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.
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.
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.
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.
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.
A charming, historic city to visit any time of year, Edinburgh is especially festive during December. Walking through its cobblestone streets takes you back to medieval days when sheep, cattle, and grain were sold in what is now the center of the city. Today, the Royal Mile includes shops, cafes, and museums. Edinburgh Castle, a must for first-time visitors, dates to the 12th century, with its dramatic silhouette overlooking the city. For those seeking holiday celebrations, the Royal Botanic Garden is decorated with lights, music, and illuminated trees. European-style Christmas markets pop up at Princes Street Gardens and George Street, offering traditional crafts, gifts, food, and warming drinks, most welcome during chilly December. The annual Hogmanay celebration welcomes the New Year with fireworks, food, and festivities. Don’t miss the delicious and ubiquitous fish chowder called “Cullen skink,” and be sure to try haggis, served with “neeps and tatties” — mashed turnips and potatoes. Buttery shortbread and whisky from the country’s more than 100 distilleries are also Scottish specialties. A stay at the elegant and historic Balmoral Hotel will enhance any visit to Edinburgh, and while you’re there, you’ll notice that Scottish actor Sean Connery was a guest, as was J. K. Rowling who finished the last Harry Potter book in one of its suites.
Oh, did you want a sunny tropical vacation that doesn’t require a passport? Done. Hurricane season is over, flights are cheap, and the water is still warm enough for swimming (and scuba diving). Almost all the tourists come here via cruise ship, which means you’re mostly not competing with them for hotel rooms -- Windward Passage, Emerald Beach, and the Bolongo are all open for business after Hurricanes Irma and Maria last year. On December 16 you can catch Jazz By The Sea down at Coral World Ocean Park, and on December 21 watch the St. Thomas Lighted Boat Parade, where contestants (boats) are judged on lights, originality, and holiday cheer.
If you are looking for something far less developed than Phuket or any other Thai island, Boracay might be for you. This gorgeous strip of sand is a bit out of the way, but partly because of that it still feels only partly discovered. You'll spend your days relaxing along White Beach or walking up and down the sandy paths that serve as the only real form of transport for most people. Many visitors come every year, and quite a few of those never seem to leave.
This is a really interesting question. If you want to avoid crowds then you have already figured out that it’s best to avoid Honolulu and I would avoid Oahu completely. The Big Island is very interesting because of the volcano and some of the other scenery, but the most beautiful islands are Maui and Kauai. I haven’t made it to Kauai yet, but everyone I know has been there and they swear it’s the most photogenic, which looks right based on the photos I’ve seen. Maui is also really gorgeous and all islands other than Oahu are uncrowded even in high season. I drove all over Maui in a rental car and loved it and I don’t think there is as much to see on Kauai. So either of those will be great choices and the weather should be almost perfect in December with warm (but not scorching) temperatures and almost no rain. Have a great trip and let me know if you have any other questions. -Roger
For a cheap destination in December that has great clothes shopping opportunities I can only think of two really good options. The closer of the two is Dubai. I’m not sure if you’ve been there before, but it has some of the best shopping in the world with every store imaginable and very good prices because duties and taxes are low. In spite of its reputation, Dubai can actually be visited quite cheaply if that is important. It’s famous for expensive hotels, but it’s got hundreds of more affordable hotels that can be pretty nice.

From December through February there are literally no European cities that could qualify as having “great weather,” except for the Canary Islands, which is listed below. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
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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