A Week-In-The-Life of Corbett Barr: Free Pursuits

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Corbett Barr is an entrepreneur and blogger who has spent the past seven months on a road trip with his wife through Mexico and the Western U.S. and Canada. You can find him at his namesake website where he writes about lifestyle design. Please enjoy a little insight into what a week-in-the-life of Corbett Barr looks like!

This post was originally published in 2009. It has since been updated for accuracy of links and content.


My wife and I are nearing the end of a 7-month-long sabbatical. We’ve been on a road trip since January of this year (mostly through Mexico) and are making our way back home to San Francisco via the Pacific Northwest. Today we wake up in my Father-in-law’s house in the woods about 45 minutes from Portland, OR.

We’ve been here visiting family for the past week. It’s our last full day here, and we’re trying to relax and catch up on rest before heading back on the road again. The day is filled with reading and a little swimming. I also manage to get a blog post written.


sunset, photo by Corbett Barr

We wake up around 9am and pack the car for a two-week trip. We’re headed up to Seattle today to stay with some friends. We used to live in Seattle, and we’re looking forward to catching up with a bunch of people. It’s only a 2.5 hour drive to Seattle, so we arrive in the early afternoon. The friends we’re staying with have planned a barbecue in the evening that some of our other friends will be coming to. In the mean time, we walk to a local cafe and order some sandwiches that we take to eat on the shores of Green Lake.

When evening rolls around, friends start to show up for the barbecue. It’s a beautiful warm Seattle Summer evening. It stays light until 10pm, and we enjoy every minute of sunlight out on the back patio. Most of us (in our early 30s) are married, but only a few of us have had a child. This is the first time we’ve been with this group of friends when there’s a kid around. We have a great time making jokes with the 3 year old until dark. Life is changing.


We can tell that our hosts feel like they have to entertain us throughout the day, but we really just want to relax. Being on the road constantly is definitely tiring, and we’ve learned to cherish little moments of down time. Rest isn’t in the cards for us today though. A couple that we didn’t get to see the night before stops by to say hi. We end up spending the afternoon playing frisbee and talking at the park. In the evening, we head out to dinner at a new Vietnamese restaurant downtown, and then pop in to a favorite bar that we used to frequent for late night drinks.


Corbett Barr and his wife, on a sailboat

Today will be another busy day. We’re meeting up with a few different people we haven’t seen in a while. We leave the house where we’re staying around noon to pick up a childhood friend of my wife’s. The three of us head to downtown Seattle for some lunch. While they catch up over a glass of wine, I head to a store to pick up some last minute items before our trip up to Vancouver B.C. tomorrow. We’re going sailing with some friends in the Canadian Gulf Islands, and I want to get some things in the States since they’re cheaper than in Canada.

After lunch, I walk a few blocks uptown to meet with an old colleague. He asked if I’d like to catch up, and also to meet a friend of his. His friend has some idea for an email startup and wants to run some things by me since I spent the past three years building an email service.

At about 6pm (hopefully after rush hour traffic), we head down to Tacoma for a baseball game. An old friend that I’ve known since middle school is the announcer for the local AAA baseball team. It’s great seeing him and his wife and newborn baby. He manages to get me to lead the crowd in the chicken dance during a break. Hopefully that doesn’t end up on YouTube.


We pack up in preparation for our trip to Vancouver, Canada. Before leaving town, we decide to head over to our favorite lunch spot, the Essential Bakery near Gas Works Park. It is well worth the trip. Our drive to Vancouver takes about 4 hours with stops and the border crossing.

The people we’re going to meet are actually new friends. We met them in Mexico in January where we were taking the same Spanish class. They’re recently retired (in their early 50s) and we were in the same town in Mexico for a couple of months. After hitting it off, they invited us to come up and go sailing for a week.


Provisioning and preparing the boat will take some time today, so we get up early and head out. We stop at a couple of grocery stores and a liquor store (beer and wine are only sold in government liquor stores in B.C.) before heading to the boat.

Sailboat at Sunset

What a beautiful boat it is! Our friends had long planned to own a boat once they retired, and they really went all in. She’s a brand new 43 foot Bavaria Cruiser. If you haven’t been sailing before, 43 feet is large, and Bavaria makes some good looking seaworthy boats. It’s going to be a great week aboard the boat with three staterooms (bedrooms), a spacious galley (kitchen) and cabin and two heads (bathrooms).

After prepping the boat, we catch lunch at the Yacht Club and then walk over to Granville Island to do some sightseeing. Granville Island is really like a big market, similar to Pike Place in Seattle. We wrap up the day at a favorite Sushi restaurant and get to bed early.

See also: Nora’s Adventures Sailing the Caribbean for Two Months


Sailing day! We have about a 30 knot sail ahead of us, which will mean about 6-8 hours on the water, depending on the winds. We board the boat and depart the dock at about 10am. The boat is pretty easy to sail (with a roller-furling head sail and in-mast main sail), and we get the hang of everything quickly. The wind is strong, but we have to sail mostly upwind today, so we arrive at Secret Cove at about 6:30pm.

Our friends have made reservations at the restaurant at the marina which happens to be run by another couple we met in Mexico earlier this year. It’s really a small world. The food and conversation is fantastic.

Everything went really well today, and we can already see how great this week of sailing will be. We’re planning to stop at about six more places along the way, with a mix of natural anchorage spots and comfy marinas. It seems like the water will even be warm enough for some swimming along the way. We can’t wait!

Corbett Barr wrote this from Portland, Oregon where he was spending the last week of his 7-month sabbatical. He’s headed back to his home base of San Francisco for the rest of the year, but plans to return to Mexico for a couple of months next Winter.

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6 thoughts on “A Week-In-The-Life of Corbett Barr: Free Pursuits”

  1. Cheers, Corbett! I’m honoured that you participated, and I’m envious of the great boating experiences you had with good friends. Keep having fun!

  2. Bum. Stop posting this sort of stuff.
    It makes me SOOOOOO jealous. (Not long now, just paid the LAST term of Private secondary school fees EVER!! – and he wants to be a ski bum…well spent hey!!)

    • @Frank – Hmm…ski bum….professional hobo…I like his style! Don’t worry, Frank – you’ll be sailing into the sunset yourself before too long!

  3. Now that is a gorgeous sunset. Wow! What a dream to sail on a luxury sail boat. I have a feeling that we will be seeing a lot of future travels ahead from Corbett after what he has experienced in the past 7 months.

    • @Dave and Deb – Tell me about it! I love to see how people travel, and how their travel habits evolve with their lives.


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