Behind the Scenes: How I Planned a Reader Trip to Tuscany

Behind the Scenes: How I Planned a Reader Trip to Tuscany

montefioralle 3In March I invited you to join me in Tuscany this October. Remember that? We’re going to be eating, sipping and hot air ballooning our way around Chianti for one glorious week, it’s going to be marvelous. When I started blogging in 2013 as a new expat in Germany I never would have believed that one day my then-sad little Blogger blog would serve as a platform for gathering travelers for a week in Tuscany. Low and behold, three weeks from today I’ll be drinking vino with 10 readers at a gorgeous Tuscan villa. In my book, this takes the cake on blog projects.

Back Story & Planning

Arianna, from Km Zero Travel, had initially connected with me over an Instagram direct message (of all places!). After a few Skype chats and kicking around a number of ideas on how we could collaborate, she suggested that we put together a trip and invite The Overseas Escape readers. Initially this suggestion seemed nothing short of outlandish. I honestly wasn’t confident that folks would be interested to join me in Italy, much less that we’d have enough to fill up her villa. I was inspired by Arianna’s confidence so I went through the motions of collaborating with her on an itinerary. I channeled my inner Margo Steves, if you will. (I’d like to promise to never say ‘Margo Steves’ again but I can’t.)

Screen Shot 2016-04-12 at 10.29.39 AMShe was delightfully adamant about ensuring that we had a truly authentic Tuscan experience. Case in point: when I asked if we could go on a bike ride she hesitated and reminded me that bike riding could be done anywhere. I then offered – what if we take a short Italian language lesson, bike ride to the market and purchase ingredients for dinner, exercising our new vocabulary? Perfect, she loved it. We went back and forth like this quite a few times before settling on the final itinerary.


With the dates, price, and itinerary nailed down I then needed to fulfill my end of the bargain – promoting it. I worked on this post for the better part of a day. I really wanted to communicate the attention to detail we’d poured into it as well as the fun, energetic vibe of the trip. This wasn’t going to be a grandparents retreat but an activity-filled journey centered around developing an understanding on what makes Tuscany so special. I choose my words verrrry carefully and hit Publish.

Escape to Tuscany with The Overseas Escape

pinterest-friendly graphic element I made for the big promotion


Within hours of posting the invitation to the trip I received two emails from travelers serious about joining us. Shortly thereafter I received more emails and the trip was eventually sold out. For a week we even considered expanding to a second villa nearby but after talking the plan over with my grandma, a well-traveled 87 year old, I decided to favor the intimacy of a small group and maintain the original plan. Fast-forward to today – we’ve all got our tickets, our meeting point at the Florence airport and even super awesome souvenir t-shirts. I can’t wait.

How this relates to you

By no means am I sharing any of this to self-promote or sell the trip. I learned something from this experience and wanted to be honest and open about it. Without Arianna’s optimism and insistence I honestly never would have dreamed of coordinating such a trip. Lesson learned. That said, I want YOU to know that no matter how wild YOUR idea is – whether it be to run a marathon, have a line at Target or write a cookbook – the only person actually holding you back is yourself. No matter how you do it, I challenge you to muster up the courage to apply yourself and ALL those amazing skills of yours to attempt something you thought was out of reach. Way back in 2014 I remember reading on World of Wanderlust that for the first year of blogging she literally just faked it until she made it. Today she probably has a million followers for each of her million hats. Whatever your angle – faking it until you make it, finding an advocate or simply, cold-turkey dropping your fears – go for it!

That said, I’d love to support YOU. Let me know what your big idea is THEN let me cheer you on to accomplish it. Tell me your big goal in comments below or email me at!

Brooklyn & Amtrak - The Overseas Escape-16

  • This is so exciting! Congratulations for putting together such a fun excursion! I wish I could join you.

    • Margo

      I’m reallllly hoping to do another one of these trips down the road so you’ll have to join us next time, okay? 😀

  • have fun on your trip! I’ll read all about it later:)

    • Margo

      You bet you will! 😀 Thanks so much, dear!

  • You go girl! Your hard work is an inspiration! I can’t wait to read about the trip, it sounds absolutely dreamy.

    • Margo

      Thanks, lovey! I expect to take no less than 1000 pictures so I’m sure I’ll have one or two to share. ;D

  • Good on you, Margo! You go for it, keep growing, and have a BLAST in Italy. I’m just sorry I couldn’t join in, but not for lack of wanting to!

    • Margo

      Just got your FB message! ECKK! So exciting! I can’t wait to visit your digs one day soon! Writing you back over there! ;D

  • I love this post, Margo!! And you know what the best thing is? Since I know you in person, I can definitely, one-hundred percent say that when you encourage us all to follow our dreams, you’re not just saying that – you actually genuinely mean every single word that your saying and I absolutely love you for it! You truly are one of the most positive and kind-hearted people I know – I miss you loads! 🙂

    • Margo

      Oh, my sweet friend. I’m soooo excited to see you SO soon! My Heidelberg visit can’t come soon enough and you’re getting a BIG squeeze asap! XO

    • I’ve never met Margo, but I agree! One of the most genuine bloggers I “know”. 🙂

      • Margo

        Gosh, thank you too Sarah! I admit there have been times that I’ve strayed from my voice in order to write what I thought people wanted to hear… but hopefully those days are long behind me. Thank you both for the love! Xo

  • Laura Leigh Wyatt

    This picture of you and Tara is the cutest!!! Love the way it’s edited too – did you use one of your presets for this? Fangirl geeking out.

    • Margo

      Ha! Yeah, sure did! I can’t remember which preset I used though! The back story on that shot is that there was a really sad headline but I told tara that I wanted to be laughing for this picture so she sarcastically read the (very sad) title aloud… which did the trick. 🙂

  • I can’t wait to see you soon and tell you the million ideas I have in my head!!!!!!!!!!!!

  • Esraa Bassiouny

    This sound great. I really want to visit Columbia one day and I am currently saving for it, finger crossed, It would really help if you have any advice for it.

    • Margo

      Oh man, I’d LOVE love love to see Columbia one day but I have absolutely no advice about South America as a whole. Sorry, dear! I definitely think you should go for it though! ;D

  • I hope you have the best time in Tuscany, the experience sounds amazing.

    Abigail Alice x

    • Margo

      thanks so much Abigail! I’m thrilled about it too! 😀

  • This is awesome!! Seriously, good on you!

    • Margo

      Thanks so much, Sammy! I really appreciate the support! 😀

  • The slow pace

    The trip sounds amazing!!! Looking forward to your upcoming posts (Because you are sharing the experience over here, no? We need to see how evertything goes!! Wonderfully, I’m sure)

    • Margo

      Oh, you bet, dear! I plan to take no less than a zillion pictures so I’m sure a story or two will trickle it’s way onto the blog. ;D

      PS. Your site looks amazing! I really love the new look and feel! Beautiful!

      • The slow pace

        Thank you! Well, we still have a lot of work to do but we try to improve it little by little when we have time :=)

  • Clint Mccool

    Sounds like a great idea and a really fun trip. Hope you plan another. Wish I’d come across it sooner. Clint from Alaska.

    • Margo

      Thanks so much, Clint! I’d certainly love to plan another – whether it be in Tuscany or elsewhere (how about Alaska!?) so please stay tuned! 😀

  • Kristin

    Wow! This is SO incredibly inspiring. I’ve been blogging for almost two years and have loved every minute of it. I hope someday I’ll be able to write a travel book and make revenue from my blog. I look forward to hearing all about this trip–thanks for sharing authentically!

    • Margo

      Absolutely, dear! I really, really am trying to be completely open on this space – about who I am and what this whole blogging biz is all about. I LOVE that you dream of writing a travel book and seriously applaud you for it. What’s holding you back? Is it the content itself or something else? I’d love to learn more about what you envision!

      • Thank you for the sincere and quick response, Margo! I’d love to learn the ins and outs of the process of writing an e-book. And this summer I will be traveling for 3 months (woo hoo!!) and hope I can turn that into a book. I teeter between focusing on practical tips (where to visit, what to see, etc.) and more reflective copy (big picture, benefits of travel for mental health, etc.).

  • Very nice read.. Inspiring… 🙂

  • So awesome that you were able to pull this together. Wish I could tag along on the trip!

  • My wife is in love with the cover picture of yours.. :))