Safely Wandering

As a Wanderer I tend to end up using a wide variety of different internet connections, while dragging my computers all over the place. One day I'm on my boat trading via my Google Fi cellular connection. The next day I'm using a local SIM card. Another day I might go to shore to use Starbucks wifi because I want to back up my hard drive or upload a bunch of content without using up my own data. Sometimes I'll be at a marina that has wifi at the dock. Point is, my computer usage and connections, are not stationary, and not secure like they would be in a land-based home on an unlimited hard-wired line.

To protect my privacy and my data, I've adopted a few different methods through the years. Below I'll list my favorites. Some of these are affiliate links, all are products I use daily.

Credit Card

Tip number one for anyone who travels and does business over the internet is to have a great credit card. Absolutely, positively, do not rely on Paypal (or similar), or debit cards to do business either in person, or over the internet. A good credit card is worth every penny you pay in annual fees.

My credit card info has been stolen half a dozen times. That's just a simple fact of life, both at home, and while abroad. Chase has made the process totally painless for me. They never question me when I tell them it's happened, again. They simply ask when the last legit purchase was made, and then everything fraudulent disappears overnight. They will also go out of their way to get you a new card quickly no matter where you are. Usually just a day or two.

Beyond theft protection, Chase gets my business for a few other reasons. I rent all my cars with their card. They will pay for any damage to the car, and will also pay if the car is stolen. I've used this twice. Once my car was sideswiped by a bus in Guatemala. The bill for that was around $600, which Chase reimbursed without question. The other was a tiny shopping cart ding in a St. Croix grocery store parking lot. The car company charged an insane $650 for that one. One call to Chase and the charge disappeared. Again, without question.

$300 travel credit. Every year Chase reimburses you for travel related expenses. This happens automatically on your bill. Travel expenses can be just about anything. Hotels, Uber, airline tickets, etc.. It doesn't take a traveler long to rack up that reimbursement.

TSA pre-check. Chase pays the $85 fee.

Once past the TSA security line my favorite card perk of all comes into play—Priority Pass Membership for airport lounges. You and a guest get to wait for your plane in a lounge with free food, drinks, good internet, comfortable couches, and nice bathrooms. I find myself arriving to the airport an hour earlier just because I know I can spend the extra time in the lounge.

Travel delay insurance. Plane, train, or automobile delayed more than six hours? Chase will pay for your food, hotel, and any essentials you need to buy.

Lyft Pink. Free subscription to Lyft's upgraded benefits. You get better cars, and 15% off each ride, all for doing absolutely nothing.

Free DoorDash subscription, means free food deliveries, means more money to tip your delivery person.

Concierge services, extended warranties, the list goes on and on. There are loads of little-known perks.

So, while the card is expensive, with a $550 annual fee, I think just about any traveler worth their salt will find the fee is more than made up for by the benefits. In addition, if you sign up and spend $4,000 in the first three months they'll give you 60,000 points to start with. That's worth $900, which pays for just about two years of annual card fees before you've even begun collecting the rest of the benefits.

Click here to earn 80,000 bonus points with Chase Sapphire Reserve and get what I consider one of the most essential pieces of travel gear.

Importantly, though, credit cards, and the rewards that go along with them, are only financially beneficial if your card balance is paid off in full each month. The only reason credit card companies can offer benefits like these is because they know that more people than not will end up in the position of paying interest each month instead of paying off in full.


A virtual private network extends a private network across a public network and enables users to send and receive data across shared or public networks as if their computing devices were directly connected to the private network. That's what wikipedia tells me, anyway. For me, it means keeping whatever I'm doing online safe from prying eyes, as well as fooling websites into thinking I'm somewhere I may not be at the time.

I use Surfshark. A number of travelling friends recommended it, and it hasn't disappointed.

If you use Netflix, Amazon Prime, Spotify, or really any sort of paid subscription for media online, then you've likely run into the "Hmmm, you don't appear to be in your home country right now" warning that lets you know you can't stream what you want because you are now in Mexico, or New Zealand, or Egypt, instead of tucked away nicely in bed at home. Set your VPN to route your traffic through your home country and your problem is solved.

I've also found that occasionally stock brokerages will cause users problems if their IP address is showing up outside of their home country. For instance, an Australian friend was on her boat applying for a new brokerage account located in Australia. At the time, however, she was in Malta. The brokerage wouldn't allow her to open the account despite repeated attempts to prove who she was and explain why she was in Malta and not in Australia. They basically said, call us when you get home. A VPN would have avoided that hassle.

Extra security and extra anonymity make a VPN worth the couple of bucks a month. This link gets you 82% off and 2 months free. The two-year plan is just $2.30/month.

Password Manager

1Password has changed my online life. Once upon a time I had one, maybe two, passwords that were reused over and over again, for years. It's a miracle I was never hacked. But hey, who can remember all those passwords?

1Password solved the problem for me and my family. One account, one password, as many devices as we want. Once you install 1password it's a simple matter to change current passwords, or to create new ones when you visit a new website. 1password creates impossible passwords, and all you have to do is remember one of your choosing. On most devices you won't even need that, you'll just use your fingerprint or facial recognition that you already use to log in to your device. 1password is my number one online time saving hack. It's so fast and easy to access websites now. Even sites I haven't visited in years.

I haven't been hacked yet, and I no longer consider that pure luck, like it used to be. However, that is not meant as a challenge!

Hard Drive Backups

Because of my lifestyle I virtually never have unlimited data, which means I can't be constantly backing up everything to the cloud. All my photography and video resides on portable hard drives, which are great... until they aren't. The hard drive fails, is lost, stolen, etc..

So, I knew I needed some sort of backup that was cloud based, but that still didn't solve the question of how I could save terabytes worth of data. Even if I was visiting family, I couldn't just leave my computer running for days on end to upload 5TB to the cloud.

iDrive solved this problem for me in the easiest way. Once a year they send me (more if you pay for them), free of charge, a large portable hard drive. You transfer whatever data you want on to that hard drive and mail it back to them. Within a couple days they will upload it to your account in the cloud. If you ever need access to it, you've got it. In addition, once you've made that first huge upload, subsequent data uploads are much more manageable. For me, they turned an overwhelming project into something simple.

I am now able to stay, mostly, backed up. If I had an always on internet connection it would be simple, but for me it still requires a manual push of the button when I'm on an unlimited connection somewhere.

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Puerto Vallarta

Living, trading, and running a business from a boat is pretty amazing. Just ten years ago the idea of doing all of this would have seemed impossible. While technically it may have been doable, it would have been a near constant headache, mostly due to internet connectivity. These days, almost nothing stands in the way of a mobile lifestyle, whether retired, or working, or some mixture of both. This past year I've gone from Bonaire to Aruba on our boat, to across the US via vintage motorhome, and am now on my boat in Mexico waiting out hurricane season. Life is different in every location, but work and trading remain the same. The world is wide open to us vagabonds.

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