With a vibrant downtown, great restaurants, culture, and a recent multi-million renovation to the Ritz Carlton, Naples, one of the areas most luxurious hotels, December is when the town really starts to get into gear. You can spend your time on the miles of gorgeous Gulf Coast white sand beaches, take an Everglades Safari, or head to the Artis-Naples which hosts world class dance, theatre, music, and comedy. And that is to say nothing of the five-star shopping.
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.
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 too am a planner, which is how I got involved in this, and so I totally understand your motivation. I think your plan sounds quite good. The weather in the places you are planning is actually fairly mild, and none of them are too far north. For some of us it’s easy to forget how far north parts of Europe are, and in those areas it’s not so much the cold but the fact that the sun rises at 10am and sets at 3pm that time of the year.
From England I would say your cheapest and best late December destination with warm weather and reasonable prices is going to be Phuket. There are some other Thai islands that might be a bit cheaper, but they would be more complicated to reach, and they’d have fewer activities for the boys. Here are some Phuket resorts good for families. You can see that the price range is wide from cheapest to most expensive. In late December it’s peak season so you’ll pay at or near the top of those ranges.
Increasingly popular, Lisbon is quite warm in summer, but November’s cooler temperatures and fewer crowds make it a pleasant time to visit. A city of hills and spectacular views, many terraces (miradouros) offer vistas for those who climb (or take a taxi) to the top. Alfama is the city’s historic district, defined by hilly, narrow cobblestone streets. The Fado Museum, in Alfama, honors Portugal’s soulful folk music and provides some background on the sounds heard nightly in the city’s fado houses and bars. Seafood is plentiful in Lisbon, and the traditional Portuguese dried salted cod (bacalhau) is on most menus along with octopus, shrimp, sardines, clams, and tuna.
As for the Northern Lights, Iceland is one to consider, and its Aurora Tourism sector is pretty famous. You can get a cheap flight to Iceland from London or most other large cities in Europe, and it’ll cost about the same as a flight to Stockholm or Oslo. If you want to stay on the continent, I’d think about Sweden, even though Norway has more northern area. Both are very expensive, but Sweden is a bit cheaper and easier to get around in.
Get acquainted with San Antonio on a River Walk boat tour as you pass restaurants, shops, historic architecture, and the Museum Reach, a 1.3-mile section with art installations and native landscaping. November weather, in the mid-60s, makes outdoor activities comfortable for exploring the city and enjoying the month’s events. November begins with Dia de los Muertos, the traditional Mexican holiday that remembers those who have passed away. Music, processions, performances, and costumed dancers will pay tribute in Pearl Park (Nov. 1-2) and Market Square (Nov. 3-4).
Capital of the UAR, Abu Dhabi combines ultra-modern structures and attractions with its ancient Arabian culture. This year, the Louvre Abu Dhabi will celebrate the first anniversary of its long-awaited November 2017 opening. Built on a manmade peninsula, its collection ranges from prehistoric to contemporary works, exploring universal human themes. The Sheikh Zayed Grand Mosque, a spectacular architectural achievement, consists of 82 domes clad in pure white marble. Its hand-knotted carpet, the largest in the world, features an intricate Islamic medallion design crafted by about 1,200 artisans. Open Saturday through Thursday, the mosque offers free admission, and visitors must observe proper dress and behavior.
My first thought was Goa, which you say you’ve been to before, but maybe you don’t realize that there are about 20 different beach areas that are different from one another in terms of vibe and types of visitors? Personally, I found that Anjuna and Vagator were both kind of mellow but also busy enough and easy to meet other people. But if you don’t like those, there are many different beaches in the south, which I’ve heard are also great and draw different groups. It’s something to think about because it doesn’t get much cheaper than Goa for beaches anywhere in the world. -Roger
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.)
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
Actually, all of my best suggestions for those things are in the article above. One challenge you’ll have is that all popular tropical destinations have their peak weeks at the end of December because so many people in cold areas have that time off. So flights to Central or South America are going to be fairly expensive, although buying soon can help. For hiking and views I think Costa Rica could be a good choice, or Nicaragua. You could also go to Bariloche in Argentina, though it’s probably not worth going all that way unless you were also going to spend some time in Buenos Aires and such.

I’ve only been to Norway in the summer and I’ve not gone skiing in Europe, so I can’t be of my help with those. Pretty much everyone who comes to this article (and this site) for December recommendations is looking for tropical destinations, so that’s what I’ve mostly provided. Sorry I couldn’t be of more help, and feel free to ask more questions if you have them. -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.

Unfortunately I’ve only been to Cartagena in Colombia, although I know of some travel bloggers who live in Medellin and love it there. The mild weather year round is one reason people love it. I don’t speak much Spanish, which is a problem in much of Latin America, but evidently there is a pretty big scene of various expats and English speakers, so Spanish isn’t so critical. In other words, I like the sound of your idea and I imagine it’ll be great, but I haven’t been there yet so I am really not qualified to give real advice. Best of luck with whatever you choose. -Roger
You still get warm ocean breezes and 70-degree temperatures, plus the Hawaiian islands go all out for the holidays. Locals host potlatch-style parties where the Christmas goose is replaced by a luau pig, and the resorts deck themselves out like tropical North Poles, including a massive tree-lighting ceremony at the Outrigger on Oahu and tree-decorating contests at Mauna Kea on the Big Island. Residents there climb to the top of the 13,000-foot-tall volcano, shovel snow into their trucks and speed back down to build snowmen in their yards before it melts.
Pay homage to the Native American heritage of the U S of A by taking in the sights and sounds of Arizona’s capital city for pure rest and relaxation before the holiday season. Phoenix anchors a sprawling, multicity metropolitan area known as the Valley of the Sun, which is highly regarded for its luxury resorts, vibrant nightclubs, designer golf courses, and long lasting sunshine and warmth—even through the winter months. Attractions include the Heard Museum and the Pueblo Grande Museum & Archaeological Park. Be sure to check them out!
The other place that comes to mind is Croatia, which also has reasonable weather in November. I’d recommend focusing on Split, which has many similarities with the more-famous Dubrovnik, but it’s easier to reach, much cheaper, and more authentic because Dubrovnik has become kind of cheesy as a cruise port. You could even take a bus to Mostar or Sarajevo in Bosnia for a couple days. The coast in that area is beautiful and there won’t be many other tourists that time of year. I hope these ideas help. Let me know if you have any other questions. -Roger
I’m sure you’ll have a great time. I don’t have any good suggestions for where to celebrate Christmas, but I’m sure you’ll have no problems finding something by just walking around or checking online. The top draw in Barcelona is the architecture, and especially the 20th Century buildings by Gaudi. I recommend the hop-on, hop-off bus tour because it allows you to see almost all of the famous buildings from the street in just a few hours. Park Guell is worth a visit, but of course the main attraction is the Sagrada Familia cathedral. Check opening times and reserve a ticket in advance if you can.

For a cheap destination in December that has great clothes shopping opportunities I can only think of two really good options. The closer of the two is Dubai. I’m not sure if you’ve been there before, but it has some of the best shopping in the world with every store imaginable and very good prices because duties and taxes are low. In spite of its reputation, Dubai can actually be visited quite cheaply if that is important. It’s famous for expensive hotels, but it’s got hundreds of more affordable hotels that can be pretty nice.
The last one is a 10 day trip for spring break 2018 most likely to be from March 9th to March 18. I’m thinking Europe but I don’t want to stay only in one country. I have so many options that I need someone to shorten the list in a way that it will work out. I want to go to Amsterdam, Rome,Venice,London,Barcelona,Zurich,Madeira,Dublin, and Madrid. (Amsterdam & Barcelona are a must).
This looks great and I wish I could be of more help. As I mentioned before, my first safari will probably be in 2017. I have a couple safari articles on this site from writers who have done them, and I’ve read a lot about the experience and the extremely positive reviews that most of them get. But having not yet done one, I wouldn’t feel comfortable offering specific advice. There are hundreds of articles on the internet that discuss these safaris, so I recommend you seek advice from someone with plenty of first-hand experience. Just be careful not to rely too heavily on a commercial safari outfitter, and try to seek advice from a travel blogger or other regular consumer. Have a great trip. -Roger
The hotel rates all over Goa are highest in December and January, but in Anjuna or Vagator they still start at around £10 per night for a private room with ensuite. The cheap places are quite shabby, so it might be worth spending more. Vagator has an amazing beach, but it’s often filled with Russians these days. Anjuna is famous for its beach raves and music scene, but I’ve honestly heard nice things about many other beach areas in Goa.
Gorgeous weather, an enviable winter suntan, and thriving dining and nightlife are obvious reasons for heading to Miami in December. Art Basel Miami Beach 2018, a contemporary art extravaganza and America’s premier art fair, is another incentive for a Miami trip. With celebrities, parties, and unmatched celebrations throughout the city, over 250 world-renowned galleries and 4,000 participating artists will display their creations and collections. The Betsy South Beach, centrally located in Miami Beach’s Art Deco district, will be a major Art Basel venue. Another noteworthy accommodation is The Setai Miami Beach, situated oceanside in South Beach. Featuring 87 Art Deco rooms and 49 ocean suites, the Setai will debut five new retail stores by the end of the year. There is no shortage of family-friendly fun in the Magic City, so named for its rapid growth from 1,000 residents to over 5 million in the past 120 years. Santa’s Enchanted Forest at Tropical Park is the largest holiday theme park in the world featuring carnival rides, shows, games, race cars, food, holiday displays, music, and dazzling Christmas lights. The Miami Lantern Light Festival at the Fair Expo Center celebrates Chinese culture, featuring food, acrobats, handmade souvenirs, rides, and huge handmade lanterns symbolic of illuminating the future and the reunion of family. 
You mention New Zealand and of course it’s summer there then, so it would be a good choice. However, all of these places will be crowded and near peak hotel rates if they are warm. So I’ll be happy to give you advice if you tell me if you’d rather visit one or more European cities in the cold season, or if you are looking for a warm place like New Zealand where it will be fairly crowded. By the way, the southern European cities such as Rome and Barcelona are lively and enjoyable that time of year, as the Christmas season goes on, and there aren’t too many tourists except for a few that travel to see their families around the holidays. So it can be a good time for southern Europe, as long as you don’t mind wearing a jacket or jumper during the day, and maybe a bit more in the evening. Give me a bit more guidance and I’ll be happy to try to help. -Roger
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