I have a bunch of Southwest Airlines miles I need to use. Where to go?

In My Humble Opinion
1

We have tons of miles saved up on our Southwest card, and they’re going to expire if I don’t plan a trip. I’m thinking sometime January/Feb, someplace warm.

Here are the places we can go (excluding cold places and ones I’m just not interested in for various reasons.)

In no particular order:

Cabo
Cancun
New Orleans
Aruba
Punta Cana
San Juan
San Fransisco
Puerto Vallarta
Charleston, SC

I’ve never been to any of these places. It would be me and my husband, we’re mid thirties, very outdoorsy, no kids. We are SCUBA certified, so if any of these places have exception diving, that would be cool.

I’d love any suggestions. Thanks!

2

Forgot to add Nassau to the list.

3

I am struggling the the exact same problem but it is a good one to have. Your potential list may be even bigger than you think because Southwest is about to expand its service into Mexico, the Caribbean and Central America and the launch date is right around the corner.

“Southwest previously had announced that it would fly from Hobby to four cities in Mexico, plus San Jose, Costa Rica, and Belize City, Belize, beginning Oct. 15 and Montego Bay, Jamaica, on Nov. 1. It began service to Aruba earlier this year.”

Service to Liberia, Costa Rica begins on November 1st and that may be one of the ones I take because I love Costa Rica. There are any outdoor activities you want in that beautiful country and the people try really hard to please.

All of your choices are good ones except maybe Cancun (because of the trashy college crowd factor). It just depends on how far you want to go and how hot you want it to be. New Orleans is a one of a kind city that is always a people pleaser. Late fall is a good time to go there because it is warm but not scorching during the summer.

Aruba is always popular with the Boston area crowd and the weather is almost always great (it is too far south for hurricanes).

4

Thanks, Shagnasty. I didn’t know they were starting service to Costa Rica, that interests me a lot. I might put off this decision for a bit.

Right now I’m leaning toward Cabo. Is a week in Cabo too long? Is there stuff to do there for that long?

5

You could fly to Cancun and take a ferry across to Cozumel. The diving and snorkeling there are excellent, and, while it does get a lot of cruise ship traffic, you can stay a little ways out of the main town and avoid most of it. We went for a week about a dozen years ago (Grandma and Grandpa flew out to take care of the kids), and had a great time.

6

San Francisco sure ain’t warm in January!

7

Average high temperature in San Francisco in January is 58 degrees, February 60 degrees.

Average high in Charleston, South Carolina in January is 57 degrees, February is 60,

Depends on where you are from if that is “warm” to you.

8

As a former scuba instructor this would be my plan for the best diving. It’s drift diving from boats. You could split time on Cozumel with time on the mainland and spend a couple days taking in the Mayan ruins if its not an all diving vacation.

Second choice would be flying to Aruba then taking the short connecting hp to Bonaire. Bonaire is more shore diving. Can get a package that includes rental truck and unlimited tanks for shore diving.

Final good diving option is the flight to Belize City. Take a local airline hop out to Caye Caulker or Ambergris Caye for a very relaxed vacation with short boat rides out to the barrier reef.

9

It wouldn’t be an all-diving vacation. Maybe 2 dives in a week or so (we enjoyed diving when we lived on Okinawa, but didn’t go nuts for it). Any thoughts on what the best of these three are in terms of non-diving activities or general atmosphere?

10

I thought that was the whole point of spending like a million dollars for a tiny appartment in CA: Amazing weather all year. Did I miss something? :smiley:

Seriously, we’re currently living in Missouri, and moved here from Maine (husband’s military). 60s in January and Feb is warm enough.

11

That’s southern CA…

12

Potatoes, potahtoes.

13

I spent a week in San Francisco in January a few years ago. It isn’t that cold at all compared to the Midwest or Northeast during the winter but it stays that vaguely cool to coldish temperature all the time. It is an amazing city although extremely expensive for most everything. You have to take that into account as well.

I can give you the shortest list of pros and cons as possible because I have been to most of the places on your list or at least have family members that have:

  1. Cabo - My parents used to go there every year because they bought a time-share there for some reason that only they can speak to. It is plenty pretty enough but there isn’t a whole lot to do unless you have a ton of money, like spending time in resorts or love wild Mexican style nightclubs. The Pacific Ocean is surprisingly cold there even during the summer so do not expect to swim in it for long if you choose it. I personally always refused to go even for free accommodations for the week because nothing there really appeals to me.

  2. Cancun - There are some nice resorts but, if you pick the wrong one, it is Girls Gone Wild combined with lots of Texans. I am not really a resort type person and you don’t sound like one either. There are more suitable places slightly away from Cancun as noted if you aren’t interested in that type of trip.

  3. New Orleans - I used to live there and it really is a world-class, one of a kind city, that lives up to its reputation. There is more than enough to see, do, eat and drink for many years let alone a single vacation. However, your expected travel dates are in January and February. Mardi Gras is February 17th this year and I would strongly advise that you stay away from Mardi Gras for your first trip if not ever. It is really intense and lasts several weeks so you would need to go mid-January at the latest. Temperatures could be almost anything at that time but expect highs about 60F on average.

  4. Aruba - This island is off the coast of Venezuela so it is a bit of a hall but it is pretty, friendly, has consistently great weather and lots of good resorts and other accommodations. I consider it just a generic vacation island but there is nothing wrong with that.

  5. Punta Cana - I don’t know much about it but my officemate swears that he will never set foot in the Dominican Republic again after his bad honeymoon experiences there.

  6. San Juan itself isn’t a very nice city but Puerto Rico in general has lost of different types of accommodations, some beaches are excellent and it will be quite warm to hot even during the winter. Old San Juan is worth checking out but your best bet is to pick accommodations well outside the city.

  7. Puerto Vallarta is similar to Cancun and the rest of Mexico’s tourist centered ports. The resorts are nice but very touristy. I had a good time there but I stayed in an all-inclusive resort the whole time. The area outside of the resort was positively third world in many places.

  8. Charleston, SC - lots of travel magazines rank this city as the #1 U.S. city for recreational travel because of food, culture, history, friendliness and cost. It is certainly worth a long visit but I am not sure if January or February is the best time for it although it probably would still be pleasant weather wise.

Other areas to consider are:

  1. Costa Rica as mentioned. The whole country is basically an ecotourism theme park set up for people interested in such things. Outdoor activities are endless. It is much safer than Mexico or most other countries period and you can drink the water. The downside is that you have to get out of San Jose to experience that and many of the roads are beyond horrible (it is not unusual to have to do river crossings in your vehicle while praying that you will make it across). The new Southwest Airlines route from Houston to Liberia would put you close to the spectacular and almost completely undeveloped Pacific Coast with warm water and all the unspoiled natural resources you could hope for. You would have monkeys, parrots, sloths, crocodiles and thousands of unique species all around you. That is a low-risk version of adventure travel and there are many ways to do it on various budgets and it doesn’t even need to cost that much. Let us know if you want to do that because some Dopers have experience with it including me.

  2. The Yucatan in Mexico - I have never been there myself but it is my parent’s new favorite place. I am not a big fan of Mexico in general but I would go there especially to see the Mayan ruins and venture off into the jungle. It is supposed to be completely different than northern Mexico. I am not sure which Southwest flight best serves that area but I know it is doable as long as you combine it with some other types of transport.

14

Cancun is a hellhole, but it’s a good jumping off point for exploring the Yucatan. With ruins, hungles, charming towns, cenotes, waterfalls and all kinds of natural wonders, there is plenty to do. When I did it, I took a Green Tortoise trip, which is a unique experience on its own. Otherwise, I’m not sure what they best way to get around nowadays is.

I’ve been to Ambergris Caye in Belize. It’s a pleasant getaway and there are some fun things to do, , but for some reason it didn’t catch my fancy as much as other places I’ve been. It’s pretty touristy, but not really a resort experience kind of place. I found it kind of an awkward middle ground. But people like it.

San Francisco’s weather is unpredictable, but “drizzly and grey” is a good bet. The temperature itself isn’t unbearable, but buildings in the region aren’t particularly well insulated, and it can get pretty miserable.

15

Of Cancun/Cozumel, Belize City/Ambergris Caye, and Aruba/Bonaire I’d pick Cancun. And I’d pick it as a jumping off point for other activities, not so much for Cancun itself.

I really liked the Mayan ruins such as Chichen Itza and Tolum can be done as day trips. Can even do Cozumel diving as a day trip if you don’t want to spend the night there. You can explore more towns of the Yucatan such as Valladolid and get a more realistic flavor of what Mexico is about… unlike the bars of Cancun.

16

I spoke to the credit card company this afternoon, and apparently with our card, points don’t expire. So, that’s both great, and also an excuse to put off travel because we have too much other crap to do, which is…kind of missing the point of having free miles. And now that I’m looking at this, I want to go somewhere.

I used to think I was a serious traveler. I backpacked Western Europe (gasp!) all by myself after I finished high school. It cost about $2000 for 2 months and 9 countries in 1999. Loved every second. Then I convinced my now-husband to backpack Peru with me. We did the Inca Trail + 3 weeks wondering around, and it was good-ish, although I found the trip difficult on account of constant sexual harassment and horrible altitude sickness. We got married in Jamaica (another 3 weeks, which was great, but we’ve seen Jamaica and don’t have any particular yearning to see it again.) Then we lived in Okinawa for 4 years, so we saw Japan.

Looking harder at Cabo…many rave reviews reference great shopping, which I suspect is not what I think of as “great shopping.” I’m a goodwill and Craigslist kinda girl. I don’t desire shot glasses and t-shirts with “Cabo” printed on them. So, I’m thinking maybe not for me.

The reason Charleston is on the list is because my husband retires in 3 years, and, get this: we can move anywhere we want. Anywhere! This is a weird concept for people who’ve been in the military for 17 years. Charleston seems…kind of nice? Maybe a place that we might want to live? I don’t know. I realize January isn’t it’s best month, probably. But we could get the gist.

I’m really thinking about January in New Orleans. We’re too old for Mardi Gras, but I think I’d like to see the city. The culture. I’ve been listening to 10 year anniversary Katrina podcasts. It’s interesting.

Also, Costa Rica, even if not for this trip, sounds fantastic. I really want to do that. Southwest is not offering flights to peruse right now to Costa Rica, unfortunately.

Anyway, thanks so much to everyone who has offered suggestions!

17

I recommend that everyone experience New Orleans at least once. There is nothing else like it in the U.S. or the world. January should be fine because a lot of people don’t understand that NYC isn’t the only city that is 24/7/365 as well. New Orleans is like that too, just in a different and more fun way. If you pick it, you will have fun no matter how the weather turns out. You have to try very hard not to.

I do highly recommend the Pacific Coast of Costa Rica as well when you can fit it in. It is surprisingly close in airline travel time yet a completely different world. There is a reason Jurassic Park was set there but it isn’t for the wine and dine cruise and resort set if you want to really experience it. They have all of that too but so much more that you cannot experience anywhere else.

18

But you married him anyway.

19

I’ve been to New Orleans a few times and I agree that it’s an amazing city, well worth visiting.

A description of the city that explains its uniqueness within the U.S. has stuck with me: Its history is not that of the southernmost American colonial city, but of the northernmost Caribbean colonial city.

20

They wear you down.

New Orleans it is. One week in January. I booked the flight, and I’m totally excited about it. I think we will try to do Costa Rica in 2017.

Thanks so much for the advice, huge help!