Rakowski's Around the World - June 2025 update @Rak_Travels

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Hadley Rakowski

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Sep 25, 2025, 9:04:42 AMSep 25
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Hello dear friends and family,

We’ve officially launched into the first legs of our global adventure—and we’re writing with hearts full of gratitude and awe. Since our last update, we’ve sold nearly all of our belongings (with just a few sentimental items tucked away, thanks to the generosity of a friend), Jordan has graduated from high school (YAY!), and Jeremiah has wrapped up his final day of work. We are now fully in it—living the journey we spent so long dreaming and preparing for. Sadly, our beloved Kenai crossed the rainbow bridge after 12 wonderful years protecting and loving our family. Our hearts are shattered, and we're at peace knowing he's not in pain and can be with us in spirit on our journey around the world.

Jordan has started a travel Instagram account @Rak_travels where he is sharing occasional updates and moments from our journey. And, we've resurrected our old family blog (https://rakowskiscoasttocoast.wordpress.com/) that Trinity crafted when we moved across the country in 2016. We are taking our time adding to it, and you will find that the first few posts are in great detail about our experiences, and as it evolves, we've transitioned to more of a summary of what we're up to. This will be the last of the emails, as we will update the blog going forward. You can sign up to receive notifications when it's been updated on the site. If you're having trouble figuring it out, ask your local teenager to help you. Happy reading!

Here’s our updated itinerary:

  • June 2025: Mexico (Southwestern Baja California)

  • July–October 2025: Vermont, then Europe (Portugal, London, Scotland, Netherlands, France, and Spain)

  • October 2025–April 2026: Southeast Asia (Indonesia, Thailand, Vietnam, Philippines, Japan) & Mallory and Trinity will join us for part of this adventure

  • May 2026: Hawaii for Trinity’s college graduation 

As always, we welcome your continued support—whether it’s local knowledge, a warm introduction, food tips, or simply cheering us on. Thank you for being part of our ever-growing circle. This journey is possible because of you.

With love and gratitude,
Hadley, Jeremiah & Jordan

ps - Please feel free to share this with others you think would enjoy it. 

---------- Forwarded message ---------
From: Hadley Rakowski <rakworl...@gmail.com>
Date: Sun, Jan 19, 2025 at 3:23 PM
Subject: Rakowski's 100 Days to Departure: The Countdown is On!
To:
Cc: Hadley Rakowski <hadleyr...@gmail.com>, Jeremiah Rakowski <jeremiah...@gmail.com>

Hello, dear family and friends,


Yesterday marked a special milestone: just 100 weekdays until we embark on our journey of world travels! The excitement and anticipation are palpable, and yes, there’s a fair share of nerves mixed in, too. As we count down the days, big milestones are quickly approaching—Jordan’s high school graduation is on June 5, and Jeremiah’s last day of work is June 6. Between now and then, our lives are a whirlwind of administrative tasks, purging, packing, donating, organizing, and letting go of attachments to physical things in preparation for this incredible adventure.


As the practical tasks are checked off, we’re diving into the fun part: planning our travels! We’re thrilled to share that we’re embracing a mix of four distinct travel styles that will give us a blend of experiences:

  1. Vacationing with Airbnbs: Comfortable and flexible, these stays will let us soak in local culture and explore at our own pace.

  2. Workaways (workaway.com): This incredible platform allows us to trade home/property support for food and accommodations, immersing ourselves fully in the cultures and communities we visit.

  3. TrustedHousesitters (trustedhousesitters.com): We’re beyond excited about caring for homes and pets as part of our travels, which will add a heartwarming element of animal love to our journey.

  4. Staying with friends or introductions: Building community through connections is a core value for us, and we’re so grateful for the people who have welcomed us into their lives—and who will hopefully welcome us into theirs!


As we prepare for this adventure, we want to extend a heartfelt invitation to you, our family and friends, to be a part of this journey. If you have any connections in the countries we’re visiting, we would be incredibly grateful for introductions. Whether it’s sharing a meal, swapping stories, cooking together, offering local tips, or even a place to stay, we’re eager to build community through connection. We’d love to learn about your contacts’ customs, food, or simply hear their life stories. Here’s our rough itinerary so far:

  • June 2025: Mexico (Southwestern Baja California)

  • July–September 2025: Vermont, then Europe (Portugal, London, Scotland, Netherlands, France, and Spain)

  • October–December 2025: Southeast Asia (India, Indonesia, Malaysia, Thailand, Vietnam)

  • January–March 2026: Philippines (open to network on any island & Mallory and Trinity will join us for part of this time)

  • April–May 2026: Southeast Asia (4 weeks—perhaps Cambodia or Laos)

  • May 2026: Hawaii for Trinity’s college graduation!

  • May–June 2026: Japan

Our journey is like the weaving of a great tapestry—every thread of connection adds strength, color, and beauty. It’s also a bit like the fabric of a trampoline: every friend, family member, or connection has helped us grow and expand. Now, as we leap (😉) into this new chapter, we’re excited to see how far this incredible web of relationships can stretch across the globe.


Hadley, ever the creative, has mastered dehydrating and rehydrating her sourdough starter so she can bake bread wherever we go. Her dream is to break bread—both literally and figuratively—with the people we meet, sharing warmth and connection around the world.


We’ve intentionally left room for spontaneity and the unexpected in our itinerary, and we know that’s where the magic happens. Your support, advice, and connections could be the key to unlocking some of the most meaningful moments of this journey. Whether it’s a restaurant recommendation, a ride to the airport, or simply cheering us on from afar, your encouragement means the world to us.


Thank you for being part of our lives and, now, part of our travels. Here’s to the next 100 days of preparation and the countless adventures to come!


With love and gratitude,

~The Rakowskis (Jeremiah, Hadley & Jordan) PS - Please feel free to share this with any of your contacts, and if you no longer want to receive updates, please reply letting us know.


---------- Forwarded message ---------
From: Hadley Rakowski <hadleyr...@gmail.com>
Date: Sun, Sep 29, 2024 at 11:10 AM
Subject: Rakowski's around the world
To:
Cc: Rak World Travel <rakworl...@gmail.com>

Hello Everyone,

For those who know us, you’re aware that we’ve spent the last 25 years climbing the professional ladder while raising our three wonderful children. Two of them have already moved on to their versions of adulthood, and our youngest is just eight months away from graduating high school.

As we face the prospect of an “empty nest,” we have engaged in some soul-searching about what’s next for us. With countless possibilities ahead, we’ve decided to think BIG and embark on a unique and exciting adventure: we are going to travel the world for an indefinite period.

Having spent our marriage in a routine that often felt like a grind—working long hours just to pay bills and support our family, seeing each other only at night and on weekends—we’ve decided to follow our hearts. We want to prioritize quality time together, explore what the world has to offer and break free from that constrained lifestyle. Additionally, we hope to show our son, who is still figuring out his path, that there’s a vast world out there with many ways to live. 

With that in mind, the Rakowski family is hitting the road! Beginning June 2025, Hadley, Jeremiah, and Jordan will set off on an adventure that will take us around the globe. We plan to explore places we’ve always wanted to see, research our family history, reconnect with old friends, meet new friends, and discover how community is fostered in different cultures.

We would love your help! If you have suggestions for places to visit or connections with people around the world who might be open to hosting us or helping us navigate new areas, we welcome any introductions. We are open to visiting any country, and some of the places we’re considering for the first year include France, Scotland, Netherlands, Spain, Portugal, Indonesia, Thailand, Vietnam, the Philippines, Jamaica, and Mexico. One of our main focuses during our travels is to find community and share cultures. We hope to connect with people in each location, share a home-cooked meal, and exchange stories about ourselves.

At this time, we plan on keeping family and friends apprised of our adventures by way of email from rakworl...@gmail.com. We'll let you know if we decide to document our travels via another means. Please let us know if you'd like to be added to our email list for updates.

Thank you for being a part of this journey!

Warm regards,

The Rakowski Family


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