If I were you I’d fly into Bali and spend a couple days in the Kuta area to get your bearings and then head to Ubud, which is in the foothills and easily reached by shuttle bus. It’s also fairly crowded, but it’s still quite nice and there are scores of little spas and yoga places and that sort of thing. Then after a few days there, head up to the northern coastal town of Lovina, which is sort of like how Kuta was 25 years ago. It’s still only partly developed and there are still many open spaces, which is no longer true in the Kuta area. It’s cheaper than Kuta, and somewhat like Boracay in how mellow it is. You could also take a ferry from Bali to the island of Lombok, which is the next large one over. Things there are also more like Boracay and less chaotic than the Kuta area. Again, I really love Bali and still recommend it, but unless you are an Australian surfer, it’s best to stay somewhere other than the general Kuta area.
The mountains of Canada include the gentle slopes of Mont Tremblant in the east to the towering ones of Whistler in the west. Note that Canadians celebrate their Thanksgiving before the United States does, which makes our neighbor to the north a particularly good place for couples who won't be visiting family during that U.S. holiday—especially if you're willing to forgo turkey and stuffing for crepes and poutine.

The three places that jump out to me are the Playa del Carmen area just south of Cancun in Mexico, the island of Puerto Rico, or Costa Rica. All of those have endless beach activities and sights and great food and everything else, and they are all well within your budget. Puerto Rico would be easiest, and probably my first choice. Costa Rica is better known for adventure activities that might suit the younger ones. There are several good resort areas along the Pacific coast that would work.
It would probably be a bit more expensive, but another idea that could be great would be to fly to San Juan, Puerto Rico, and rent an apartment for two weeks. It’s a wonderful place that is family friendly, and rental apartments can be good deals. It’s obviously peak season there as well so nothing will be cheap. But the weather will be fantastic and the beaches are great, even in and near the city. I hope this helps. Let me know if you have any other questions.
I’ve spent a few weeks on Boracay, but not in early November. From what I’ve read, the monsoons there are usually not too bad, and it’s mainly a matter of a couple of hours rain in the afternoon on the bad days. Throughout the Tropics it’s very rare to get rain all day on any given day, and I’ve spent many months in those areas during rainy seasons. So early November isn’t ideal, but if it’s the only time you can go I still think you’ll enjoy it. One nice thing about Boracay is that the hotels are all basically on the beach or right off the beach, so even if it does start raining you can be back in your room in like 2 or 3 minutes. Best of luck with this. -Roger
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.

You’ve been to Cancun, but have you been to Playa del Carmen? Personally I much prefer it because PdC is a lovely tourist town with hundreds of little hotels and restaurants and bars, unlike Cancun, which is mainly a long string of high-rise beach hotels that are so spread out that you are nearly trapped in your own hotel. It’s about an hour south of Cancun airport by taxi or shuttle. That would be another of your cheaper options, partly because flights into Cancun are pretty cheap. It will be the tail-end of the rainy season in all of these places, but that usually just means a 30-minute rain storm a few afternoons each week.
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
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.
Steamed pumpkin sautéed and seasoned with fresh orange juice makes a tasty fall or winter side dish. Pumpkin steamed in the pressure cooker is easy to peel and dice and the steaming liquid can be used as a flavorful liquid in another recipe. You can pressure cook spaghetti squash this way too: use the same timing, but tease out the “spaghetti” flesh with a fork instead of dicing it.
Sunny SoCal may be beautiful all year-round, but the more-than-mild temperatures of November make it an even more stellar choice for those hoping for not-too-harsh sun, sand, and sea to chase away any impending winter blues. Head on over to the world-famous Santa Monica Pier or shop till you drop at Third Street Promenade. Of course, there’s also the good old beach itself, where you’ll find surfers, beach babes, locals, and tourists alike mingling festively together at Pacific Park amusement park, the outdoor gym at Muscle Beach, or on the historic Looff Hippodrome Carousel-- there’s also Bergamot Station in the heart of the city, which houses several art galleries to check out.
As for flight connections, Barcelona and Madrid should have decent connections to Toronto and Delhi, while Casablanca (Morocco’s largest airport) probably does not. So Spain is the better choice by that standard. On the other hand, you can get to Morocco by ferry from Spain in a short time, so you could go to Spain and also visit Morocco for a day or two.

Even cheaper than that is Cartagena, although the flight would probably be a bit more expensive. Cartagena has a gorgeous walled colonial Old City filled with cool hotels, shops, and restaurants, and it’s a 10-minute cheap taxi ride to a strip of beachfront hotels in a modern neighborhood. It helps if you know Spanish in both places, but Playa del Carmen has so many English speakers that it’s easy to get by on that alone. Those are my best picks in our region for inexpensive places that are fun with a lot to offer a solo traveler or small group. Let me know if you have any questions. -Roger

Really my first bit of advice is that the best place to get a really nice hotel that is on a beach or a hill and has the other nearby and also has great weather in December is Phuket, Thailand. You could go almost anywhere in southeast Asia in December and get good weather and low prices. But Phuket has over 1,000 hotels and hundreds of those are wonderful fairly luxurious hotels or villa complexes that could be perfect for a romantic honeymoon stay.
Venice can get pretty cold and they also have those famous Acqua Alta floods in winter, so read up on that before you go. But Rome and Munich should be easy to visit in December. One suggestion I will make is to consider visiting Rome for 3 or 4 nights and then base yourself down on Sorrento for the remaining 2 or 3 nights. Rome is one of those cities that is crowded and chaotic even in winter, to the point that just crossing the street can be frustrating, so many people get tired of that after they’ve seen the main sights. And Sorrento, on the other hand, is a lovely small city that is close to Amalfi, Pompeii, Naples, and the Isle of Capri, so it’s an ideal base to visit all of those. Sorrento is also cheaper than Rome, and a surprising number of locals speak English there, so it’s easy and pleasant. That time of year I’m not even sure if the tourist buses are running to Amalfi, although the local ones will be.

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
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