Most people who read anything that I post online know me via my start-up, Outseta. But outside of work a lot of my free time and energy goes into scheming... scheming up where my next adventure will take me!

My wife and I have settled into a routine where we travel for 6 months out of every 24. We both love to travel but we now have twin 3-year old boys, so a fully nomadic lifestyle simply isn't in the cards for us at this point. This is the next best thing and our rationalization is simple...

If we do this until we're about 70, we'll end up going on something like 20 trips of a lifetime.

These are not extended vacations—their an opportunity to live and work in different places, while experiencing different cultures, with some degree of regularity.

This is keeps my life interesting, is good for my soul, and is an amazing opportunity for my kids, too. While I think school is generally good for the sake of socialization, I seriously question its merits when it comes to learning. I believe that the education my kids will get from living abroad frequently is more valuable than any public school education in spades.

Also, I actually enjoy the process of planning these trips. I research locations and search for Airbnbs obsessively. 

We're about to embark on our third such trip on May 1st. While we could fly by the seat of our pants in the past, traveling with two crazy three year olds requires extensive planning. 

They need a situation conducive to sleeping. You can't just throw them in a cab. Flying with toddlers is tough.  

So our schedule this time is meticulously planned—we try to stay in each location for two weeks to a month to provide the kids with some degree of structure.

Starting in May, I'll be returning to my favorite place on earth—the island of Sifnos, Greece. We discovered it on our last trip, stayed for 3 weeks, and vowed to return. I may very well end up here.

We'll be on Sifnos for three months, and many of our friends and family are coming to visit—everyone from my parents who don't travel internationally much, to two of our best friends who are staying with us as their wedding present. These are trips of a lifetime for our friends and family too—it's really cool that we get to share these experiences with them this summer.

After three months in Greece we're planning to stay in a small winemaker's village in southern France, a pedestrian only town of about 200 residents tucked on the side of a mountain.

After that we will have been in the European Union for 90 days, so as US citizens we need to leave. We're headed to the west coast of Scotland for the month of August, then to Nova Scotia, Canada for the fall. Our full itinerary and some commentary is below.

May 3 - May 10 (Athens)

We're flying into Athens and staying with my business partner, Dimitris, and his family for a week.

May 10 - May 25 (Sifnos, Greece)

We're staying for most of our time on Sifnos in Kamares, the main port and my favorite place on the island. One nice benefit of traveling in Greece is how affordable it is—this AirBnB is brand new, super comfortable for a family of 4, and costs about $120/night.

    May 25 - June 25 (Sifnos, Greece)

    We're traveling on a budget—this is the one splurge. We rented this big place for a month to host our friends and family.

    June 25 - July 2 (Paros, Greece)

    Dimitris says his favorite Greek Island is Paros, so we're taking a ferry over there for a week to check it out. This place is more modest, but has a private beach for the kids and a restaurant and yoga studio next door.

    July 2 - July 12 (Kamares, Sifnos)

    Back to Sifnos for 10 days to host my wife's family.

    July 15  - July 29 (Vieussan, France)

    I've definitely never stayed anywhere quite like this before—this one is a flyer of sorts. As a pedestrian only town, the kids can run wild and there's a river that runs through the property. 

    I have minor concerns about the mosquitos in July, but we'll see. This place is only $89/night.

    August 5 - August 19 (Oban, Scotland)

    Oban is a good launching pad for exploring western Scotland and easily accessible by train. The Jacobite Steam Train, aka the "Harry Potter" train is also in the area—a major event for my kids. 

    Scotland is pretty damn expensive—especially in August. That said, we need to leave the European Union, by all accounts the scenery is second to none, and Scotland is generally heading back in the direction of the United States.

    August 19 - August, 25 (Cove, Scotland)

    We're throwing in a stay with a Scottish family in an 1850's Victorian mansion for good measure. This is also super cheap—$99/night!

    August 26 - September 11

    After Scotland we fly back to Boston, where we'll visit family and friends for a few weeks before heading up to Nova Scotia.

    September 11 - October 9 (Nova Scotia)

      Nova Scotia is a place I've never been but have always wanted to explore. We're staying for a month in small town called Chester on the Atlantic coast.

      That's what we've got planned so far—I couldn't be more excited. This type of trip requires a massive amount of coordination, but what else am I doing when my kids go to sleep every night?

      Another benefit of planning so far in advance is the cost of all the flights, Airbnbs, and transportation is actually slightly cheaper than our average monthly expenses living in San Diego. We purposely stick to a budget of our regular monthly expenses when planning these trips, so from a financial perspective our lives remain unchanged.

      I couldn't me more excited to explore all of these new places—and I couldn't me more excited for my third trip of a lifetime.