First Draft: An Itinerary For the Next Big Adventure

It’s taken a few weeks, but we’ve put together what we think is a good plan for two years of travel! We started off thinking we would figure out a year’s worth but somehow we just got going and couldn’t stop at a year.

I’m sort of happy we did this because it gives me lots of think about when it comes to planning and how much we should save in advance. There’s a big splurge in the second year which will require extra advance saving, but now that we know we’re better prepared to work on a monthly budget for that.

Before we started putting together an itinerary, we set three simple ground rules:

  • A minimum of 30 days in each location
  • Include at least one “long weekend” or getaway to a nearby location (around four or five days)
  • Ninety days in Japan each year
  • Special attention given to the weather and time of year; i.e., other than going to New England in December to spend Christmas with our daughters, no northern visits in the winter, no southern visits in the summer, and so forth.

Locations we have not visited yet were the priority, but there are some return visits. We also wanted the order we traveled to make some kind of geographical sense with not too many long flights in between.

After much deliberation and back and forth, here’s the first draft of an itinerary for the next Big Adventure. We’re pretty sure some things will change as we move closer to 2023, both because of costs and because lots can happen during two years that we have no way of knowing now.

photo credit: Danae Dal Bianco/Unsplash

We’ll start with an month-long stay on the island of Crete in Greece, with a long weekend in Athens and possibly a trip to Santorini.

photo credit: Fatih Yurur/Unsplash

From Greece we’ll head to Istanbul, a place both of us have longed to visit.

photo credit: Julia Solonina/Unsplash

Instead of returning to Rome, we’ve decided we would rather go north and spend a month in Verona, with easy access to Venice, Vincenza, Padua, and Milan.

photo credit: ERROR 420/Unsplash

Next is Western Germany. We wanted to stay in Amsterdam for a month, but lodging is very expensive there so instead we’ll make Amsterdam a long weekend visit. We’re thinking of staying in either Cologne or the area around Frankfurt so we can also go back to Strasbourg for a few days.

photo credit: Candy Good/Unsplash

We’re heading back to the UK after Germany, for just 30 days this time. We can’t decide whether to return to the Cotswolds or instead stay in Derbyshire, but it’s looking like the Cotswolds may be too expensive for a month’s stay (last time Airbnb covered the cost). We plan to rent a car this time, so a trip back to Blockley for a long weekend would be doable from Derbyshire and probably more affordable. We also want to add on a week in London at the end of our stay to see the things we missed before. After nearly missing our flight out of London in 2019, we want to make sure as well this next time we’re already in London before our flight!

England will be followed by a 90-day stay in Tokyo. We hope to find lodging this time nearer to our son’s new home but there currently don’t appear to be any affordable rentals in the area. Sangenjaya, the neighborhood where we stayed before and love, would not be as convenient as before but still doable. There are nonstop flights from London to Tokyo, and this will be where our air miles will come in handy, to upgrade to comfortable seats for the long flight(s).

photo credit: Clifford/Unsplash

If all goes as plans we will leave Japan in mid-December, and head back to New England for a month to spend the Christmas and the New Year’s holiday with our daughters, and re-provision before setting out again. Japan to the east coast of the U.S. will be another long journey, but we are already thinking that unless we find a fantastic fare to Boston we will break up the trip with a short stay in Portland so we can get together again with friends.

At the beginning of 2024 we want to return to Buenos Aires, not only because of a strong desire to experience more of the city, but because it will be summer there! We would like to visit Iguazu Falls this time, if possible, so that’s one idea for a long weekend getaway. We missed seeing Colonia del Sacramento in Uruguay on our last visit, another great getaway (it’s just across the river, and a World Heritage site), or maybe spending a few days in Tigre, a natural area on the northside of Buenos Aires. Tierra del Fuego would make a wonderful long weekend visit as well.

photo credit: Miranda Garside/Unsplash

Following Argentine our destination will be Mexico for 60 days, spending the first month exploring Mexico City, and the second in San Miguel de Allende, which would have been our destination following Japan in 2020.

photo credit: Scott Walsh/Unsplash

Leaving Mexico, we will head north again, this time to Canada! Our idea is to spend 30 days somewhere in the Maritimes, 30 days in Montreal, and finish with 30 days in Vancouver. We would rent a car during our stay in the Maritimes but otherwise rely on public transportation in the other two cities.

photo credit: Ondrej Machart/Unsplash

Another l-o-n-g journey awaits us when we leave Canada because we want to head back to Australia for 60 days! We will break our 30-day rule here as there’s several things we’d like to do, and this is probably the last time we’ll go to Australia. We’ll start with a week in Sydney, then travel to Adelaide in South Australia for a 30 day stay. The train made a stop in Adelaide on the way to Sydney during our last visit and we were enchanted by what we saw. At the end of our stay we’ll board The Ghan for hopefully 10 days of travel through the center of the country, with stops in Alice Springs and overnight visits to Uluru and other sites in the outback, and finishing the journey with a short stay in Darwin. Afterwards we’d like to visit my brother and other family in Queensland. A train journey tour package would be our only big “splurge” this time around.

Then it’s back to Tokyo for another 90 day fall stay. While we love seeing the cherry blossoms, the changing leaves, autumn foods, and the chance to celebrate our son’s and granddaughter’s birthday make the fall a great time for us to be there.

We’ll end 2024 with another stay in New England for the holidays.

After coming up with that itinerary, we decided it was time to stop although we have some ideas of where to go after that. There are so many places we want to visit but those can wait until later!


49 thoughts on “First Draft: An Itinerary For the Next Big Adventure

    1. Fingers are crossed on both hand, toes as well, that we can pull this off without any changes, or at least nothing major. Hopefully by 2023 Covid will be under control worldwide.


    1. Thanks! Getting a plan in place makes it seem not all that far off – we have a lot to do to get ready, and hopefully I can keep all the preparation work interesting.


  1. Hi Laura. I havent been commenting much lately but have to chime in today. I have a house in Crete and you can stay there if you like. Its in a little village in the mountains with no-one that’s speaks English and i think you would probably need to rent a car. Nowhere near Chania (in the photo) though. Email me or facebook message if you want to. Liz x

    Liked by 1 person

    1. We had to make changes to our itinerary before we set off the last time, so there will most likely be changes to this one as well, but for the most part we think it’s pretty solid. We’ve got our fingers crossed on both hands!

      Liked by 1 person

      1. As we all know now, there are things beyond our control. You might have to change plans, and maybe some great opportunities will come your way. As I said, I am thinking positively for you and your family.


  2. Sounds awesome. I have a suggestion. From Montreal fly to Calgary and then rent a car and drive to Vancouver. It’s a beautiful drive through the mountains, but I’m biased 🙂


    1. This is a great suggestion! I checked on the price of a one-way rental car out of Calgary and as long as we keep the cost in mind as we budget we could do this. I would LOVE to see Banff NP and of course the entire drive through the mountains on the way to Vancouver would be amazing. Thank you!!

      Liked by 1 person

      1. We first checked Costco rentals and for a change they were VERY expensive. So, I checked on Expedia and found that Thrifty and Budget had more affordable rentals for that time of year, something we could afford. We try to make those reservations early too because you get a better rate rather than waiting until the last moment. As soon as our dates firm up those will be some of the first reservations made. We very much want to make this drive!


      2. I didn’t even know Costco rented cars! Let me know if you need any info in your planning. I’m in Banff, Lake Louise and area a lot and know it well.


      3. Thank you! I will be in touch when we are a few months out – we really want to do this.

        We have always found the best car rental prices through Costco in the U.S. – they’re worth checking out (and if you have an executive membership, what you pay for a rental applies to you rebate!).


  3. How lovely! If you are centered in Nova Scotia, the rest of the Maritimes are all within a few hours drive. There are so many back roads to explore. I recommend going “The Hawk” beach in Southwestern NS. One of the most beautiful places I have every seen.


    1. The Maritimes were at the top of our list for a Canada visit, and we are open to any and all suggestions of where to stay and places to see while we’re there, especially since we’ll have a car. Thanks for this suggestion – it’s already gone into our list of places to see and things to do!


      1. One more hint. If you are planning to go to Prince Edward Island (which of course you should!) you only pay when you leave the island. Your best value is to take the car ferry over and come back via the Confederation Bridge. It is a fair bit cheaper to do it that way, as opposed to the alternative.


  4. I am so in love with this idea! We are moving in a similar direction of 30 day stays going forward, because our days of bouncing from place to place are less appealing as we get older. And, our daughter, SIL and granddaughters leave next week for a three year assignment in Germany via the Navy, so an annual 90 day stay near them is in our future as well.

    We’ve been to most of the places on your itinerary. I’ll just give a shout out to considering staying within the Netherlands, even if it’s outside of Amsterdam, because the whole country is that amazing. Really, such an enchanting country, and on our list for a 30 day return stay for sure. The trains there seem to run with Swiss-procession, so commuting in from outside of Amsterdam should be quick and easy. And the costs for food, groceries, museums, etc. didn’t seem crazy high as compared to, say, Switzerland. Anyhow, just my two cents. 😊


    1. Our 90-day stays in Japan near family were absolutely magical. We felt like we had time to relax and really get to know more about Tokyo and the pace of life there. The hard part was saying goodbye when the time came – we wanted to stay longer. Germany will be exciting as you’ll be in striking distance of so many other places in Europe.

      Our long stays in other places last time (Florence, Strasbourg, England) convinced us that this was the way for us to go this time. We often found ourselves tired and frustrated when we stayed less than that, and that we didn’t get to see or do everything we wanted, or really get to know a place.

      We spent several days going exploring the Netherlands, but the cost for a full 30 days was always just too much for our budget. If we found affordable lodging it was often way off the beaten path. So, we decided to make Amsterday and the surrounding area a “longer weekend” – we’ll probably spend four or five days there before returning to our home base. You’re right about Switzerland though: crazy expensive.


  5. How wonderful! I will probably have moved back to Ankara when you visit Istanbul but, I would definitely drive and meet with you when you do visit. You definitely gave me something to look forward to.


    1. I am so hopeful we can get together in Turkey – I would love to meet up after all these years. If you have any suggestions for a “long weekend” excursion for us in Turkey, let us know – we are very open to suggestions.


      1. Wow! Looks like a fascinating area to visit. I’m guessing there would be flights from Istanbul, and maybe organized tours of the area? Thank you for this – lots to think and dream about!


  6. What a wonderful adventure. You have to make a stop in Ontario when you are in Canada. You need to go to cottage country. Muskoka, Haliburton, or Georgian Bay. These areas are only a couple of hours north of Toronto and the scenery is breathtaking with the lakes and the Canadian Shield. Sunset over Georgian Bay rivals any in the world. Also, Ontario is home to the longest freshwater beach in the world. Wasaga Beach.


    1. We are already trying to figure out how we can make this happen. We’re pretty sure we’ll be flying into Toronto from Mexico City if things go as planned, so this could be something we can possibly fit in before heading to the Maritimes. Thank you!


  7. Wow! Such a wonderful sounding itinerary! It will be interesting to follow along with you via the blog!


    1. We are very motivated to make this happen, and hope Covid will be under control worldwide by the time we set off. I hope the next couple of years will pass very quickly!


  8. I can hardly wait until your trip to Mexico and Argentina!!!!! So fun! I had been thinking about doing 90 day stays near my 2000 miles away granddaughter, so I think it is fabulous you are going to Japan a lot!!!


    1. We absolutely LOVED Buenos Aires the last time we visited and wished we had spent more time there. It was a no brainer that we’d go back this time. If not for COVID we would still be in Mexico, or just getting ready to leave – we had planned to stay for a year to rest, and see more in the area. So it was a given this time as well. And what can I say about Japan? It will always be the last thing taken off our list – we’re already antsy that we haven’t been there in over a year now.


  9. Isn’t it amazing that two years seems so long but when there are eight 30-day slots a year (3 months in Japan and one month in NE) that there seems to be too much world and not enough time?!

    Looks like you’ve done a great job of thinking about weather and the 90 day Shengen limit.

    Before Covid, I had a two year nomading trip mapped out that also included a month on Crete in Chania. I was pulling data in late 2019/early 2020 and my spreadsheet shows the cost of a OW flight from Athens to Chania was $114 on SkyExpress and took one hour on a direct flight. After Crete I was planning to fly to Cyprus for a month.

    Years ago I was working outside of Venice and spent a weekend split between Bassano del Grappa and Lake Garda. Bassano has gorgeous handpainted pottery plus, as the name implies, is known for grappa. The lake was incredible but very touristy and expensive (Sirmione). Both look like easy trips from Verona. Smart to be keeping to northern Italy in June. The Dolomite mountains are very unique and worth a trip.

    Australia in their winter sounds perfect!

    A couple of thoughts for holidays in Boston-area – Plimouth Plantation stays open through Thanksgiving weekend. My son and I spent two Thanksgiving dinners at the Plantation and they were very memorable. The Plantation is divided into two parts: English settlers and a Wampanoug village, which is staffed by bloodline Wampanougs. I know you have Mayflower blood in your veins and might find the Plantation very interesting. There are several “living” museums in New England beyond Plimouth Plantation and include Sturbridge Village in central MA and Mystic Seaport in CT. Mystic does evening lantern tours for the holiday season. Sturbridge also offers special events for Xmas. Several of the “summer cottages” in Newport, RI stay open through the holidays and are totally decked out with decorations. All easy day trips from Boston.

    I can’t wait to read more details as you flush this out and then follow along with you!


    1. First, thank you for all the information about NE and things to do there in the winter. We haven’t started to look at housing rentals there, but can already imagine that Boston will be too expensive, so we may end up in either Maine, Connecticut, or western Massachusetts. Who knows? We’ll probably be arriving sometime in mid-December (that’s the plan anyway), but oh would I love to attend that Thanksgiving dinner! I’d definitely fall on the side of the English settlers, but would still choose to eat on the Wampanoug side. I still think we need to visit no matter when we go. All of the other things sound right up our alley.

      We’re really please and excited about our destinations this time. I read somewhere else about Bassano, so we will be doing more investigation. There’s an AF base (Aviano) in the area, so we’ll be able to top off prescriptions when we’re there and it’s located close to Dolomites, so we’d also check into what their recreation office offers.

      We think we can pull this off as long as COVID comes under control. The next two years are both going to go extremely slowly and extremely fast, if. you know what I mean.


      1. Both Portsmouth, NH and Providence, RI are one hour from Boston. Amtrak is direct from Providence to downtown Boston and many people commute. PVD will be easier living without a car then NH. CT will also be challenging without a car.

        You might want to look for housing at the ends of the “purple line” commuter rail for Boston. Here’s a link to the overall system map for MBTA.

        That being said, the Berkshires, in Western Mass are charming, but probably challenging without a car.

        I can’t wait to be a voyeur as you continue to refine, research, and share your plans!


      2. These are good locations for us to know, especially in the coming years when we plan to spend a month near the girls over the winter holidays. Our girls don’t think at our ages that we are a good fit for year-round living back east, so we are continuing to think about where to settle whenever we give up traveling again.

        Brett and I have near daily discussions about the itinerary, costs, etc. It’s so much fun to be doing this again!


  10. This sounds like so much fun! No wonder you’re so excited to become a nomad again.
    I’ll put a world map up on the wall in front of my desk to follow you along. Bring on 2023!!!


    1. We’re excited and happy about the itinerary we’ve come up with – it’s very motivating! 2023 often looks a long way off, but from past experience it’s going to come around faster than we expect – we have a lot to do to get ready!


  11. If you are going to be in Germany anyway, it would be a shame to miss Berlin. It’s an amazing city. You would need more than a weekend though!


    1. Berlin was in strong contention for where to stay in Germany, but we eventually settled on the Rhine area because of its proximity to Amsterdam and Strasbourg. I also very much want to visit Cologne (Koln). We may try and squeeze in a visit to Berlin, but it would sadly only be for four or five days if we do.


      1. You could do Berlin via train! We did it in a weekend- like all big cities, there is always more to see.
        I highly recommend the military hotel Edelweiss in the Alps. I know you prefer air bnb- but it might be a good stop. You can train into Munich (which I love) and get a train or bus to Garmish. Like all military hotels, they book up fast.They offer a ton of day trips to the area I will be there for my birthday a year from September!

        Your itinerary looks amazing. I am interested in seeing how it goes in South America. That is one place we have not visited, but am very keen on doing in the next five years.


      2. We’ve looked at doing this, even going over for a just three days or so. It will depend of course on time, money, and energy, but we would very much like to visit Berlin if possible.

        We LOVED Buenos Aires when we visited before, and a return trip has long been a priority. With a 30-day visit there is so much more we can see and do (we were only there for 10 days before).


  12. If you are going to land in Toronto, Niagara Falls, Ontario is less than a 2 hour drive away – the Niagara Escarpment area is beautiful. I have lived in Niagara Falls all my life and seen the falls in all seasons many times, all are beautiful.


  13. How exciting. So for your week in Sydney, you are welcome to stay with us. Save the $$$ on accommodation. While there’s no night life, the city and beach are a train ride away and we are on the train line.

    As to the Rhine, although Köln is big, I didn’t like it much. (Shhh. Don’t tell my aunt.) Koblenz, where the Rhine joins the Mosel, is a small town with easy access up snd down the Rhine and Mosel. I loved Mainz even more.


    1. Thank you for the invitation – we would love to stay with you. Lots of time to chat, drink, etc. LOL. We may just take you up on it! We did love our little apartment in Potts Point too – it was a great location.

      We are starting to zero in on Mainz as a good location – they seem to have more affordable rentals there, and it’s close enough to get over to Strasbourg as well as up the Rhine and to Koln. I really only want to go there for a day to see the cathedral and the area surrounding it. I read a fascinating book a few years ago about a major WWII tank battle between the U.S. and Germany and ever since have wanted to see the place myself to understand it better (the Germans had the better tanks and were favored but the U.S. somehow pulled off a victory even with all the odds against them).


      1. OK, both Mr S and I loved Mainz. Had two of the best dinners in Germany there. So much to see in the little town. And a quick train ride to Frankfurt airport. In the centre of town, Gutenberg museum of printing – he was from Mainz. Roman boats. Roman ruins. The only memorial to WWII in Germany that admitted their responsibility and that loss was actually freedom. Koblenz wins for quick trip by train to Trier (which is a MUST see for Roman ruins) and Köln and Moselle wine towns.

        As to Sydney, I’d love to share some sights of natural beauty or let you explore whatever it is you want to see alone.


      2. I’ve read how easy it is to pick up a ferry or similar service on the Rhine from Mainz or other places, an affordable and easy way to get to other towns/sites if you’re staying for a while. I had no idea there were so many Roman ruins – they are one of my favorite things to investigate. Seeing the Colosseum, Forum, and surrounding area in Rome was a dream come true for me.

        There are only a few things we’d really like to do again in Sydney. One is visit the zoo again as it was so hot the day we were there before. We saw quite a bit, but also missed a lot as well and would like the chance to do it again under better weather conditions. The views were spectacular, and the animals fascinating to us. We’d also like to try the beach walk again from Bondi and see if we could get a little further along this time – the heat drove us off before and we didn’t get very far. I would still like to do the backstage tour at the Opera House if possible (Brett is not as keen). We would be very open to seeing places of natural beauty in and around Sydney though. I am greatly looking forward to getting together with you and setting the world straight once again.

        Liked by 1 person

  14. Can’t wait and time is speeding by. Can’t believe it is almost May. You’ll be traveling in no time.


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