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
Another option is Chiang Mai, Thailand, which has wonderful weather in December as long as you don’t require constant heat. It is popular with tourists and expats, but it’s not an overly touristy city so it never seems too crowded. Other options in that general area to consider are Luang Prabang, Laos, and Siem Reap, Cambodia. Let me know if any of these sound interesting and I can provide more info if you need it. -Roger
If you are looking for pleasant weather in December you might also consider the Canary Islands. They have good connections to many destinations. You would probably have to change planes in Dubai, Abu Dhabi, or Qatar on your way to Delhi, but the flight will at least be fairly cheap. Good luck with this and let me know if you have other questions. -Roger
The Maldives is amazing for relaxing beach holidays and it’s within your range. The tricky thing for most people is that it’s quite expensive for a shorter trip. Of course the Maldives is famous for its water villa resorts, and those water villas start at around US$350 per night. Nearly all of those resorts also have island villas and rooms and those can start at as low as US$100 per night, but you also have to pay for a speedboat or sea-plane transfer from Male Airport to your resort. That can be as low as US$100 per adult for the closer speedboat islands, and up to US$600 per adult for the more remote sea-plane islands. On a shorter stay, that obviously adds to the price. Speaking of that, I run another site all about overwater bungalows and I have links from an article on this site about the cheapest overwater villas in the world. Have a look at that list as it will show you the more affordable options in the Maldives, as well as even cheaper options in Malaysia and elsewhere.
Hmmm…there may not be a Wow Factor in Puerto Rico, especially if you are that used to Caymen. I was thinking more about a really nice place that was easy and with great weather. Costa Rica could have the Wow Factor, however. The country is something like one-third national parks and it is packed with great scenery and adventure activities. It is the zip-lining and canopy tours capital of the Americas, so there are many great options along those lines. And there is the volcano and hot springs and really nice beaches. I’m not sure what you’d consider a Wow Factor, but Costa Rica is probably the most Wow destination other than Hawaii.
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
If you really want to see the city up close, visit in November or December, when the crowds have dispersed. Hotel prices are comparatively low, and gondoliers are more appreciative of customers. And once you have your fill of religious art, head for the Peggy Guggenheim museum, which displays 20th-century American and European art in a home and garden setting. Note: October through January is the time of acqua alta, when Venice may flood. Usually it's not severe, and the city puts up wooden walkways for visitors and residents to traverse the water.
New Zealand is an excellent option in December, as it’s before the Christmas crowds and just before the summer holidays there. The best and most popular way to explore New Zealand is to rent a camper van or a car and drive from one “holiday park” to another. Auckland is a pretty generic city so it’s not worth spending more than 1 or maybe 2 days there. Just fly in, and rent a vehicle to leave the next morning, and drive south. The North Island has a lot to see, but the South Island is even more scenic and pleasant. You can take a ferry between the two with your vehicle.
The most important holiday in Japan is oshogatsu (New Year), and the month leading up to it is packed with fun festivals and markets. Standouts are Shimai Kobo (December 21) and Shimai Tenjin (December 25) both of which offer great ceramics and handicraft shopping, in addition to lots of good things to eat and drink. From December 8 through the 17th, thousands of lanterns will be placed around Arashiyama, including in the enchanting bamboo forest. If you’re there on New Year’s, you’ll catch the famous the bell-ringing ceremonies -- get up real early and see the monks at Kyoto’s largest temple, Chion-in, or drop by a small-scale local shrine instead.

As December begins in the Caribbean, the hurricane season is officially over and the weather is pretty much perfect by any standard. Punta Cana is the Dominican Republic's most popular resort areas, especially for those who aren't particularly interested in absorbing the local culture. This is a resort area with wonderful beaches and not much history.
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
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.
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