Always happy to hear that people find this useful. If you are looking for a driving holiday with warm weather in December I think you’ve already narrowed down the best choices. New Zealand will be ideal, although maybe not for more than two weeks or so. As you might know, the South Island is more scenic than the North, but the North has many great things to see and do as well.
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.
Heading east, India could be a possibility, although it’s not for the faint of heart. As a resident of Singapore, I assume you know a fair bit about India. Outside of Mumbai, it’s all quite cheap and the weather will at least be good. Personally, I love the southern state of Goa, and it has everything you are looking for, without the insanely crowded conditions of India’s big cities.
Unfortunately, it can be a bit complicated and time consuming to reach any of these Philippines resort areas. I don’t think I’d recommend doing more than 2 of them in a 8 to 10 day trip. The nice thing is that they are very secluded-feeling once you get there because they are so out of the way. Partly for that reason, I think staying for 4 or 5 days each is very nice.

Thank you for the kind words. If you’ve got 30 days in Thailand I would recommend spending more time in Bangkok and probably in Chiang Mai as well. Bangkok is huge and in December the weather is actually quite nice, so two days seems way too rushed. As for which islands to consider it sort of depends on why you don’t want to go to Phuket. Phuket is the largest and busiest island and it’s got just about everything that the rest of the islands has. I can understand not wanting to spend time in Patong Beach, which is the shopping and nightlife capital, but there are many other wonderful beaches and towns on Phuket that are quite different from that.

As for key events in December, I typically avoid those sorts of things myself, so I’m not a good source on that. I actually visited Rio de Janeiro during Carnival, by accident, and it drives hotel prices so high and also crowds that it’s probably the worst time to visit unless you specifically want to spend all night watching the parades. And Oktoberfest, as another example, literally triples the prices of hotel rooms in Munich, so it’s only worth it if you REALLY want to get involved in the Oktoberfest thing yourself. But plenty of other travelers love to go witness the biggest events, and I assume they love it, so there is no right or wrong.
Oh, did you want a sunny tropical vacation that doesn’t require a passport? Done. Hurricane season is over, flights are cheap, and the water is still warm enough for swimming (and scuba diving). Almost all the tourists come here via cruise ship, which means you’re mostly not competing with them for hotel rooms -- Windward Passage, Emerald Beach, and the Bolongo are all open for business after Hurricanes Irma and Maria last year. On December 16 you can catch Jazz By The Sea down at Coral World Ocean Park, and on December 21 watch the St. Thomas Lighted Boat Parade, where contestants (boats) are judged on lights, originality, and holiday cheer.

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.


If you are going for one week I wouldn’t go all the way to Thailand, but if it’s two weeks I think it’s worth it. It takes most of a day in each direction, but flights are often reasonably priced, and everything there is cheap once you get there. I’ve actually lived in Thailand for 6 months and have visited many more times and it’s actually very easy and stress free once you are there. All the important signs are in English and nearly everyone you’ll encounter as a tourist will speak enough English to help you as well. You can get around by train or VIP bus for cheap, or fly to the islands for cheap. It’s very safe there as well. You could spend a few days in Bangkok and then head to one of the islands or take a train up to Chiang Mai.
What a fantastic site you have. I am in Dallas, TX and looking for a 7-10 day getaway in late November or any time in December, depending on when my passport renewal comes in. I am going solo and have a reasonable budget. My goal is relaxing mostly but as a solo upper 40’s male, it wouldn’t be bad to run into some people (and ladies) to visit with some of the time. I thought of SE Asia but travel time burns up much of the trip. Do you think all-inclusives are worth it? And any recommendations for places I won’t be overrun with families and screaming kids?

I’m not really an expert on surf destinations and even less so on skate parks, although I am aware of many places that do have good surf beaches. From Ireland I think your two best bets would be either Rincon, Puerto Rico, which has the best surfing in the Caribbean and is good for longer rentals like that. You could get a reasonably priced flight into San Juan, which is also a really nice place with some surfing and great beaches, and then hire a car for the drive to Rincon.
Two of the easier other choices would be London or Madrid. From Amsterdam you can take a train to Brussels and then change for the Eurostar train to London, or you can fly. From London to Barcelona you’d want to fly for sure. If you chose Madrid you can go to Amsterdam and then fly to Barcelona and then take a train from Barcelona to Madrid in only 2.5 hours.
Not surprisingly, the weeks around Christmas and New Years are literally the busiest of the year in Goa, so either book a hotel way in advance or be flexible once you arrive. Some towns, like Calungute, are lined with package hotels that fill up completely, but other towns, like Anjuna and Vagator, are usually booked in person or by email, so you can often find a place just walking around. If you are in the mood to tour around, Mumbai has great weather during December, and Delhi has warm days but cool evenings this time of year. Goa has some of the best beaches in December in all of Asia, so give this one a serious look.
Without knowing more about your interests, my top suggestion would be to focus on Sydney and Melbourne and the areas around both. The Blue Mountains near Sydney are also nice for a couple days or so. The main challenge you’d have in seeing a lot of Australia is that it’s all so spread out. You can hire a car for Melbourne and Sydney and that whole area, but it’s better to fly to get to Uluru (near Alice Springs) or Brisbane or Cairns/Great Barrier Reef or Perth. You’d be driving for days in between those places if you started from the southeast area where most people live.
Yes I travelled a bit by train in southern India, I got lucky on my first few journeys with lack of people, then I hit some Indian holidays and it was hellish. I remember the trains being booked up for all the upgraded a/c and upper class carriages. One time even the Indians were fainting on the over packed carriage so you can imagine the heat for little old gringo me!
Australia is so large and varied that one cannot simply say ‘go to Australia in November’ and expect everything to be fine beachy. That said, November is probably as close as it gets to being perfect weather country-wide. The tropical rainy season in the North hasn’t properly settled into humid downpours yet, while the cooler southern states of Victoria and Tasmania are shaking off the winter frost and basking in warmer days. Vino and meals are taken al fresco, outdoor music and food festivals pop up everywhere, and beaches across the country begin to buzz.
As for my own Top 10 destinations in general, that’s a tough one for someone like me because I can’t help but factor costs into the equation. For example, I really love Amsterdam and I even lived there for awhile, but it’s also very expensive and maybe not a great choice for everyone. And it’s also hard to avoid cliches for a list like this, because I honestly feel that most of the places on these sorts of lists are great.
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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