and Dubai are all classics for a reason, delivering scorching temperatures throughout the shivering depths of December and January. But that also means they’re very popular — and if you find yourself lusting after a hot vacation every winter, chances are you’ve already been to a few of them, anyway.

If you’re looking for new winter vacation ideas, consider these 12 unexpected locales for a warm-weather getaway.

Penang, Malaysia

Pier Over Sea Against Cloudy Sky,Penang, Malaysia
The waterfront in George Town, Penang. SIMONLONG/GETTY IMAGES

With a latitude of about 5 degrees north, this little island just off the western coast of Malaysia guarantees heat year-round. Following big rains in what we’d call fall, the weather is most ideal from December through February. Think highs in the mid-80s and lows in the mid-70s in December, with things warming up a few degrees in the months following. Humidity is notoriously lower than the rest of the year, making things quite pleasant.

Sun seekers can find plenty of it on the sandy beaches encircling the isle — though note the Malacca Strait is not the place to swim, due to jellyfish. The pools at many hotels offer fabulous places to dip instead.

The destination is a hot spot for culture seekers and foodies. There are dozens of Bib Gourmand eateries, not to mention a couple that are Michelin-starred, and street food stalls and markets galore, promising spicy, smoky and exciting flavors plus delicious refreshments such as nutmeg juice.

As a major trading port, Penang embraces several distinctive cultures and religions. Four of the most famous houses of worship are found on the same road, dubbed the Street of Harmony. It’s part of the UNESCO World Heritage Site of historic George Town, where visitors of all ilks mingle happily, posing with iconic street art, riding trishaws and shopping for everything from Chinese medicinal herbs to handicrafts to clothing.

TPG tip: Opened in February 2025 on George Town’s Millionaire’s Row, The Millen Penang, Autograph Collection, is an uber-glamorous city hotel that also offers island resort panoramas, especially from its clear-sided ninth-floor lap pool. Rooms and suites come with free-standing bathtubs overlooking the turquoise water. Rates start at $198 or 39,000 Marriott Bonvoy points per night this winter.

La Gomera, Spain

San Sebastian on La Gomera. ROSSHELEN/GETTY IMAGES

Gran Canaria, Fuerteventura, Tenerife and Lanzarote are well known in the world of winter sun-seeking, thanks to their prime position off the coast of northwest Africa. (Average highs range from 70 to 79 degrees in October, dropping to the mid-60s to mid-70s from December to March.)

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All of these bigger Canary Islands are usually safe bets, weatherwise. But there are eight main islands, and La Gomera, the second smallest, is one to carefully consider. Temperatures typically swing from around 67 to 77 degrees during winter, and the days are typically mild, dry and pleasant. Expect black-sand beaches on which to lie (or play), epic cliffs to hike and plenty of mirador viewing points for the perfect holiday snap — plus the dramatic, UNESCO-listed laurel forests of Garajonay National Park for a day trip adventure.

It’s also worth boating to the even smaller El Hierro or the peaceful La Graciosa, which claims to be one of the world’s only places to have eschewed asphalted roads. Its dirt roads are ideal for cycling.

TPG tip: Small islands like La Gomera don’t have major chain hotels, so for a points booking, opt for “the island of eternal spring,” Tenerife, and its warm pink The Ritz-Carlton Tenerife, Abama, which has plentiful swimming pools plus a massive spa. Rates start at $334 or 69,000 Marriott Bonvoy points per night this winter.

Zanzibar, Tanzania

A dhow passing Bawe Island in Zanzibar. BRUNO MORANDI/GETTY IMAGES

Off the coast of Tanzania is Zanzibar, an archipelago where visitors can embrace a double dose of fascinating culture and sparkling, untouched beaches. January and February are particularly good times to go, with (typically) less rain than in December and temperatures heating up into the 80s, reaching the low 90s.

Highlights include the main island, Unguja, and its old trading quarter, Stone Town — now a UNESCO World Heritage Site for its “cultural fusion” of African, Arab, European and Indian influences, seen in the architecture, as well as its historic role in the ending of the slave trade. Jozani Chwaka Bay National Park is also home to a rare, endangered primate, the Zanzibar red colobus. Beyond Unguja, snorkeling among the coral reefs of the private Chumbe Island, where guests can spend the night in solar-powered eco-bungalows, is quite the experience.

TPG tip: Be in the middle of all the action in Stone Town at the 67-room Park Hyatt Zanzibar, with a zero-edge pool hovering over the beach. Rates start at $392 or 25,000 World of Hyatt points per night this winter.

Related: Plan the ultimate African safari with these 12 bush-to-beach destinations

Valletta, Malta

The Senglea Marina in Valletta. DADO DANIELA/GETTY IMAGES

OK, so Malta will probably not be roasting hot in winter. Expect the low 60s to be your average high; January is typically its coldest month. That said, it’s likely to be a good 30 degrees toastier than U.S. cities on the Eastern Seaboard, and rain is at a minimum, while snow is virtually unheard of. This is all thanks to the archipelago’s location in the Mediterranean Sea, set off the coast of Italy, Tunisia and Libya.

You can secure a touch of winter sun just about anywhere in Malta, from the historic town of Mdina to the cool, lagoon-skirted islands of Gozo and tiny Comino. Still, the yellow-hued capital Valletta is a great place to start — with the scenic waterfront to mosey along, a 16th-century cathedral, the Fort St. Angelo site and the picturesque Upper Barrakka Gardens, not to mention nearby towns such as Sliema to explore. TV and film fans will love it here, too, for Valletta has starred as a filming location in “Game of Thrones,” “Troy” and “Gladiator,” among others.

TPG tip: The attractive boutique hotel Rosselli, part of Mr & Mrs Smith, gets major points for ambience. It features luscious furnishings, custom floral wallpapers and private two-person saunas in a 17th-century estate. Rates start at $255 or 18,125 World of Hyatt points per night this winter.

Dominica

woman walking on trail in the middle of jungle
Hikers will enjoy walking the Waitukubuli National Trail. DAVID MADISON/GETTY IMAGES

As the rainy hurricane season ends in November, winter is an excellent time to visit the Caribbean nation of Dominica. Average temperatures at this time of year can hover around 87 or 88 degrees, and the water is similarly warm at 78-80 degrees, perfect for snorkeling and diving.

As a tropical island country, it (obviously) has beaches. But if all you want is somewhere to lie on the sand, Dominica isn’t the best fit for you as there’s much to see and do. Exploits include spotting the island’s colorful birds and sperm whale watching — it boasts the world’s first protected Sperm Whale Reserve — to uncovering seemingly endless natural beauty, including lush forests, nine live volcanoes, and numerous waterfalls and hot springs. In Morne Trois Pitons National Park, take a long hike to the natural, steam-spraying 183-degree Boiling Lake. Long-distance walkers will thrive here by embarking on the 112-mile-long Waitukubuli National Trail.

TPG tip: Splurge on the sustainable and exclusive 10-villa boutique resort Secret Bay, with rates for the Mr & Mrs Smith hotel starting at $1,631 or 135,250 World of Hyatt points per night this winter. Or choose InterContinental Dominica Cabrits Resort & Spa, inside Cabrits National Park, for rates starting at $385 or 84,000 IHG One Rewards points per night.

Related: How Dominica and other destinations are doing sustainability right

The Algarve, Portugal

The Algarve. GONZALO AZUMENDI/GETTY IMAGES

Continental Portugal’s southernmost region, the Algarve, has something for every traveler. If you want to stay in a hotel and spend a week lounging by the pool without a care, you’ve got plenty of options along the coastline. If you’re after world-class beaches, breathtaking views and nightlife, try Lagos or Albufeira. Want a city break that isn’t Lisbon or Porto? Try Faro instead, with its historic Old Town. Does all of the above sound great? It’s fairly easy to explore the Algarve, its beaches and charming coastal towns by car.

But just how hot can Portugal be in December? Well, it’s similar to Malta, with an average high of 63 degrees in December, with things getting significantly chillier in the evenings at around 47 degrees. It’s about the same in January and February. Still, it’s one of the warmer places in Europe at this time of year, so while you may not be in a T-shirt 24/7 or full bathing suit mode, you’ll have a chance of escaping the U.S.’s colder daytime temperatures, and Portugal is known for having in excess of 300 annual days of sun. You’ll also get to avoid the summer crowds.

TPG tip: Conrad Algarve, near Ria Formosa Nature Park and in the golf mecca of Quinta do Lago, offers thoughtful amenities, a lovely spa and a Michelin-starred restaurant, Gusto by Heinz Beck. Rates start at $236 or 68,000 Hilton Honors points per night this winter.

Curacao

Klein Curacao Island. CHIRAPRIYA THANAKONWIRAKIT/GETTY IMAGES

Curacao is the “C” in the Caribbean’s ABC islands — with the “A” being Aruba and “B” being Bonaire. All three are ideal winter sun destinations, enjoying average high temperatures in the mid-80s throughout December, January and February. Indeed, this is the peak season for travel, but it’s well worth it.

You’ll find white sandy beaches, clear-as-day water and resort-style hotels in Curacao, but you don’t want to miss the chance to go diving or explore the island, which is part of the Netherlands. The influence is visible in the Dutch-inspired architecture of the UNESCO-listed capital, Willemstad, painted in cheerful candy colors and lined with lively cafes. February is a great time to visit, as the annual Carnival takes place that month over changing dates each year, when the island is at its most spirited.

TPG tip: Renaissance Wind Creek Curacao Resort is one of the best-rated resorts in historical Willemstad and has its own infinity pool. Rates start at $290 or 46,000 Marriott Bonvoy points per night this winter.

Agadir, Morocco

RAUL C/GETTY IMAGES

Resort city Agadir on Morocco’s south coast is a fine option for winter sun. The temperature hovers around an average high of 70 degrees — though the lows are high 40s and low 50s — with the sea staying just warm enough to dip your toes in without yelping (somewhere around 65-ish).

Agadir is known for its long stretch of golden beach (Plage d’Agadir), but it also has local souks to explore, a recreation of an old medina to marvel at, cultural museums to take in and half a dozen golf courses (if that’s your thing). You’ll also be within close travel distance (30 minutes) to the fishing village of Taghazout, known for its excellent surfing (best for experienced surfers in the winter) and scenic beaches, as well as road-tripping distance (approximately three hours) from the historic port city of Essaouira.

TPG tip: On a soft, sandy beach in the middle of town — equipped with cute thatched umbrellas and plump loungers — the Sofitel Agadir Royal Bay Resort is an attractive Moroccan-styled choice. Rates start at $223 per night this winter. Sofitel hotels are part of the Accor Live Limitless loyalty program, which is free to join.

Iguacu Falls, Brazil

Iguacu Falls. MEKDET/GETTY IMAGES

Expect high temperatures in the region to average 91 degrees (and perhaps the odd rainfall) in Brazil throughout November (the end of spring) and December to February (summer). This makes it an ideal time weatherwise to visit one of the South American country’s greatest natural wonders: Iguacu (or Iguazu or Iguassu) Falls.

The gushing falls can be seen from Brazil or Argentina in their respective Iguacu and Iguazu national parks. They are a cloudy, plunging spectacle, stretching across 8,858 feet and dropping 269 feet (at their tallest) into the river below, combining into the world’s largest waterfall system. OK, you won’t lie on the beach getting a tan, but you will see one of the world’s most impressive natural sights. In Brazil’s park, which spans more than 457,000 acres, there are opportunities to explore the jungle and, if you’re lucky, see the local wildlife, which includes giant anteaters and giant otters.

TPG tip: With a poolside Brazilian grill and spa, the legendary Hotel das Cataratas, a Belmond Hotel, Iguassu Falls is the most epic stay in the park with exclusive access to the falls. Rates start at $883 per night this winter, or book through Amex Fine Hotels + Resorts for late checkout and a $100 on-site dining credit, among other perks.

Funchal, Portugal

Aerial view of Funchal in Madeira, Portugal
CICERO CASTRO/GETTY IMAGES

Funchal, the capital of the autonomous Madeira archipelago, is an easy place to while away a few days. Enjoy a relaxed trip to the farmers market, a stroll around the vibrant Madeira Botanical Garden and the pretty cobbled streets of Zona Vieja, or ride on the Funchal cable car before savoring a long lunch and a spot of wine tasting. Football (soccer for Americans) fans can even visit an entire museum dedicated to the city’s superstar son, Cristiano Ronaldo, showcasing some of his many trophies.

Suppose you have more than a few days to spare. In that case, this Portuguese island has plenty more to explore, from its unique walks along miles of levadas (water channels built for irrigation) to Porto Moniz’s natural pools and Santana’s traditional thatched houses. Often touted as a year-round destination due to its position on the northwest coast of Africa, you can expect to experience decent temperatures from autumn into early winter in Funchal — i.e., an average high of 75 degrees in October, 73 degrees in November and 68 degrees in December. Expect slightly chillier evenings, though, and the odd flash of rain.

TPG tip: The renovated Dreams Madeira Resort, Spa & Marina is half an hour from Funchal and has all the makings of a relaxing sunny holiday. Rates start at $191 or 23,000 World of Hyatt points per night this winter.

Related: Dear TikTok, stop calling Madeira a dupe for Hawaii

Cape Town

V&A Waterfront, Cape Town. PETER ADAMS/GETTY IMAGES

When seeking winter sun, don’t forget about the Southern Hemisphere’s gems, such as Cape Town, the vibrant city of fewer than 5 million people that seems to have just about everything a person could desire. There are magnificent beaches, some with natural sea pools, others with surfing waves and still others with cute African penguins. Be sure to climb Lion’s Head with something to toast at the top at sunset, or take the Aerial Cableway up to iconic Table Mountain.

There are showstopping restaurants and abundant wineries, epic scenic drives and more somber historical sites (Robben Island), places to see wildlife (Cape Point Nature Reserve) and places to geek out over plants (Kirstenbosch National Botanical Garden).

You can expect an average high temperature of 77 degrees in December and about 81 degrees in January and February, and just a couple of days of rain, though it’s always wise to pack a light layer for when the wind inevitably picks up. And for sunbathers, the city is blessed with fabulous swimming pools, especially in the luxury hotels around the V&A Waterfront.

TPG tip: The iconic Cape Grace — A Fairmont Managed Hotel has location, location, location on its side, but also stunning interiors, artworks, and vibrant restaurant and bar scenes that highlight the best of South African cuisine and concoctions. Rates start at $1,181 per night this winter. Fairmont hotels are part of the Accor Live Limitless loyalty program, which is free to join.

Rajasthan, India

Amer Fort or Amber Fort in Jaipur, Rajasthan, India. KRIANGKRAI THITIMAKORN/GETTY IMAGES

It’s easy to assume much of India is swelteringly hot all year, but visitors can anticipate incredibly pleasant weather in the wintertime. It’s still sunny, of course, but cooler. (Think a January average high of 72 degrees in Rajasthan, with nights dropping to a refreshing 50-ish degrees on average.) The humidity is down, the rain is almost nonexistent (think one day per month), and you can comfortably ride in that open-air electric rickshaw without sweating through your clothes.

Since many of the spectacular highlights — decadent and ancient palaces, forts, temples and historical museums — in Rajasthan’s main destinations, including the terra-cotta pink-toned Jaipur, brilliant blue Jodhpur and an artificial lake-filled Udaipur, are not air-conditioned, this is the absolute best time to sightsee. It’s also the ideal season for safaris in Ranthambore National Park. The sun brings the wildlife, particularly elusive tigers, out from the brush to bask in it.

TPG tip: Stay in the fairy-tale environs of Six Senses Fort Barwara to immerse in Rajasthani magic — landscapes, design, food, temples, tea — and make time for Ayurvedic treatments in the gorgeous women’s palace turned spa. Rates start at $1,083 or 152,000 IHG One Rewards points this winter.

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Recent Reviews


Real estate investors regularly pursue new ventures that require substantial upfront investments before generating any revenue. A successful investor might purchase land for a luxury resort, spend hundreds of thousands on architectural plans and permits, and begin construction on facilities designed to serve paying customers. These early expenditures represent legitimate business development costs, incurred with the genuine expectation of future profits.

But what happens to these costs when construction defects or other problems prevent these ventures from ever opening their doors? Can expenses incurred in planning and developing be deducted as trade or business losses? The answer depends on whether the taxpayer was actually “engaged in carrying on any trade or business” when the losses occurred.

The recent Root v. Commissioner, T.C. Memo. 2025-51, case addresses when ambitious real estate projects fail before operations begin.

Facts & Procedural History

The taxpayers selling their family business in 2008. Prior to this, during the 1990s, while still running their business, the taxpayers began planning their next venture: a recreational ranch and guest lodge in Oregon.

The planned lodge would combine fishing with equestrian activities and hospitality. Beginning in 1995, the taxpayers purchased four parcels of land totaling over 90 acres, including waterways, pasture, and farmland. They invested in property improvements, including waterway restoration to enhance fishing opportunities.

In September 2000, the taxpayers contracted with an architect to design a lodge, guest wing, council house, and barn. Construction began in 2003. The scope of work included the main house, council house, and garage, with the total project representing a substantial investment in what was intended to become a commercial hospitality operation.

Problems emerged almost immediately after the lodge received its certificate of completion in May 2006. Snow and rain caused flooding, revealing serious defects in windows, roofing, and weatherproofing. By 2007, the taxpayers discovered hundreds of bats living in the walls along with rats and mice, creating foul odors throughout the structure. A forensic architect later determined that the foundation was defective and the main fireplace was structurally unsound.

County officials condemned the lodge as unsuitable for occupancy in 2010 after receiving reports of the structural defects. The lodge was eventually demolished. The taxpayers sued their contractor and architect to recover their losses. They ultimately recovered approximately $3 million through arbitration and litigation but paid approximately $4 million in legal fees.

Throughout this entire period, the lodge never hosted overnight guests. The taxpayers never obtained an innkeeper’s license, hired hospitality employees, or developed booking systems. While they did host occasional events on the property between 2002 and 2009–including television filming, fundraisers, and dog trials–none involved stays at the lodge.

The taxpayers initially filed their 2014 tax return listing the husband’s principal business as a consulting business reporting more than $300,000 in gross receipts. However, in May 2018, they filed an amended return claiming a $5 million dollar loss related to the lodge project. They carried portions of this claimed net operating loss to their 2017 and 2018 returns, claiming carryovers of $3 million each year. The IRS examined the tax returns and issued a IRS Notice of Deficiency disallowing the net operating loss carryovers in full and imposing accuracy-related penalties for both years.

Trade or Business Requirements Under Section 165

Section 165(c)(1) allows individual taxpayers to deduct losses “incurred in a trade or business.” This requires the taxpayer actually be engaged in a trade or business when the loss occurs. This is different than the rules under subsection (2), which does not have a trade or business requirement.

The distinction between business losses under Section 165(c)(1) and investment losses under Section 165(c)(2) has significant implications for tax treatment and carryover rules. Business losses (under subsection (1)) can generate net operating losses that may be carried back or forward to offset income in other years, while investment losses (under subsection (2)) are generally limited to offsetting capital gains and may be subject to different timing restrictions. Additionally, business losses (under subsection (1)) aren’t subject to the investment interest limitations that can restrict the deductibility of losses from investment activities. Understanding these distinctions becomes particularly important for real estate activities and rental properties that may qualify for special tax benefits like the Section 199A deduction.

Despite these consequences, neither the tax code nor regulations define the phrase “trade or business.” One has to turn to the court cases for the definition. In Commissioner v. Groetzinger, 480 U.S. 23 (1987), the Supreme Court said that determining trade or business status requires examining all facts and circumstances in each case. Courts apply consistent standards across different code sections, including Section 162(a) for business expense deductions and Section 165(c)(1) for business loss deductions.

These court cases start with the concept of trade or business as something that extends beyond simple profit-seeking activities. Many taxpayers engage in profit-motivated transactions that don’t rise to trade or business level.

The courts have developed a three-factor test for establishing trade or business status. First, the taxpayer must undertake the activity with genuine profit intent rather than personal or investment motives. Second, the taxpayer must be regularly and actively engaged in the activity, demonstrating continuity and regularity rather than sporadic involvement. Third, the taxpayer’s business activities must have actually commenced, meaning the business has begun functioning as a going concern.

This third factor often proves most challenging in cases involving failed or abandoned ventures. For this factor, the courts distinguish between planning and preparation activities–which don’t constitute trade or business operations–and actual business activities that do qualify for trade or business treatment.

When Do Business Activities Actually Begin?

The leading court case for establishing when business operations commence is Richmond Television Corp. v. United States, 345 F.2d 901 (4th Cir. 1965).

In Richmond, the Fourth Circuit held that “even though a taxpayer has made a firm decision to enter into business and over a considerable period of time spent money in preparation for entering that business, he still has not ‘engaged in carrying on any trade or business’ until such time as the business has begun to function as a going concern and performed those activities for which it was organized.”

This standard requires more than research, investigation, or extensive preparation. The business must actually engage in the activities for which it was designed, even if those activities don’t immediately generate revenue or profits. A business can qualify as operational while losing money, provided it’s performing its intended functions and holding itself out to serve customers.

The distinction between pre-opening expenses and business operations becomes particularly important for hospitality ventures like hotels, restaurants, and lodges. These businesses typically require substantial investments in facilities, equipment, and infrastructure before serving their first customer.

Courts analyze whether the business has crossed the threshold from preparation into operations by examining specific operational indicators. Does the business have systems for accepting customers? Has it obtained necessary licenses and permits? Does it have employees or infrastructure capable of delivering services? Has it begun marketing to potential customers or holding itself out as available for business?

The Lodge Project Was Not a Trade or Business

In the present case, the U.S. Tax Court found that the taxpayers’ lodge venture never crossed the line from preparation into actual business operations. Despite substantial investments exceeding $5 million and genuine business intentions, the lodge failed to meet the Richmond Television standard requiring that the business “function as a going concern and perform those activities for which it was organized.”

The lodge never performed its core hospitality function of housing paying guests. The taxpayers themselves acknowledged that the lodge was never in a condition to provide lodging for paying customers. Beyond the construction defects that ultimately led to condemnation, the venture lacked basic operational infrastructure. There was no booking system for accepting reservations, no website for marketing services, no revenue processing capabilities, and no customer service procedures. The taxpayers never obtained the required innkeeper’s license or hired hospitality staff.

The court systematically rejected each of the taxpayers’ proposed business commencement dates. The 1995 land purchase couldn’t establish a hospitality business when no lodging facilities existed. Construction beginning in 2003 represented preparation rather than operations since a lodge cannot house guests while under construction. Even after construction was completed in 2006, the lodge never opened to paying customers. A single open house event in 2006 was insufficient because promotional activities don’t constitute carrying on a trade or business when the facility remains incapable of generating revenue.

The conditional use permit obtained in 2009 also failed to demonstrate business commencement. While permits may be necessary for business operations, obtaining permits alone doesn’t prove that operations have begun. The permit contemplated additional construction that never occurred, and the existing lodge remained unsuitable for occupancy.

The court’s analysis was strengthened by comparing this case to Todd v. Commissioner, 77 T.C. 246 (1981), where a similar IRS audit revealed that abandoned real estate development plans don’t constitute trade or business activities. In Todd, a taxpayer’s “plans to enter the business of renting apartments were never realized,” making the resulting losses from abandoned plans non-deductible as business expenses. The policy underlying net operating loss provisions – allowing businesses to “set off their lean years against their lush years” – doesn’t apply when there were no operational years at all.

The taxpayers also failed the regular and active engagement test. The occasional events hosted on the property were too sporadic and disconnected from hospitality operations to establish ongoing business activity. During the construction period, the taxpayers were simultaneously operating their primary fruit processing business, and after selling that business, one spouse continued leading another company. By the time they might have focused on the lodge, construction defects had made the facility uninhabitable, shifting their attention litation and remediation rather than business development.

The Takeaway

The decision helps explain when activities become trade or business operations for tax purposes. The case shows that substantial investments, genuine business intentions, and professional development don’t create trade or business status when ventures never become operational. Construction defects, permit delays, and market conditions that prevent business opening don’t transform preparation costs into business expenses, regardless of amounts involved or underlying business legitimacy. Taxpayers contemplating similar ventures should focus on establishing operational capabilities as early as possible in development processes. While construction problems may prevent full operations, having booking systems, customer infrastructure, and revenue collection mechanisms might strengthen arguments that trade or business activity has commenced.

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