At the Kimpton Rowan Hotel, admire the appealing outdoor art while you have a quick bite at Juniper Table or head to the roof for dinner at the 4 Saints with its menu of seasonal Mediterranean-style dishes. From the restaurant and rooftop High Bar, you’ll feel as if you can reach out and touch the San Jacinto Mountains. The Palm Springs Art Museum, Indian Canyons, golf, casinos, luxurious spas, and the Palm Springs Aerial Tramway to the mountain top are just a few of the many things to do. Visitors can fly into Palm Springs International Airport or drive about three hours from Los Angeles.
Traveling around India is a shock to the system, but it’s not as bad as it looks. If you pay a bit more for the AC3 class on trains (air-conditioned, 3 bunks per side of the compartment), or AC2, it’s pretty comfortable and civilized. Mumbai is worth a couple days before you’ll be desperate to get out, but many parts of Rajasthan are much nicer and fascinating.

That really depends on your starting point. Most of the cheapest places are in Asia, but the flight would be quite expensive if you are in North America or Europe. If you are in the US, your best bets for cheap places with good weather that time of year will be the non-resort towns of Mexico, or even the resort towns if your budget is a bit higher. Let me know your starting point and more about what you are looking for and I can give you a more complete answer. -Roger


The only places I’ve visited in Brazil at this point are Rio de Janeiro and the Iguazu Falls area. Both of those areas are very nice and justifiably popular. Aside from those, I hear a lot of mixed things about Brazil. I’m sure I’ll explore more of the country at some point, though I’m in no rush. Among other things, English isn’t widely spoken in Brazil (and in Latin America in general). You might know as much about the country as I do, aside from those places I’ve visited.
As far as finding work on the road, the only decent-paying job that is fairly easy to get that I’m aware of is teaching English, but I think those gigs tend to last at least a few months. Right now Thailand is trying to get rid of any foreigners who are working in hotels and bars without permits, so Cambodia might be better at the moment. I’m one of the thousands of people who work online while traveling, and it seems much easier to make a decent living that way compared to working in hostels and such. Good luck with whatever you decide, and maybe I’ll see you on the road at some point. -Roger
That definitely helps! Though I think I was quite unclear in the first place. Being in the same region is definitely not a constraint. We’ve been considering Africa as well, for example! Also, a couple of days of beach time is also sort of desirable, and we’re not really into visiting cities as such. Ideally, we wish to have some time to spend on beaches/resorts/hotels along with some time in a place like a safari or something.
For those looking for an even calmer slice of paradise without all the holiday festivities, try Waimei on Kauai’s southwestern shore, which offers calm waters and sandy beaches that are especially attractive in the early winter months. Get away from all the gloomy weather of the East Coast by trying out a Waimea vacation rental—it’ll definitely make for makes the perfect base to explore all Kauai has to offer.
My best recommendation would be somewhere in the islands of Thailand. December has very pleasant weather with warm days and nights that can be a bit chilly (for some people). Best of all, it’s a very beautiful place and the tourist infrastructure makes it easy to get around speaking English and with very few headaches. The largest island is Phuket and it has famous nightlife in the Patong Beach area. In fact, the nightlife is so notorious that many people think it’s too much so they avoid the place. There are many other beach areas that are quiet and still close enough to go into Patong once in a while.
If you are going to that region I suggest you visit a site called travelfish.org, which is by far the best website on SE Asia and it’s run by a friend of mine who lives in Bali. They have busy forums where you can ask questions and quickly get them answered by experts on every imaginable topic there. I’m happy to help more as you are planning, so let me know if you have any other questions. -Roger

While the Caribbean destination tends to overflow with families during the holidays in December, go a month earlier and you’ll be treated to sunny days sans screaming kids, plus less expensive airfare. “November is my one my favorite months. The hustle and bustle of high season hasn't kicked in, average temperatures are in the 80’s, and the water temperature is lovely,” says Michael King-Hew, the proprietor of Kamalame Cay, a private island resort in the Bahamas. King-Hew specifically suggests for the resort's annual wellness retreat. “It’s the perfect way to get rested and in shape before the start of the hectic holiday season.”

And as you mention, Bali could actually work for you. I’ve spent two Decembers in Bali, and December is quite a bit rainier on average. Still I had a great time and it was sunny most of the days. The rain in the tropics (and Bali is almost ON the equator) tends to come down in 30-minute bursts rather than drizzling all day, so it’s usually pretty easy to avoid. The best part of Bali is there are loads of things to see and do, and the nightlife is excellent. The Kuta Beach area is fun for at least a few days, but I wouldn’t spend too much time there. You should also spend a few days in Ubud, which is very touristy but also interesting. And you could spend some time in Lovina, which is along the northern coast and it has all of the charm of Bali from 20 years ago before most of it got overbuilt. With all the temples and other local attractions, there is always something interesting to do, which is not true of many other places with great beaches and nightlife. Let me know if you have any other questions. -Roger


I’ll be happy to try to help, but I’d really need to know your starting point because there are cheap places in different corners of the world, and it’s not worth flying halfway around the world to try to save US$20 per day. In mid December through January for beaches you should consider Thailand and perhaps also Vietnam. I’ll give you more information once I know where you are starting from. -Roger
From December through February there are literally no European cities that could qualify as having “great weather,” except for the Canary Islands, which is listed below. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
I think Sri Lanka would be wonderful for 2 weeks in December. The rainy season typically ends early in December, but even when it’s still going it tends to be quick downpours, as you are no doubt familiar with if you’ve been all over southeast Asia. Still at this point there are very few hostels with dorm beds and not even many cheap budget hotels, but at the age of 30 you are probably happier with normal hotels anyway. Value is quite good in Sri Lanka as long as you can spend at least US$30 or so per night, and hopefully a bit more. Food is also quite cheap in general, although there are still surprisingly few tourist-oriented restaurants in many towns so it feels a bit undiscovered. Just don’t spend much time in Colombo and preferably focus on the mountain areas, and I think you’ll love it.
My other two suggestions are San Juan, Puerto Rico and Cartagena, Colombia. Both cities have really wonderful colonial districts and modern resort districts nearby. San Juan is more expensive, but still reasonable, and it has far better beaches. Both have a bit of rain in November, but it tends to come and go quickly. You’ll get similar rainstorms in most of the Caribbean in November, so it’s a bit tricky. I hope this helps. If you had something else in mind let me know and I’ll try again. -Roger
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