If you are looking for an all-inclusive resort with reasonable airfares from Chicagoland, your best bets will be in Punta Cana, Dominican Republic, or the Cancun/Playa del Carmen area. Both have everything on your list, except perhaps wild life, depending on how you define that. You can get cheaper flights into Cancun, and there is a wide variety of offerings once you are there. If you don’t think you want to leave the hotel much, then stay in the Cancun hotel district or along the Maya Riviera nearby. But if you want to interact with a real and lovely town, then stay in Playa del Carmen or over on Cozumel. There are many nearby activities and some very interesting ruins.
Hi Roger, Just wanted to thank you for taking the time to compose this list. I always refer to your destinations (with great weather) lists prior to booking future-dated vacations. I was a little worried that you didn’t mention Bali but there was more than enough in the comments to reassure me that it would be a great spot to visit in December. I also saw your other post for places to visit over Christmas and NYE. Thanks again!
As for Europe, it’s the low season there at the end of the year and you might be able to find a reasonable flight. Have a look at my list of best Europe destinations in December for weather and comments about each of the better places. If money is tight then Europe can be challenging because getting from place to place can add quite a bit to the daily total. I think two weeks in Spain and Portugal could be very nice, with reasonable weather and relatively low prices. Let me know what you think and I can try to help you more. -Roger
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.
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.
In addition to the obvious perks of pleasant weather and fewer tourists, off-season rates at accommodations are abundant. Voted No. 1 continental U.S. island by Travel + Leisure readers for the third time in 2018, Hilton Head has much to offer visitors. One of the most popular activities, perfect with autumn temperatures, is biking on the more than 60 miles of pathways covering the island, including along 12 miles of beaches. Bird watchers will keep busy spotting egrets, sandpipers, wood storks, sea gulls, pelicans, and ospreys. Well known as a golfer’s paradise, the Hilton Head Island area boasts more than 33 courses.
Montego Bay is home to one of the Caribbean's busiest airports in addition to a few hundred hotels and resorts, so it's an ideal destination for even a shorter getaway in November. The rainy season is over but the busy holiday peak season doesn't begin until just before Christmas, so the weather is perfect and hotel prices are still very low. Flights should be cheap from most hub cities as well, so even a long weekend is within reach for budget travelers this month.
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).
Once the scorching temperatures and monsoon rains of summer have subsided, November is the perfect time for exploring this kaleidoscope of colour and culture. Due to India’s size and terrain, you can still expect some variation across the country, but travels through Rajasthan and the Golden Triangle will be mostly dry, clear and balmy with a maximum of 30c (86F). Perfect for tiger-spotting in Ranthambhore, camel rides in Pushkar, and admiring the shimmering Taj Mahal!
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
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?

The best places in December with good weather and that are inexpensive and also fairly close to India are Sri Lanka and Thailand, and they are both mentioned in the article above. Sri Lanka is obviously closer and you have many nice and scenic areas in the hills as well as the beach areas along the southern coast. But Sri Lanka has many similarities to India, as you may know.
Portugal does have one of Europe’s best autumn climates, but as you’ve noticed November can be a bit rainy. That said, in my experience it rarely rains for long periods in that part of Europe so I think it’s very unlikely that a big part of your trip would be “rained out.” Also those cities have lots of great indoor attractions so if you see that it’s supposed to be clear in the morning and drizzly in the afternoon, you can plan to explore neighborhoods in the morning and plan to visit a museum or castle in the afternoon. It’s a bit of a crap-shoot and generally Portugal has nicer weather than most of the rest of Europe at any given time. I hope this helps. -Roger

November is a perfect time to visit Bermuda, with temperatures in the mid-70s and pink sand beaches that are less crowded than in high season. There are many ways to explore the 21-square-mile island, from under the sea where you can snorkel or dive among coral reefs or shipwrecks to the Bermuda Railway Trail, an 18-mile abandoned rail bed that winds through scenic landscapes and shorelines. The Crystal Caves take you into an underground world with a subterranean lake and white limestone stalagmites. The 36-acre Botanical Gardens, established in 1898, inspired John Lennon during a two-month Bermuda stay that led to his Double Fantasy album.
Either way, my favorite warm-weather destinations near North America are San Juan, Puerto Rico, Playa del Carmen, Mexico, and Puerto Vallarta, Mexico. All 3 of them have very interesting towns that are also on lovely beaches so you have nightlife and culture mixed with beaches and water sports and whatnot. You might get low 30s for daytime highs in October, but it cools off in the evenings and it’s pretty nice. Let me know how that sounds and if you have other ideas I can add more information if you like. -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.
Christmas markets sprout up all over the country this month, and from the smallest towns to the biggest cities they’re a great place to mingle with locals, learn about regional handicrafts, and sample seasonal delicacies. Depending on the venue, you can find anything from medieval reenactments to outdoor concerts. But they’re usually at their prime once darkness has set in and the fairy lights are out in full force (which means there’s also time in the day for museum visits and city touring before indulging in the market flurry). Some travelers skip dinner altogether for a smorgasbord of yuletide samplings at the wooden market huts!
As for Indonesia vs. Philippines, I’ve been to Bali quite a few times but I haven’t been to Bandung. And for the Philippines I’ve spent time in Manila and in Tagaytay just to its south, and I don’t think I’d recommend those for a longer trip. And I also spent two weeks on Boracay Island, which is quite nice, but it’s small and also a place I wouldn’t recommend for a longer trip like yours. For information on Indonesia you might go to my friend’s site – travelfish.org – which is an excellent resource. Unfortunately, they don’t cover the Philippines yet. Best of luck with what you end up doing. -Roger
Thank you for the kind words. Interestingly, had you not included that you’ve been to Costa Rica, I’d say that was the obvious suggestion because they really do that sort of thing well and it’s at least a bit better organized than its neighbors. And if you were less concerned over travel time, I’d have some interesting suggestions for you in Asia. However, as you know, it takes nearly a full day just to get to Asia from the US or Canada, and then a few days to adjust, so you might be best off saving that for later.
Traveling around India is a shock to the system, but it’s not as bad as it looks. If you pay a bit more for the AC3 class on trains (air-conditioned, 3 bunks per side of the compartment), or AC2, it’s pretty comfortable and civilized. Mumbai is worth a couple days before you’ll be desperate to get out, but many parts of Rajasthan are much nicer and fascinating.
Let’s get started. For the November trip you are going to have a lot of competition for those flights and hotels because those are prime Thanksgiving flight dates. I would normally recommend Puerto Rico, but they won’t be ready for visitors until next year from what I hear. Just a few days ago I published a new article on which Caribbean destinations have no hurricane damage. There are a lot of great choices, including all of the busiest ones, that were untouched by the storms. You might also consider Cartagena, which is probably the cheapest option once you get there. It’s got a wonderful walled historic town area, and it’s a short bus or taxi ride to the modern area with beach hotels and such. The sand there isn’t great, but the value is very good. I wouldn’t go outside of Cartagena at the moment.

Wine aficionados will enjoy sipping Argentina’s well-respected wines, Malbec, a rich red wine, and Torrontes, an aromatic white. Malbec is a perfect match for Argentina’s beef dishes, and Torrontes would make a delightful partner to Milanesa, whether veal or chicken, pounded thin, breaded, and fried. The country’s cuisine demonstrates the influence of Italy; about 3 million Italians migrated there during the late 19th and early 20th centuries. Pizza, pasta, and helado, an ice cream similar to gelato, are as much a part of the cuisine as their asados, barbecued beef grilled on a parillo. Consider a stay at the historic Savoy Hotel, WorldHotels Collection in the artsy Avenue Corrientes area with its elegant neo-baroque lobby, adorned with chandeliers and frescoes.
I’m happy to try to help. It’s hard to say whether one 30-day trip would be better than several shorter trips. On one hand, it’s much more efficient to go for a month because it obviously saves you all the going back and forth. Also, one week is a short time to go 7 or 8 time zones away, as it takes pretty much an entire day each way, and at least a few days to adjust to the time change. Hmmm…
The idea of holidaying in a country where the depths of winter are approaching may seem a little counter intuitive but stick with us. The aurora borealis, or Northern Lights, is the best light show on Earth, and a trip to Iceland in November is the perfect ticket to see them. Explore thermal geysers, stunning waterfalls, and epic glaciers by day then stay up late and watch the skies dance with green light by night. Just make sure you pack your thermals though – the average day time temperature only reaches highs of 4c (40F)!
Thank you for the kind words. Interestingly, had you not included that you’ve been to Costa Rica, I’d say that was the obvious suggestion because they really do that sort of thing well and it’s at least a bit better organized than its neighbors. And if you were less concerned over travel time, I’d have some interesting suggestions for you in Asia. However, as you know, it takes nearly a full day just to get to Asia from the US or Canada, and then a few days to adjust, so you might be best off saving that for later.

Escape the cold weather to sunbathe on the beaches in Rio de Janeiro and ring in the New Year with a fun celebration on Copacabana Beach. And while you're near Copa, visit the neighborhood and beach that inspired the song, “The Girl from Ipanema.” Don’t overlook the other beaches, including Baixo Baby for families, Praia do Arpoador for surfers and Sao Conrado Beach if you want to leap from nearby peaks and go hang gliding.
Morocco certainly qualifies as an exotic destination, and it could be fun to do some holiday shopping at their world famous markets. If there’s time, Abu Dhabi’s unique surroundings would make a memorable pre-holiday excursion. Or enjoy spring in New Zealand along with their fresh seafood, wines, and beaches. In Buenos Aires you can watch tango dancers while sipping a glass of Malbec — or get up and dance. Bermuda’s convenient location, sunshine, luxurious hotels, and November events give visitors plenty to do, but a lounge chair by the pool will be pretty inviting as well. The same can be said for Palm Springs, where it’s warm enough for poolside relaxing or al fresco dining and cool enough for cozying up to an outdoor fireplace at night. Warm weather awaits in Belize along with a clear blue sea ideal for snorkeling and diving.
If you know where you’re going far enough in advance, you can contact your resort or vacation destination and explain your dietary needs with an employee. The vast majority of destinations, including ours, are opening up their menus to try and make them more friendly to those with food allergies and special dietary needs. While keto/low carb aren’t always on those special menus, the fact that they have special menus at all shows that vacation spots recognize that there are a lot of different dietary needs and are willing to help people who can’t or won’t eat the standard fare.
It is this quintessential destination-- nestled conveniently between Boston and Cape Cod-- that’s known as “America’s Hometown,” offering not just a glimpse into our national history, but an array of enjoyable activities from water sports to golfing to whale watching to ghost tours. During the fall you can even take trolley or culinary tours, or witness live cranberry and pumpkin harvests. It’s a November getaway to remember for sure.
Amazing post! I am taking vacation the last two weeks of November. I am planning to visit Germany for the first week. I also want to soak in some sun and enjoy the beach life during the second week of my vacation . Initially I wanted to go to Spain, but after reading your post I’m a bit discouraged because is not going to be warm enough . I love to sunbathe and outdoors activities . Just as running, hiking, tennis etc . Also I love to learn new cultures and fit in with the locals. Keep it economical .I been to must of the Caribbean and wouldn’t mind revisiting . But open to new warm destinations that would make sense. I would love to hear some of your suggestions .Thank you in Advance and safe travels..
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