Thanks for all of this Roger! It looks like in the comments you mention Portugal a couple times and I wanted your opinion – we’re looking at the first two weeks and probably focusing on Lisbon to Porto (since we know it will be too cold to do the beaches in the south). While Portugal seems to be highly recommended, I keep seeing conflicting information about November being rainy – we definitely don’t want to spend 2 weeks in the rain but in your experience what are the chances of that? Thank you!!
Yes, it's high season and rates edge up, but that's only because everyone wants to make the scene and flee cooler climes. Whether you prefer a hotel right on the beach, one in the midst of Miami's trendy Art Deco or Wynwood art district, or a tower with horizon views and vast swimming pool, there's a place for you. And each December, Art Basel in Miami Beach brings together artists with knowledgeable collectors and gallerists.

As for your Europe trip, I highly recommend spending 3 nights in any city you visit. If you change cities every day or every other day you’ll end up spending most of your holiday on trains or in airports rather than seeing the places you flew all that way to see. So if Amsterdam and Barcelona are musts, I would add exactly one other city if you’ve only got 9 days. Unfortunately it’s not on your list, but the best and easiest one to add between them is Paris. There is a train from Amsterdam to Paris in a bit over 3 hours, and another high-speed train to Barcelona from Paris in 6 hours 27 minutes with no changes. Paris is easily one of the most impressive European cities for tourists, but if you’ve been there before and don’t want to go again you can obviously choose something else.

Cancun is at the north end of the Riviera Maya, which also includes the island of Cozumel, so this is a huge area with over a thousand hotels to choose from. All that competition keeps prices down until the high season begins, so November is still a buyer's market. There are even ruins nearby and other cultural opportunities, so it's not all about sitting on the beach here. If you prefer a high-rise hotel overlooking a beach then stay in Cancun itself, but if you prefer to stay in a friendly town with many restaurant and shopping choices then head to Playa del Carmen, just a bit to the south, instead.
Say Hydrated – This is a no-brainer and one of the most significant challenges for me. I never drink enough water, but it was hot this week in Florida when we were at Disney, and I could tell such a difference in how I felt when I was hydrated. I felt like it made it easier to stay strong and stick to eating low carb/keto as it helps to quench false hunger.
Spear fishing, kayaking, and zip lining across the jungle are popular activities. At Hol Chan Marine Reserve, you can safely snorkel alongside sharks and stingrays. The Belize Barrier Reef is a favorite destination for snorkelers and scuba divers and one of the most diverse ecosystems on the planet. Experienced divers may want to plunge into the famous Great Blue Hole of Belize, designated one of the top 10 diving sites in the world by famed French explorer Jacques Cousteau. Family-friendly activities include cave tubing down the rivers of the Belizean rainforest, sailing, bird watching the over 600 species of birds, canoeing, horseback riding, or just relaxing on a beautiful sandy beach. Romantic sunset cruises are a wonderful adult option. Travelers can stay at beachfront properties like Banyan Bay Suites and Grand Colony Villas for an authentic Belize experience.

You would probably get some rain in Cartagena in November, but mostly in the first half of the month, and even then it tends to come down in short bursts rather than all day, so it’s usually easy to avoid. I love Cartagena for trips like this because the walled historic part of the city is really lovely and fun, with plenty to see and do. The nearby beaches are big, but the sand isn’t white and fluffy, so they won’t make too many “best beaches” lists. It’s also very cheap there, and especially at the tail end of the off season like that. As long as you don’t mind the possibility of a couple of quick rain storms, it should be great.
I like your comment about how “rainy seasons” are almost always overstated. I totally agree based on my own experiences and research, although there are a few places where they should be taken more seriously than others. On my most recent December trip to Bali (2.5 years ago, I think), I spent 30 days there and the rain only became a problem that one time I mentioned. It was just an insane cloudburst while taking a minibus from Kuta to Ubud, and in the end it’s actually probably my best Bali story. Aside from that, it’s very humid during Bali’s wet season, but even that really didn’t slow me down. The thing is, in Bali you are usually on or near the beach or a hotel pool (feeling the breeze) or in your air-conditioned room. Or you might be touring around to see temples and rice terraces and whatnot, and everything is outdoors and beautiful. When it does rain it’s usually over in 15 minutes, but often the rain comes over night. That kind of humidity can be a killer when visiting a city, but for me it’s a small issue on a tropical island like Bali.
As for Malaysia, you could book online and it might cost a bit more, but more things go by a fixed price in Malaysia so it might not be much different. Personally I’d probably book tours through my hotel once I got there, just as in Vietnam. But there is a BIG difference between the countries in that Malaysia is a much richer country and there are very few scams to worry about. Vietnam is still fairly poor and they were communist for so long that people got used to trying to scam people a bit as the only way of getting ahead. So the good news is that Vietnam is a gorgeous country with excellent food and very low prices on almost everything. But the bad news is that you have to be more careful in Vietnam because people will try to overcharge you if they can, even though it still might seem cheap to you. That’s one reason I like to book with hotels, because they put the reputation of the hotel on the line when they book something for you, and they can’t afford to get a string of bad reviews by charging an extra US$5 on a cut-rate tour. I hope this helps. Let me know if you have any other questions. -Roger

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).
If an apartment isn’t your thing, or you have to book a hotel for your business trip, then there is one upside: the food. Typically hotels will include some sort of breakfast, and occasionally some sort of dinner plan. In Portland, we stayed at a great hotel that included both. Breakfast usually consists of pastries, waffles and oatmeal – but they almost always have eggs, bacon, and sausage ready to go on your plate.
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?

While the Caribbean destination tends to overflow with families during the holidays in December, go a month earlier and you’ll be treated to sunny days sans screaming kids, plus less expensive airfare. “November is my one my favorite months. The hustle and bustle of high season hasn't kicked in, average temperatures are in the 80’s, and the water temperature is lovely,” says Michael King-Hew, the proprietor of Kamalame Cay, a private island resort in the Bahamas. King-Hew specifically suggests for the resort's annual wellness retreat. “It’s the perfect way to get rested and in shape before the start of the hectic holiday season.”

From exquisitely decorated storefronts to the amazing Rockettes Christmas show at Radio City Music Hall, New York City attracts thousands of tourists every December. Visit the Big Apple during the holidays! It’s a sight to behold. We recommend visiting Rockefeller Center to go ice skating, go shopping at new pop-up shops or just enjoy a cup of hot chocolate at Serendipity 3.


Looking to shake up the traditional holiday season table? We’ve got just the foodie forays for you this festive month. Tuck into a spicy blend of fabulous flavours at Malaysia’s hawker food stalls, where bright bowls of creamy laksa (noodle soup) and deliciously deep-fried lor bak (pork or prawn wrapped in tofu skin, deep fried and served with dips) will soon do away with any cravings for Christmas pudding. With tourist numbers low, now is the ideal time to visit Spain’s Basque Country, seeing out the year with a plate piled high with pintxos (tapas); or check out Cuba’s capital, exploring the crumbling, colonial architecture with a rum-based cocktail in hand.


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.
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.
In Cambodia the best place by far is the Angkor Wat temples just outside of Siem Reap. Siem Reap itself is a nice town with plenty to see and do, but 3 or maybe 4 days should be enough. Otherwise you have Phnom Penh, which isn’t too special, or Sihanoukville, which is a pleasant beach town that doesn’t really match up to most of what you are used to in the Philippines.

Mexico’s spectacular Día de Muertos (Day of the Dead), bewitches Mexico City at the start of each November. Donning the skeleton face paint for the mass parades in the main Zócalo square is a must, but take time to step back from the party and seek out more intimate family celebrations where deceased loved ones are honoured with candles, sugar skulls and, of course, tequila. If you’d prefer to relax with a rum, then Barbados in November may be more to your tastes. The sugar-cane liquor is thought to have originated here in the 17th century and continues to be the local tipple of choice. Toasting the sunset from one of the island’s magnificent beaches is a quintessential experience.
Really my first bit of advice is that the best place to get a really nice hotel that is on a beach or a hill and has the other nearby and also has great weather in December is Phuket, Thailand. You could go almost anywhere in southeast Asia in December and get good weather and low prices. But Phuket has over 1,000 hotels and hundreds of those are wonderful fairly luxurious hotels or villa complexes that could be perfect for a romantic honeymoon stay.

We were able to sit down in the store, relax, and eat our salmon and cheese  (pictured above) – separately of course! As you eat, you can watch them hand make their cheese through a glass window, showing exactly what they do in their process to get the food you’re eating in front of you. An experience in itself that I definitely would recommend to anyone visiting this city!


That said, I think going to Siem Reap in Cambodia would also be a great idea. And Vietnam is also really wonderful, especially that time of year. Hanoi is quite chilly in December and Saigon is still very warm. It’s worth visiting both of those along with Halong Bay near Hanoi and Hoi An in the center of the country on your way between them. You could easily spend 10 days in Vietnam or more.
Hi great site it’s very helpful! My husband and I are looking to do a last minute vacation to somewhere with warm beaches next mid November (14-21). We live in California so don’t want to travel to far more than 8 hours flight. We’re looking into Kauai, Cancun, Costa Rica. Weve been to Maui and Oahu, Puerto Vallarta and recently Bahamas last November. Any recommendations? Thanks in advance!
As for the alcohol thing, I’m a bit of a drinker myself, so it’s hard to offer advice to an AA person. I guess one factor could be that there are many places around the world where alcohol is so cheap and the days are so warm that many people drink during the day AND at night. If I were in your shoes, I’d probably want to avoid those places. Probably the easiest places to go would be Muslim countries and India because there is little or no drinking culture there, so they have endless evening alternatives that don’t revolve around drinking.
I’ll be happy to try to help, but I’d really need to know your starting point because there are cheap places in different corners of the world, and it’s not worth flying halfway around the world to try to save US$20 per day. In mid December through January for beaches you should consider Thailand and perhaps also Vietnam. I’ll give you more information once I know where you are starting from. -Roger
As for the alcohol thing, I’m a bit of a drinker myself, so it’s hard to offer advice to an AA person. I guess one factor could be that there are many places around the world where alcohol is so cheap and the days are so warm that many people drink during the day AND at night. If I were in your shoes, I’d probably want to avoid those places. Probably the easiest places to go would be Muslim countries and India because there is little or no drinking culture there, so they have endless evening alternatives that don’t revolve around drinking.
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.

By the way, Costa Rica is quite different from the popular countries of South America itself (Peru, Argentina, Brazil etc), so it’s a different experience and not much of an introduction. I think in 12 days you could have a great time in several areas of Costa Rica, and maybe also spend a few of those days in Panama or Nicaragua. As always, feel free to ask more questions if you have them. -Roger
Later in the month, the day after Thanksgiving begins Christmas season with the Ford Holiday River Parade and Lighting Ceremony. Decorated floats wind through the illuminated trees and bridges along the river. Luminaria, San Antonio’s annual free contemporary arts festival (Nov. 10-11) will take place in Hemisfair and other downtown venues, unveiling a special program at the Mission San Jose, a UNESCO World Heritage Site. San Antonio has been recognized as a Creative City of Gastronomy by UNESCO’s Creative Cities Network. Influences of Mexican, Spanish, German, French, and Native American cuisine and ingredients combine to form the city’s culinary heritage, increasingly attracting foodies to its hundreds of unique restaurants.
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.
It’s only fitting that the closest big tourist destination to the North Pole would do Christmas up big. Reykjavik feels almost like a mini-New York in December, with the Oslo Christmas tree standing sentinel over the city and a public skating rink in Ingolfstorg Square. Seeing the northern lights is never a guarantee, even during days of near-perpetual darkness, but your odds are much greater in winter. On the other hand, who needs ’em when you have 13 official Santas walking around town posing for pictures? The Christmas Village at Hafnarfjordur is a top weekend destination for both locals and the newfound throngs of American visitors. Just beware their holiday tradition of eating ruinously smelly fermented skate.

Flights, on the other hand, can be pricey if you buy too early. My recommendation would be to book a resort soon and then put a fare-alert on the flights so you’ll get an email when the fare drops. For the Caribbean the cheapest fares are usually only 2 or 3 weeks out, and since that is a slow period you really shouldn’t have any problem (unless you are trying to go on popular Thanksgiving dates). Most likely the resort prices won’t change much as November approaches, so you could probably wait on that as well. There will definitely be empty rooms when you get there, so the resorts usually don’t start pushing up rates when they will be partly empty. Best of luck on this. -Roger
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.

Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.
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
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Keto Diet practitioners who overeat a little on vacation shouldn’t chastise themselves too harshly. Life is about balance, and the Keto Diet helps practitioners regain control over their eating habits, but it shouldn’t be an overbearing burden. As long as you can get back to your diet plan after vacation, and you don’t use your holiday as an excuse to go back to your old way of eating, eating outside of what your Keto Diet plan recommends doesn’t have to be a huge problem.

Walking along the city's tree-lined streets, you'll notice that Spring is in full bloom come November, with vibrant jacarandá flowers dripping down over building facades. The weather is balmy and hotel rates are slightly lower for "shoulder season," which makes it the perfect time of year to plan a visit. Buy tickets to a soccer match, check out one of the world's most beautiful bookstores (El Ateneo Grand Splendid), and catch a tango show at a local theater. Looking for more inspiration? Check out our "10 Things to Do in Buenos Aires" guide.

That was very nice of you to take the time to mention this. Interestingly, I’ve been to Bali exactly twice so far (going again in early 2016) and both times have been in December. As you have probably noticed, the rainy season in Bali can be VERY rainy at times, which is why I didn’t put it on the list during the worst months. I still clearly remember standing in almost 2 feet of water trying to push the minibus I was riding in to a dry enough area to start the engine again. That was on the way to Ubud, but most of the time the rain isn’t problematic and I’d go back again again in December if given the chance. Just don’t expect any Christmas decorations or celebrations because they pretty much ignore it there, even in tourist areas. Have a great trip. -Roger
If you are more interested in nature and adventure than culture, then the top choice would be Costa Rica. The country has many beautiful national parks and it’s filled with things like zip-lining and canopy tours, just to name a few things. There are also volcanoes and surfing beaches and much more, plus a very good backpacker infrastructure of cheaper hotels and hostels.

If you are interested in a place that isn’t focused on beaches in that area then I’ll point you to some recent answers just above where I mention the charms of Chiang Mai in northern Thailand, or Luang Prabang in Laos, and/or Siem Reap in Cambodia. All of those are wonderful places with temples and other sights, and they are quite affordable once you are there as well.

I am from Chennai, India. Me and my wife are planning to spend about 8 days in SE asia around christmas time. Based on your inputs we are looking at either Vietnam or beaches of thailand. We are on a strict budget constraint so which one of these two will be a better option as far as budget goes ? And if it is thailand beaches, where do you suggest we go to avoid over crowding and for budget deals during christmas ? Thanks in advance 🙂

My second vacation meal was dinner that night. After walking almost ten miles at the park, the hotel, and spending the late afternoon swimming in the pool, we did dinner at the hotel restaurant before heading back to the park to ride a few things one last time. Dinner (Meal 2) consisted of pot roast with carrots and mushrooms (I asked them to go light on my carrots and they did a very good job of it), and a side salad that I again topped with salt, pepper, and blue cheese dressing.


This sounds like a really fun trip you have in mind. I think the challenge is that most of Europe is much closer to 50F than 80F in November, and a good chunk of Europe is already colder than that. I’m running a new series highlighting the best places in Europe (and Asia) to go each month of the year, and I think that the best Europe destinations in November would be helpful to you. Another tricky thing is that you’ve been to many of the warmer places already, and I do understand your boyfriend’s desire to go someplace that neither of you have been.
We are looking to travel somewhere warm in December of this year, for approximately 3-4 weeks. We are originating from Canada – Alberta, to be exact, and have done a fair bit of travelling throughout our lives, however, we are now bringing along our 4 year old son. With that in mind, I suppose our biggest concerns are now flight durations and safety (in our younger years and without children, these weren’t so much a factor, but definitely are considerations now).

As for Costa Rica, I think it would be ideal for what you have in mind. It’s by far the most tourist-friendly (and English speaking friendly) country in that area, so it’s a great starting point. Belize is pretty easy as well, although there is far less nature to enjoy. Panama and Nicaragua are a bit cheaper and have similar things to offer, but Costa Rica has the best infrastructure and nature parks, so it’s less stressful for a first-timer. The snorkeling is better on the Caribbean coast, I believe, but the better tourist beaches are on the Pacific. The country is pretty quick to get across, so you could easily spend a few days on both sides, plus another few exploring the rain forests and volcanoes and such.
We were able to sit down in the store, relax, and eat our salmon and cheese  (pictured above) – separately of course! As you eat, you can watch them hand make their cheese through a glass window, showing exactly what they do in their process to get the food you’re eating in front of you. An experience in itself that I definitely would recommend to anyone visiting this city!

The Canary Islands are always an option and the weather in November is pretty decent. I spent almost a month on Tenerife a couple years ago and I thought the nightlife was mostly pretty cheesy, although at least the drinks are cheap. I think in summer the nightlife there might be good, but in the other months I think it’s pretty quiet because it’s mostly older visitors from northern Europe.

Cartagena is a lovely place as well, but another reader just pointed out that the US government has a new travel warning to all of Colombia as of June, 2017. The US has travel warnings to many countries that people still safely travel to every day, but it is something to consider. Many years ago Colombia had quite a few problems, and yet Cartagena was always okay because it is this little cruise port and tourist city far away from the major urban centers. Seeing this, I would think twice myself, although I wouldn’t rule it out, but I also wouldn’t go anywhere except Cartagena at the moment.
The fastest high-speed trains between those cities only take 2.5 hours, although most departures are closer to 3 hours. Definitely take the train and also buy the ticket as far in advance as possible for the lowest fare. Not only is it FAR quicker than flying (and of course the coach), but it’s far more comfortable and more enjoyable. This is a link to the official Spanish rail site. The scenery isn’t all that special, but it’s still interesting. Have a fantastic trip. -Roger
That was very nice of you to take the time to mention this. Interestingly, I’ve been to Bali exactly twice so far (going again in early 2016) and both times have been in December. As you have probably noticed, the rainy season in Bali can be VERY rainy at times, which is why I didn’t put it on the list during the worst months. I still clearly remember standing in almost 2 feet of water trying to push the minibus I was riding in to a dry enough area to start the engine again. That was on the way to Ubud, but most of the time the rain isn’t problematic and I’d go back again again in December if given the chance. Just don’t expect any Christmas decorations or celebrations because they pretty much ignore it there, even in tourist areas. Have a great trip. -Roger
Lovers of historic architecture should consider tiny Malta in November, which still basks in glorious warm weather as much of Europe starts to shiver. The baroque palaces, churches and fortifications of its harbour-hugging capital Valletta look much the same as they did 400 years ago, and are extra lovely when observed from a traditional dghajsa (open boat) water taxi. If a life on the high seas has always appealed, then charter a course for the Cayman Islands come November, when the serene Caribbean isle hosts Pirate Week, a fun-filled festival that includes costume contests, street dancing and a horde of swashbucklers ‘invading’ the island and capturing the governor.

Thanks for all of this Roger! It looks like in the comments you mention Portugal a couple times and I wanted your opinion – we’re looking at the first two weeks and probably focusing on Lisbon to Porto (since we know it will be too cold to do the beaches in the south). While Portugal seems to be highly recommended, I keep seeing conflicting information about November being rainy – we definitely don’t want to spend 2 weeks in the rain but in your experience what are the chances of that? Thank you!!


If the Caribbean sounds better, I’ll recommend Puerto Rico. The area around San Juan is fairly crowded, although not nearly as crowded as a typical resort area that is loaded with hotels. And there are many smaller resort towns on other parts of the island where people usually rent a condo for a week or two. In a town like Rincon you won’t get crowds, and you will get great beaches.
A trip to glittering New York City during the holiday season is exciting, and it’s the perfect place to finish gift shopping while enjoying the festive atmosphere. Ice skating under Rockefeller Center’s fabulous Christmas tree and watching the high-kicking Rockettes are holiday traditions for New Yorkers and visitors alike. Or come at the end of the month for an unforgettable New Year’s Eve watching the ball drop among the crowd in Times Square. If a little bit of country is more your style, you’ll love Austin in December. Whether you travel far or stay close to home, a December trip can be the perfect gift to yourself.
The mountains of Canada include the gentle slopes of Mont Tremblant in the east to the towering ones of Whistler in the west. Note that Canadians celebrate their Thanksgiving before the United States does, which makes our neighbor to the north a particularly good place for couples who won't be visiting family during that U.S. holiday—especially if you're willing to forgo turkey and stuffing for crepes and poutine.

Overall this is a perfect time of year to visit almost anywhere in Argentina. When December arrives things really start filling up and all the locals are on their own holidays, so November is the ideal mix of great weather that isn't too steamy, and modest crowds and prices. With Argentina's recent inflation and currency devaluation, it can be hard to know how expensive this trip will be, but for most people it will be cheaper than in recent years.
The final month of the year marks the time when people in northern climates start looking around for an escape to the sun. Fortunately, there are big parts of the world that have their best weather of the year at this time, and are very cheap as well, once you get there. The best places to visit in December are of course close to the equator or even below it.
One more destination to consider is Dubai. Its beaches are a small part of the charm, and the whole place is very impressive. Shopping is probably the most famous activity, but there is plenty more, and flights there are quite cheap from Delhi. Hopefully one of these options sounds good. Either way, feel free to follow up if you have other questions. -Roger
My top recommendation would be San Juan, Puerto Rico. It offers a wonderful mix of history and culture and nightlife and great food, alongside excellent beaches and abundant activities. Hotels and rental apartments are mostly in the mid-range for the Caribbean, but food and drinks and most other things are great value. You could get a place in the Condado area, which is close to the lovely Old San Juan neighborhood and plenty of nightlife all around. And then perhaps you could rent a car and stay for a few days at one of the smaller beach towns elsewhere on the island. You wouldn’t even need a passport, although it does feel fairly exotic while you are there. But because it’s part of the US, it’s also well organized and safe. Most people you’ll meet will speak at least some English, and many are fluent, so it’s easy even if you don’t speak Spanish.
If you’re a bit more on the timid side, you can always use Yelp and TripAdvisor to get good insights on places people have visited. As a disclaimer, some of the ratings may not be accurate on these sites, so make sure you go through and read some of the more recent reviews that people have written. We did this for a few of the places we visited and had no issues.
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