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Traveling can be stressful and time-consuming, so I wanted to share a list of the stuff I try and offload when I’m on the road.

1. Hotel and Flight Research

In this case, I’m staying at the conference hotel, but I often don’t because it’s sometimes overpriced.

Hey, I don’t blame them — they’ve got a captive audience.

So I’ll have Fancy Hands look into nearby places that might be more affordable within walking distance. I don’t mind walking a couple blocks to save $100 or more over the course of my stay.

When I’m traveling with my wife, we tend to stay in Airbnbs to have a little more space and get more of the “local” experience. A virtual assistant is great to help you narrow down your initial search and to get an idea of what’s available.

VAA Bonus: Get $25 off your first Airbnb stay.


2. Flight Check-In

I find myself flying Southwest a lot because they have a decent hub here in Oakland. But because of their cattle call boarding, it sucks to get stuck with the dreaded “C Pass” and have a middle seat in the back.

I get around this by having Fancy Hands check in for my flight 24 hours in advance. It’s one less thing for me to have to remember to do, and especially useful while I’m at a conference or event and don’t want to be interrupted to check in.

An “A” boarding pass every time 🙂

3. Meetup Location Research and Reservations

Although I don’t think I’ll have time for it on this trip, I try and host informal meetups with readers and people I know in the cities I’m visiting.

So far this year I’ve hosted dinner and drink meetups in Phoenix, Washington DC, Fort Worth, and most recently, Chicago.

I like to have a VA do the initial research and if they find a great spot, make the actual reservation.

For my Chicago trip, I trialed a service called OkayRelax, and my assistant Ainee came up with several options that met my criteria:

  • Downtown location close to public transport.
  • Able to accommodate a group of 10.
  • Outdoor patio seating.
  • Lots of beer on tap.
I’ve also used virtual assistants to scrub my database for subscribers within 45 minutes of a location based on their IP address, so I could send an invite only to those people who lived or worked nearby. This is really cool if you have customers all over the country.

4. Check Local “Rules”

In Chicago, the activity I was most looking forward to was a baseball game at Wrigley Field.

Still, you never know what you’re allowed to bring into stadiums these days in terms of outside food, beverages, and backpacks.

So I texted GoButler (a free SMS assistant) “are you allowed to bring outside food into wrigley field?”

Right away they responded with a detailed outline of what was and was not allowed to bring into the ballpark.

(Yes, our food was allowed, but we made sure to get a Chicago Dog too.)

5. Suggestions of Fun Things to Do

Sure, I could go on TripAdvisor myself, but occasionally this request uncovers some cool lesser known attractions.

Last year in Spain, the Fancy Hands assistant who picked up the task happened to have done a study abroad semester in Madrid and had some fun suggestions for us.

I’m OK “burning” a request on something like this to see what comes back. I know, pretty wild. That’s the extent of my gambling persona 🙂

6. Airport Transportation Options

I always feel more confident if I know exactly where to go and what to do once I land. For that reason, when I’m arriving at an unfamiliar airport, I like to have a virtual assistant research my ground transportation options.

The results vary like crazy. In Fort Worth, my best option turned out to be a Lyft ride across town for $43. When I land in Charlotte tomorrow, an airport express bus will drop me 4 blocks from my destination for $2.20.

Bring exact change, they advised.

VAA Bonus: Get $20 off your first Lyft ride.


7. Keep the Wheels Spinning While I’m Away

Keeping tabs on the business and being available to help put out fires while I’m gone is probably the most important travel task.

Having that assistant (or assistants) on hand makes the trip much more stress-free, and in some cases, enables the trip in the first place.

What I Don’t Outsource

I still haven’t had a VA complete a plane or hotel reservation on my behalf.

That’s just one thing I really feel better about doing myself, double-checking the dates and times, and just making sure it’s exactly what I want.

I don’t know, maybe that’s being a little controlling and I should relax more, but when it comes to making big and often non-refundable purchases like that that could make or break the trip, I’m OK doing it myself.

What do you think?

Your Turn

What do you outsource when you travel? Anything I missed?

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