Which Risk to Take: Fees or Expensive Flights?

My husband and I planned a cruise for 2018 with my family. Due to kids and school schedules, we have to go during Easter. We'd be flying into San Juan the Wednesday before Easter weekend.

My job won't officially approve the vacation until February 15th. I bought cruise insurance to minimize my loss if we have to cancel the cruise.

I don't know what to do about flights. Should I buy now and risk having to cancel or switch flights, costing what will probably amount to hundreds in fees? Or should I wait until February 15th to book international flights for the end of March (right before a major holiday)?

I realize it's ultimately my decision to make, I was just hoping for some educated opinions from frequent travelers.

Thanks!

I guess it depends on the airline and their change fees. Some only charge a flat rate while others charge the difference in airfare.

You could also purchase a refundable fare. Will cost you more, but you can cancel without penalty.

If you get insurance you will need the kind that allows "cancel for any reason". Again this costs more and usually only covers 70-80% of the total trip cost.

Southwest flies to San Juan now and 2 of the perks with Southwest is that they don't charge a change fee and also free baggage. If you had to change or cancel the flights you'd have a year from date of purchase before you would lose the money. BTW San Juan isn't international since it's a US Territory so if you don't have passports you can still fly there.

I've been considering Southwest. I have $400 worth of points to use with American Airlines, but it is tempting to buy tickets with Southwest that include the 'reusable funds' option. At least we'd be able to fly somewhere else later in the year if we had to cancel the cruise.

My job won't officially approve the vacation until February 15th. I bought cruise insurance to minimize my loss if we have to cancel the cruise.

 

I think that you have a very bad employer if they can't approve the vacation before February 15.

Is it possible for you to find another job?

I think that you have a very bad employer if they can't approve the vacation before February 15.

 

Is it possible for you to find another job?

I see that you are in Sweden. Let's just say American labor laws are not as generous as Sweden's. If someone where to change jobs now, they aren't going to eligible for vacation in March/April.

I see that you are in Sweden. Let's just say American labor laws are not as generous as Sweden's. If someone where to change jobs now, they aren't going to eligible for vacation in March/April.

It's not a matter of USA labor law, which doesn't regulate when one can get vacations. It's a matter of company policy.

In my heavy working days, I regularly negotiated for vacation in the months shortly after joining the company. It may not have been paid time off, but I almost always got what I wanted.

What kind of insurance did you get that covers boss not approving vacation? That could be more of a risk than the flights. I'd talk to my boss if I were in the same situation.

It's not a matter of USA labor law, which doesn't regulate when one can get vacations. It's a matter of company policy.

 

In my heavy working days, I regularly negotiated for vacation in the months shortly after joining the company. It may not have been paid time off, but I almost always got what I wanted.

Works if you are in a job high enough up the food chain. Don't suggest you try it if you are an hourly worker or many other jobs.

I see that you are in Sweden. Let's just say American labor laws are not as generous as Sweden's. If someone where to change jobs now, they aren't going to eligible for vacation in March/April.

I know that labor laws are different but don't think this is about laws.

If another company wants you they might let you go on a cruise just to be able to employ you.

I can book a cruise without asking for vacation first because if my boss should say no I can get another job. It's not about different laws.

I don't say that everyone can do that, not in America and not in Sweden.

Don't suggest you try it if you are an hourly worker or many other jobs.

I agree with this but I don't know what the OP is working with.

I see that you are in Sweden. Let's just say American labor laws are not as generous as Sweden's. If someone where to change jobs now, they aren't going to eligible for vacation in March/April.

But if you get a new job now, you can always tell them that you have a family trip scheduled already planned. No, you won't get paid for it, but I don't think most would refuse to let you go.

Although I love traveling, I don't think I'll be quitting my job anytime soon for a vacation.

Someone pointed out that Puerto Rico is considered a domestic flight. For whatever reason I didn't consider this. Maybe it just feels international? Either way, I have $400 in credits/points and free bags with American Airlines. Worst case scenario, I have to change the trip dates with American, costing $400. So it will basically balance out the credit I have with them.

I'm thinking I'll book with American now with the knowledge that I may have to pay the change fee in the future instead of worrying for several months about the cost and availability of last minute flights, which was my primary concern.