My son and his family are taking me to all inclusive resort in Cancun next week. I want to bring my iPad to read my email, ebooks, the Oregonian newspaper, YouTube, etc… and Tidbits, of course! My son thinks I should leave it home.
So I am looking for comments/opinions from this knowledgeable group.
Bring the iPad or leave it home?
Jane
Of course, any time you travel with valuable electronic devices you’re at some risk of loss (by whatever means). But I’d say in an all-inclusive resort in Cancun the risk is not super high. It’s a pretty competitive niche; resorts are very self-motivated to provide very good security for their guests. OTOH, if I were to go to a bar in town at night for a margarita, I probably wouldn’t tote the iPad along. 
I agree with @fischej and would ask: if you did lose it, how bad would that be?
Here’s one way you could think about the choice. Which would feel more painful to you: not having access to your non-vacation routine while on vacation or losing your iPad and having to replace it?
Another angle: use a family member’s laptop/tablet/phone for a hour or so each day.
I’d suggest bringing actual books you’ve been meaning to read for a while, and if it’s only a short-ish stay, take a break from reading the news and any moving pictures.
Your fellow TBTalkers will miss you of course but your can catch up when back by using the ‘Unread’ and ‘Latest’ views.
Haven’t heard about the Oregonian for a while. I started my newspaper photography years straight out of Uni at the Statesman-Journal just down the way in Salem… Maybe the digital paper also has a way to catch up on unread stories.
I suggest leaving the digital materials home. Enjoy the vacation!
I’ll side with your son here. Take a break from the digital world for a short time. Your son probably would like you all to spend time and enjoy interacting with each other rather than everyone staring at a screen and ignoring the others.
You should absolutely bring your iPad if you want to (as you state is your preference).
Has he given you a reason why he thinks you should leave it at home? If so, is his reason persuasive?
In general, I think your son should decide what he wants to bring with him and let you decide what you want to bring with you.
My feeling is that the OP’s question is more complex than a yes-or-no choice because a lot of objective and subjective things are involved. For example, personality traits, comfort level with airport security practices, experience with international travel and border crossings, and planned trip activities.
My son is concerned about theft. While we are staying at an inclusive resort in Cancun his family has gone to for 3 years, he said the safe is small. I am not worried about the airport. But I am worried about being in Mexico and not knowing the security at the resort. He also said it will be very hot and I can’t take it to the pool, either. Maybe he’s right and I should leave it home. On the other hand…
For me, vacations are about maximizing enjoyment and minimizing worry. I get enough worry and hassle in my day-to-day life! So if I think something will add stress to a trip—say, trying to get to an AirBnB after a 20 hour flight or hoping an old daypack will survive a couple of weeks of hard use—I try to avoid bringing or doing that thing.
I’d download a few good books # & podcasts and turn wifi off at the resort. It is not rude to read a paper book so why not an iPad?
If there is something urgent you can always connect through the resort wifi IF it is secure (eg WPA2).
A passcode protected iPad should be reasonably secure if lost or stolen but make a backup to a Mac or iCloud before you go in case you need to replace it (but you are probably already there by now!)
#The Murderbot Diaries!
Hotel/resort Wi-Fi systems rarely have any encryption. There is usually a captive portal, but that’s just meant to keep out non-hotel-guests, not to actually secure anything.
But the odds of someone attacking your device over the Wi-Fi is low (no matter where you go). The real risk is someone snooping on your data, which is a risk no matter what the Wi-Fi security may be. So either use a VPN or make sure not to read/write any sensitive data over links that are not HTTPS-encrypted.
Fortunately, most web sites these days are HTTPS, so the risk is much less than it was in the past.
Addendum
FWIW, when I travel, I always bring my laptop (a MacBook Air). I bring along a few personal financial documents so I can access them when away. I create an encrypted disk image and transport the documents in that image, to protect against someone stealing the computer. I mount the image (without storing the password in my keychain) when I need to access the contents and immediately unmount it when I’m done with those documents. I also recommend using FileVault and powering off the computer when it’s not in use, which will add additional protection on top of the encrypted disk image.
When I need to access a sensitive site (my banking and investment accounts), it is always over an HTTPS connection with strong encryption, so I’m not worried about that being compromised.
My biggest fear is the computer being physically stolen. Fortunately, nearly every hotel I’ve stayed in has a safe at least big enough to hold a MacBook Air, although some have been too small for a larger computer. If you’re not sure, you should be able to phone the hotel and ask if your room has a safe, and what the dimensions are - this will give you enough information to make an intelligent decision.
It’s Cancun, for crying’ out loud. The news will available when you return home. Enjoy!
Yeah, That’s it right there. If you’re going to be stressed everyday you’re out of the hotel it’s not worth taking. Last trip I did I only brought my iPhone. I wanted to have one trip where I didn’t head back to my room and was on my iPad. But this was actually an extended weekend type of trip. Not a week long one.
Two words: Kindle Paperwhite. Available cheap at sites like Woot.com.
Kindle App on iPhone and iPad. But I prefer print books.
Is your son bringing any devices?
Unplug if you can.
No. My son is only bringing his iPhone. That is what I am bringing, too. I leave in a few hours!
The Internet is full of videos on how easy it is to open standard hotel room safes without the combination. I can’t vouch for their accuracy, but they at least look plausible.