Eight days in Chile? Global tour specialist Abercrombie & Kent has a 40-percent-off deal for Cyber Monday.

Black Friday is fine for Tinkertoys and turtlenecks, but savvy travelers know the best deals happen on Monday.

Get your credit cards (and passports) ready: Cyber Monday is Christmas come early for travelers looking to score big on their next trip. If sifting through thousands of sales seems daunting, don’t worry. We’ve scoured the very best hotel, tour, and flight discounts for you. From half-price Caribbean villas to African safari expeditions, these are the Cyber Monday deals you won’t want to miss.

Azores Getaways

Often called the Hawaii of Europe, the Azores is home to lush coastlines of waterfalls, volcanoes, and pristine beaches. Spend a week at this tropical Portuguese archipelago, just four hours from the East Coast, at the bargain-bin price of $499. This includes round-trip flights from Boston, seven nights in four-star hotels, and select meals. Bonus: New direct flight routes to/from JFK are coming in 2018, so keep your eyes peeled for low-cost airfare from New York City as well.

Deal only available Monday, November 27.

The Peninsula Hotels

Leave it to the elegant Peninsula Hotels to list one of the most over-the-top Cyber Monday steals. Rooms and suites at The Peninsula New York and The Peninsula Chicago cost 30 percent less, while the brand’s Beverly Hills, Chicago, and New York locations sell spa packages with free upgrades, massages, facials, and personal training at a 25 percent discount. Gift cards to their on-site restaurants and spas are reduced by 10 to 20 percent, too.

Deal available Friday, November 24, to Monday, November 27. 

Abercrombie & Kent

Abercrombie & Kent’s annual holiday sale cuts 40 percent off its private journeys to far-flung destinations around the world, such as Botswana, Vietnam, Peru, Russia, Egypt, Thailand, and Jordan. For a total savings of $2,800, your best bet is the eight-day tour of Chile, where you’ll travel from the vibrant capital city of Santiago to the rugged Torres del Paine National Park. A stay at the design-forward Explora Patagonia lodge comes with more than 40 excursions, including guided nature hikes and gaucho-led horseback rides around the region’s glacial lakes and snow-capped peaks.

Deal available Monday, November 27, to Friday, December 1.

AlSol Cap Cana Resorts, Dominican Republic

This all-inclusive resort group rolls out the red carpet for rock-bottom rates. Set on 30,000 oceanfront acres in the Dominican Republic, AlSol Tiara Cap Cana features 10 restaurants and bars, swim-up pool suites, and a range of free activities: Spanish lessons, beach bonfires, wine tastings, and cooking classes among them. There’s also the smaller, more secluded AlSol Del Mar, the family-friendly AlSol Luxury Village, and the sprawling Villas at Cap Cana by AlSol. All four properties are 50 to 59 percent off—dropping some rooms to $104 a night. In addition, you’ll receive a free bottle of champagne, plus spa and dining credits (applicable to specialty on-site restaurants separate from the all-inclusive package).

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Deal only available Monday, November 27. 


You can pocket more than $2,000 if you book with andBeyond. For Cyber Monday, the company is deducting 30 percent from its small group trips: a six- to eight-night Mobile Camping Safari Expedition in Botswana, a 13-day Snow Leopard Journey in India, and a five- to eight-day East Africa Photographic tour through the Serengeti National Park in Tanzania or the Maasai Mara National Reserve in Kenya. Get on it while it lasts.

Deal only available Monday, November 27, and a 20 percent deposit must be made within 14 days after booking.

Destination Hotels

Destination Hotels is taking 40 percent off all its properties from coast to coast, including Carmel Valley Ranch in California, Stowe Mountain Lodge in Vermont, Wailea Beach Villas in Hawaii, Vail Residences at The Talisa in Colorado, and the Cliff House in Maine. Washington, D.C.’s Embassy Row Hotel even throws in free valet parking, a daily $10 food and drink credit per room, and yoga sessions on the seasonal rooftop—all for as low as $106 per night.

Deal available Thursday, November 23, to Wednesday, November 29, for travel between December 1, 2017, and December 1, 2018. The Embassy Row Hotel deal is available for travel until August 2018. 

Nayara Springs, Costa Rica

Perched atop Costa Rica’s rainforest, this adults-only retreat spells romance for couples seeking a honeymoon hideaway. Check into one of the 35 open-air cottages, which have outdoor showers, Arenal Volcano views, plus terraces with hammocks and plunge pools fed by mineral hot springs. The best part: A four-night visit with breakfast and daily yoga classes will save you $1,050.

Deal only available Monday, November 27, for travel in May 2018 and between August 16 and November 15, 2018.

Villas at Sailrock Resort, Turks and Caicos

A quick 25-minute flight from Providenciales brings you to the brand new Sailrock Resort on quiet South Caicos. Here, the beachfront bungalows have coastal-chic decor (reclaimed wood furniture, beige fabrics) and feature floor-to-ceiling glass sliders that open onto private infinity pools and a 1.5-mile stretch of powdery white sand. One- to four-bedroom villas are half price during a four-night minimum stay (breakfast included).

Deal available Friday, November 24, to Monday, November 27, for travel between January 3, 2018, and November 19, 2018 (blackout dates apply).

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The Cosmopolitan of Las Vegas

Rates like this are rare at The Cosmopolitan, one of the Strip’s most popular hotels. The massive two-tower building features three pools, a world-class spa and hammam, a famous nightclub, a seasonal rooftop ice rink, and a 300,000-square-foot entertainment complex with 16 award-winning restaurants. Rooms are buy one night, get the next one free—leaving you with plenty of extra cash for the casino.

Deal available Friday, November 24, to Monday, November 27, for travel between December 2017 and April 2018. 

Marigot Bay Resort, St. Lucia

For a budget-friendly Caribbean escape, look no further than St. Lucia’s Marigot Bay Resort. Guests who book a minimum of three to five nights will receive 50 percent off the hillside suites, which have canopy beds and outdoor hot tubs overlooking the marina. The resort itself is home to three stylish restaurants, two cabana-lined infinity pools, and a spa.

Deal available Friday, November 24, to Monday, November 27, for travel between November 24, 2017, and March 30, 2018.


Cheap airfare isn’t hard to find on Cyber Monday, as long as you’re flexible with your destination and travel dates. Carriers such as American, JetBlue, United, Alaska, Southwest, Frontier, and Spirit all offer discounted domestic flights, starting at $30 each way. For international travel, Delta, Emirates, Norwegian, and WOW are known to have the most wallet-friendly deals, with round-trip fares to South America and Mexico from $100, Europe from $200, and Asia from $500. Just keep in mind that seats sell out fast, so don’t hesitate if you see a good price.


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