I’m not a gambling person, for sure!  I’d much rather have an actual thing or an actual experience, than the HOPE of winning money to purchase a thing or a great experience.  But…not gonna lie…I have fun playing the game “What if I won the Lottery”….and today, I’m sharing with y’all my little secret….If I Won the Lottery, Here’s Where I Would Travel!


Belmond Trains

If I Won the Lottery Belmond Dining Car

PC: Adventures All Around


If I Won the Lottery, I’d travel by luxury train!  According to the Belmond web site, “It all began in 1976, when we received the keys to the legendary Belmond Hotel Cipriani in Venice. A year later we began collecting the carriages for the Venice Simplon-Orient-Express, which launched in 1982 to whisk intrepid travelers to La Serenissima in style. Since then we’ve grown to a carefully curated collection of travel adventures, each with a rich story to tell.”


If I Won the Lottery Belmond Luxury Train

PC: Adventures All Around


France, Ireland, Italy, and the UK…there’s travel-by-train destinations available through Belmond for all these gorgeous countries.  How fabulously old school and glamorous!!!!


Rent a Castle in Scotland

If I Won the Lottery Scottish Castles to Rent

PC: Elysian Estates


Recently I was lost in the rabbit hole that is Pinterest, and came across an article about renting a castle in Scotland.  I know you can rent gorgeous villas in Italy, and all over Europe, but a castle?  Like a real castle?  Come on….!  With heat and running water…and beefy dudes in kiltes…a la Outlander….Turns out, that’s a thing….and www.celticcastles.com had an UNREAL menu of options!


If I Won the Lottery Scottish Castle Bedroom

PC: www.celticcastles.com

And y’all….they sleep a ton of people, because…well, because it’s a CASTLE.  Duh.  I think if we all go in together, and If I Won the Lottery, this is totally doable!


Witness the Birth of Our Nation

If I Won the Lottery Lexington and Concord

OK….this is TRUE confession time!  When my kids were young, and there was just no way to travel like I can now, I would create “fantasy travel plans.”  Yes, I am that dorky, and yes, being a Travel Planner has been in my DNA for a lonnnngggg time!  Here’s a trip I started working on in the 1990’s….starting in Jamestown, I want to travel New England, not totally geographically, but basically along the timeline of the Birth of our Nation.  Starting with the first colony, and ending around 1778 ish.  And, yes all you American History people out there, including my husband who shakes his head at me when I talk about this fantasy trip, I realize that history was happening simultaneously in many locations.  What I’m talking about is the BIG events.  My husband and I visited Lexington, Concord, and Plymouth last fall, and I got a taste of what this trip could be, and wrote about it as a guest blogger on my friend Tanya Foster’s Blog….but there’s SO MUCH MORE to see.


If I Won the Lottery Old North Church Boston


Why do I need to win the Lottery to do this trip….well, my fantasy is gorgeous New England Inns the whole time…maybe a driver…probably a historical guide…and…you know I’m going to be looking for travel treasures the whole time!  I wrote about some of my past finds in this post….so If I Won the Lottery, I’d have the spending cash to get all the things!


Harvest My Own Olives

If I Won the Lottery Il Falconiere


This fantasy is a tiny bit more involved than that.  My If I Won the Lottery fantasy begins with a gorgeous Tuscan Villa, complete with several bedrooms, a pool, a view, a chef…and I am there for a good solid three months in the Fall.  I’ll read a lot, needlepoint a lot, drink a lot of wine, visit my friends at Il Falconiere a lot, and participate in an olive harvest!


If I Won the Lottery Italian Villa


I want to shake the trees, gather the olives, take them to the local press, stay up all night with the locals eating and drinking all night, and taking back to my fabulous villa my very own stock of first-press olive oil.  Bellisimo!

If I Won the Lottery….that’s what I’d do…..what would YOU do????

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