For anyone considering a multi-destination South American trip in November, Santiago should definitely be looked at. The daytime temperatures should be pleasant and warm, and it's bone-dry all summer, so it's a great combination. Hotels in Santiago don't have their peak price season until New Year's, so in November you'll easily be able to find a very good rate at one of the nicer places.

In India I’ve always had good luck with the trains by booking at least a couple days in advance, and also being flexible and only going when an AC3 ticket is available. As you know, the actual train stations are nightmares. But every hotel has a person who can fetch a ticket for you by going through the back door and bribing someone at the train office. Like a AC3 ticket might cost US$20, and for an extra US$4, your hotel will go buy it for you and it’ll be waiting at the front desk later that day. It’s a pretty sweet system.
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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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

November is a month of transitions: weather is cooling in most places, and as the days move towards Thanksgiving, momentum picks up and we’re rushing headlong into the winter holidays. It could be a good time for a trip, whether you’re looking for warm weather, taking advantage of cheap shoulder season rates, exploring a new exotic destination, or heading to the southern hemisphere to trade autumn for spring. Or you just might want to begin the holiday season early, get a head start on gift shopping, and jump right into winter’s chilly weather. Travel during November has something for everybody.

Two other suggestions would be India or Sri Lanka. Except for a few beaches in Goa, neither of those attract the party crowd, and both are excellent for scenery and culture. India is cheaper as long as you minimize time in Mumbai and other big cities, but that is good advice for many reasons. Sri Lanka is a bit better organized, and on your budget it is good value and easily affordable. There are good beaches along the south coast of Sri Lanka, but India is probably better for beaches.

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.
The 2nd option is a bit early in the year. The Greek Islands are cold and mostly deserted until mid April or so, and the good weather really starts in May or June. This is true in Mallorca as well. The Canary Islands are much farther south so they have acceptable beach weather almost all year, although you might get some cooler days in March as well. Even still I wouldn’t really recommend them for a younger person. In my opinion, the Canary Islands are pretty boring because the majority of visitors that time of year will be retired people from northern Europe who just want to sit in the sun. The nightlife tends to be cheesy and/or weak if you can find it at all. Let me know if you have any other questions. -Roger
When you mention, “not too touristy”, the first thing that comes to mind is San Juan, Puerto Rico. I’m not sure if you’ve been there already or not, but one great thing about it is that the “tourist” areas close to Old San Juan are filled more with apartments than with hotels, unlike Cancun, where it’s nothing but hotels and timeshares. I can highly recommend the Condado neighborhood, which does have some large hotels but is mostly apartments for expats and seasonal visitors. There is even a free bus that goes from there to the heart of Old San Juan, which is a gorgeous colonial town filled with great restaurants, bars, and interesting attractions.
Warm weather, Caribbean beaches, and fascinating history beckon visitors to this coastal city during December. Once a 16th-century Spanish port, Old Town Cartagena, surrounded by ancient stone walls, is a UNESCO World Heritage site. Visitors strolling through its streets will see original Spanish Colonial architecture among new restaurants, restored homes, and boutique inns. From street food to upscale restaurants, Cartagena offers the best in local seafood, meat, and fresh fruits. In December, the city becomes a festival of lights, with nativity scenes, decorations, and holiday celebrations culminating with New Year’s Eve fireworks. Holiday shoppers will want to take home gifts of colorful handcrafts sold at markets throughout the city, with special Christmas markets arriving in December. Colombia supplies nearly 90 percent of the world’s emeralds, and a quality gem from a reliable source would make a memorable keepsake. Nearby Rafael Nunez International Airport makes arriving by air quite convenient, and visitors will find a range of lodging in and around Cartagena. For a luxurious vacation, the new Conrad Cartagena offers four pools, a private beach club, a golf course, seven restaurants, tennis courts, a spa, and stunning ocean views from every room.

On the morning of our last day we hit the hotel cantina again for another round of breakfast bowls and bacon (Meal 5), which I had with fatty coffee. Afterwards we headed out for our final day. After riding a few things and checking out some of the tours, we found a place for a late lunch/early dinner at around 4 pm. This was the only sit-down, table service place we patronized on the entire trip and it was worth it. The menu didn’t seem to have a lot to offer the carb-conscious, but after explaining briefly to my server that I avoid carbs and sugar, I settled on the Kobe beef burger, bunless, and the server offered to replace the side of fries or rice with a bowl of stir fried veggies. My plate arrived (Meal 6) and looked gorgeous! The veggie bowl consisted of onions, peppers, mushrooms, snow peas, baby bok choy, and some carrot sticks which I mostly ate around. After stirring in a smidgen of the offered soy sauce and Sriracha, I must say I was greatly pleased with this side. The chef also garnished my plate with a small sample of cucumber salad, which was delicious. The burger was as thick and round as a steak and was probably the best restaurant bunless burger I’ve ever had. It was served with a sesame-soy sauce mayonnaise as a condiment which really complimented the burger well. This was probably my favorite meal of the trip and it was well worth the price and effort of sorting through the menu.
From the Art Deco architecture to fabulous restaurants and nightlife, Miami is truly a city that appeals to every type of traveler. Art and culture lovers should plan a trip during Art Basel, which officially kicks off on December 6. The weeklong affair attracts celebrities, tastemakers, and bold-faced names, who come for the world-renowned art exhibitions, but stay for the swanky parties and events. Be sure to book a hotel well in advance, as prices skyrocket and availability becomes increasingly limited.
Over in the Americas, meanwhile, it’s all about downhill thrills. Mt Hood, an 11,250ft (3429m) stratovolcano in Oregon’s Cascade Range, has North America’s longest ski season, with good quality powder dumps arriving in earnest at the beginning of November (before the real ski crowds descend). Runs are split fairly evenly between grades, making it a great spot for skiers of all abilities. Those looking to really ramp up the thrill factor, however, should head south to Nicaragua, where volcano boarding – tobogganing down their slopes – provides a one-of-a-kind adrenaline rush.
Two other suggestions would be India or Sri Lanka. Except for a few beaches in Goa, neither of those attract the party crowd, and both are excellent for scenery and culture. India is cheaper as long as you minimize time in Mumbai and other big cities, but that is good advice for many reasons. Sri Lanka is a bit better organized, and on your budget it is good value and easily affordable. There are good beaches along the south coast of Sri Lanka, but India is probably better for beaches.
Since flights to Mexico City from the US and Canada are usually quite cheap this time of year as well, this could be a perfect short cultural holiday. This city has great shopping, dining, and nightlife, and the central historic and tourist districts are far safer than most people would expect. There are ruins just out of town as well, so a bit of everything is available.
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