One of the best things about Puerto Vallarta is that, unlike most of the Caribbean destinations, this is a real historic town rather than a purpose-built resort community. That means that there are small and authentic (and cheap) restaurants catering primarily to locals, so you get a much more authentic experience if you prefer one. The hotel zone close to the airport is modern and posh, but you are a short taxi ride away from the lovely center of town.
I know Italy is the world’s top wine producer and they obviously make a lot of olive oil as well. I’ve seen on many travel shows how it’s fairly easy to visit the olive oil places, and of course most wineries have places where you can see the process and taste it. The thing is though, that even Sicily is quite chilly in December so they might close down for the season. You definitely won’t get sunbathing weather in December at all. I would say you are best off in May, June, September, and October to get good weather and not have to deal with the insane crowds in July or August. Tuscany is the easiest to reach of the 3, but because of that its beach towns are most likely to be crowded in those warm months. I hope this helps and let me know if you have any other questions. -Roger
Weirdly enough, Central America and South America aren’t really known as top “culture” destinations, as the colonial history has mostly wiped out the indigenous history in the larger places. There are Aztec, Maya, and Inca ruins and sights, but not really enough to build a whole trip around. I’d say the most interest of those would be the Inca culture of Peru, specifically around Machu Picchu and the valley around Cusco. Alternatively, visiting Argentina is pretty much like visiting Europe from a culture standpoint. It’s quite nice there and prices are low if you know about the blue market for currency, but otherwise it may not be what you are looking for.

Take Meal Times in Stride – Although I had intentions of planning keto/low carb meals by researching restaurants beforehand, especially at Disney, that never happened. Did I mention I have four kids? Yea, I don’t have a lot of downtime. Even so, I never had any problem finding foods that I could eat at restaurants. When we were out and about in Orlando, if we were thinking about eating at a restaurant that I hadn’t eaten at before, I looked their menu up online in the car before walking in. As long as they had a keto/low carb option, it was a go. I wasn’t picky. In fact, I ate either a bunless burger or bunless grilled chicken club almost every day at Disney or Universal. When my kids wanted to order pizza one night at our condo, I ate the toppings off with a fork. When they wanted Mexican food, I enjoyed Chicken Fajitas on a bed of lettuce. Whatever my family wanted, I found a way to make it work, and I never felt deprived. We typically ate breakfast at our condo, a late lunch (at Disney or Universal if it was a park day), then a late dinner out. By doing so, we also saved a great deal of money since eating inside the park can be so expensive. Since we stayed off site, the dining plan wasn’t an option.
As Christmas approaches the city will fill up much more, so if you can go early in the month you'll be much better off. But even if you can't go before the last week of the month you'll still find Mexico City to be a tremendous bargain compared to pretty much anywhere else in North America. It's a great shopping destination, and not just for goofy souvenirs, so that's something to think about as well.
Of course in November you can pretty much forget about Europe if you want warm weather and little chance of rain. Fortunately you can go almost anywhere in Latin America and through many parts of Southeast Asia on a cheap flight, and you'll be in the sun with shockingly low prices, easily making the flight duration and cost worthwhile. The best holiday destinations in November are found all over the world, which you'll see on the list below.
As you suspected, this is a tricky one. Most of the places that would work for you are having a very rainy month in November, so it’s not a good time. Thailand would actually be a good choice if you can deal with the travel time. The rainy season there ends in October and yet the crowds don’t start appearing until December, so you get low hotel prices with nearly perfect weather. As mentioned, all of the good options in Central or South America have a wet season in November. Argentina could be a good option, as November is late spring there, and it has everything you are looking for. The flights to get there are also fairly long though.
I think a side trip or two will be a great idea. Singapore is a large and very interesting city, but you can see everything that you want in maybe 3 days or so. You have almost limitless options if you include the possibility of a flight. Even though Singapore itself (especially hotels) is kind of expensive, you can get cheap flights to all points of Asia from there, and the airport is awesome. Air Asia and Tiger are two great low-cost airlines with many flights out of Singapore, so you could check their destinations and find something good.
For those from the Northern hemisphere in need of decent a blast of winter sun, the picturesque coastal town of Essaouira is the perfect place to put your feet up and relax. Fresh-caught fish sizzles on beachside grills, whitewashed houses with blue shutters lend a Mediterranean vibe, and you can lose hours wandering through the dozens of art galleries and workshops.
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.
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
Lastly, while you’re stocking up on your morning coffee or mid-morning snack, you can many times see hard boiled eggs, snack-size cheeses, and small packs of nuts available in the display cases. While this is common in gas stations and convenience stores, more and more coffee shops and cafés are offering elevated versions of these as well. These are a quick and easy way to get some keto food while you’re sightseeing or running to a meeting.

I haven’t followed the Zika list, but I do understand the concern. Since you aren’t big beach people, you might just bring jackets and go to a more romantic city like Paris, and then maybe down to Nice for part of the trip and something a bit different. I’m not sure if this is helping, but if you have any questions about any of this I’m happy to keep trying. -Roger
Orlando’s theme parks are a major draw for families (and big kids, too!), but this iconic experience doesn’t necessarily come cheap. During the pre-Christmas November lull, however, hotels often offer attractive discounted rates, meaning potential savings and – more importantly for the kids – less time spent standing in line. Those looking for a more alternative American adventure should consider the island of Puerto Rico in November. While there’s a chance of rain (but a greater chance of balmy beach-lounging days), the out-of-season discounts are as appetising as the island’s take on Thanksgiving dinner: turkey stuffed with mashed plantain.
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