It looks like you’ve been to most of the more popular options for winter holidays already, and since you listed them I assume you want to go somewhere new. The one that is missing, which I think could be perfect for you, is the Guanacaste area in northern Costa Rica. The weather will be perfect and you should be able to get a reasonably priced flight into nearby Liberia Airport. There are a variety of smaller towns along those beaches, and Tamarindo might be the most famous. They offer a mix of traditional hotels and resorts in smaller towns along with newer 4-star and 5-star hotels on large properties that tend to be away from the towns. The weather will obviously be similar to Panama, as long as you were on the west coast. Costa Rica is the adventure capital of Latin America and one-third of the country is national parks, so there is plenty to see and do. There isn’t much history there, but you can’t have everything.
Another destination that might not exactly have “great” weather in December, yet deserves to be on the list, Sharm el-Sheikh is famously Egypt's most popular Red Sea beach resort. Those following the news might still hesitate to book a trip here, whether that is a rational decision or not. But at the very least this is one to consider in the future, as it's an amazing bargain once you get here.
Italy should be at least a bit warmer than England this time of year, but not by all that much in a typical year. Also, if you only have about 9 days I think I’d try for no more than 3 or perhaps 4 total cities (Venice can be appreciated in about 24 hours if you are in a hurry). And of course, Paris and Amsterdam will both be quite chilly, so I think I’d save those for another trip. My recommendation would be to spend the whole trip in Italy so you aren’t so rushed. Do Rome for at least 3 nights and Florence for 2 or 3 nights, and then Venice for 1 or 2 nights. You could still have time to pop down to Sorrento for a couple nights to see Naples and Pompeii and whatnot.
Yes, these lists are reviewed and updated at least once a year. I’ve been adding new cities each year and even removing a few that have become too expensive to be on a “cheap” list. Personally, I’m an obsessive travel planner (which is why I do this for a living) and I like planning at least a few months in advance. You usually get the cheapest flights around 3 months out, although it can range from 2 to 5 months for longer flights. In other words, now is a great time to plan a November trip.
Vacationing to Sicily during Italy’s traditional “off-season” has been trending in recent years, according to American Express Travel. What gives? Well, for starters there's Sicily's fabulous Mediterranean setting, as well as its rich baroque aesthetic and festive Catholic traditions. Plus, the crowds are more manageable than they are in the summer, which makes travel for families and large groups a breeze.

Interestingly, I had not seen that June travel warning. It’s hard to know what to think of it. On one hand, the US State Department has official warnings like this to many places, including quite a few that people safely travel to every day. And also, even when Colombia had its problems for all those years, Cartagena was considered safe because it’s this tourist beach town and the drug and FARC problems had nothing to do with it. My best guess is that Cartagena itself would be fine and perfectly safe, but I wouldn’t rent a car and drive around the highways myself at this point. Sadly, I think it might be best to save Cartagena for another time when there is no known threat.


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
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.
There’s also Mad River Valley in Vermont, another place to spot amazing hues of fall foliage within Green Mountain National Forest, which provides one of the most gorgeous November vacations. Enjoy quiet seclusion in the small towns near and around Central Vermont for a once-in-a-lifetime chance to see autumn’s last breath and the birth of winter white splendor. Plus, November also happens to be primetime for skiers in Vermont and surrounding Eastern states. Enjoy a slice of wondrous heaven this Thanksgiving holiday.
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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