Lanikai, which translates to, "Heavenly Sea," is a beautiful sandy beach on the windward side of Oahu, located about 30 minutes from downtown Honolulu.
Susan Seubert
By Stirling Kelso
January 9, 2015

Cold weather got you down? Perhaps you’d like to get away someplace warm this winter. Or maybe you’re already thinking about your summer vacation destination. No matter when you’d like to escape, this 12-month calendar will help you find the best getaway—and the best deals. (Also check out these travel resolutions that can help you save time, money, and hassle all year long.)

Click here for 2016’s guide to the best places to travel.

January: Cruise the Caribbean

Sun seekers aboard the Caribbean Princess
Jordan Confino—Flickr

Why Now: January is the ideal time to sail the balmy Caribbean, says Carolyn Spencer Brown, editor of “You avoid the December holiday crowds, and pricing is quite affordable,” she says. Indeed, many cruises are 50% or more off peak rates.

What to Do: For a small island and beach-oriented trip, book a sailing in the eastern Caribbean, which includes destinations like Turks and Caicos, as well as the British and U.S. Virgin Islands. Or, if you prefer to visit ancient ruins, scuba-dive, or do some ziplining, check out the western route, where you may stop in Playa del Carmen, Mexico; Roatán, Honduras; and Belize City, Belize.

How to Save: Starting at $309 per person, Princess Cruises’ four-night eastern Caribbean trip, which departs Jan. 22 from Fort Lauderdale, is up to 50% off its holiday price. (All rates are as of January 8.) The ship offers a poolside movie theater, history lectures, and yoga, and stops in the Bahamas and Princess Cays, the liner’s 40-acre private island.

For a more luxurious pick, Peter Lloyd of Century Travel recommends a 10-day western Caribbean sailing on the Oceania Riviera. Departing from Miami on January 14, the ship stops in Key West, Cozumel, and Belize City. Onboard, indulge in a treatment at the Canyon Ranch spa and dine in any of nine restaurants. The trip starts at $2,699, about half off holiday and summer rates.

February: Ski Lesser-Known Mountains

A snowboarder enjoys the fresh powder at Montana's Bridger Bowl.
Ben Pierce—

Why Now: Skiing on the edge of the season can mean bargains, but it’s hard to predict whether the snow will play along. Instead, pick a smaller-name resort in-season; you’ll find reliable conditions and savings of 20% or more (avoid Presidents’ Day weekend).

What to Do: Some of the country’s best powder falls in Colorado, Utah, and Montana. Fortunately, you don’t need to pay through the nose to ski it. Just find the right mountain, buy your lift tickets online and in advance, and go hit those slopes.

How to Save: In Colorado, try Monarch Mountain, three hours from Denver and located in a microclimate that gets hammered with snow, says Colorado-based travel writer Jayme Moye. Advance lift tickets start at $57 a day, vs. $110 for Vail.

Thinking about Park City? Visit Ogden’s Powder Mountain, which gets over 500 inches of natural snow a year, instead. Lift tickets are $69 (vs. $105 in Park City)—or free when you book a package at the Ben Lomond Suites (from $144).

Big Sky, an hour south of Bozeman, is Montana’s most high-profile resort. However, many locals prefer to head north to Bridger Bowl, where lift tickets are just $52. (They’re $103 at Big Sky.) Plus, since you’re only 20 minutes from the city, you can stay in Bozeman, where boutique properties like the C’mon Inn start at an affordable $99 a night.

March: Escape the Spring Breakers in Oahu

A view of the Pacific from Makapuu Trail
Courtesy of Hawaii Tourism Autho—Tor Johnson

Why Now: Since many schools go on spring break in March, it’s a tough month for deals in fair-weather destinations. The Hawaiian island of Oahu is a surprising exception. Waikiki, the popular beach neighborhood in Honolulu, on the island’s south side, sees an average rate dip of 10%, vs. July and August, according to hotel research firm STR.

What to Do: Oahu is Hawaii’s most populous island, but you can find open countryside and quiet beaches outside Honolulu, says Marilyn Clark with Lighthouse Travel. Take the five-mile hike at Kaena Point, the westernmost tip of the island, where you’ll see albatross and whales.

Check out free events such as the Honolulu Festival (March 6-8), a cultural celebration that highlights Hawaiian art, dance, and music. Stay up for the Honolulu Night Market on March 21, when local designers and chefs line the streets of the city’s Kakaako district with food and fashion stalls.

How to Save: Rooms with partial ocean views at Honolulu’s Sheraton Princess Kaiulani are $225, half off the high season. Farther inland, rates are even lower: the Coconut Waikiki hotel, a 10-minute walk from the beach, has rooms from $169 (vs. $209).

Visiting in March could mean airfare savings as well: As of early December, nonstop flights from Los Angeles to Honolulu started at $660 in March, vs. $810 in July.

April: Hike Peru’s Sacred Valley

Andean weavers in Cuyuni, a village outside of Cuzco
courtesy of Paragon Expeditions

Why Now: April marks the end of the low season in southern Peru’s popular Sacred Valley region. If you’ve always dreamed of seeing the sun rise over Machu Picchu, now’s a great time. April’s short but frequent showers limit crowds and keep prices slightly lower than usual. Plus, the markets will be overflowing with harvest-time bounty, and the countryside is vibrant from the past few months of rain, says Holly Wissler, a trip expert for tour operator Paragon Expeditions.

What to Do: Obviously, you must visit Machu Picchu, the Incan emperor’s estate dating to the 15th century. A limited number of people are allowed in daily, so go with a tour group or buy your entrance tickets at least three months in advance.

In Cuzco, the region’s largest city, enjoy historic sites like the Plaza de Armas, which dates to the Incas, and there are more modest delights too, like a glass of chicha, a fermented-corn drink, at Picanteria and Chicheria Valia.

How to Save: Paragon’s eight-day Machu Picchu and Sacred Valley tour is $3,298, $500 less than in peak season. You’ll tour the iconic ruins, meet Andean weavers, and visit the strangely beautiful tiered salt mines outside of Cuzco.

Another eight-day trip, the Classic Machu Picchu from Knowmad Adventures, is a manageable $2,160 in April ($200 off regular price). Standout outings include a visit to Sacsayhuaman, an Inca fortress of massive rock walls, just north of Cuzco, and a chance to browse through the artisan goods at the Sunday Urcos Market.

May: Safari in Kenya

Rhinos in Nakuru National Park in Kenya.
Luis Davilla—First Light

Why Now: May, the tail end of the green, or rainy, season, is one of the best and most affordable months to take a safari. While the dry landscapes of high season make it easier to spot big game, visitors arriving this month will enjoy wildflowers and lush scenery, says Kent Redding of Africa Adventure Consultants. Even better, he says: “It’s birthing season, so you’ll see baby animals.”

What to Do: Safari, of course! Depending where in Kenya you go, and what outfitter you choose, you could see everything from elephants and rhinos to zebras and impalas. Another important consideration: Will you travel by land or air? Air is speedier and more convenient, while staying earthbound will save you the biggest bucks.

How to Save: For a splurge, pick Africa Adventure Consultants’ Kenya Unforgettable safari, a private nine-day trip by small plane. You’ll stay at camps such as Amboseli National Park, famous for its huge elephant herds, and Samburu National Reserve, where you’ll see northern species such as Grevy’s zebra and the reticulated giraffe. This once-in-a-lifetime getaway totals out at $7,494 per person, a $1,785 savings from the high season.

For a more manageable price tag, opt for smarTours’ 12-day Kenya Wildlife Safari; it’s $3,599 for May departures, $1,000 below peak season. This group trip drives from camp to camp, visiting gems such as the Maasai Mara National Reserve and Lake Nakuru National Park, home to a rhino reserve and massive flamingo flocks.

Airfares, too, tend to be affordable in May, according to flight search site Recently, roundtrip flights from Chicago to Nairobi started at $765, vs. $1,542 in July.

June: Road-Trip Along Coastal Maine

Portland Head Light, a historic lighthouse
Clarence Holmes—First Light

Why Now: While much of New England is shifting into summer mode by June, it still feels like spring in northerly Maine, with highs in the low 70s, long sunny days, and fields of wildflowers coming into bloom. Vacationers won’t start flooding into the state in earnest until July, so you’ll find fewer crowds and reasonable prices. At many of Maine’s coastal lodges, June rates are up to 35% lower than in peak summer, says Greg Dugal of the Maine Innkeepers Association.

What to Do: Take advantage of the relatively clear roads with a drive along scenic Route 1, which runs up the coast toward New Brunswick. Not sure where to start? The 158-mile stretch between Portland and Acadia National Park is particularly pretty. Along the way, be sure to put down several of the state’s famous lobster rolls (Hilary Nangle, author of the Moon Maine guidebook, recommends McLoons Lobster Shack on Spruce Head Island).

Make time for a couple of leisurely detours. Stop in Boothbay to see the lovely Coastal Maine Botanical Gardens ($16). Further north, drive down St. George peninsula to take in the views from Marshall Point lighthouse.

How to Save: Point Lookout Resort, located in Northport, knocks $45 off the peak-summer price of its gorgeous pine cabins, complete with porches and fireplaces (from $206). In Rockport, check out the Samoset Resort. The property, on 230 waterfront acres, has an 18-hole golf course, spa, and pool, and a wide range of outdoor sports courts. June rates start at $239, compared with $339 in August.

July: Visit Mexico’s Heartland

A sunset view of San Miguel de Allende
Luis Davilla—First Light

Why Now: While you could also head to Mexico’s Caribbean coast for July deals, San Miguel de Allende, located in the Bajío Mountains, is a better choice. Rather than suffer the humidity of the coast, you’ll enjoy daytime temps in the mid-70s and cool evenings. Still, tourism to the area does slack off in the summer, so there’s plenty of cheap lodging to be had.

What to Do: San Miguel is famous for its colonial architecture. Get your design bearings with the House & Garden tour (Sundays, $20), which takes travelers inside many of San Miguel’s historic homes, suggests Zachary Rabinor, CEO of Journey Mexico. The city is also home to a range of superb restaurants, serving up everything from traditional enchiladas to newer spins on the classics, like short ribs in mole sauce. Then there’s the street food: you’ll find cheap eats—bean soup and stewed pork or chicken ($4) at Mercado el Nigromante, a relatively tourist-free market, says Alberto Aveleyra of Artisans of Time tours. For gifts, visit Mercado Ignacio Ramírez for brass handicrafts.

How to Save: For an ultra-affordable stay, book Casa Gutiérrez, a colorful guesthouse where rooms with private baths start at $32, down more than 40% from spring rates. According to, you’ll get the best fares to Mexico by booking three months out. And don’t forget to check fares into Mexico City, three hours away, as well as the closer Querétaro airport.

August: Unwind in the Maldives

A sea turtle in the Maldives
Courtesy of Coco Bodu Hithi

Why Now: This island nation, off the tip of India, is one of the world’s most striking—and expensive—vacation spots. During the summer rainy season, though, resort prices drop by 30% to 40% and some hotels start throwing in free extras, says Justin Parkinson, a Maldives specialist with Linara Travel. While travelers can expect three to five showers a week in August, he says, storms are typically short and clear quickly.

What to Do: The diving and snorkeling in the Maldives are world-class. The crystal-clear waters are home to whale sharks, rays, sea turtles, and more. In most cases, your resort will arrange for a dive (typically $80 to $150).

How to Save: Is staying in a private overwater bungalow on your bucket list? Seven nights at Coco Bodu Hithi, located on an island in the northern atoll, costs $4,900—still a whopping sum, but more than 30% cheaper than in high season. All villas are tricked out with their own terraces and private pools.

Guesthouses, legalized in the Maldives in 2011, are a more affordable alternative, says founder Raki Bench. He suggests the Arena Lodge on Maafushi, a South Malé atoll, priced at $119 a night, including meals and snorkeling gear. A caveat: The Maldives is a Muslim country, so alcohol is banned in residential areas, and people cover up on public beaches. However, many guesthouses have day rates with resorts (from $30), where guests can have a cocktail and break out their swimwear.

September: Hit the Beach on the Emerald Coast

Riding bikes on the watersound boardwalk
Jean Allsopp

Why Now: There are few places more picturesque than Florida’s Emerald Coast, especially the section edged by Highway 30A, east of Destin. The 28-mile road links a series of sugar-white sand beaches and manicured towns, both of which are packed throughout the summer months. But come September the families clear out, prompting hotel prices to drop and leaving you plenty of room to enjoy the clear blue-green ocean and 80° days.

What to Do: Explore the various coastal towns, each with its own vibe. In Seaside, known for its pastel houses (you may recognize them from The Truman Show, which was filmed here), visit Modica Market to stock up on essentials. Then, stroll to the beach for a pleasantly sandy picnic. For a more active afternoon, hike along dune-flanked trails in deer lake State Park (entrance fee: $3), next to WaterSound Beach. Nearby Rosemary Beach is known for its New Orleans–style houses and charming shops.

How to Save: Lodging prices typically dip 10% to 20% in September. For a splurge, rent a one-bedroom cottage in Seaside, where starting rates fall 17% in September to $350 a night. Or choose one of the area’s affordable inns. Rooms at the Hibiscus Coffee and Guesthouse in Santa Rosa Beach start at $125, down 15% over August rates. Plus, you’ll get a dynamite free breakfast; past visitors rave about the cinnamon-roll French toast and spinach frittatas.

October: Tour Artsy Toronto

Toronto downtown panorama view from Centre Island, restaurant in foreground.
Andrew Rubtsov—Alamy

Why Now: Fall temperatures can be cool in Toronto (think highs in the low 60s), but for culture vultures, October is an ideal time to visit. Oct. 3 is Scotiabank Nuit Blanche, a contemporary arts festival when cultural institutions, from museums to artist-run centers, open their doors and offer free access to their collections. Plus, arrive before mid-month and you’ll catch some beautiful fall foliage.

What to Do: Learn your way around with a free walking tour of downtown, offered by the Royal Ontario Museum. Or, for something a bit more neighborhoody, explore the city’s Queen West district, known for its galleries and independent boutiques, says art consultant and city guide Betty Ann Jordan. While you’re there, be sure to check out the Stephen Bulger Gallery, where you’ll see historical and contemporary photographs by the likes of Vivian Maier and André Kertész. The space includes a 50-seat theater and hosts free films on Saturdays at 3 p.m.

Music fans should also plan to visit the steel-and-glass Richard Bradshaw amphitheatre, which hosts biweekly performances by the Canadian Opera Company.

For a break from the city, take in the fall colors on Centre Island, a residential isle just a 15-minute ferry ride ($7) from downtown.

How to Save: In October, hotel rates dip by 10% or more compared with the summer high season. Rates at the 586-room InterContinental, for example, are 30% lower at $166. At the Gladstone Hotel, a redbrick Victorian on Queen Street West, industrial-style rooms with exposed brick walls start at $131 (vs. $197).

November: Take In Savannah’s Southern Charm

A row of classic Savannah homes.
Bill Stamatis—Getty Images/iStockphoto

Why Now: Savannah is best known for its 19th-century architecture and oak-lined streets. However, the city also has an impressive modern design scene, thanks in large part to the Savannah College of Art and Design (SCAD), which has campus buildings all over town. The crowds that flood the city earlier in the year start to thin in November, yet the weather stays pleasant, with highs in the low 70s.

What to Do: Immerse yourself in the region’s design history with a walking tour from Jonathan Stalcup, founder of architectural Savannah. His in-depth itineraries ($30) detail Savannah’s progression from Georgian buildings (when we loved the English) to Greek Revival mansions (when we loathed the English).

The city is also a shoppers’ paradise, stocked with one-of-a-kind delights, says editor Heather Henley of Check out Satchel for unique leather handbags and Folklorico for crafts from a range of countries.

Finally, be sure to sample the city’s culinary scene, which ranges from Low Country classics to newer additions, like Florence, an Italian spot recommended by Stefanie Dasher, who blogs about the city on “Try the black bucatini pasta with a pork sausage ragu ($20).”

How to Save: Savannah’s popularity as a convention destination keeps hotel prices relatively stable, but, according to STR, the average rate does slide 10% in November as tourists head to even warmer climes. Look carefully, and you’ll find more impressive deals: At Brice, for instance, a new property with four- poster beds and a chic, all-white library, rates start at $179, down from a peak of $399. The no-frills Holiday Inn express, ideally located in the historic district, has rooms from $125 (vs. $172 in April).

December: Spend the Holidays in Madrid

A giant Christmas tree illuminates the Puerta del Sol in the centre of Madrid.
Gerard Julien—AFP/Getty Images

Why Now: Madrid rings out the year in high style. Serrano, a top shopping street, shows off lights and festive window displays, and the city’s many churches set up glowing nativity scenes, says Virginia Irurita, founder of travel company Made for Spain. Madrid is already a steal compared with other European capitals (the average hotel rate is about $100, vs. $179 in Rome), and lodging rates dip 20% in December.

What to Do: Get in the holiday spirit with a choral or organ performance at the Almudena Cathedral or one of the free Christmas concerts hosted by the Prado Museum, says Irurita. Then, indulge in the other thing Madrileños worship—food—at the cozy new Ultramarinos Quintín, part market, part restaurant. Don’t miss the bacalao-stuffed croquettes, shrimp, and fried potatoes.

Shopping for holiday gifts? Skip the weekend crowds at the city’s famous Sunday Rastro flea market; the best vendors are open all week long, says Madrid-based journalist Andrew Ferren. Among his favorites: La Recova, which carries home-decor items, and la Brocanterie, the place to find mid-century furnishings. Afterward, duck into Lhardy for a cup of hot caldo, or bouillon, mixed with sherry, Ferren says.

How to Save: For affordable accommodations, check out, a Madrid-based chain of unique properties throughout the city. Simple double rooms at Room Mate’s centrally located Mario hotel cost $73 in December, compared with $98 in summer. Planning a holiday splurge? Opt for Urso Hotel & Spa, housed in a former palace. The property has gotten a lot of attention for its elegant custom furnishings and hydrotherapy spa pool. Rates start at $205, down about 20% from March.

January 2016: Explore Artsy Asheville, N.C.


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