Once again, it's worth noting that the first half of December will be cheaper and far less crowded than the time around Christmas, so if it's possible you should come early for best value. Still, compared to, say, Miami Beach, Cancun and the other Mexican resort towns are far cheaper and at least as fun as well. By the way, Cancun is mainly just a strip of high-rise hotels along a lovely beach, while Playa del Carmen (about an hour south) is a real tourist-friendly town with smaller hotels as well as hundreds of restaurants and shops to choose from.
There are not one but a cornucopia of hotspots to check out in the Aloha State come November. First, Oahu, which has, throughout the years, been transformed by Asian-Pacific locals from a holiday outpost into a globalized, cosmopolitan destination that offers all the glory of paradise in one locale. You’ve got the allure of the Island landscape, plus the buzz of modern living mixed in a relaxed, slow-paced daily lifestyle near the shores. It is (along with Honolulu) the center of the Hawaiian universe, and will no doubt sprinkle excitement into any Thanksgiving celebration. You might even want to go all out by getting a taste of authentic, fantastic Hawaiian flavor by cooking that turkey in a traditional imu (underground oven)! Those who want to work off all that feasting can hop on into the Turkey Trot 10 Mile Run on Thanksgiving morning and then spend Black Friday enjoying the annual Waikiki Holiday Parade—instead of braving those restless shopping crowds.

I’ve yet to do an African safari, although that is probable next year for me, and I know quite a bit about it from reading and publishing articles on them. That certainly would be a Wow thing to do. They tend to last around 5 days, so you could do that in conjunction with a visit to South Africa itself. That is another that I’ve yet to reach, but people rave about Cape Town and many other places in that country.
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
I totally agree about the solo traveling thing being down to luck in many cases. Right now I’m on a long trip around Europe again, and from one night to the next I might meet a bunch of interesting people, or be sitting there alone in a sea of locals with no interest in chatting with foreigners. At least in a place like Goa, everybody is on holiday, so I’ve had good luck meeting people.
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.

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


Oh no. I don’t mind rain but that would be a little disheartening. I come from a tropical place and it wasn’t until I moved to Canada that I realized that “rainy seasons” don’t really mean much. More so, I went to Punta Cana last October during the cold period and it was gorgeous every day, and what little rain fell was usually overnight or little drops that you could stay on the beach unbothered.
More good news comes with the fact that there are two other great resort areas that are each about 90 minutes by shuttle from Montego Bay Airport, so you can almost as easily reach Ocho Rios or Negril, both of which have a different vibe that you might prefer. Bargain hunters will also find pretty amazing prices at the all-inclusive resorts, particularly those in Montego Bay and Ocho Rios. If you prefer a quiet beach area lined with smaller hotels, restaurants, and bars, then head to Negril.

Hotels in Buenos Aires are starting to reach their summer peak prices in November, especially toward the end of the month, but still they are a fantastic bargain by European or North American standards. The weather in November is also pretty much perfect, and while there's always a threat of rain in BA, it's mostly an indoor city so it shouldn't be too much of an inconvenience.
The subtropical climate of Hong Kong means that summers are particularly hot and wet, and spring is warm and humid. November is the sweet spot, with clear, sunny days and mild temperatures. During your trip, you'll want to take a traditional junk boat ride on the harbour (seen here) and check out the sweeping city views from Victoria Peak, which you can reach by tram. Another can't miss? Stockton, a hidden speakeasy-style whiskey bar in Central.
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
Thank you, and I’ll be happy to try to help. But first I have to mention that ALL of Europe is quite cold in December and there are no beaches that are anywhere near warm enough to even spend time on, much less go swimming. The only place that could possibly fit the bill is the Canary Islands, which is off the northern coast of Africa although technically part of Spain. It’s reasonably warm there during December, and there is quite a bit to do.

Another reason to consider Dubai is that the busy airport has cheap non-stop flights coming in from almost every major airport in Europe and Asia. As a result it's popular to book long weekend trips of 3 or 4 days to Dubai, where you can enjoy some sunshine and shopping before flying back home where it gets colder by the day. You might also consider stopping for a few days in Dubai and then moving onto somewhere else with cheap direct flights such as the Maldives.
Always happy to hear that people find this useful. If you are looking for a driving holiday with warm weather in December I think you’ve already narrowed down the best choices. New Zealand will be ideal, although maybe not for more than two weeks or so. As you might know, the South Island is more scenic than the North, but the North has many great things to see and do as well.

You might also consider Malaysia and perhaps a stop in Singapore. Malaysia is actually more modern than Thailand so everything is easy and reliable. They have cheap VIP buses that are very comfortable. Penang in the north is really nice and also interesting. Kuala Lumpur is a modern and pleasant big city. A bit south of that is the colonial town of Malacca, which is also very nice and worth a look. Going south from there you can reach Singapore in a few hours, and that is an amazing city, although accommodation there is expensive.
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.

Another reason to consider Dubai is that the busy airport has cheap non-stop flights coming in from almost every major airport in Europe and Asia. As a result it's popular to book long weekend trips of 3 or 4 days to Dubai, where you can enjoy some sunshine and shopping before flying back home where it gets colder by the day. You might also consider stopping for a few days in Dubai and then moving onto somewhere else with cheap direct flights such as the Maldives.
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.
If you’re a fan of cheese, this place is really fun. It’s a quaint little shop that’s right across the street from Pike’s Place Market. With hundreds of competitive awards under their belt over the last decade, you know their cheese is going to be good – and they do too. They let you sample different varieties of cheese before you buy it, so you know exactly what you’re getting into.
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.
Traveling around India is a shock to the system, but it’s not as bad as it looks. If you pay a bit more for the AC3 class on trains (air-conditioned, 3 bunks per side of the compartment), or AC2, it’s pretty comfortable and civilized. Mumbai is worth a couple days before you’ll be desperate to get out, but many parts of Rajasthan are much nicer and fascinating.
And you mention that you’ve been to Cancun and Yucatan, but just in case you haven’t been to Playa del Carmen or Cozumel, those could also be worth a look. They are both much more real tourist towns as opposed to Cancun, which is primarily a long strip of high-rise hotels and time-share buildings on a beach. I hope this helps. Let me know if you have any other questions. -Roger
In South America, and you start getting into some longer flights here, the best and safest places are Argentina, Peru, and Chile. I’m not sure if this helps you much, but at least it should let you know that you were thinking along the right lines already, and there are no obvious places that you’d overlooked. Let me know if you have any other questions. -Roger
This diverse and rapidly growing capital city of Texas is known for its live music scene, world class museums, beautiful outdoor spaces, pleasant weather, fine dining, and nightlife. A little bit city, a little bit country, Austin has no shortage of December activities for all. The Zach Theatre presents a rocking adaptation of the Dickens classic "A Christmas Carol" from Nov. 21 through Dec. 30, guaranteed to have you dancing in your seat. In its 56th year, Ballet Austin’s annual production of "The Nutcracker" returns to the Long Center Dec. 7-23. Holiday shoppers gather at the Blue Genie Art Bazaar to purchase unique handmade gifts including paintings, photography, jewelry, clothing, and more. Zilker Park transforms into a glittery wonderland with more than 2 million lights, 40 displays, interactive experiences, food trucks, and live music on two stages. The Armadillo Christmas Bazaar, an art and music festival, runs from mid-December through Christmas Eve with live music, two full bars, and local food specialties. Over 175 national and local artists display paintings, sculptures, woodworks, and an assortment of handmade gifts. Winter Wonderland at the Circuit is great family fun with holiday lights, a skating rink, Santa’s Village, petting zoo, carnival rides, and of course, live music. In the heart of downtown, the historic Driskill Hotel celebrates with an enormous Christmas tree and seasonal music. On Sunday, Dec. 16, Austin’s best bakers will share their holiday cookie collection, with the event’s proceeds supporting the Driskill’s traditional charity, “Cookies for Caring,” benefitting the community.
Flights, on the other hand, can be pricey if you buy too early. My recommendation would be to book a resort soon and then put a fare-alert on the flights so you’ll get an email when the fare drops. For the Caribbean the cheapest fares are usually only 2 or 3 weeks out, and since that is a slow period you really shouldn’t have any problem (unless you are trying to go on popular Thanksgiving dates). Most likely the resort prices won’t change much as November approaches, so you could probably wait on that as well. There will definitely be empty rooms when you get there, so the resorts usually don’t start pushing up rates when they will be partly empty. Best of luck on this. -Roger

The rainy season in Cartagena winds down by early November, so this is an ideal time to come, especially toward the end of the month if you can get cheap airfare before and/or after Thanksgiving. The temperatures are pretty much the same here every day of the year, so the key is to work around the autumn rainy season to when it's dry but before hotels fill up.
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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