Another consideration is that Thailand is generally easier to get to with far more flights that are often cheaper, and Thailand also has FAR more beach options because of its long southern coastline and especially the islands. The posh beach areas on Phuket are typically the most expensive beach hotels in Thailand, but there are other more remote beaches in Phuket with lower prices so it’s worth a look. Aside from Phuket you should also look at Ko Samui, Ko Pha Ngan, and Ko Phi Phi. You might also look at the town of Pattaya, which is the closest beach resort to the Bangkok Airport. Parts of town have a lot of single foreign men in certain bars at night, but most of the town is actually quite family friendly and very good value. Let me know if you have other questions. -Roger
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
Dubai has pretty much perfect weather in November, and this is really the first month since April when it's not scorching here. Fortunately, the crowds are also light because most people wait until Christmas to start traveling to warmer places. Dubai can be incredibly expensive if you have a big budget, but it doesn't have to be. You can get good deals on non-chain hotels and even apartment hotels this month, and if you skip the hotel restaurants and the fancier places in malls, you can eat well on a modest budget here.
Fortunately, it rarely rains at all in Cairo, so even though December is one of the wetter months, that means nothing and you are unlikely to see even a drop of rain. Hotel prices do reach their peak in Cairo starting late in December, so it's best to go early in the month if possible. Egypt is definitely one of the cheapest places to travel in December, and the weather is surprisingly nice as well.
Thank you so much for the kind words and I’m always happy to hear that people find this information useful. As far as Turkey in December is concerned, I wouldn’t recommend it. I actually lived in a small town near Antalya on the Mediterranean for a bit over a year and I was surprised by the fact that almost everything closed down around 1-November and didn’t start opening again until March or April. Actually, I think Istanbul would still be enjoyable in December and so would Bodrum or any of the other larger cities including Antalya. But anywhere on the coast will be a ghost town and I’m pretty sure that Cappadocia would also be mostly shut for the winter. Ephesus probably stays open, but similar to Cappadocia, the attractions are all outdoors and they can get pretty fierce rainstorms in winter.
This is a tricky one. Pretty much every destination in the Tropics has its peak rates of the year during the weeks you have in mind. That said, there are still some fairly cheap destinations in the Caribbean, even at peak rates. However, since you live in South Florida and understandably don’t want to go someplace even hotter during the only semi cool time of the year, it sounds like you are ruling out most of the Tropics.

If you are really only going for 4 or 5 days you only have time to visit one or maybe two cities anyway. I’d say that Lisbon would be ideal and you’d have time also for a short visit to Porto or the Algarve in the south, or at least the historic small town of Sintra, which is near Lisbon. Lisbon has fantastic weather for Europe and it’s a lovely city with plenty to see and do.
It's been said Jackson Hole is where Aspen meets Palm Springs. Ski season, however, really starts in mid-December. There's world-class—not to mention some of the most vertiginous—skiing in the continental U.S. Plus, miles and miles of trails and nature to enjoy less vertically trekking through Grand Teton National Park and Yellowstone National Park. To put much of this at your fingertips, the Four Seasons Jackson Hole has a ski concierge and is a ski-in/ski-out property.
Trekking in Nepal during peak season might not sound like the most sensible choice for penny-pinching backpackers. But you can still enjoy the ideal weather without spending a fortune on in-demand hotels and expensive permits if you're happy to swap big-name trails, like Everest Base Camp and the Annapurna Circuit, for quieter treks to Kanchenjunga Base Camp and around the Langtang Valley. Idyllic conditions (dry but not witheringly hot) are also on offer in Rajasthan, one of India’s most vibrant and varied states. Chug between notable, attraction-rich cities like Jaipur, Jodhpur and Udaipur on an atmospheric and wallet-friendly Indian train, snacking on spicy pakoras and sipping sugary chai en route.
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