As for Costa Rica, I think it would be ideal for what you have in mind. It’s by far the most tourist-friendly (and English speaking friendly) country in that area, so it’s a great starting point. Belize is pretty easy as well, although there is far less nature to enjoy. Panama and Nicaragua are a bit cheaper and have similar things to offer, but Costa Rica has the best infrastructure and nature parks, so it’s less stressful for a first-timer. The snorkeling is better on the Caribbean coast, I believe, but the better tourist beaches are on the Pacific. The country is pretty quick to get across, so you could easily spend a few days on both sides, plus another few exploring the rain forests and volcanoes and such.


Let’s just say that November in Colorado is a truly exciting time of year. The city of Denver hosts several hot annual events, including Mile High Holidays, The Starz Film Festival, and the International Wine Festival. There’s also Denver Arts Week, which is a week-long celebration of the visual and performing arts held during the same month. What’s more is that snow aficionados looking to get an early start on winter sport fun should make resort reservations come November. The earlier you claim those spots, the cheaper the prices tend to be.
Jamaica Montego Bay, Negril, Ocho Rios Martinique Martinique Netherlands Antilles Bonaire, Curaçao, St. Martin/Sint Maarten Puerto Rico Rincón, San Juan Saint Kitts and Nevis St Kitts Saint Lucia St. Lucia Trinidad and Tobago Trinidad and Tabago Turks and Caicos Islands Turks and Caicos Virgin Islands, British Tortola Virgin Islands, U.s. St. Croix, St. Thomas
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There are always those travelers who celebrate the end of summer and the opportunity to don a sweater and take out the wool scarves and quilted jackets. For them, Iceland would be a perfect destination, with a chance to see the Northern Lights and adorable sled dogs. Montreal is another place with a winter chill, and at the end of the month, you might even find an early Christmas market. San Antonio gets into the holiday spirit at the end of November as well. Sedona offers chilly nights and gorgeous scenery, while Hilton Head Island still enjoys autumn weather and activities.
This is a huge question and I’d need to know more about your preferences and your budget to answer it properly. But I can give you a short version here. In my opinion, which is matched by many other people, the most interesting and dramatic cities in Europe are London, Paris, Amsterdam, Rome, and Venice. Visiting those would require about 16 days to do it properly because you’d want to spend 3 or 4 days in each city, except maybe only 2 days in Venice because it’s quite small.

Even when those quick rain storms come, you can see them forming and head indoors for a while. Nearly every hotel on Boracay is on the beach or within 200 meters of the beach, so it’s really easy to stay dry. If you stay along White Beach (where most hotels are) I think it would be easy to meet other people if you choose as well. Let me know if you have any other questions. -Roger
Thank you for the kind words. Interestingly, had you not included that you’ve been to Costa Rica, I’d say that was the obvious suggestion because they really do that sort of thing well and it’s at least a bit better organized than its neighbors. And if you were less concerned over travel time, I’d have some interesting suggestions for you in Asia. However, as you know, it takes nearly a full day just to get to Asia from the US or Canada, and then a few days to adjust, so you might be best off saving that for later.
As with other Caribbean resort destinations, the weather in Montego Bay is perfect in December, and the first half of the month is still cheap for flights and resort prices. The weekend before Christmas is when peak season here starts, and if you book early enough you can still get a good deal then, but don't expect many last-minute bargains during that period.
It’ll definitely be too chilly in Portugal or Malta to go in the water in November, and Malta has almost no beaches anyway. I really like Malta a lot, but it’s not a great beach destination. It will be warm enough in the Canary Islands, but the flight from Atlanta would be long and expensive because you have to change planes in Madrid. Also, I find the Canary Islands to be pleasant and the weather is wonderful, but it’s kind of boring there compared to the other places we are discussing.

I haven’t heard much about Zika in quite some time, but I just checked the current CDC map and evidently it’s still out there. I also remember hearing that it’s really only pregnant or potentially pregnant women that are at much risk, so perhaps that is what you are implying with the kids in their 30s. I’m no expert on Zika and I’ve visited many places on the map in recent years without much worry.


In addition to the obvious perks of pleasant weather and fewer tourists, off-season rates at accommodations are abundant. Voted No. 1 continental U.S. island by Travel + Leisure readers for the third time in 2018, Hilton Head has much to offer visitors. One of the most popular activities, perfect with autumn temperatures, is biking on the more than 60 miles of pathways covering the island, including along 12 miles of beaches. Bird watchers will keep busy spotting egrets, sandpipers, wood storks, sea gulls, pelicans, and ospreys. Well known as a golfer’s paradise, the Hilton Head Island area boasts more than 33 courses. 

If an apartment isn’t your thing, or you have to book a hotel for your business trip, then there is one upside: the food. Typically hotels will include some sort of breakfast, and occasionally some sort of dinner plan. In Portland, we stayed at a great hotel that included both. Breakfast usually consists of pastries, waffles and oatmeal – but they almost always have eggs, bacon, and sausage ready to go on your plate.
I like your comment about how “rainy seasons” are almost always overstated. I totally agree based on my own experiences and research, although there are a few places where they should be taken more seriously than others. On my most recent December trip to Bali (2.5 years ago, I think), I spent 30 days there and the rain only became a problem that one time I mentioned. It was just an insane cloudburst while taking a minibus from Kuta to Ubud, and in the end it’s actually probably my best Bali story. Aside from that, it’s very humid during Bali’s wet season, but even that really didn’t slow me down. The thing is, in Bali you are usually on or near the beach or a hotel pool (feeling the breeze) or in your air-conditioned room. Or you might be touring around to see temples and rice terraces and whatnot, and everything is outdoors and beautiful. When it does rain it’s usually over in 15 minutes, but often the rain comes over night. That kind of humidity can be a killer when visiting a city, but for me it’s a small issue on a tropical island like Bali.
As for key events in December, I typically avoid those sorts of things myself, so I’m not a good source on that. I actually visited Rio de Janeiro during Carnival, by accident, and it drives hotel prices so high and also crowds that it’s probably the worst time to visit unless you specifically want to spend all night watching the parades. And Oktoberfest, as another example, literally triples the prices of hotel rooms in Munich, so it’s only worth it if you REALLY want to get involved in the Oktoberfest thing yourself. But plenty of other travelers love to go witness the biggest events, and I assume they love it, so there is no right or wrong.

Unsurprisingly, the end of December is the beginning of the peak season for resort prices, so those who are able to come earlier in the month will be getting better deals. Still, the all-inclusive resorts are locked in heavy competition all year so this area can be a great deal compared to the alternatives, even in high season. If you are looking for where to go in December for an all-inclusive beach holiday, this is your best option for most people.


I’m happy to try to help. It’s hard to say whether one 30-day trip would be better than several shorter trips. On one hand, it’s much more efficient to go for a month because it obviously saves you all the going back and forth. Also, one week is a short time to go 7 or 8 time zones away, as it takes pretty much an entire day each way, and at least a few days to adjust to the time change. Hmmm…
Thank you. If you are looking for an all-inclusive or large resort hotel on a beach, you can’t do any better than Punta Cana for value and facilities. You can also find really nice resorts in the general Cancun area, and the flight would probably be cheaper, but the nightly rate would be quite a bit more. Both have really nice beaches, although with Cancun you have to pay attention to the specific location because not every resort is on a wide stretch of sand.
I haven’t followed the Zika list, but I do understand the concern. Since you aren’t big beach people, you might just bring jackets and go to a more romantic city like Paris, and then maybe down to Nice for part of the trip and something a bit different. I’m not sure if this is helping, but if you have any questions about any of this I’m happy to keep trying. -Roger
If you are referring to days trips and that sort of thing, it will be much cheaper if you book once you get there. In Vietnam in particular it’s amazing how cheap tours can be if you book them through your hotel. I once did a 6-hour bus tour to Mỹ Sơn, which is near Hoi An, and I think I paid about US$6. It even included a boat ride and a basic lunch. That same day tour online would probably cost US$30 because the booking company takes a share and there is very little competition.
If you book a resort hotel from home you'll probably think Goa hotel prices are much higher than you were expecting, but if you book a family-run place once you arrive you'll still find fantastic bargains. It's probably wise to book a few nights online before you get to India, because it can be incredibly confusing at first. After that you might be able to find a similar place for half the price by just checking around the same area.
Hotel prices definitely go up in around Christmas so it's best to come early in the month if that's possible, but it's still a pretty good bargain even during the peak weeks. Book early if you can because the better and cheaper hotels will fill up first, of course. Also consider a side trip to the Mendoza wine region, Patagonia, or the amazing water falls of Iguazu.
Thank you very much Roger. I truly value your insight and am taking into consideration everything you’ve noted above. I’m going to check out the link you posted as well. That just reassured me that Bali would be great during that period. I’m thinking principally of staying in Ubud, Sanur or Seminyak for the type of trip I have in mind which is equal parts warm weather, walking/discovering, culture and some beach life. I’d love to visit Thailand but it’s just not the right time. At this point, I’m more intrigued by all of the many, still remote islands of Philippines than the chaotic lifestyle in Thailand. Perhaps, that’s just me still reeling from my trip to India a few months ago.
If a warm weather getaway sounds appealing, consider seeking the sun in Cartagena where summer is approaching. The South American city offers history, Christmas spirit, and unique gifts for holiday shopping. Sun-drenched Phuket, Thailand’s popular island, is a place to relax during the day and party at night. St. Bart's in the Caribbean is recovering nicely from hurricane damage, an ideal spot for a winter vacation. Miami’s December weather is perfect for a warm Christmas, and Art Basel, early in the month, is an exciting time for fans of contemporary art. In Santa Barbara, a few days of pampering might fit the bill, or you can join in their holiday festivities throughout the month. Death Valley, in the middle of the Mojave Desert, offers a respite from the crowds and a chance to enjoy quiet days and starry nights.
If the Caribbean sounds better, I’ll recommend Puerto Rico. The area around San Juan is fairly crowded, although not nearly as crowded as a typical resort area that is loaded with hotels. And there are many smaller resort towns on other parts of the island where people usually rent a condo for a week or two. In a town like Rincon you won’t get crowds, and you will get great beaches.
The park we visited has an app you can download on your phone that allows you to reserve a table at any table service restaurant on their property ahead of time. The app also lists the daily breakfast, lunch, and dinner offerings at every single food establishment on site. There really is no excuse for settling for the popcorn or french fries when you can easily find a place with compliant options if you’re willing to look and tweak a bit. A lot of other theme parks are either offering similar apps or putting their information online for those who need to research their options ahead of time. If your destination is the beach or a famous city, check out what’s in the area online, or call your hotel to get an idea.

If you're determined to travel during the holiday periods, though, book your vacation flights, hotels, and cruise far in advance. If it works with your schedule, fly on Thanksgiving Day or Christmas day; those are the least crowded days of the holiday season. And if at all possible, avoid traveling during weekends, on the days right before or after the holiday, and late in the day. It's not only crowded at airports but also northern storms can wreak havoc and create weather delays that cascade across the system.


Never thought of Moscow as a Winter destination! It is quite the place to go especially after the world cup hype. I second Rajasthan, India as one of the best places to travel in December. Love this list, Wendy. I have even listed Rajasthan and other offbeat places to travel in December and January over here: https://www.thegonegoat.com/inspiration-and-tips/2018/11/29/the-best-places-to-travel-december-january
As the year winds down the parties amp up, none more so than in Scotland’s capital, where Hogmanay celebrations see flaming torches, fireworks displays and night-long parties take over the usually quiet cobbled streets. Slightly more sedate, the Caribbean’s southernmost island Trinidad simmers with stirring Spanish-style musical performances as the locals usher in the start of the dry season.
On Monday morning we arrived at our hotel, dropped our stuff in the room, and headed out to our first stop. We had a light breakfast at home, and mine consisted of a fatty coffee and 2 pieces of bacon. So we were all pretty hungry by around 1 pm. We headed to one of the food joints nearby, and I found a southwest grilled chicken salad (Meal 1) on their menu. After asking them to hold the black bean relish and sugary dressing, I ended up with a decent sized bowl of salad mix topped with half a grilled chicken breast and a good-sized scoop of chopped avocado. I topped it off with salt, pepper, and a packet of blue cheese dressing.
It would be hard to beat Chiang Mai for its combination of great November weather and low prices. Even though it's officially the start of the high season for hotels, the beginning of the month is usually very slow anyway, so bargains are common. Hotels in Chiang Mai are among the best bargains in the entire world, so even if you do have to pay full price for a room it'll be cheaper than a dorm bed in most European cities.
My other two suggestions are San Juan, Puerto Rico and Cartagena, Colombia. Both cities have really wonderful colonial districts and modern resort districts nearby. San Juan is more expensive, but still reasonable, and it has far better beaches. Both have a bit of rain in November, but it tends to come and go quickly. You’ll get similar rainstorms in most of the Caribbean in November, so it’s a bit tricky. I hope this helps. If you had something else in mind let me know and I’ll try again. -Roger 
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