Thank you. I think Kauai, Cancun, and Costa Rica could all be good choices for you. You’ll be looking at the last month (more or less) of the rainy season in each of them, but in the Tropics that usually means at most a few quick thunderstorms per week that typically last only 30 minutes or so. Kauai would be the most expensive of the three, although the most beautiful as well, and the easiest to visit since Spanish isn’t necessary at all.
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.

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
I’m hearing very mixed things about Cuba visits. The main downside for Americans is that you still have to go as part of a package deal, and those packages are all incredibly expensive for what you get. It sounds like the Cuban government is charging very high taxes and fees on companies selling tours to Americans, so they are really only popular among people who are especially curious about visiting Cuba. In other words, they are poor value unless it’s at the top of your list already. I hope this helps. Let me know if you have any other questions. -Roger
Brazil, on the other hand, has a famous problem with petty crime in tourist areas so I wouldn’t recommend it for a woman and young child. Another to consider is Puerto Rico, which has a lot to offer including great weather, and it’s also more or less part of the US, so it’s fairly safe and well organized. Hotels in Puerto Rico are a bit expensive, but you should be able to get an apartment rental in the San Juan area (gorgeous, by the way) for a modest price if you are staying for more than a few days. Let me know if you have any other questions. -Roger
It’s unfortunate and heartbreaking how many times I have recommended San Juan, Puerto Rico in the last few years. Once they get the power back on I’m sure it’ll be back to normal fairly soon after that, but I’m guessing probably March or later. And fortunately, Nate missed the Cancun area for the most part. Have you considered somewhere in the Cancun/Playa del Carmen/Cozumel area? I’m particularly fond of Playa del Carmen, and that flight to Cancun should be pretty reasonable for you.
I’ll be happy to give you some suggestions, but it would really help to know your starting point and approximate budget. At this moment I am writing this reply from Cancun, which could be perfect if you are in or near the US, but if you are in another part of the world there will likely be better choices. Although thinking about it, even if you are in Europe, a place like Cancun might still be best. Let me know and I’ll give you my best answer and an alternative or two. -Roger
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.
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.
Actually, most of the popular European cities have fairly mild winters, in that they don’t spend much time below freezing and snowstorms are rare as well. It’s hard to make suggestions without knowing about your tastes, but I will tell you that the most popular European cities are London, Paris, and Rome, and none of them get snowed in often. If you are going to Italy, you should also go to Florence and maybe Venice as well.
Fortunately, it rarely rains at all in Cairo, so even though December is one of the wetter months, that means nothing and you are unlikely to see even a drop of rain. Hotel prices do reach their peak in Cairo starting late in December, so it's best to go early in the month if possible. Egypt is definitely one of the cheapest places to travel in December, and the weather is surprisingly nice as well.
While the most recent hurricane has hit some areas of Florida pretty hard, most people know that come wintertime, the further down south or towards the desert you go, the warmer the weather will be. This tried and true fact makes November one of the best times to visit Florida, especially for travelers wanting to engage in lots of opportunities for nature-viewing. You won’t need binoculars in the Sunshine State to spot the sight of wintering birds at Florida’s Merritt Island National Wildlife Refuge -- they make an annual pit stop along the major migration corridor located near Cape Canaveral. You and the entire fam can also stare at a colorful gathering of pink roseate spoonbills that hide out in various estuaries around the area come November.
Those who adore the holidays and don’t mind the cold (the average high is around 48 degrees) might consider an end-of-year trip across the pond. Arguably Europe’s most festive destination, December in London promises charming Christmas markets, show-stopping Christmas trees, and streets covered in twinkling lights. A number of posh hotels, like 45 Park Lane and The Dorchester even have Christmas-centric packages available to get you into the holiday spirit.
My recommendations depend on your starting location so for now I’ll just assume you are starting somewhere in the USA. If you are looking for a really nice beach AND really good night life your best choices are the Cancun area, Puerto Vallarta, and San Juan, Puerto Rico. If you are in the eastern US or Canada it’s probably faster and cheaper to go to Cancun and if you are in the west Puerto Vallarta is better. San Juan will be more expensive because there just aren’t many cheap hotels in the good parts of the city. For the Cancun area I would recommend Playa del Carmen (about an hour south of Cancun Airport) because there are fairly cheap hotels near the town center, which is packed with bars and restaurants. In Cancun itself the best nightlife is in the heart of the hotel zone, and all of the hotels there are pretty expensive. Let me know if you have any other questions. -Roger
From the Art Deco architecture to fabulous restaurants and nightlife, Miami is truly a city that appeals to every type of traveler. Art and culture lovers should plan a trip during Art Basel, which officially kicks off on December 6. The weeklong affair attracts celebrities, tastemakers, and bold-faced names, who come for the world-renowned art exhibitions, but stay for the swanky parties and events. Be sure to book a hotel well in advance, as prices skyrocket and availability becomes increasingly limited.
Thank you for the helpful comment. Interestingly enough, I’m in Tenerife at the moment (for a month). I probably will add Tenerife when I update the November list in a couple months, and I already have it listed in much of the year on the other lists. But calling this place “Europe” is a bit of a stretch. There are islands in the Caribbean run by France, Netherlands, and Britain that are also full territories of those countries, and you could just as easily call those “Europe” using the same definition. Still, I appreciate you taking the time to comment. -Roger
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.
Picking your next destination isn’t easy, but there’s a better way than spinning a big globe, closing your eyes and slamming your finger down (it’ll probably end up in middle of the Atlantic, and wifi there is patchy to say the least). Introducing our ultimate month-by-month destination guide: your no-fuss list of places to go, things to see, and good weather to chase around the world.
Increasingly popular, Lisbon is quite warm in summer, but November’s cooler temperatures and fewer crowds make it a pleasant time to visit. A city of hills and spectacular views, many terraces (miradouros) offer vistas for those who climb (or take a taxi) to the top. Alfama is the city’s historic district, defined by hilly, narrow cobblestone streets. The Fado Museum, in Alfama, honors Portugal’s soulful folk music and provides some background on the sounds heard nightly in the city’s fado houses and bars. Seafood is plentiful in Lisbon, and the traditional Portuguese dried salted cod (bacalhau) is on most menus along with octopus, shrimp, sardines, clams, and tuna.
Sri Lanka doesn’t really have a good infrastructure for budget travelers at this point. There are loads of nice hotels if you are willing to pay US$40 or more per night, but almost nothing below that except for a few hostels. I haven’t been to Palawan but I have been to Boracay and Palawan can’t be too much cheaper. Boracay doesn’t have many budget options either, so my guess is that Thailand or Cambodia is your best bet.
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