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.
Hmmm…there may not be a Wow Factor in Puerto Rico, especially if you are that used to Caymen. I was thinking more about a really nice place that was easy and with great weather. Costa Rica could have the Wow Factor, however. The country is something like one-third national parks and it is packed with great scenery and adventure activities. It is the zip-lining and canopy tours capital of the Americas, so there are many great options along those lines. And there is the volcano and hot springs and really nice beaches. I’m not sure what you’d consider a Wow Factor, but Costa Rica is probably the most Wow destination other than Hawaii.
You’ve got a pretty good budget so you can afford to go almost anywhere, assuming you are okay with renting one or two houses or villas instead of 4 hotel rooms. If you are willing to fly all the way to Asia, your best bets would be Bali or one of the Thai islands, probably Ko Samui or Phuket. In all of those places you should be able to rent a house or villa near the beach and then do activities and day trips very easily.

You mention New Zealand and of course it’s summer there then, so it would be a good choice. However, all of these places will be crowded and near peak hotel rates if they are warm. So I’ll be happy to give you advice if you tell me if you’d rather visit one or more European cities in the cold season, or if you are looking for a warm place like New Zealand where it will be fairly crowded. By the way, the southern European cities such as Rome and Barcelona are lively and enjoyable that time of year, as the Christmas season goes on, and there aren’t too many tourists except for a few that travel to see their families around the holidays. So it can be a good time for southern Europe, as long as you don’t mind wearing a jacket or jumper during the day, and maybe a bit more in the evening. Give me a bit more guidance and I’ll be happy to try to help. -Roger


The truth is, Rio de Janeiro will make this list for at least 8 months of the year, as the weather is always pretty good and the prices are still reasonable compared to Europe and North America. November is still well into the sweet spot, as the high season for hotels doesn't begin until December. This means bargains are often available at some of the luxury places along the beach, which won't be true again until April.

However, I would probably recommend staying closer to the US, unless you are really interested in the Asian cultures or that kind of experience. If you are mainly just interested in family time and a fairly easy holiday for all, and you aren’t specifically interested in getting to know an Asian culture and its food, I think I’d stay in the Americas.


I know Italy is the world’s top wine producer and they obviously make a lot of olive oil as well. I’ve seen on many travel shows how it’s fairly easy to visit the olive oil places, and of course most wineries have places where you can see the process and taste it. The thing is though, that even Sicily is quite chilly in December so they might close down for the season. You definitely won’t get sunbathing weather in December at all. I would say you are best off in May, June, September, and October to get good weather and not have to deal with the insane crowds in July or August. Tuscany is the easiest to reach of the 3, but because of that its beach towns are most likely to be crowded in those warm months. I hope this helps and let me know if you have any other questions. -Roger
As you begin to cross off the final 31 days on your calendar you may be tempted to put away the passport and swap those itchy-footed escapades for quiet nights in. But with nearly a year of adventures behind you, why stop now? December is jam-packed with high-octane adventures on mountain peaks and coursing rivers; indulgent escapes with mulled wine, rum cocktails and spicy Malaysian street food galore; walks on the wild side with kaleidoscopic creatures and soaring giants; and countless seasonal celebrations whisking you from the sunny Caribbean to Santa’s hometown.
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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