Few people travel between Thanksgiving and Christmas—specifically, from the Tuesday after Thanksgiving to the Thursday or Friday before the peak Christmas rush—so you can enjoy substantial savings off peak-season rates (four nights for the price of three, seven nights for the price of five) and your chances of an upgrade are good—if you book through a Caribbean specialist with clout.
Yes I travelled a bit by train in southern India, I got lucky on my first few journeys with lack of people, then I hit some Indian holidays and it was hellish. I remember the trains being booked up for all the upgraded a/c and upper class carriages. One time even the Indians were fainting on the over packed carriage so you can imagine the heat for little old gringo me!
One thing about Cancun that is interesting. Cancun itself is essentially a very long beach sticking out into the Caribbean that is lined with high-rise hotels and time-share properties. Except for a busy area at the corner of that peninsula, most of the hotels are spread out quite a bit, so there aren’t many things that most guests can walk to. Many people love it and are happy to basically stay in their own hotel most of the time, and maybe take a taxi down to that busy corner area once in a while. Personally, I’m a much bigger fan of Playa del Carmen, which is a full-on tourist town about 50 miles south of Cancun. It’s got hundreds of small hotels, restaurants, bars, shops, and everything else a visitor wants. The beaches aren’t quite as nice, but I find the town to be very fun and vibrant. Also, up and down the coast from south of Playa del Carmen to north of Cancun there are large resorts that are far from each other and on huge properties. Many of them are all-inclusive, so that is another option.

Turkey has bars all over Istanbul and the other tourist cities, but there are also cafes and tea shops and that sort of thing that are filled with locals (and some tourists) all evening. In Dubai and Abu Dhabi, the only bars are attached to hotels (and there are a LOT of them), but almost no locals drink, so there are unlimited evening alternatives. Other nearby Muslim countries such as Oman and Bahrain are similar, except with far fewer tourists (and drinkers).
Not surprisingly, the weeks around Christmas and New Years are literally the busiest of the year in Goa, so either book a hotel way in advance or be flexible once you arrive. Some towns, like Calungute, are lined with package hotels that fill up completely, but other towns, like Anjuna and Vagator, are usually booked in person or by email, so you can often find a place just walking around. If you are in the mood to tour around, Mumbai has great weather during December, and Delhi has warm days but cool evenings this time of year. Goa has some of the best beaches in December in all of Asia, so give this one a serious look.
Those who find a healthy dose of decadence aids the de-stressing process should make a beeline for UAE capital Abu Dhabi, where infinity pool-rimmed spa hotels offer a taste of the world of the rich and famous amid guaranteed November sun. In Madrid, it’s the laid-back lifestyle of the madrileños that draws travellers, who can browse works by Picasso in the Reina Sofia, quaff Tempranillo in grand plazas and tuck into warming cocido madrileño (traditional chickpea stew), without the stifling crowds of summer.
You would probably get some rain in Cartagena in November, but mostly in the first half of the month, and even then it tends to come down in short bursts rather than all day, so it’s usually easy to avoid. I love Cartagena for trips like this because the walled historic part of the city is really lovely and fun, with plenty to see and do. The nearby beaches are big, but the sand isn’t white and fluffy, so they won’t make too many “best beaches” lists. It’s also very cheap there, and especially at the tail end of the off season like that. As long as you don’t mind the possibility of a couple of quick rain storms, it should be great.
Malta would have decent weather as well, but I think the nightlife there is pretty dead during the colder months because they don’t get many visitors. They don’t have proper beaches as well, as the coastline is mostly these huge rocks. If you really want a warm beach in December your best bet is the Canary Islands, and even then it can be slightly chilly in December. But the nightlife in Malta is pretty dull, since so many of the visitors are retired Europeans.
The Bali thing is also kind of a mess for those on low budgets. Kuta is a headache, and pretty much the opposite of what is so beautiful about the rest of the island, but it’s also where nearly all the really cheap beds are located. If you go a bit north in that same area into Legian and Seminyak, it’s nicer, but prices also go up. And Ubud is nice, but also more expensive for hotels and such. I’ll probably rent a place in Seminyak for a few weeks, which won’t be cheap.
My fiance and I plan to travel for a month starting Oct. 20. We’re thinking about selecting a region that would allow 4 destinations with great food, outdoor activities (hiking, swimming, horses, yoga, etc), nice accommodations that don’t break the bank, and some sight-seeing. We’re planning to get married on the trip, too. Any suggestions? Super appreciate your insight!

There are many other Thai islands that could also be ideal and have what you are looking for. Another option is Boracay Island and I mention it because I spent an evening hanging out with some guys visiting from Saudi Arabia and they liked it a lot. The weather won’t be “cool” but it should be nice, and they do have very good nightlife in the Boat Station 1 area.

November brings the annual Vodafone Mexefest Music Festival (Nov. 24-25), a gathering of popular artists in venues throughout Lisbon. The Lisbon & Sintra Film Festival, in its 12th year, is a celebration of cinema with directors, actors, artists, musicians, and writers in town for the event (Nov. 16-25). Billed as the “largest technology conference in the world,” Web Summit began in 2010 as a way to connect industry and the technology community (Nov. 5-8). The year’s new wine and the ripening of chestnuts are celebrated with the Magusto, on Nov. 11, St. Martin’s Day. The holiday spirit becomes apparent at the end of the month, with colorful lights and roasted chestnut vendors along the streets.

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