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!!
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Even cheaper than that is Cartagena, although the flight would probably be a bit more expensive. Cartagena has a gorgeous walled colonial Old City filled with cool hotels, shops, and restaurants, and it’s a 10-minute cheap taxi ride to a strip of beachfront hotels in a modern neighborhood. It helps if you know Spanish in both places, but Playa del Carmen has so many English speakers that it’s easy to get by on that alone. Those are my best picks in our region for inexpensive places that are fun with a lot to offer a solo traveler or small group. Let me know if you have any questions. -Roger
My recommendations depend on your starting location so for now I’ll just assume you are starting somewhere in the USA. If you are looking for a really nice beach AND really good night life your best choices are the Cancun area, Puerto Vallarta, and San Juan, Puerto Rico. If you are in the eastern US or Canada it’s probably faster and cheaper to go to Cancun and if you are in the west Puerto Vallarta is better. San Juan will be more expensive because there just aren’t many cheap hotels in the good parts of the city. For the Cancun area I would recommend Playa del Carmen (about an hour south of Cancun Airport) because there are fairly cheap hotels near the town center, which is packed with bars and restaurants. In Cancun itself the best nightlife is in the heart of the hotel zone, and all of the hotels there are pretty expensive. Let me know if you have any other questions. -Roger

This diverse and rapidly growing capital city of Texas is known for its live music scene, world class museums, beautiful outdoor spaces, pleasant weather, fine dining, and nightlife. A little bit city, a little bit country, Austin has no shortage of December activities for all. The Zach Theatre presents a rocking adaptation of the Dickens classic "A Christmas Carol" from Nov. 21 through Dec. 30, guaranteed to have you dancing in your seat. In its 56th year, Ballet Austin’s annual production of "The Nutcracker" returns to the Long Center Dec. 7-23. Holiday shoppers gather at the Blue Genie Art Bazaar to purchase unique handmade gifts including paintings, photography, jewelry, clothing, and more. Zilker Park transforms into a glittery wonderland with more than 2 million lights, 40 displays, interactive experiences, food trucks, and live music on two stages. The Armadillo Christmas Bazaar, an art and music festival, runs from mid-December through Christmas Eve with live music, two full bars, and local food specialties. Over 175 national and local artists display paintings, sculptures, woodworks, and an assortment of handmade gifts. Winter Wonderland at the Circuit is great family fun with holiday lights, a skating rink, Santa’s Village, petting zoo, carnival rides, and of course, live music. In the heart of downtown, the historic Driskill Hotel celebrates with an enormous Christmas tree and seasonal music. On Sunday, Dec. 16, Austin’s best bakers will share their holiday cookie collection, with the event’s proceeds supporting the Driskill’s traditional charity, “Cookies for Caring,” benefitting the community.
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.

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.

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.


The second option you have is food trucks – although you really have to be weary on this one. Don’t be afraid to ask them what the ingredients are, as the food is made fresh and they’re usually proud to tell you what’s in their food. Luckily, we encountered a Paleo food truck while in Portland called Cultured Caveman (pictured below) that served some keto friendly items.
Interestingly, December though February do get a bit cool in Cairo, so it's not a great winter break, but in November it's still pleasantly warm and bone-dry so you can enjoy the outdoors for long periods of time. If you don't mind staying in a locally-owned hotel you can save a lot of money and see some old-world charm at the same time. Reservations in advance aren't necessary, but it's best to book your first couple of days just to avoid all the confusion once you arrive.
Being from Mumbai you can be forgiven for not realizing how unappealing beach areas are when the air temperatures are only a bit above freezing. Seriously, even beach on the European mainland is totally deserted by November 1, and many of the local hotels and restaurants are closed by then until April or so. Now, if you are mainly after the novelty of being on a beach in the European winter, you can certainly go and still find open hotels and restaurants. If I had to recommend one place to consider it would be Spain’s Costa del Sol, which is the resort area around Malaga. The average high in December in Malaga is 17, and the average low is 8. You’d be the only one on the beach, which might be kind of nice. It’ll also probably be windy. If you were going to do that I’d recommend staying in Malaga itself, which does have a nice beach area in the city, and since it’s a city the hotels and restaurants will all be going.

Hi Roger, I plan on being in boracay on Nov 6th and am just concerened about the weather. Is the start of Nov too close to the end of the monsoon season ? I don’t mind a bit of rain but ideally want to be able to spend a few hours on the beach with sunshine per day. Looking at pics it seems to be mostly clouded over all the time. Do you get sunny clear skies around that time ? I just can’t seem to get a clear answer online. Any advise would be much appreciated
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.
Located off the coast of East Africa, the Seychelles—an archipelago consisting of 115 islands—is about as close to paradise as you can get. Crystal clear water, lush jungles, and powder-fine sand make it the ultimate early winter escape, particularly for romantic getaways. Book one of the 30 breathtaking pool villas at Six Senses Zil Pasyon, which is among the region's top luxury resorts. The hotel is situated on a private island that offers prime territory for snorkeling, sailing, kayaking, and hiking—plus, the spa has scenic pavilion-style treatment rooms that are worth the trip alone. Health conscious guests will be particularly impressed by the property's new "Eat with Six Senses" program, which is intended to make travelers leave vacation without the guilt that comes with overindulging. There are four tailor-made treatment plans that focus on sleep, detoxing, fitness, and more, depending on the issues you prefer to address.
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