Okay it is cold and rainy outside. It even snowed a week or so ago. Like I said in my Amazon giveaway post, it’s time like these where I start thinking about somewhere warm.
This is how I feel and this is NOT how I WANT to feel
So where can I go on the cheap? I am tracking my mileage balances with Award Wallet, and I’ve got plenty to go somewhere. I even talked with a friend about bartering some airline miles for babysitting, and even have the potential to go somewhere the weekend of December 6th (or maybe in early January).
But where to go and how to get there? I know there’s a bunch of smart people out there and while I’ve got a few ideas, maybe someone else has even better
The Ground Rules
- It has to be somewhere warm. Like beach warm. Florida is okay but we already took a getaway trip to Miami for free last year.
- We could do the weekend of December 6th, or sometime in January
- I have enough miles / points to do anything (within reason)
- Leaving from CVG or surrounding airports (DAY, IND, CMH, SDF all options) in case you want to use Southwest
- Hotels that use points preferred.
- The “winner” of the contest is not necessarily the one who uses the fewest points, but who comes up with the best trip for the points spent.
Views from the Hilton Fort Lauderdale
Option 1: Avios
I can get most places in the Caribbean for 24,000 miles roundtrip. It’s either 4500 to CLT / PHL / DCA and then 7500 to the final destination, or 7500 to MIA and then a 4500 Avios hop to places like San Juan, Grand Cayman, Jamaica, etc.
Option 2: United
I’ve written before about the Caribbean Hopper on United, which is 17,500 miles for a one-way from the US to the Caribbean that allows an open jaw and a stopover.
Option 3: ANA
ANA is moving to a new zone-based award chart starting next year, but for now, they have a distance-based award chart.
So for 4,000 miles (which can get me to most places in the Caribbean when I connect through Houston), it’s only 22,000 miles roundtrip.
Kenny at Miles4More has a great series talking out about the sweet spots to the Caribbean on ANA.
Option 4: Southwest
I have the Southwest Companion Pass, which lets me travel for half price essentially. The one annoying thing is that Southwest does not fly out of my airport of choice (Cincinnati), but there are a few other airports within an hour or two.
Southwest goes to several warm locations, though prices are pretty high for the weekend of December 6th. Also, I’m not sure why the fees on Southwest were so much higher than on other airlines (since I’d assume that taxes / fees like airport / immigration fees would be constant across all airlines)
Hotels
Obviously points-based hotels would be best, though I do have some Barclay Arrival points that I could use for non-points lodging like was mentioned by the Carolina Travel Girl at FT4RL.
Something on the IHG Point Breaks list for December or January would be spectacular.
So….
Basically I want to go somewhere warm as cheap as possible. Who can make it happen? Leave a note in the comments! I can’t promise any tangible “prize” for this contest, but if you come up with a truly amazing plan, I’ll figure something out.
This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as thepointsguy.com. This may impact how and where links appear on this site. Responses are not provided or commissioned by the bank advertiser. Some or all of the card offers that appear on the website are from advertisers and that compensation may impact on how and where card products appear on the site. Any opinions expressed in this post are my own, and have not been reviewed, approved, or endorsed by my advertising partners and I do not include all card companies, or all available card offers. Terms apply to American Express benefits and offers and other offers and benefits listed on this page. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more. Other links on this page may also pay me a commission - as always, thanks for your support if you use them
User Generated Content Disclosure: Points With a Crew encourages constructive discussions, comments, and questions. Responses are not provided by or commissioned by any bank advertisers. These responses have not been reviewed, approved, or endorsed by the bank advertiser. It is not the responsibility of the bank advertiser to respond to comments.
Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
I can get you to Palm Beach in a matter of minutes!
http://palmbeachtan.com/cincinnati-kenwood-Montgomery-Road/
Hmmm I’m not sure that’s quite what I was looking for 🙂
Do the job yourself lazy asshole
LOL thanks for taking the time to comment. Nobody said you had to play
@Don Please, try to remember that Dan is a real person. I know it’s hard, but give it a shot, OK?
Dan, I’m going to suggest something incredibly crazy to you, meaning NOT cheap. I’m assuming you are not taking an entire crew, right? How about 3 nights in Montego Bay, Jamaica staying in Holiday Inn All-Inclusive. You would have to go in January, since December date is way too expensive.
I checked the dates for January 10-13, leaving Saturday and coming back on Tuesday. If you fly from IND, it’s about 18K Rapid Rewards points roundtrip (plus tax), less with Companion pass. The flight does leave at 6:45 AM, but you would get to Jamaica early in the day to maximize your value.
IHG property is available for those dates, but costs 35K points per room (gasp!). So, you would need 2 rooms per night if taking the kids with you. But, you get all the food, plus kid’s club included. Your wife will thank you, I promise. I know you have a ton of IHG points, so with co-pay option you should have enough for 3 nights. No, it’s not cheap, but remember, you can now get Chase bonus every 24 months. I have a feeling that this property will go up on points in the future. It’s a good deal in high season, and would give you and your wife a true vacation. Think about it, man!
Hmm that is intriguing. CMH-MBJ I can get as low as about 14,000 points all-in, though fees again are about $120 / person.
I would assume there is a resort fee with this, but I didn’t see it?
Thanks for commenting (and defending me against anonymous Internet trolls 😀 ) – it’s always good to have different options.
I got this.
We are going to have to be cognizant of the Traveler’s Triangle, which I sum up as “You can’t always get what you want, but you can get most of it.”
Option A: Mexico
Here’s the key to this trip: You have to fly from a hub. So we’ll base this trip on your flying out of ORD. Driving Cincinnati to ORD is pretty manageable. I just did it and more yesterday to get to the family’s home in Southern Wisconsin in time for Thanksgiving Dinner.
Flight: Southwest is a non starter. With this little time, and the fact that SW redemption values are based on ticket prices, means you’ll be paying quite a bit for tickets for next weekend. So let’s focus on Avios. Fixed, distance based is the way to go as it sounds like you want to be in the Western/Northern Hemisphere.
Flights:
December 6th: There’s a flight out of ORD to CUN at 6:25. 10k Avios a person, 7 seats left.
December 8th: CUN to ORD is wide open. 7 Seats left at 10k/a pop.
Lodging: The Marriott Casamanga is 35k Marriott points a night, with plenty of availability. We stayed there earlier this year for 1 night. It was great. Wonderful spot on the beach, and you can also use the great pools at the JW Marriott that is attached. Also, take a cab to Bovino’s Churascarrio. Great Brazillian Steakhouse, and you are more likely to see locals there than extranjeros. They will pay for your cab back.
While you are there, do yourself a favor and do the “Xenotes” excursion. We are so glad we did this. Check both of my recommendations on Trip Advisor.
The Casamanga has a shuttle from the airport.
All in, if it’s just you and the wife: 40k Avios + 105,000 Marriott Points. Assuming you are on top of your UR, you can likely swing this pretty manageably. If you need to, you can use the Barclaycard to cover some of the Hotel stay.
Same itinerary is available in early January.
This is such a solid plan, I am half tempted to do it myself! But, then I don’t have the baby sitting…
Working up a Bahamas itinerary shortly…
Now we’re talking! This is the spirit of what I was talking about. I think that the weekend of December 6th is out at this point for a variety for reasons.
I was musing the possibilities of Southwest to Aruba which looked like it had some decent prices from CMH on some weekends in January – about 20,000 points total (since I have the companion pass). And maybe the Club Carlson hotel there for a 2 for 1 stay.
Aruba looks to have about $75 / person taxes and fees though 🙁