Spend the past two days discussing your ideas. Group thoughts; Is that adventurous and cultural enough? We want a “wow” factor. We have vacationed in Cayman Islands about a dozen weeks since the kids were little (been there done that.). We have ruled out Asia only because don’t see a huge Wow factor for the amount of travel. What about African Safari? Still not ruling out your ideas, just want to know what is Wow about Puerto Rico? Costa Rica?
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
First of all, applause to all your kind help (and your time). My 8 years old boy and I want to travel in December to a warm country and I am a little bit nervous to be only two of us since my hubby could not join us. I am just wondering if Costa Rica (or Brazil) safe to travel for a woman alone with young kid? Any other safe countries in your mind (with affordable price)? We live in D.C and don’t want to fly too far like Asia, Australia, etc. We have been in Dubai and Mexico.

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
Hi Roger I was hoping to travel to either Bali or Thailand over Christmas into New years… our dates are a little bit flexible. I am having a hard time finding good deals on airlines. When is the best time to book and which are the airlines you recommend. If Asia is to expensive for airfare any other suggestions .We want to go to some place warm and have activities, We have been to Mexico and Hawaii already
You’ve been to Cancun, but have you been to Playa del Carmen? Personally I much prefer it because PdC is a lovely tourist town with hundreds of little hotels and restaurants and bars, unlike Cancun, which is mainly a long string of high-rise beach hotels that are so spread out that you are nearly trapped in your own hotel. It’s about an hour south of Cancun airport by taxi or shuttle. That would be another of your cheaper options, partly because flights into Cancun are pretty cheap. It will be the tail-end of the rainy season in all of these places, but that usually just means a 30-minute rain storm a few afternoons each week.
Thanks for all of this Roger! It looks like in the comments you mention Portugal a couple times and I wanted your opinion – we’re looking at the first two weeks and probably focusing on Lisbon to Porto (since we know it will be too cold to do the beaches in the south). While Portugal seems to be highly recommended, I keep seeing conflicting information about November being rainy – we definitely don’t want to spend 2 weeks in the rain but in your experience what are the chances of that? Thank you!!
Another option would be Cambodia and/or Vietnam. The town of Siem Reap, which is just next to the Angkor Wat Temples is the real highlight. Phnom Penh is worth a quick look, but not on a shorter trip. Vietnam itself is a wonderful and gorgeous country, and you can see a lot of the highlights in 10 days or so. It’s also very cheap, even around Christmas. You could fly into Hanoi and then go see Ha Long Bay, and then take a train down to Hoi An. After that you could go to Nha Trang for the best beach experience or the hilltown of Sapa. The city of Ho Chi Minh City is quite crowded and you might not like it for more than a day or two.
The 2nd option is a bit early in the year. The Greek Islands are cold and mostly deserted until mid April or so, and the good weather really starts in May or June. This is true in Mallorca as well. The Canary Islands are much farther south so they have acceptable beach weather almost all year, although you might get some cooler days in March as well. Even still I wouldn’t really recommend them for a younger person. In my opinion, the Canary Islands are pretty boring because the majority of visitors that time of year will be retired people from northern Europe who just want to sit in the sun. The nightlife tends to be cheesy and/or weak if you can find it at all. Let me know if you have any other questions. -Roger
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
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