There is no better time than December to discover a still (somewhat) under-the-radar part of the Caribbean. This verdant, five square mile island has seen a lot of activity recently, from a new mega yacht club to a Soho House to the Mandarin Oriental's first property in the Caribbean. More is on the horizon for this picturesque piece of paradise, but go before everyone else discovers it.

November is a perfect time to visit Bermuda, with temperatures in the mid-70s and pink sand beaches that are less crowded than in high season. There are many ways to explore the 21-square-mile island, from under the sea where you can snorkel or dive among coral reefs or shipwrecks to the Bermuda Railway Trail, an 18-mile abandoned rail bed that winds through scenic landscapes and shorelines. The Crystal Caves take you into an underground world with a subterranean lake and white limestone stalagmites. The 36-acre Botanical Gardens, established in 1898, inspired John Lennon during a two-month Bermuda stay that led to his Double Fantasy album.
The food, including its famous ceviche dishes, is a particular highlight here, and the tourist district of Miraflores is packed with interesting and cheap restaurants. Basic and cheap hotels are in the same neighborhood, so it's a better alternative to the historic center of Lima for most people. By the way, the rainy season in Cusco starts in December, so the trails can sometimes be cut off, although many people go anyway.
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Heading east, India could be a possibility, although it’s not for the faint of heart. As a resident of Singapore, I assume you know a fair bit about India. Outside of Mumbai, it’s all quite cheap and the weather will at least be good. Personally, I love the southern state of Goa, and it has everything you are looking for, without the insanely crowded conditions of India’s big cities.
The other place that comes to mind is Croatia, which also has reasonable weather in November. I’d recommend focusing on Split, which has many similarities with the more-famous Dubrovnik, but it’s easier to reach, much cheaper, and more authentic because Dubrovnik has become kind of cheesy as a cruise port. You could even take a bus to Mostar or Sarajevo in Bosnia for a couple days. The coast in that area is beautiful and there won’t be many other tourists that time of year. I hope these ideas help. Let me know if you have any other questions. -Roger

Bali is wonderful, or at least parts of it are, but they now have a volcano issue and those flights are very long and never cheap. Machu Picchu is incredible, but it’s a place you visit for half a day or so, and they actually have their rainy season at the end of the year, so it’s actually not one of the better times to go. Actually, you might consider a trip to Argentina, which is warm that time of year, though rarely scorching. Buenos Aires is a wonderful city that is pretty good value now, and you can also visit the Mendoza wine region and Iguazu Falls and Bariloche, which are all even a bit cheaper than Buenos Aires.
Even if you can't sunbathe, the weather is still reliably pleasant all the time, with almost no rain. Weekly and monthly apartment rentals here are very popular, but there are plenty of hotels and hundreds of restaurants for those coming for shorter periods. If you want to be with the most English speakers you'll want to focus on the southwest area of the island around Los Cristianos and Playa de la America.
In colder weather it’s probably better to focus on the great cities rather than places more known for scenery and outdoor activities. If your budget is generous then my top choice would be London, Paris, and Amsterdam. You could fly into any of those and then visit the others by high-speed train. The train that connects London to Paris and Amsterdam is called the Eurostar, and the earlier you buy your tickets the cheaper they will be. Paris and Amsterdam are linked by normal high-speed trains, which are also cheapest when you buy early. Speaking of that, your dates are prime travel dates over the Christmas holidays so the airfares will be kind of expensive and they will only go up from here. In other words, buy as soon as you can.
Most hotels these days include at least a small refrigerator, and some even include a full kitchen and stove. This is great because it allows you to shop locally for some fresh food options. Search online for nearby farmer’s markets or grocery stores and see if you can pick up some local meats or fresh veggies to have in your room. This is more likely to be an option in the warmer months.
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.
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
Capital of the UAR, Abu Dhabi combines ultra-modern structures and attractions with its ancient Arabian culture. This year, the Louvre Abu Dhabi will celebrate the first anniversary of its long-awaited November 2017 opening. Built on a manmade peninsula, its collection ranges from prehistoric to contemporary works, exploring universal human themes. The Sheikh Zayed Grand Mosque, a spectacular architectural achievement, consists of 82 domes clad in pure white marble. Its hand-knotted carpet, the largest in the world, features an intricate Islamic medallion design crafted by about 1,200 artisans. Open Saturday through Thursday, the mosque offers free admission, and visitors must observe proper dress and behavior.
In spite of its image of being blazing hot all the time, December in Cairo can actually be on the cool side, at least in the evenings. This is great though because almost all the important sights are outdoors and requite a lot of walking between them. For 9 months of the year it can get very hot doing that, so these few cooler months are ideal for visiting the famous sights.
I know what you mean about how easy everything is in Thailand, with a 7-Eleven on every corner. But I don’t know the current visa situation because it’s changed recently and might change again. Still, I think they are mainly trying to cut off the people who try to stay forever on consecutive Tourist Visas, and they are still welcoming of the 60-day visits. I hope so anyway because I might be heading there this winter myself.

Located just 90 minutes from New York City, the quaint Caribbean island is home to fantastic beaches—like the famed Horseshoe Bay and Elbow Beach—plus a unique style all its own. A balanced mix of charming British heritage and laid-back tropical vibes, Bermuda has, in recent years, become a hotspot over the holidays. The weather is typically temperate (expect temperatures in the 70s) which makes it a perfect destination for golf-lovers, families, and anyone looking for a quick weekend escape.
The Bali thing is also kind of a mess for those on low budgets. Kuta is a headache, and pretty much the opposite of what is so beautiful about the rest of the island, but it’s also where nearly all the really cheap beds are located. If you go a bit north in that same area into Legian and Seminyak, it’s nicer, but prices also go up. And Ubud is nice, but also more expensive for hotels and such. I’ll probably rent a place in Seminyak for a few weeks, which won’t be cheap.
As December begins in the Caribbean, the hurricane season is officially over and the weather is pretty much perfect by any standard. Punta Cana is the Dominican Republic's most popular resort areas, especially for those who aren't particularly interested in absorbing the local culture. This is a resort area with wonderful beaches and not much history.
Another option is Thailand, and Phuket has the most family-friendly beach areas. You could get a family hotel room at one of the many beach resorts that has a Kids Club in addition to swimming pools and the beach itself. Those are my top suggestions for a family trip that is also suitable for an anniversary. I hope this helps. Let me know if you have any other questions. -Roger
Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.
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