If this were last year I might have also suggested San Juan, Puerto Rico or Cartagena, but both of those have issues at the moment. If for some reason you don’t like what you see in Costa Rica, there are also some really nice resorts in Panama, especially in the San Blas Islands area. Aside from those you’d probably have to fly longer than you prefer. I hope this helps. -Roger
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.
From exquisitely decorated storefronts to the amazing Rockettes Christmas show at Radio City Music Hall, New York City attracts thousands of tourists every December. Visit the Big Apple during the holidays! It’s a sight to behold. We recommend visiting Rockefeller Center to go ice skating, go shopping at new pop-up shops or just enjoy a cup of hot chocolate at Serendipity 3.
During the holidays in Europe, Christmas pop-up markets open in November, bringing intoxicating tastes and aromas (mmm...gingerbread) that brighten even dreary-weather days. On Viking Cruises, for example, the Danube Waltz itinerary enables passengers to experience a variety of markets, which are great places to shop for affordable holiday gifts. Vienna and Budapest both host multiple markets, and each one is different and features different merchandise. Smaller Passau has a more intimate market, and you get to stroll through a charming town to reach it.
Cancun is at the north end of the Riviera Maya, which also includes the island of Cozumel, so this is a huge area with over a thousand hotels to choose from. All that competition keeps prices down until the high season begins, so November is still a buyer's market. There are even ruins nearby and other cultural opportunities, so it's not all about sitting on the beach here. If you prefer a high-rise hotel overlooking a beach then stay in Cancun itself, but if you prefer to stay in a friendly town with many restaurant and shopping choices then head to Playa del Carmen, just a bit to the south, instead.
Early in your message you say the last week of November, and then later you mention “late December,” so I’m not sure which it is. But if it’s late November, I think Italy could be a great option, as the weather there is still quite nice, at least in the south. You could go to Venice for a day or two and then Florence and Rome, and then maybe spend 5 or so days in Sorrento. I spent 5 days in Sorrento in mid November two years ago and the weather was very nice, even if it wasn’t warm enough to sit on the beach.
As for alternatives, you might have a look at my recent article with my recommendations for the best places to go in Asia in December. It’s got many more choices than the article above, with weather information for all of them. Closer to India, I think Sri Lanka is very nice in December, although it’s somewhat similar to India in many ways and you may want something more exotic. In that case I think Thailand and Malaysia are the best choices for family holidays.
With a vibrant downtown, great restaurants, culture, and a recent multi-million renovation to the Ritz Carlton, Naples, one of the areas most luxurious hotels, December is when the town really starts to get into gear. You can spend your time on the miles of gorgeous Gulf Coast white sand beaches, take an Everglades Safari, or head to the Artis-Naples which hosts world class dance, theatre, music, and comedy. And that is to say nothing of the five-star shopping.
There are many other Thai islands that could also be ideal and have what you are looking for. Another option is Boracay Island and I mention it because I spent an evening hanging out with some guys visiting from Saudi Arabia and they liked it a lot. The weather won’t be “cool” but it should be nice, and they do have very good nightlife in the Boat Station 1 area.
This sounds like a really fun trip you have in mind. I think the challenge is that most of Europe is much closer to 50F than 80F in November, and a good chunk of Europe is already colder than that. I’m running a new series highlighting the best places in Europe (and Asia) to go each month of the year, and I think that the best Europe destinations in November would be helpful to you. Another tricky thing is that you’ve been to many of the warmer places already, and I do understand your boyfriend’s desire to go someplace that neither of you have been.
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.
By early December the rainy season is pretty much over in Cartagena, and it cools down just a bit more as well, so the weather really doesn't get any better than this. As with most others on this list, right around Christmas you'll find that hotels get more expensive and are more crowded, so if you can go earlier in the month you'll be paying less and dealing with fewer crowds.
A few months ago, my girlfriend and I went on a small vacation through Portland and Seattle. I wanted to document all of the food I was eating to share the experience and to provide some tips and tricks with all of the curious folks out there. Being ketogenic while being on vacation is one thing – but eating well while staying keto is another, and I’ll show you how to do it.
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