Great site and info. My husband and I travel a lot to the Caribbean and Costa Rica. We live in Atlanta. Flights are really high to either place and much of the Caribbean is out at the moment due to the hurricane damage to many islands. I hate to pay close to 3k to go to costa rica (1800 is just the flights). I have thought about trying somewhere new and we are all over the place. We want to book now and go early November. I have read a lot about Rio. My husband is nervous about the safety and cleanliness. Same with Cartagena. I think both would be great places. It sounds like you feel both are fairly safe as long as you are a smart traveler. We love the beach and heat. I thought about Iceland just for a change of pace but looks like it is cold and a little too dark in November. Looks like we missed it by a month or two. And I would have to see the Northern Lights or it’s a no go. Then thought about Lisbon/Malta/Canary Islands depending on how good of a deal we could get, but I am a little worried about the weather being a little too cool to actually get in the water. Any suggestions or ways to narrow down our search or any other places I may want to consider?? We usually travel in September to avoid crowds in most places but we are traveling late this year and looks like it’s not the greatest time to chose a place to go.
It’s only fitting that the closest big tourist destination to the North Pole would do Christmas up big. Reykjavik feels almost like a mini-New York in December, with the Oslo Christmas tree standing sentinel over the city and a public skating rink in Ingolfstorg Square. Seeing the northern lights is never a guarantee, even during days of near-perpetual darkness, but your odds are much greater in winter. On the other hand, who needs ’em when you have 13 official Santas walking around town posing for pictures? The Christmas Village at Hafnarfjordur is a top weekend destination for both locals and the newfound throngs of American visitors. Just beware their holiday tradition of eating ruinously smelly fermented skate.
The biggest single highlight in the region is the Angkor Wat temples near Siem Reap in Cambodia. It’s one of the most impressive tourist sights in the entire world, and Siem Reap is a fun and mellow town that you can linger in for a while. Vietnam is really lovely and cheap as well. The food there is excellent, as it’s a fusion of French and traditional Asian. You can go from Ho Chi Minh City in the south on the train to Hoi An near Da Nang, and then up to Hanoi to see Halong Bay. I wouldn’t start in Vietnam because it can be a bit trickier than the others. In the rest of the region it’s easy to book tours and buses and such, but in Vietnam the travel agencies are a bit harder to trust, so you have to be more careful. Things there are very cheap though, so even if you pay more for a reputable agency, it’ll still be cheap.
Being from Mumbai you can be forgiven for not realizing how unappealing beach areas are when the air temperatures are only a bit above freezing. Seriously, even beach on the European mainland is totally deserted by November 1, and many of the local hotels and restaurants are closed by then until April or so. Now, if you are mainly after the novelty of being on a beach in the European winter, you can certainly go and still find open hotels and restaurants. If I had to recommend one place to consider it would be Spain’s Costa del Sol, which is the resort area around Malaga. The average high in December in Malaga is 17, and the average low is 8. You’d be the only one on the beach, which might be kind of nice. It’ll also probably be windy. If you were going to do that I’d recommend staying in Malaga itself, which does have a nice beach area in the city, and since it’s a city the hotels and restaurants will all be going.

Europe in general and Greece in specific are not ideal in January because it’s cold and many sights are closed. I’d go to Thailand, which has a great variety of things to see and do, and January is the best weather month. Spend at least a few days in Bangkok and then either go to one of the islands like Phuket or Kho Samui, or head up to Chiang Mai for its temples and shopping and outdoor activities. You could even head over to Siem Reap to spend a couple days seeing Angkor Wat. Let me know if you have other questions. -Roger

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Yes, I’ve been to all of the Nordic countries, but mostly during the summer months. However, I know that those Northern Lights tours are popular and well established. On one hand, you know you’ll be visiting areas where there is only a bit of sunlight in the middle of each day, so it won’t be great for general sightseeing. But the cold months are also the best Northern Lights months, and if you want to see them then it’s your best bet.
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
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.
The biggest single highlight in the region is the Angkor Wat temples near Siem Reap in Cambodia. It’s one of the most impressive tourist sights in the entire world, and Siem Reap is a fun and mellow town that you can linger in for a while. Vietnam is really lovely and cheap as well. The food there is excellent, as it’s a fusion of French and traditional Asian. You can go from Ho Chi Minh City in the south on the train to Hoi An near Da Nang, and then up to Hanoi to see Halong Bay. I wouldn’t start in Vietnam because it can be a bit trickier than the others. In the rest of the region it’s easy to book tours and buses and such, but in Vietnam the travel agencies are a bit harder to trust, so you have to be more careful. Things there are very cheap though, so even if you pay more for a reputable agency, it’ll still be cheap.
December is a popular month to go cruising around Hawaii and Mexico. It’s an ideal family trip, especially with most kids in the US out of school for the holidays. Experience the Hawaii’s tropical paradise. Pick a popular cruise liner and visit ports of call like Nawiliwili on Kauai, Honolulu on Oahu and Kona on the Big Island. If the Caribbean floats your boat, we recommend taking a cruise to explore Mexico’s Costa Maya, Cozumel, Ensenada, Acapulco, Cabo San Lucas, Puerto Vallarta and more.
I’ve spent a few weeks on Boracay, but not in early November. From what I’ve read, the monsoons there are usually not too bad, and it’s mainly a matter of a couple of hours rain in the afternoon on the bad days. Throughout the Tropics it’s very rare to get rain all day on any given day, and I’ve spent many months in those areas during rainy seasons. So early November isn’t ideal, but if it’s the only time you can go I still think you’ll enjoy it. One nice thing about Boracay is that the hotels are all basically on the beach or right off the beach, so even if it does start raining you can be back in your room in like 2 or 3 minutes. Best of luck with this. -Roger
My second vacation meal was dinner that night. After walking almost ten miles at the park, the hotel, and spending the late afternoon swimming in the pool, we did dinner at the hotel restaurant before heading back to the park to ride a few things one last time. Dinner (Meal 2) consisted of pot roast with carrots and mushrooms (I asked them to go light on my carrots and they did a very good job of it), and a side salad that I again topped with salt, pepper, and blue cheese dressing.
If you are looking for an all-inclusive resort with reasonable airfares from Chicagoland, your best bets will be in Punta Cana, Dominican Republic, or the Cancun/Playa del Carmen area. Both have everything on your list, except perhaps wild life, depending on how you define that. You can get cheaper flights into Cancun, and there is a wide variety of offerings once you are there. If you don’t think you want to leave the hotel much, then stay in the Cancun hotel district or along the Maya Riviera nearby. But if you want to interact with a real and lovely town, then stay in Playa del Carmen or over on Cozumel. There are many nearby activities and some very interesting ruins.
Prices go up a bit when you go south into Malaysia, but it’s worth it if you’ve got the money. You might even consider Myanmar as well, which I’ve yet to visit, but I keep hearing great things about. It’s honestly the perfect time of year there. By April it’s insanely hot (the hottest month of the year), but December through February is lovely. It’s all quite safe as well, as long as you keep your wits about you. I’m happy to help with more information if you need it.
Blisteringly hot in summer, Tokyo is a breeze in the cooler months. Fight the dizzying jet lag and head out for the world's best sushi or ramen, shop in the city's amazing department stores, and visit the parks surrounding the Imperial Palace in the center of the city. Escape the crowds somewhat by heading to Yanaka Ginza, which retains a bit of old Tokyo and has plenty of places to eat and shop. Do make time for a side trip to Hakone, where you can visit a Shinto shrine and see magnificent Mount Fuji on a clear day.
Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex.

If I had more information about destinations in East Africa that would qualify I would love to include them. But unfortunately, it’s one of the few regions I haven’t been to myself, and according to every source I hear, very few foreigners are visiting as well. I know many (especially wealthy) people do the safaris in that region, or they walk up Kilimanjaro, but outside that it still sounds like there is almost no tourist infrastructure or even a backpacker scene. If you know things to be different, please let me know because I’m very open to it. -Roger
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.
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.

The mountains of Canada include the gentle slopes of Mont Tremblant in the east to the towering ones of Whistler in the west. Note that Canadians celebrate their Thanksgiving before the United States does, which makes our neighbor to the north a particularly good place for couples who won't be visiting family during that U.S. holiday—especially if you're willing to forgo turkey and stuffing for crepes and poutine.
As for the hurricane, it’s true that it did go through that area a few days ago, but I think that was the first one in almost 10 years to do so. In other words, it’s an extremely rare event, and even when it does happen, they know about it long in advance so everyone is evacuated or safely sheltered. Also, the “Hurricane Season” technically goes through the end of November, but November hurricanes are actually far rarer than the earlier months. Personally, I love to book into places like Punta Cana during that season because the weather is the same about 95% of the day, and prices can be half as much as December or January.
Let’s get started. For the November trip you are going to have a lot of competition for those flights and hotels because those are prime Thanksgiving flight dates. I would normally recommend Puerto Rico, but they won’t be ready for visitors until next year from what I hear. Just a few days ago I published a new article on which Caribbean destinations have no hurricane damage. There are a lot of great choices, including all of the busiest ones, that were untouched by the storms. You might also consider Cartagena, which is probably the cheapest option once you get there. It’s got a wonderful walled historic town area, and it’s a short bus or taxi ride to the modern area with beach hotels and such. The sand there isn’t great, but the value is very good. I wouldn’t go outside of Cartagena at the moment.
While the Caribbean destination tends to overflow with families during the holidays in December, go a month earlier and you’ll be treated to sunny days sans screaming kids, plus less expensive airfare. “November is my one my favorite months. The hustle and bustle of high season hasn't kicked in, average temperatures are in the 80’s, and the water temperature is lovely,” says Michael King-Hew, the proprietor of Kamalame Cay, a private island resort in the Bahamas. King-Hew specifically suggests for the resort's annual wellness retreat. “It’s the perfect way to get rested and in shape before the start of the hectic holiday season.”
Costa Rica is kind of the Thailand of Latin America in that they have great tourist infrastructure and it’s the easiest place to get around. They also have a lot to offer with the beaches on both coasts and many natural sights and activities, plus of course the Arenal volcano, which is a really nice area. San Jose is best as a place to just pass through on your way somewhere else. 
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