Seven Reflections After Our Second Consecutive Annual Trip of a Lifetime

We just spent over a month in Milan, Italy; Stresa, Italy; Zakynthos, Greece; Ithaca, Greece; and Kefalonia, Greece.  You might say we had a one-week trip in Italy to prepare us for three-plus weeks in Greece’s Ionian Islands.  Milan had delicious food, our first Italian lake experience on Lake Maggiore in Stresa surpassed every expectation, and sailing around three new Ionian Islands brought us to some of the most beautiful beaches.  We are lucky to now be living the life we slowly curated over the past decade.  For us, that life includes a lot of travel!

Our May-June travels lasted more than a month and happened a year after our last month-long trip to Sicily in 2025.  We love the month-long trips and plan to keep them in our regular travel rotation.  The European style of vacation is correct.  We should all take a month off to enjoy summer and make memories.

But we also do not think one month of summer for travel is enough.  We spent more than three months of 2025 traveling and should end up with similar statistics by the end of 2026.  Getting to travel as much as we want adds perspective about how to travel not just to escape but to improve your life, whether at home or traveling, as a whole.  Here are seven takeaways following our second annual “trip of a lifetime” where we left the country for a month or more:

1. Save more money than you need for the travel you plan.

We live in an age where many travelers want to take extravagant trips, regardless of the cost.  About a quarter of travelers charge their trip to their credit card and carry a balance from trip expenses, accumulating credit card debt in order to fund travel.  At a minimum, make sure you have the money to pay for your travels before traveling!  The stress of debt when you come home can completely ruin the restorative effects of travel.

Beyond having enough to cover the trip, you should have some contingency money because you always need to be prepared for something to go wrong.  When I studied abroad in Egypt, I only saved enough money to cover my trip without any extra.  I was 21 years old without a lot of spare money, so enough was the best I could do at the time.  My roundtrip plane tickets cost about $1,000, thanks to an overnight layover in the London airport that I could tolerate 14 years ago but not today.  My parents told me that I would eventually be responsible for the cost of the plane ticket, but they paid it initially so I could keep that $1,000 to use in case of emergency.  It was June 2012:  , Egypt had just gotten through the Arab Spring and was holding its first democratic elections after the revolution.  Having a little extra in case I needed to relocate in a hurry made sense.  When no emergencies occurred that summer, I reimbursed my parents for the $1,000, but I had the safety of a little extra just in case.

While I did not need that extra money in Egypt, we needed the extra money this year.  On the day we were supposed to take a train from Milan to Stresa, Italy had a nation-wide train strike.  We ended up getting an expensive rental car to make the journey because I was not missing a single night at the luxury lake hotel with a much more expensive nightly rate than we usually pay (thanks to booking with points!).  Instead, we paid for that very expensive rental car and got to the hotel a little earlier than planned.

There were lower-dollar changes on our trip as well, including the ferry rates between Zakynthos and Ithaca due to poor customer service from the ferry booking company we talked to in Zakynthos.  Even if you only encounter small dollar changes, they can add up to stress if you save only exactly enough money for your travels.

We save way more.  In fact, I have a high-yield savings account called “Extravagance,” with the sole purpose of providing money to spend on our most extravagant month-long trips.  The fund had about $12,000 in it before the trip, and it now has about $7,000 afterwards.  In other words, we spent extravagantly but still did not spend even half of what I set aside.  Knowing there is money if we need it is a big part of what makes travels feel free and extravagant.

2. Spend on what matters, and save on what does not.

While we spent extravagantly, we also spent intentionally.  We walked into our five-star Stresa hotel expecting to do laundry there.  The couple of times we have had laundry done at a hotel, it was usually a per kilogram rate that allowed us to easily wash lightweight workout clothes.  This was not the case at La Palma Hotel in Stresa.  (I am about to criticize their laundry service but want to note that I would absolutely go back, loved this hotel, and would recommend it to anyone!  It is probably the nicest hotel I have ever had the pleasure of visiting.)  Laundry at the hotel cost 2 euros for a pair of socks, 2 euros per pair of underwear, 3–5 euros per shirt, and more for nicer pieces of clothing.

We ended up taking our dirty laundry to a laundromat in town.  The laundromat was an eight-minute walk from the hotel, and we started it before dinner, switched it to the dryer between dinner and gelato, and then brought the laundry home when we were done eating.  Dinner, gelato, and the laundry cost less than the laundry alone would have at the hotel.

The laundromat we opted to use in Stresa because we refuse to pay five euros to wash a single shirt.

Even when we stay at a glamorous hotel, we remember to spend on what matters and save on what does not.  Waking up to the view of Lake Maggiore and the Italian Alps mattered.  Sitting in a sauna with a view of the lake mattered.  Lounging on the lake itself mattered.  Eating granita while watching the boats go by mattered.  Having our laundry done at the fancy hotel did not matter.

The gorgeous view of Lake Maggiore that made us feel like royalty, who refused to pay excessive laundry fees.

This same concept had led us to enjoy more dinners out in Sicily than ever before, but we still limited our dinners out in Taormina because that town was more expensive.  In our eight days there, we had pizza two of the nights we went out to dinner and enjoyed one dinner with a beautiful view of Mount Etna.  Otherwise, we enjoyed breakfast or lunch out instead and prepared meals at home at night because the price of a pasta in Taormina was double the price of a better pasta in Cefalu the day after we left Taormina.

On the other side of the equation, we spent some large sums of money this year on our first and second private boat tours ever.  In Zakynthos, you cannot travel to some of the most beautiful spots on the west coast unless you are in a small boat with an experienced guide.  Public tours with 10 or more passengers are too large to navigate the caves, making private boat tours the only option to see the bluest waters and sea caves.

While I still will not pay five euros to wash one shirt, I will absolutely spend 400–500 euros for five hours of these gorgeous waters in this cute boat with my own skipper at my own pace:

Calypso Boat Rentals in Zakynthos will show you the most beautiful swimming spots and caves on the island if you stop in Zakynthos on your travels.

3. Travel improves health. 

I always felt like travel improved my health and made me feel better generally.  Since getting a Whoop in late 2024, I have actual data supporting this feeling.  My health statistics improve dramatically when I am traveling, and this is more pronounced when I travel for longer periods of time.  On the day I am writing this, my heart rate variability (HRV) is 60 ms and my monthly average HRV is 66 ms.  In fact, I have had an HRV above 100 ms exactly six times in just over a year and a half with Whoop.  Each of those days was while traveling: Three were in Sicily in May and June 2025, one was on our Caribbean cruise in August 2025, and two were on our recent travels to Greece in June 2026.  Each of these trips also included days where my typically-60-something ms registered above 95 ms.  Each of these trips was also longer than a week and included ideal ratios of relaxation and adventure.

My lowest resting heart rates follow a similar trend, so much so that I joke the second my average resting heart rate registers as 50-something bpm instead of 60 bpm, I know I am in vacation mode!  Traveling lets my resting heart rate fall to below 55 bpm, while everyday life typically has too many stressors to keep it below 60 bpm regularly.

For me, travel is also a time when I can bring up Vo2max in my rugby offseason with long and controlled Zone 2 runs to see tourist attractions.  If you have not experienced a tourist run, bike, hike, swim, or kayak on vacation, I highly recommend it!  Whatever your activity of choice, there are places you can see better when travelling by foot or paddle than by a tourist bus.  By contrast, my Vo2max usually dips a bit during my competitive season when wear and tear prevents the extra miles required to maintain a high Vo2max, and prioritizing muscular durability becomes more important.

Beyond fitness, the world as a whole offers healthier food choices than American pub fare or Doritos on the couch.  Eating the local cuisine wherever you go is almost guaranteed to improve your health.  Exposure to different fruits and vegetables bolsters the plant diversity of your diet.  For me, this is as simple as putting apricots on my oatmeal when in Italy or Greece in June because they are in-season and delicious.  At home, I typically have berries.  Both options are foods with health benefits, but consuming a variety of foods offers additional health benefits.

Finally, switching from your mental reality of focusing on work, kids, or whatever responsibilities you have at home is refreshing and important.  When your decision-making shifts from scheduling dozens of tax returns to where to go for dinner, your brain gets a much needed reset.  Instead of practice planning, the planning becomes whether to go to the beach all day on Tuesday and the mountain hike followed by a wine tasting on Wednesday or to flip those days based on weather.  Importantly, recovering from decision fatigue only happens if you allow yourself to travel slowly, and the health outcomes support taking a slower pace.

4. Travel leaves me with more future travel plans rather than fewer.

Some people think about travel as a list of world highlights to check off over time.  The “bucket list” approach to travel sends everyone to the Pyramids, Colosseum, Eiffel Tour, and Taj Mahal.  I can confirm that all of those places are wonderful to visit, but when I listen to all the Americans on the flight from Athens to DC describe their trips to Santorini, I cannot help feeling sad for them that they will never even know Kefalonia exists.

When Americans think of Greece, they think of the Parthenon in Athens, white houses cascading down the cliffs of Santorini, and parties with beach days in Mykonos.  And maybe gyros.  But there are 119 Greek islands that are inhabited all year and more than 200 Greek islands with some kind of population at least part of the year.  There is so much more than Santorini and Mykonos, but if you look at Santorini and Mykonos as boxes to check off on your bucket list, you miss all the other islands.

I first saw Corfu on a cruise with my parents and thought it was the most beautiful water I had ever seen.  This made me suggest it to Patrick as our honeymoon destination, and we loved it.  Corfu also introduced me to the Ionian Islands generally.  This island chain off the west coast of Greece has this unmatched electric blue water, tons of breathtaking beaches framed by cascading cliffs, and mountain views that let you see the shape of every surrounding island.  Corfu inspired us to go to Zakynthos, Ithaca, and Kefalonia this June.  This year’s trip made us see that our 23 days in these islands was not enough.  Years from now, we want to come back and experience all of the Ionian Islands from the sea to hit a couple more of those hidden beaches while returning to some of our favorite ports explored by land.

This feeling of travel inspiring more travel is not unique to the Ionian Islands, as beautiful as they are.  Our month in Sicily included a day trip to Vulcano.  Vulcano had three main attractions we wanted to see.  We wanted to climb the volcano, experience the hot springs beach, and visit the black sand beach on the opposite side of the island.  The black sand beach was probably my lowest priority, but I found myself in awe over its beauty and the feel of the water.  This one-day excursion taught us that we were not done with Vulcano, and that the Aeolian Islands deserve their own dedicated travel experience in the future.

When you stay at home, you only know about the famous bucket list destinations you have not visited.  When you travel, particularly when you travel slowly, you realize the world is so much more than those destinations.  Each place you experience shows you how little you have experienced and how much more there is out there.  I love the way travel pushes our worldview to expand with ease.  Every box I check off leaves me drawing five new boxes I did not know existed.

5. “Trip of a Lifetime” labels are too much pressure.

While travel naturally broadens your perspective, planning one big “Trip of a Lifetime” closes the door on this potential perspective expansion.  Instead of exploring new destinations with an openness to learning there is more to the world than you ever knew, a “Trip of a Lifetime” usually aims to have you see what you already determined are the most important places to visit.  This limits how travel can improve you and your life before the travel begins.

A “Trip of a Lifetime” label also puts too much pressure on one particular travel adventure.  If anything goes wrong, it can feel like the entire trip is ruined because a “Trip of a Lifetime” is supposed to be perfect!  But if you are on another fun month away, just like you were the year before, a nation-wide strike in Italy is just something you adapt to overcome rather than an event that ruins your perfect trip.

I know not everyone can travel for a month every year, even if I think the month-long holiday standardized by white-collar Europeans should be available to everyone.  Given your constraints, I encourage anyone to find an amount of travel that is achievable for them on a continuous basis.  Travel should be something you can keep coming back to over time, even if it means shorter durations.  Let every travel adventure stand alone with its unique benefits, and let it inspire your next trip rather than being the one big trip.

6. Book your next travel adventure before you embark on your trip.

Coming back from an amazing trip is difficult when you have no future travel on your schedule.  To make coming back easier, schedule your next trip before you even embark on your current trip!

Friends have asked me if it was tough coming back from our month in Italy and Greece, but I went to a rugby tournament to cheer on my teammates the day after I landed back in the United States.  Two days after landing, I attended a friend’s birthday and moving (boo!) party.  Five days after landing, I was back on a plane to visit my dad in Connecticut.

And some bigger travel is also already planned.  Before leaving for Milan, we knew we had a California baseball and beach vacation planned for later this summer, a Caribbean cruise booked on the new largest ship in the world in November, and a Las Vegas Thanksgiving trip with Patrick’s family.  We also had plans without bookings for shorter trips to the beach in Ocean City, Baltimore for baseball games, and Baltimore for a rugby matchup between the top two teams in the world.

At a minimum, have the next trip or event booked.  When your life feels like one big adventure filled with travel and events with friends and family, the joys of travel spread to every piece of your life.

7. Add your favorite parts of travel to your daily life.

When the benefits of travel spread to our daily lives, we become better and healthier people.  I started to notice habits I like in the travel version of myself that I wanted to bring to my daily life.  When I travel, I am eager to get up and start some morning cardio because I am excited for the adventures I have planned that day.  The sooner I run, the sooner I get to go on a luxury boat tour, hike a scenic gorge, see a white peacock in a beautiful island garden, or plant myself on the beach.  Back home, I struggled to incorporate the same morning cardio because I would sometimes be dreading a task I had to do after the run.  None of it was actually about the run—it was about how excited I was for the post-run activity.

To adjust, I started adding more events to look forward to in daily life.  Since we have schedule flexibility, we have some mid-week beach days or hikes on the calendar that add similar energy to our travel excursions.  Escaping the routine of daily life and incorporating something new every week infuses travel energy into our lives.

There are smaller differences too.  When traveling, I almost always eat breakfast outside on whatever balcony, porch, or beachfront table I have available.  I have a lovely little balcony at home and can do that here too, but I often just do not because it is not my habit.  Coming home this year, I am making a point to eat breakfast at a slower pace outside on the balcony to start my days with the simplicity I feel when traveling.

The pieces of travel that enrich your life will be different than mine, but taking a piece of your travels home will make you appreciate your little world more every day.