4 Shockingly Affordable Last-Minute Holiday Trips

When to Go: Dec. 31-Jan. 7. San Juan remains relatively affordable throughout the year thanks to its airport, which has the cheapest average fares (per mile) of the 75 busiest hubs in the U.S., according to the Department of Transportation. In a recent search, flying from Chicago early on New Year’s Eve costs a manageable $550. Hotels are also affordable compared with many Caribbean hotspots. On Hotels.com, four-star properties in San Juan start at $206 a night during the first week of 2015, vs. $304 in Montego Bay, Jamaica, and $341 in Punta Cana in the Dominican Republic.

What to Do: You can’t go wrong wandering the blue cobblestone streets of Old San Juan. Stop by the massive Castillo San Cristóbal fort ($5) and the Museo de Arte de Puerto Rico ($6), one of the Caribbean’s largest museums. On Calle del Cristo browse shops such as El Galpon, which sells authentic Panama hats (prices from $60).

Next, head to Santurce, an up-and-coming area full of hip bars and eateries. “It’s always packed with locals,” says Ryan Ver Berkmoes, author of guidebook Lonely Planet Puerto Rico.

Hit the beach at nearby Ocean Park and Condado. For less than $20, you can rent a chair, buy a couple of cold beers, and feast on empanadas sold by street vendors. For a wilder dose of nature, explore the hiking trails and waterfalls at El Yunque National Forest, an hour outside the city. A guided tour is $60, including transportation from San Juan.

Interested in another good day trip? Try Playa Luquillo, the mile-long crescent of surf and sand about an hour east of San Juan. The beach here has a fun, social atmosphere and is known for its food vendors, says Ver Berkmoes. So grab a tasty fried snack and check out the scene.

How to Celebrate: The city’s biggest New Year’s party, complete with fireworks, happens at the Puerto Rico Convention Center (discounted tickets are $65 on Gustazos.com). For something more low-key, head back to Santurce and its central square, ringed with open-air bars and cafés, to toast 2015 with a $3 piña colada.

Jan. 6 is Día de Los Reyes, or Three Kings Day. Expect parades and festivals with food and live music (but keep in mind that some stores and restaurants will be closed).

Where to Stay: In San Juan, Le Consulat is a great bargain in the Condado luxury district, where it’s surrounded by hotels charging upwards of $300 a night. At $127 for a double, you get free Wi-Fi, a simple, modern room, and an outdoor pool. For a bit of a splurge, Ver Berkmoes recommends spending a couple of nights at the Gallery Inn, where each room is decorated with art and antiques. Doubles start at $220 a night.

When to Go: Dec. 19-26. Why not spend Christmas in the City by the Bay? The weather is temperate, most attractions are open, and hotel prices actually drop, says Chris McGinnis, a travel blogger for the San Francisco Chronicle. For instance, last year, rates at the city's big convention hotels hit an annual low of $170 or less from Dec. 19 to 25, vs. a full-year average of $241, according to the visitors bureau. Plus, with the usual tourist hordes thinned, museums are less mobbed, and reservations at top restaurants are easy (or at least easier!) to snag. Flights, too, are reasonable this time of year. We found nonstop flights from Chicago starting at $305.

What to Do: Skip touristy Fisherman's Wharf and check out the futuristic de Young Museum ($10; closed on Dec. 25), which displays 27,000 works from the 17th to 20th centuries. Don't miss the observation tower. It has stunning views of Golden Gate Park. Nearby, the California Academy of Sciences houses an aquarium, a planetarium, and a living rainforest dome ($35).

The city is "brimming with sublime food," says Michele Bigley, author of the Fodor's San Francisco guide. In the buzzing Mission District, Bigley recommends La Taqueria for a behemoth burrito ($7) before catching a movie at the Roxie, one of the oldest theaters in the nation. Cap the night with a cocktail at Trick Dog, where drinks are named for local landmarks ($12).

Visit the Ferry Plaza Farmers Market to see the NoCal bounty. “Occasionally you’ll spot famous chef Alice ­Waters shopping there,” says Anna Roth, food and drink editor of SFWeekly. In the same building, she recommends Hog Island Oyster Co. for seafood stew and, of course, oysters ($18 to $20).

How to Celebrate: Through March, an art project using 25,000 LED lights will illuminate the cables of the Bay Bridge. Check it out from the amazing Top of the Mark bar on the 19th floor of the Intercontinental Mark Hopkins. For a more athletic option, glide over the city’s largest outdoor ice-skating rink, set along the waterfront on the Embarcadero ($14 with skates).

On Christmas Eve, indulge in an old-school meal at the House of Prime Rib, a city institution. “During the holidays it’s all decked out,” says Roth. “You’ll spend $40 or so for an entrée, but at least the martinis are cheap!”

Where to Stay: For a unique property in the heart of things, try the Herbert Hotel. Located just off Union Square, the Herbert has bright, sleek rooms (ask for one with a private bathroom) and hardwood floors. Doubles are $259 a night through Dec. 20 but drop to $155 Dec. 21–25. Prefer something with more of a neighborhood feel? The quaint San Remo Hotel offers rooms with windows from $99, though you will need to share one of several bathrooms.

When to Go: Dec. 15-22. Mexico’s Yucatán Peninsula can get pretty busy at the end of the year. According to American Express Travel, Cancún is 2014’s most popular international destination for both Christmas and New Year’s. That appeal has some upsides—every major U.S. airline offers direct flights to Cancún. However, it also means crowds and, according to hotel researchers STR, a December average daily rate of $227.

For holiday travelers, Bacalar is an escape from that tourist frenzy. This small town overlooking Laguna Bacalar, or the “Lagoon of the Seven Colors,” is 3½ hours from Cancún, and 35 minutes from Chetumal. During the holidays, ­Bacalar hotels ­average a manageable $123 on ­Hotels.com. To visit, fly into Cancún and rent a car (about $40 a day) or take the $55 bus. Flights tend to be cheaper earlier in December, says Zachary Rabinor, CEO of tour operator Journey Mexico; we found one for $414.

What to Do: Tour Bacalar’s beautiful old Spanish fortress, Fuerte de San Felipe de Bacalar ($4, free on Sundays), originally built to protect the town against pirates. Later, hang with the locals at the town’s popular balneario (swimming facility); entry $2. The area is lined by small eateries and has plenty of thatched umbrellas where you can take a break from the Caribbean sun. Or, for just $1.50 an hour, rent a bike from Cocomoco rental shop and pedal along the bay. Obviously, you should be eating as many tacos as possible; the fish and shrimp options at La Playita are not to be missed (from $4).

The town also makes a great base for exploring the Mayan ruins of Chacchoben ($4), a 45-minute drive away. The site, closed to the public until 2002, is home to stone structures dating to the year 800—some still showing signs of their original red paint. Mexico’s biggest cenote (a natural sinkhole), the 300-foot-deep Cenote Azul, is about a mile outside of town—the water is so clear you can see down to the sparkling-white sand floor. Entrance $1, life vests $3.

How to Celebrate: Get in on the holiday spirit by checking out the town’s tree lighting. Then shop for locally made gifts at handicraft shops in the town center or near the entrance to the cenote. Also be sure to sample traditional Mexican Christmas goodies such as ponche (warm tropical-fruit punch stirred with cinnamon sticks), romeritos (sprigs of the romerito plant served with potatoes and mole), and bacalao (salted cod).

Where to Stay: The recently opened Bacalar Lagoon Resort ($115) consists of seven spacious cabanas set on a freshwater lagoon; snorkeling gear is available gratis. Nearby Rancho Encantado is a great value at $125. The rooms have thatched roofs, air-conditioning, and cool tile floors. Guests can get an outdoor massage, kayak on the lagoon, or just kick back in one of the property’s many hammocks.

When to Go: Dec. 25-30. For a ski trip that doesn’t break the bank, Dan Sherman of Ski.com recommends Keystone, the most affordable of Colorado’s Vail Resorts properties. In late December, a single-day advance-purchase lift ticket at Keystone costs $99, compared with $129 at Vail or Beaver Creek. Plus, Keystone is just 90 minutes from Denver, allowing visitors to fly into a large airport with well-priced flights. Trim the cost of your airfare even further by flying on Christmas Day, when flights from Chicago start at $245, vs. $315 on the 24th.

What to Do: Hit the mountain! Keystone offers an impressive mix of terrain, from “long-groomed cruisers” to the “trees and bumps of North Peak,” says Harold C. Jenkins, a travel agent at Corporate Vacations American Express Travel. The resort is also home to Colorado’s biggest night-skiing program, with the slopes open until 8 p.m. during the last week of the year. “Watching the sunset from the top of Dercum Mountain is spectacular,” says Sherman.

Buy your lift tickets at least a week in advance; you’ll save up to 25% off same-day rates. Feeling a little rusty? Ski School lesson prices drop around 20% when you book two days ahead (about $130, though 2014 holiday prices are still being finalized). Kids 12 and under ski free, with none of the holiday blackouts you see at other resorts.

For a break from the slopes, spend an afternoon in Breckenridge, a half-hour away. Grab ­coffee at local favorite Cuppa Joe and check out the stores and galleries in this former mining town.

How to Celebrate: You’ve been burning calories, so go ahead and splurge on a nice meal. In the village, Ski Tip Lodge offers a four-course prix fixe ($75), with dessert served by the toasty fireplace. Or hop a gondola to Der Fondue Chessel, located at the top of North Peak. You’ll get a full Bavarian meal—including fondue, of course—for $59 a person.

What time and place could be more appropriate for a sleigh ride? The resort offers hourlong rides that wind through Soda Creek Valley and include hot apple cider (adults, $30; kids, $20). Afterward, swing by Keystone Lodge to check out the model village carved out of chocolate.

Where to Stay: Unlike most resorts, Keystone is just a ski area, with no standalone town. While that results in fewer off-mountain activities, it also means most lodging is just minutes from the slopes. A two-bedroom condo at the Gateway Mountain Lodge, a five-minute walk or free shuttle ride from the lifts, starts at $419 per night. (Compare that with a two-bedroom in Vail, which starts at about $900.)

Prefer a standard hotel room? The Inn at Keystone ($235 a night for a double) is also walking distance from the slopes and has a rooftop hot tub with views of Keystone Valley.

No matter where you’re going this season, these four air-travel strategies will save you time, money, and hassle.

Check in the day before. Not only is online check-in your best chance at switching to a better seat (airlines release some prime spots 24 hours in advance), but if the flight is oversold, it reduces your chances of being bumped, says Wendy Perrin, travel advocate for TripAdvisor.com.

Get in the fast lane. Planning to travel a lot in 2015 and beyond? Apply for TSA PreCheck, the program that allows you to go through expedited security lines without removing your shoes, coat, belt, or laptop. Membership costs $85 and lasts for five years.

Load up on apps. Use your airline’s app to get the latest on your flight. MyTSA will update you on security wait times, and GateGuru is great for sussing out airport amenities.

Bookmark flightstats.com. Canceled flight? Use this site to vet your options, says Perrin. Flightstats will show you which airports and planes are delayed so you can look for a route that works for you, rather than blindly accepting whatever the airline rep suggests.