30 days and counting





It's starting. Our semi-nomadic lifestyle. Our plan is to live in different places around the world for 6 months to a year. On the official list so far is:

  • Big Island of Hawaii
  • Kauai
  • Bonaire
  • Italy
I won't bore you with the unofficial list as it is long and just may make you jealous.

The plan is to experience these places, not just visit them. Experience them as a resident and truly get to know the culture and the people. It was Bob's idea and I immediately thought it was brilliant. 

Our planned travel lifestyle will last until one or more of these events happen:

  • We are sick of the travel
  • We find a place we just can't leave
  • Our kids want or need us in a single place
  • One or both of us cease to exist
OK, that went dark fast, but I think you get the gist. We don't have an end date, but we do have a start date. September 27, 2024. That is the day I (or we) fly from the Chicago area to the big island of Hawaii.

Who We Are



Our names are Bob and Toby. We have been dating for 8 years now, but never fully lived together until a year ago. We are late 50's / early 60's with 6 adult kids between us ranging in age from 18 to 27. 

We both have an "I'm in" attitude which has taken us around the world finding new adventures including fabulous trips, learning (and re-learning) how to dive, innumerable music festivals, learning to sail and sailing two summers on Lake Michigan, learning to wind surf, skiing, and traveling halfway around the world to lounge in luxury and dive in the Maldives. 

In August 2023 I left my beautiful loft in downtown Chicago overlooking the Chicago River and with a great view of Lake Michigan to move to the suburbs and move in with Bob - a town we call Crestfallen Hills (it is legally Crest Hill). We moved into Bob's dad's house and our job over the last year has been to update it, sort through his dad's stuff, and sell it in a year with the intent of moving to Hawaii by Fall 2024.

She Said: Why I Thought This Was A Brilliant Idea

Back in the day I was in consulting and got to live, on someone else's dime, in a number of places around the world. I enjoyed experiencing those cities as a resident and learning more about the people and the culture. I got to:
  • Meet Wayne Gretzky at a bar
  • See the northern lights from Thunder Bay Ontario
  • Make the streets of London my home - and the shopping!
  • Hang at the coolest bars in Manhattan, NY including McSorley's (IYKYK)
  • Perfect my driving with the cabbies in New York
  • Travel around Europe visiting cool out-of-the-way locations not typically on a tourist agenda
  • Run in a 5K on Mount Washington in PA (hilly isn't even a strong enough word)
  • Fly in first class with Mike Ditka
  • Chat with one of the members of the Super Bowl winning Pittsburgh Steelers Iron Curtain Defensive team from the 1970's

He Said: Why Bob Thought This Was A Brilliant Idea

Bob finally spoke, and here is his story

My Mom always had wanderlust....she was the stereotypical bird in a cage that always looked beyond her daily life. My Dad, not so much, but more about him later. 

My Mom was super adventurous; skydiving, skiing, sailing, and traveling every chance she got. The problem was she had a medical condition that significantly impaired her since I was 9 years old. But it never stopped her and she was lounging on a beach in Belize 6 months before she passed away, getting her hair braided, enjoying a cocktail, and yucking it up with the locals.

Travel begets travel.....the more you travel, the more you want to travel. And she passed on that "same bird in a cage" attitude to me. 

My Dad however was perfectly content to live the entirety of his life within 20 miles of where he was born. Adventurous in his own way, but never a traveller, and always worried whenever anyone he cared about got on an airplane. I'm sure that's part of the reason he and my mom weren't long for each other.

When your kids are small, there's a million reasons not to travel, and we get sucked into the daily grind, but always looking outside the cage knowing there's something better out there. Well now my cage is open. I've been an empty nester for a whole 6 weeks, my employment allows me to work from anywhere, and I have a partner in crime that not only tolerates but encourages my silliness. I'm done with the cage, lol, and I want to see the world. When I told people my master plan, I would get one of two responses, either a "that's awesome!" or a "I could never do that". I see both my Mom and Dad in their responses. I respect both but we're on our way, full steam ahead! 

Fast Forward

To get out, we had to deal with a lot of legacy.

  • get rid of stuff
  • store stuff
  • get the house ready to sell
  • have fun - always important
  • continue to fulfill our obligations

And Then Life Went To 11



We decided to get married so, in addition to working and getting this house ready, we added planning a wedding to occur at our first destination. 

That takes us to: 

Did I have a spreadsheet of all the stuff to be done and the deadlines? Of course I did! If you want a copy, I'm happy to share.

The Conundrum

This is the interesting part. What do you bring when you are renting a furnished place and will have access to a car. My list of things to bring gets shorter and shorter each day. Yes, I want my standing desk. No, it's too heavy to ship. We are almost down to clothes, important work equipment like laptop and printer, scuba gear, golf clubs, and pickle ball paddles. Anything else we buy or live without. Crazy right? I did add back my road bike. The biking in Hawaii is supposed to be grand and I would like to partake.

I know you are wondering what we are doing with our furniture. That has been a combination of:
  • Sell - old furniture no longer in use and grandpa's furniture
  • Transition to family members - family heirlooms, things our kids want
  • Discard - that old patio sofa that is falling apart. And if I keep it, who am I keeping it for
  • Store - my desk I love, that huge mirror from my bedroom, standing desk that isn't going to make the trip, etc,...
If all of this is making you exhausted, you are not alone. I can't wait to arrive and have nothing to do but plan the wedding - and after that, nothing to do but have fun and work.

So Hop Aboard!

Well this is the origin story and the beginning of our blog detailing our travels, troubles, and adventures. Welcome and hop aboard the Bob and Toby Everywhere All At Once Train. 


Location: Crest Hill, IL, USA

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