Dreaming of a dream trip?

How to book your dream trip in 3 easy steps

How I finally took my dream solo trip to Greece:

My instagram post from shortly before my trip.

I’ve had the urge to travel to Greece for many years.  After my first year of university, lost somewhere in between my dual passions of theatre and archaeology, I decided to take a gap year and travel to Greece, Italy, Egypt, and maybe a few other places (but primarily Greece).  I charted out where I wanted to go.  Airbnb was new, affordable, and exciting, and I planned some places I wanted to stay.  I started a blog, “Quest for Vitality” – I wanted to focus on fitness adventure during my trip.  I never went.

8 years later, and Greece started popping up again in my life.  I was cast as Sky in Mamma Mia, I played Assassin’s Creed: Odyssey, I read Madeline Miller’s excellent new book Circe, and I was reminded it is time to go.

My first idea, in this later stage in my life where I work in the tourism industry with small groups and have an appreciation for small group travel, was to join a sailing trip with G Adventures and visit a couple islands.  I found the trip I wanted, but I have a tendency for overcommitment – between my Yoga Teacher Training, another play I was in, various retreat and family commitments, I couldn’t line up scheduled dates with my own free time.  I didn’t book.  I waited.

Later, I thought “let’s just have a look at flights.  I have two weeks I can get away here – let’s see what’s possible,” and that’s when it all unfolded.  I used a combination of Hopper and Kayak.com to find good flight prices, and I noticed the flight home was significantly more affordable if I got one with a layover in another major city in Europe.  I looked into it, and a path was born – I would:

  • Fly from Toronto to Athens, explore the mainland of Greece.
  • Ferry from Athens to Mykonos, to enjoy some island life.
  • Fly from Mykonos to Rome, get a taste of another culture for a few days.
  • Fly from Rome, home.

All for cheaper than flying round-trip Toronto-Athens.  It just felt right – so I booked the flights within half an hour.  An hour after that, I’d booked myself into hostels for each of the major locations I’d visit.

Over the next week, I decided to check out Airbnb Experiences – an amazing gateway for affordable, EXCELLENT, small group or private experiences with local guides.  I saved so many experiences to my wishlist, I had to find a way to organize my thoughts.  I used a multi-tabbed spreadsheet to sort out my favourite experiences, and designed two sample itineraries for myself to work on.  I slowly started to turn cells “green” as I booked experiences on the platform.

I will blog another day about Airbnb Experiences in general – it is the best way to experience a new place.  I only had one incident where something was canceled (my Delphi day trip with a private guide) and it happened well before my trip so I found some other options in time.  Everything I experienced through Airbnb Experiences was top-notch.

I then sat back and was ready to go.  My first night in Athens was phenomenal – at the City Circus Hostel I shared a glass of wine with other travelers to break the ice, and we hit the streets of a festival celebrating the full moon at the acropolis, where there was live music & free entry to the acropolis museum.  I made about 10 new friends, which really set the stage for doing things together and finding community as a solo traveler.  Some of us stuck together for the majority of the trip – new faces were added in over time, and many of us just so happened to book the same ferry to Mykonos.

Based on my experience, I have 3 steps to share:

  1. Consider the cities you want to go to, and look at what Airbnb Experiences are available there first. Save a few to some wishlists to book later.
  2. Find cheap flights.  Plan to arrive in your destination around noon, as most check-ins are at about 2pm.  Book them.
  3. Find your accommodation – Airbnb if traveling with friends or want solo time, choose a hostel if you want to be social and find community.  Just book it – the rest will come.

This is part one of a short series reflecting on my dream trip.  Stay tuned!

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