In Laos, Luang Prabang is a really lovely city, and Vang Vieng is nice, but Vientiane is kind of plain and probably not worth a stop. I don’t think I’d recommend Laos for a multi-generational trip, unless you just want to fly into and out of Luang Prabang. Laos is really interesting for backpackers and adventure travelers, but it’s behind the times for family travel.
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.
Regarding Thailand, I’m not familiar with any islands that are beautiful and not touristy. Phuket has beaches all over the island and many of them are isolated so the only guests are those staying at the resort in front of them. If you search other travel sites, including travelfish.org, which I think is the best site for southeast Asia and it’s run by a friend of mine, you can find more information about more obscure Thai islands. One challenge could be that you might have to take two or three total flights and then a ferry ride to reach them.
Spend the past two days discussing your ideas. Group thoughts; Is that adventurous and cultural enough? We want a “wow” factor. We have vacationed in Cayman Islands about a dozen weeks since the kids were little (been there done that.). We have ruled out Asia only because don’t see a huge Wow factor for the amount of travel. What about African Safari? Still not ruling out your ideas, just want to know what is Wow about Puerto Rico? Costa Rica?

Uruguay is an interesting place. It seems to be a less modern and less developed version of next-door Argentina. Buenos Aires is a larger and more interesting city than Montevideo. There is a town there called Colonia, which is worth a couple days if you like old and charming cities. But most people who go to Uruguay either go to one of the posh beach resort towns (mainly Punta del Este), or they go to the tourist cattle ranches, which are surprisingly popular. If you haven’t been to Argentina yet you might find that it has more and different options, such as the Mendoza wine region and the mountain resort town of Bariloche.
It's getting cold out there, so consider a journey that leads you into a warm museum. Whatever your interest, there's bound to be a specialized one to engage it. If art and sculpture are your passions, discover some favorite art museums around the world. And consider that you can make a day of it soaking up culture as many contain surprisingly good restaurants to visit in between your viewing.

Located on the north Pacific coast of Costa Rica, the 15-mile peninsula is home to lush jungles, postcard perfect beaches, and five-star hotels. It is decidedly remote (the nearest “town” is a 45 minute drive away) but sometimes, remoteness is exactly what a winter getaway calls for. Though Papagayo is the kind of place where you might be tempted to never leave the confines of your resort—there’s an Andaz, a Four Seasons, and a community of luxury villas to rent—it also caters to adventure lovers, with activities like ziplining, jetskiing, and four-wheeling through the jungle. Stick with later in the month to avoid any lingering rain (rainy season goes from May to early November.)
My best recommendation would be somewhere in the islands of Thailand. December has very pleasant weather with warm days and nights that can be a bit chilly (for some people). Best of all, it’s a very beautiful place and the tourist infrastructure makes it easy to get around speaking English and with very few headaches. The largest island is Phuket and it has famous nightlife in the Patong Beach area. In fact, the nightlife is so notorious that many people think it’s too much so they avoid the place. There are many other beach areas that are quiet and still close enough to go into Patong once in a while.
Thank you, and I’m always happy to hear that people find this useful. Buenos Aires is a wonderful city and it feels very modern and very European, at least compared with most of the rest of South America. I would think that bringing a baby there would be similar to bringing one to, say, London or Paris. Rio de Janeiro is perhaps the most beautiful city location on earth, and it’s got some very rich areas (mostly along the beaches) and many dodgy areas. They also seem to struggle more with infrastructure there so bus service isn’t very modern and that sort of thing. That said, I haven’t been since they hosted the World Cup and Olympics and I’ve read that much of the situation has improved. Long story short, I think you might just have to be a bit more careful in Rio when choosing a hotel and neighborhood and that sort of thing, but generally I think you’d be good.
If you book a resort hotel from home you'll probably think Goa hotel prices are much higher than you were expecting, but if you book a family-run place once you arrive you'll still find fantastic bargains. It's probably wise to book a few nights online before you get to India, because it can be incredibly confusing at first. After that you might be able to find a similar place for half the price by just checking around the same area.
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
Since flights to Mexico City from the US and Canada are usually quite cheap this time of year as well, this could be a perfect short cultural holiday. This city has great shopping, dining, and nightlife, and the central historic and tourist districts are far safer than most people would expect. There are ruins just out of town as well, so a bit of everything is available.
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