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
As for alternatives you might consider Argentina, where of course it will be late spring in November. Buenos Aires is a wonderful city and recently they’ve been going through a financial meltdown again so their currency has dropped a lot, making things unusually cheap again. You could spend 3 or 4 days in Buenos Aires and the rest in the Mendoza wine country or Iguazu Falls or Bariloche for some adventure. From everything I have heard it’s all safe and civil there, so it’s just a matter of the local currency going down in value.
The Maldives is amazing for relaxing beach holidays and it’s within your range. The tricky thing for most people is that it’s quite expensive for a shorter trip. Of course the Maldives is famous for its water villa resorts, and those water villas start at around US$350 per night. Nearly all of those resorts also have island villas and rooms and those can start at as low as US$100 per night, but you also have to pay for a speedboat or sea-plane transfer from Male Airport to your resort. That can be as low as US$100 per adult for the closer speedboat islands, and up to US$600 per adult for the more remote sea-plane islands. On a shorter stay, that obviously adds to the price. Speaking of that, I run another site all about overwater bungalows and I have links from an article on this site about the cheapest overwater villas in the world. Have a look at that list as it will show you the more affordable options in the Maldives, as well as even cheaper options in Malaysia and elsewhere.
Thank you very much Roger. I truly value your insight and am taking into consideration everything you’ve noted above. I’m going to check out the link you posted as well. That just reassured me that Bali would be great during that period. I’m thinking principally of staying in Ubud, Sanur or Seminyak for the type of trip I have in mind which is equal parts warm weather, walking/discovering, culture and some beach life. I’d love to visit Thailand but it’s just not the right time. At this point, I’m more intrigued by all of the many, still remote islands of Philippines than the chaotic lifestyle in Thailand. Perhaps, that’s just me still reeling from my trip to India a few months ago.

Hotel prices remain low through all of November for the most part, so you'll have a good shot at deals at 3-star and above beach resorts that are trying to fill rooms during the slow season. Even if you are paying near the high season rates the hotels and everything else are bargains here compared to almost anywhere else. Cartagena is one of the cheapest places to travel in November on a beach, and you'll get less rain as the month goes on.
hi we have 3 boys age, 9, 7 and 5. we want to go on a two week holiday anywhere ( not europe or africa)over december for christmas and new year. we are from england. where is the cheapest to go/ fly to for a beach holiday and some day trips to experience the culture of the country? some tips on where to stay,best towns for families, and is package holidays better than booking everything individually? many thanks

More good news comes with the fact that there are two other great resort areas that are each about 90 minutes by shuttle from Montego Bay Airport, so you can almost as easily reach Ocho Rios or Negril, both of which have a different vibe that you might prefer. Bargain hunters will also find pretty amazing prices at the all-inclusive resorts, particularly those in Montego Bay and Ocho Rios. If you prefer a quiet beach area lined with smaller hotels, restaurants, and bars, then head to Negril.
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).
Cambodia could work because Siem Reap is inland and the amazing Angkor Wat temples are worth a full day or two, and the town of Siem Reap itself is quite nice. You could actually combine a couple days in Siem Reap with a few days in Bangkok, and take a (cheap) luxury bus between the two. Bangkok is a really fascinating city with a lot to see, plus it’s a great transport hub. The other main non-beach option in Thailand is the city of Chiang Mai, which is wonderfully inexpensive with quite a bit to see. It’s even a bit cool during December, so that might be a nice change of pace from India. Many people are also going to Myanmar these days, although I haven’t been yet so it’s hard for me to recommend it. I’d say if you combined 2 or even 3 of these places you could have a very interesting holiday.
We are a couple that are trying to find our honeymoon destination. We start from Italy so south America is kind of out cause the plane tickets are just too much. We love adventures nature, not so much for cities…and we’ve been to thailand sri lanka philippines and my partner now wants something little bit different to see, different scenario 🙂 im in love with Asia 😉

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
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.
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.

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.
November brings the annual Vodafone Mexefest Music Festival (Nov. 24-25), a gathering of popular artists in venues throughout Lisbon. The Lisbon & Sintra Film Festival, in its 12th year, is a celebration of cinema with directors, actors, artists, musicians, and writers in town for the event (Nov. 16-25). Billed as the “largest technology conference in the world,” Web Summit began in 2010 as a way to connect industry and the technology community (Nov. 5-8). The year’s new wine and the ripening of chestnuts are celebrated with the Magusto, on Nov. 11, St. Martin’s Day. The holiday spirit becomes apparent at the end of the month, with colorful lights and roasted chestnut vendors along the streets.
×