Stressing myself out! Opinions please.

Birdie dog

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Our ABD to Italy and Switzerland is happening this September. I live in SC and my daughter lives in NY. We purchased our air (through Delta) from JFK to Milan from ABD. Now that the trip is confirmed, I need to buy my air from CHS to JFK. There are tons of flights, but I know I'm overthinking it. I plan on flying in to JFK super early (giving myself some breathing room) and purchasing a day room at JFK.

I have two air credits on JetBlue that would pay for the flight. That's been my plan all along. But, now I'm super paranoid with all the cancellations they've been making, that I'll be stranded.

I have enough SW points for the trip, but I don't think they do direct flights to JFK and I don't want to chance my luggage being lost.

I have enough American points... but again, lots of cancellations recently.

I don't have Delta points, and their flight is the most expensive. But, that's who I'm flying to Milan on, so (maybe?) they'd link my flights. I'm also not hearing about the number of cancellations like the other airlines.

We're flying into Milan a day early to sightsee and I've even considered booking my CHS- JFK flight a day early just to remain unstressed about connections. (I think I'm pretty much over-reacting with this but with everything so unpredictable these day, UGH). Anyway, what would you do?
 

Then pack carryon only. EVERY plane trip, whether direct, non-stop, or connecting, has a chance for luggage to be lost.
We're doing northern Italy and Switzerland and I don't think all the things I need (hiking shoes, winter coat, clothes for dinner, jeans, sweaters, and layers) will fit in a carry on only.
 
We're doing northern Italy and Switzerland and I don't think all the things I need (hiking shoes, winter coat, clothes for dinner, jeans, sweaters, and layers) will fit in a carry on only.
Not my point. There is ALWAYS a chance luggage gets lost. I've had a family member lose luggage when she took a single 90 minute flight. The airline never loaded it on the plane. So if you're not willing to chance your luggage being lost, you need to go all carry on. If you check luggage, you're taking a chance.
 
I have a few tips for you. Firstly, wear the coat, a sweater, the jeans on the plane. And your hiking boots if you can. I have a pair of lightweight hiking boots I use in Europe that are much more comfortable on the plane than my other pair. I typically pack for 2-3 weeks or longer in a carryon (and I wear plus size women's clothing).

If you need to check a bag, and you are traveling with someone else, split your stuff into your bag and their bag. This way if one of the bags is temporarily lost, you both have some clothes to wear.

Also, concerning this specific ABD trip, if you plan on buying expensive stuff in Italy and claiming back the VAT, you won't be able to do it, as the border crossing from Italy (EU) to Switzerland (non-EU) does not have customs agents (at least not on the train). A friend of mine did this trip and bought loads of designer clothing in Milan and could not claim back any of the VAT because of this. With VAT often being 20% of the price of the item, this was a harsh blow!
 
I have a few tips for you. Firstly, wear the coat, a sweater, the jeans on the plane. And your hiking boots if you can. I have a pair of lightweight hiking boots I use in Europe that are much more comfortable on the plane than my other pair. I typically pack for 2-3 weeks or longer in a carryon (and I wear plus size women's clothing).

If you need to check a bag, and you are traveling with someone else, split your stuff into your bag and their bag. This way if one of the bags is temporarily lost, you both have some clothes to wear.

Also, concerning this specific ABD trip, if you plan on buying expensive stuff in Italy and claiming back the VAT, you won't be able to do it, as the border crossing from Italy (EU) to Switzerland (non-EU) does not have customs agents (at least not on the train). A friend of mine did this trip and bought loads of designer clothing in Milan and could not claim back any of the VAT because of this. With VAT often being 20% of the price of the item, this was a harsh blow!
I read something about a person taking the train into Germany to get the vat back since they were in Basel. That might be worth it for someone with a huge total, and if it works. I guess it is worth checking out if there are plans to go on a major shopping spree.
 















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