If the Caribbean sounds better, I’ll recommend Puerto Rico. The area around San Juan is fairly crowded, although not nearly as crowded as a typical resort area that is loaded with hotels. And there are many smaller resort towns on other parts of the island where people usually rent a condo for a week or two. In a town like Rincon you won’t get crowds, and you will get great beaches.
We’re a couple and are planning a 5/6 nights trip [around Christmas] from India to some place that is slightly reasonable and wonderful, of course! What we’ve been considering till now is Maldives or Cambodia or Thailand. Can you suggest anything around these or even completely different from these? The reason why we haven’t been able to finalize till now is that we’re trying to find a destination other than beaches, which isn’t as easy as it appeared!

There’s really nothing like the holidays in Manhattan. December tends not to be too cold in New York -- you may actually pine a bit for snow as you mosey past Fifth Avenue shops, peering in at the elaborate holiday window displays. The rink at Rockefeller Center gets crowded, but catch it midweek and you’ll have room to skate a lap beneath the most famous Christmas tree in the world. And if you’re still picking up last-minute gifts, you really can’t beat the shopping in this town. Even usually gruff New Yorkers seem to have a brighter spirit this time of year, and carols echo through the subway stations thanks to the city’s many transit musicians. There’s no better time to go and bask in the Home Alone 2 Christmas vibes.
Myself and my girlfriend are looking at travelling to a sunny destination during the first 12 days of December. We like beach and city vacations. Being from South Africa where it is warm in December we would prefer something different to our own culture. We’ve been to Thailand and Malaysia but never India, Sri Lanka or Vietnam. What would you recommend? Thanks Esteen
Hawaii, as you probably know, would be great for what you have in mind, except that there are no cheaper options there at all. After that I agree with you that there are places in Mexico that could work. One in particular that I like a lot is the area around Playa del Carmen, which is just south of Cancun. It’s a lively and tourist-friendly town, instead of a strip of big hotels like Cancun, and there is a wide range of activities and accommodations in different price ranges.
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The final month of the year marks the time when people in northern climates start looking around for an escape to the sun. Fortunately, there are big parts of the world that have their best weather of the year at this time, and are very cheap as well, once you get there. The best places to visit in December are of course close to the equator or even below it.
Similar to so many on this list, Cape Town begins its busy season in the second half of December, so November is ideal in that the weather is nearly perfect and you don't have to worry about high-season crowds or prices. This is a city that has things available at almost any price level. Many of the hotels cater to the 4-star resort crowd, but there are also plenty of hostels and cheap hotels so backpacker-types should be able to get by on a low budget.
Bali has nice weather in the first half of November and it’s very family friendly as long as you don’t stay on the nightlife streets of Kuta Beach. That is possibly your best choice. Dubai has great weather in November as well, and it’s very kid-friendly. There are shopping malls there that also have huge and modern play centers that are sort of like amusement parks there. And there are nice beaches as well. It’s unfortunate that the weather close to India limits your choices that time of year, but either of those could be great and they are both fairly affordable with frequent flights. Let me know if you have any other questions. -Roger
I think the best place for what you want is Thailand. You can choose from Phuket or Ko Samui or one of many other islands, and they all have nice beaches and good nightlife at a very reasonable price. There are other places in Asia that have warm December weather, but Thailand’s tourist infrastructure is better than the others so it’s just much easier to get around and do what you want. Let me know if you have any other questions. -Roger
In November you can find excellent resort deals all over the Dominican Republic, but Punta Cana is typically the first choice, especially if you are looking for an all-inclusive resort with all the luxury extras at a great price. The resort is actually a collection of little beach areas on the eastern tip of the island, so it's very secluded and well away from some of the confusion closer to the capital city.
In SE Asia you have many choices, but probably the best choice for a family would be Phuket, Thailand. It’s more expensive than Goa, but the infrastructure there is much better. Patong Beach is the biggest town on the island and the main tourist hub, but for a family I’d recommend Karon Beach or Kata Beach, both of which are just a bit south of Patong, and both lovely.

Another option is Thailand, and Phuket has the most family-friendly beach areas. You could get a family hotel room at one of the many beach resorts that has a Kids Club in addition to swimming pools and the beach itself. Those are my top suggestions for a family trip that is also suitable for an anniversary. I hope this helps. Let me know if you have any other questions. -Roger
Oh, did you want a sunny tropical vacation that doesn’t require a passport? Done. Hurricane season is over, flights are cheap, and the water is still warm enough for swimming (and scuba diving). Almost all the tourists come here via cruise ship, which means you’re mostly not competing with them for hotel rooms -- Windward Passage, Emerald Beach, and the Bolongo are all open for business after Hurricanes Irma and Maria last year. On December 16 you can catch Jazz By The Sea down at Coral World Ocean Park, and on December 21 watch the St. Thomas Lighted Boat Parade, where contestants (boats) are judged on lights, originality, and holiday cheer.
Surprising to some people, December can actually be a bit cool in Mexico City, especially at night. Its elevation keeps it mild all year, but at least the rainy season is totally over by December, so it's an ideal month for a cheap cultural holiday, perhaps combined with a trip to one of Mexico's many beach resorts. You can get cheap flights between Mexico City and Cancun or Puerto Vallarta, for example.
Located off the coast of East Africa, the Seychelles—an archipelago consisting of 115 islands—is about as close to paradise as you can get. Crystal clear water, lush jungles, and powder-fine sand make it the ultimate early winter escape, particularly for romantic getaways. Book one of the 30 breathtaking pool villas at Six Senses Zil Pasyon, which is among the region's top luxury resorts. The hotel is situated on a private island that offers prime territory for snorkeling, sailing, kayaking, and hiking—plus, the spa has scenic pavilion-style treatment rooms that are worth the trip alone. Health conscious guests will be particularly impressed by the property's new "Eat with Six Senses" program, which is intended to make travelers leave vacation without the guilt that comes with overindulging. There are four tailor-made treatment plans that focus on sleep, detoxing, fitness, and more, depending on the issues you prefer to address.
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