Where's someplace warm and cheap to spend a week or so over New Years

November 25, 2013 8:51 AM

I've been thinking recently that it might be fun to spend 4-7 days in a warm part of North America to ring in the New Year with my girlfriend. I'd love to find a place to get away, warm up from the Chicago winter and maybe sit on a beach if I can.

I've never done something like this before, so I really have no clue how I might go about booking flights and hotels and all the other sundries. I've also never flown to a place where I haven't also been going to for work or family reasons, so this whole process of booking a hotel is a bit new, along with deciding where to go.

I'd love to query the hive mind about potential destinations that aren't going to break the bank. If possible I'd like to keep it around $1200 for flights and accommodations, though the maximum would be around $2000. (I'd also like to hear that I'm crazy and there's no way I'm going to get anything worthwhile for that price so I should either budget more or think of going some other time; alternatively I'd also like to know if I'm cutting it too close, that I should have booked it earlier and that I should instead plan for February or March or whatever)

Really the only requirements are warm, with a beach and the ocean nearby and the budget. It'd be ok if there were other things to do close by, but that's a plus and not something that's necessary.

We both do have valid passports, so it doesn't need to be US specific locations as well.

posted by Carillon to Travel & Transportation (15 answers total)

Google Flights has a thing where you can supply your location and travel dates, and it will display the cost of a round-trip flight to various locations on a map. So far I have only used it for daydreaming, but I really like the interface.
posted by showbiz_liz at 8:56 AM on November 25, 2013

I was looking at Puerto Rico last year due to a business trip, and was surprised by how inexpensive it is to go from Chicago to San Juan. It looks like the holidays are not a good time for that, but something to keep in mind for another time.
posted by wotsac at 9:11 AM on November 25, 2013

If you really are that bothered by the complication of booking flights and hotels you might want to check into package deals. Check the various airline websites, as well as Expedia and other other major travel sites. You pay one price, hotel and airfare is covered, and maybe food and drink too if you go to an all inclusive resort.
posted by COD at 9:14 AM on November 25, 2013

If you have a Costco membership, you can find good package deals online.
posted by rabbitrabbit at 9:20 AM on November 25, 2013

In your situation, I would definitely suggest looking for a package deal. It's expensive to go somewhere warm and cheap over the holidays so all inclusive is the way to go.

You can do this yourself online if you want to spend the time but in your case I would
ask around for recommendations and go to a travel agent with your criteria and book a vacation right then and there.

I have done this with great success on last minute vacations with a similar budget.
posted by Snazzy67 at 9:32 AM on November 25, 2013

I was going to suggest: go to Puerto Rico.
Failing that, maybe go to San Diego or someplace similar in Southern California?

But yeah, you're looking at peak season prices with not much lead time, so it'll be expensive. Be prepared to jump on a good deal if you see one.
posted by RedOrGreen at 9:59 AM on November 25, 2013

Perhaps a 5- or 7-day Caribbean cruise.

Cruises get a bad rap sometimes, but I've been on three and I've had lots of fun. They're good for people who don't want to plan out every aspect of their trip, you'll get to visit different places and beaches, and it's usually romantic for couples.
posted by girlmightlive at 10:11 AM on November 25, 2013

I would advise against cruises (cramped, claustrophobic, no beach, storms, mercy of ship authorities).

San Diego - too cold for beach enjoyment

Puerto Rico - great option
southern Florida and the keys - also good options
posted by Kruger5 at 10:51 AM on November 25, 2013

We went to Puerto Rico in July and absolutely can not wait to go back. We spent a week in San Juan and surrounding areas and there was more than enough to do, and it was no more expensive than normal life here in Houston, if not less. I am guessing that if you get out of the city it'll be even cheaper.

Puerto Rico is also easy because your cell phones work, most people speak English, and there are no currency issues.
posted by Brittanie at 11:14 AM on November 25, 2013

New Year is a fun time to travel, but it is crowded and you'll pay a premium, but for $2,000 you shouldn't have a problem.

I've used AAA and Travelocity to book travel packages and have been very pleased with both. I will 100% recommend the American Airlines Vacations. Most of their packages end up on Travelocity, but because you book with American, there's NO NONSENSE with any of it. I have saved a butt-load, and there's no blind bidding or any of that mess. Before confirming a hotel, check it out on Trip Advisor.

Here are some ideas:

1. Las Vegas. Decently warm, lots to see and do. Tons of great deals on packages that include flights, hotel and car. American Airlines Vacations has a deal with airfare, the LVH Hotel on the strip and a Budget rental car for $724 each. Leave Saturday Dec 28, return home Jan 4.


2. Cozumel. They've got a couple of places flight/hotel for $900-$950.

3. Bermuda. Just scrapes the top edge of your budget, $2300 for the week, but less for less time.

4. Cruises. Check the site, they have a lot. I like Norweigan because you can just be a bum. No dressing up unless you want to. Lots of choices.

This is the highest of the high season for warm places, but there are options in all 4 of the above mentioned places.

For my money, I'd either do the cruise (includes meals) with my second choice being Las Vegas. If you don't have a passport, then pick Vegas.

I also checked Florida and that's outrageously expensive!
posted by Ruthless Bunny at 11:16 AM on November 25, 2013

I live in San Diego. At this time of year you aren't swimming in the ocean here without a wetsuit. It's beautiful, sunny and chillier than people think. It was 60 degrees this morning when I went for a walk. Chilly! (Or not, depending on where you live.)

I think you're looking for a vacation package in the Caribbean.
posted by 26.2 at 1:01 PM on November 25, 2013

Thanks all! It looks like Puerto Rico is a great option so I'm talking dates with the GF and we'll be taking a trip soon!
posted by Carillon at 1:05 PM on November 25, 2013

Try cheapcaribbean.com -- some of the packages include airfare and meals.
posted by AppleTurnover at 2:24 PM on November 25, 2013

Mexico? Flights to Ixtapa/Zihuatanejo (ZIH) look to be available sub $600 apiece. Maybe packages are available as well. Both towns have plenty of decent accommodations for well under $100/nt. I always start with airbnb.

FWIW, we flew in, rented a car and drove to Troncones where we had a fabulous time. But no need to go that far. You can and should absolutely manage sans vehicle hassles for such a short trip.

On that note, do everything in your power to make the trip as long as you can.
posted by AnOrigamiLife at 1:39 AM on November 26, 2013

If you decide on Puerto Rico and are on the hunt for casual r & r, consider spending some time on the neighboring island of Culebra. Accommodations generally run under $200 per night, the beaches are great, and the vibe is totally relaxed. If I were planning to return to PR, I'd spend most of my time on Culebra, and tack on a couple of nights in Old San Juan at the beginning or end of the trip. Enjoy!
posted by kayzie at 4:17 AM on November 27, 2013