Planning next year's vacations +airline miles q

[waverly]

We have about 325,000 miles on Southwest, and I have companion pass but I think only until Jan 1.  Not sure how that works with booking dates exactly.  DH no longer has that job so we won't be getting more miles.

Hawaii was on his radar, and we could do almost 2 weeks over Christmas break, and only pay for lodging and use up most of the points.  I've been before.  He's never been.  Lodging would likely be pricey. 

He never was interested in the Caribbean before, but now he is, so we could also do (no date determined) Bahamas, Grand Cayman, Turks and Caicos, Montego Bay or Aruba.  We've never been to the Caribbean, so we don't know much about it. Just listing the ones that sound the best.  Does anyone have suggestions as to which island?  Also I think we would prefer to rent a house rather than go to a resort. 

Or we can keep the points and do multiple smaller trips such as Yellowstone next summer, weekends away to NYC, DC, or whatever interest us.  What would you do? 

We are not doing spring break flying next year.  We are planning on a driving trip.  So no Florida spring break for us next year.  

We've been using our massive amount of points for farther away places (San Diego, Seattle in the last 2 years), so I don't feel like I have to go all the way to the west coast of the U.S. So lately, we've been trying to cross off places we haven't gone to yet like Maine or just getting away like NC in March. 

[sdlaura]

I would plan your vacations based on where you want to go rather than worry about using the points - since they don’t expire and you won’t be earning at the same rate in the future.

I have a lot of points too but it never seems like they’re enough - even though southwest has a great program in my opinion. I just booked holiday cross-country flights for my family (4 seats since I have the companion pass for the 5th) and it cost 180,000 points. I even picked the ‘cheaper’ dates. Ugh!

[traveltheworld]

I can't remember - are you on the east coast?

I've only been to Hawaii, Bahamas, and Jamaica. I liked them all. Hawaii is the easiest though. We always rented our own place in Hawaii; whereas we've always stayed at a resort in the other two. Personally I think 2 weeks is a bit long - depending on how long it takes you to fly there. Personally I'd do 1 week - 10 days, a a few other smaller trips like Chicago, NYC, Boston, etc.

[supertrooper1]

I do love Hawaii, but lodging and food are expensive.
I've only been to Puerto Rico in the Caribbean and loved it.
I would probably do as many smaller trips as my points would allow instead of one big trip.

[waverly]

We are in the Midwest. Trips to the west coast and Florida (for spring break) are typically 200,000. NC was something like 60,000. So if we have a bunch of little 60k flights we could do quite a few trips.

True 13 days is a bit long I was just thinking the weather is so crappy here. 10 days probably makes more sense though.

[librarychica]

Jun 11, 2019 20:14:25 GMT -5 waverly said:

We are in the Midwest. Trips to the west coast and Florida (for spring break) are typically 200,000. NC was something like 60,000. So if we have a bunch of little 60k flights we could do quite a few trips.

True 13 days is a bit long I was just thinking the weather is so crappy here. 10 days probably makes more sense though.

I love the idea of a bunch of little trips, if your kids are good fliers. Try to save a long weekend for adults only if you can.

[2chatter]

I’d do a couples trip and a family vaca - we love the Caribbean. What about Europe? We are starting to plan a Greece and Croatia trip for next May.

[librarychica]

Jun 12, 2019 9:14:33 GMT -5 2chatter said:

I’d do a couples trip and a family vaca - we love the Caribbean. What about Europe? We are starting to plan a Greece and Croatia trip for next May.

I have heard Croatia is wonderful.

[sdlaura]

Jun 12, 2019 9:16:18 GMT -5 librarychica said:

Jun 12, 2019 9:14:33 GMT -5 2chatter said:

I’d do a couples trip and a family vaca - we love the Caribbean. What about Europe? We are starting to plan a Greece and Croatia trip for next May.

I have heard Croatia is wonderful.

Croatia is wonderful! At least it was when I went 12 years ago . Amazing islands, inexpensive and uncrowded.

But can’t use southwest points for Europe.

[mommyatty]

I’ve been to Grand Cayman. It’s lovely. Especially if you snorkel or dive.

[2chatter]

I loathe Southwest - I would almost rather walk. It didn’t occur to me they don’t have a points partner program for Europe, but it totally makes sense!

The Caymans are pretty family friendly, but you will spend all you save on flights in the cost difference of things there - $18 gin and tonics, lunches I don’t think we managed for under $50 for the two of us. The best thing there is that you can rent a car and explore the entire island safely - we snorkeled all the popular spots.

[waverly]

2chatter, he could fly out of Midway which is much closer than O'Hare. New job is much less travel, and the other office location Southwest doesn't fly to, so he is using United, I think, but those points will not rack up fast, but maybe in 5 years we could go to Europe.

It sounds like certain islands will be super pricey. Maybe it make sense to do 3 smaller trips a year.

[rere]

We loved Aruba. It is routinely rated one of the safest and friendliest destinations and it was true. We loved the people and were able to explore the entire island. You don't have to worry about storms because it rarely rains. Beautiful blue water.

A few friends have been to the Caymans, and based on their pictures and experience, I hope to take the family there in a couple of years. The water looks amazing.