Greetings, newbie member here, first post so be gentle and all that.

Anyway, I figured I'd consult with some experts as to what I should do about an upcoming vacation at a friend's place in San Juan with regards to cigars. Maybe you can help me out.

My background: I'm a rookie cigar aficionado of the most casual variety. After researching things a while back I bought a box of maduros to enjoy during the week leading in and week after my wedding almost a year ago and really enjoyed them. I've eased off them since then and still have some left in the humidor. My smoking habits are to slowly enjoy one when company is around that would enjoy one or brought a few themselves to share. Probably once a month or so when I'm not on vacation.

My taste: I can smoke for about an hour without losing interest. I liked the maduros that my local cigar shop owner pointed me towards. I can't recall the brand/make/size off the top of my head but they were of average size and shape and in the same price range as H Upmans or so. Maybe robusto size? Not pyramid or torpedo profile. My cutter is a xikar that has been a pleasure to use compared to the crappy double guillotine I see others using. Well worth it.

My situation: Since I'll be on vacation for a week+, and I may be sharing a few with friends while I'm there I'm looking into if it'd be better to take some with me or to just buy some when I get there. I have no idea about the market or the availability of cigars there. Please note, I am not trying to make this thread about cuban cigars and/or procuring them. I'm not sure I'd have the palate to appreciate them and I'm not down for dealing with sellers claiming to have X but is really Y and on and on and on.

My questions:
1) Would it be better to take a handful of cigars down there with me or to seek out a vendor while I'm there?
2) If I can get good cigars there at a reasonable (or even excellent!) price where should I go to procure them? We'll be basing our travels out of my friend's family home in San Juan (near old San Juan I think) so bonus points for finding something there that isn't far out of the way or a travel inconvenience to the group of friends I'll be traveling with. We will be traveling a fair bit so other locations are fine as well, just maybe more random in nature.
3) Any tips for traveling with cigars would be appreciated. If I do decide to travel with some I was just going to pack them into a ziplock inside a ziplock with the moisture device shoved in there as well. That, some extra propelyne glycol, a zippo, and my cutter would go into the checked bag for the flight over. I'll have to check on that zippo but it shouldn't be an issue in the checked bag I think....

I saw the following thread (as well as a few others) related to Puerto Rico and didn't see any of this stuff addressed specifically so forgive me if I missed this being brought up already. I did try to search first.

Bonus points, aside, and maybe I should just make another thread... Anyway, I tried to search this but didn't see anything obvious and got a high noise to signal ratio with my search. I'm looking at making a leather cigar case in this style. I've got some veg tan leather hides that I got from a Tandy leather store and all the tools I'll likely need. I'm currently attempting to mold some of the cut pieces into a workable shape but a nice DIY guide would be great.

Thanks for the help!
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Welcome to CA.

1) Probably best to take your own, that way you know you'll have something you enjoy to smoke with you. Finding cigars there that you enjoy should be considered a bonus.

2) I saw some comments about shops in one of the threads you linked to.

3) The double zip-lock bag will work. You could also pick up a small cigar caddy or herf-a-dor from one of your local shops or online. These will help prevent your cigars from being crushed. No need to pack extra PG solution, the cigars will be fine for a week. Or pick up a 65% boveda pack from your local cigar shop. You can take your cutter as a carry on and I'd recommend just picking up a bic lighter to carry on with you as placing your zippo lighter in checked baggage is against TSA regulations because the liquid zippo fuel is highly combustible. Such being said, if you pack it, it might make it though security unnoticed, or it might be confiscated.

PS: Puerto Rico is a US territory, Cuban cigars can't legally be sold there.
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Thanks!

Yep, aware, reason number forty-two I wanted to make it clear that's not what I was after.
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42? 42! Only 42? Should be at least #39.
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And with regards to the lighter, I'll probably go the bic/matches route you mention now that I think about it.

It seems the TSA policy is as clear as mud on this one.

Zippo says it's fine for the most part:On all domestic flights and most international flights, one fueled Zippo windproof lighter is permitted in the passenger cabin. On all domestic flights up to two previously fueled Zippo windproof lighters, in an approved container, can be stowed in checked luggage. New, never-fueled Zippo lighters can be stowed directly in checked luggage.
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Yeah, the transport containers are hit and miss. You're counting on that the agent who finds it in your luggage is familiar with them and interprets them to be safe and not a hazard under the lighter fluid / flammable liquid clause. TSA is going to do what they feel is necessary for safety, quoting what Zippo says about the containers to them is likely just going to cause you more headaches.

To me, it's just not worth the hassle. A bic lighter is $1.50 and I couldn't care less if they decide to confiscate it. I'd be ticked if I lost a $30+ zippo and the $20 case.
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I just came back from Puerto Rico yesterday and brought with me a bunch of cigars, a Palio and bugatti lighter. No problems in or out.
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Awesome.

You have any positive [cigar related] experiences on the island? Store or vendor in particular that was noteworthy?
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Have fun and make sure you visit one of the biobays, it's one of the most fascinating things I've ever seen in my life.
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I've never had a problem with checking my torch. Hell, one time(in my much more naive days) I checked a can of Colibri butane too. Not so much as an inspection note on the flight there or back. It really depends on the TSA agent, but I've yet to be burned. Does this mean I'll bring my Xikar Trezo in my luggage? No. Will I risk bringing one of my Ronsons? Why the heck not, they're cheap enough.
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Have done, hope to do again with friends. Sad to say they're dying and being encroached upon with light pollution from all I hear. Dad says they were way brighter when he was there too, so there's the 50 year viewpoint as well.

It really is amazing and we may do some of the ones on the main island as well.
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They have the Cigar House in Old San Juan. Never been there but heard is a nice place. I just brought some sticks from my personal stash.

Weather was great BTW
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I am going to be in in San Juan for my first time tomorrow and I am really looking forward to it.
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You are go to love it Michael. Make sure you walk all the streets, but always be aware of your surroundings.

Safe Travels
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Stopped in Old San Juan during a cruise about a year and a half ago. It was a great place. Enjoy!
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A few pics: coming into San Juan, our ship (Disney Fantasy) from Fort San Juan, our ship in port, and the Bacardi Bat.
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Second pic
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Third pic
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Fourth
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Cool place. I went back in March. Would LOVE to go back. We toured Bacardi and Don Q.
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