We wanted this time around to be different.  We weren’t buying a starter-home/starter-boat.  We wanted something that could be our home on the water—around the world—for the next 20+ years.  With this in mind, we went into our search with the mindset that our next boat would be “the one” that would begin the next season of our life journey.  Here’s how we got started!

The search always starts with searching.  And that began months—and in many respects—years—before we got a broker involved.

Researching Sailboats

Damian’s go-to sites were bluewaterboats.org, sailboatlistings.com, and yachtworld.com.  He also religiously browsed sites that came up when googling the phrase: “best bluewater sailboats for a good price.”

Damian’s research was based on reviews, specs, and descriptions outlined on sailing forums, blogs, and comments.  He enjoyed anonymously reviewing the responses to sailboat-purchasing-banter from a myriad of sailors all over the world.

Damian valued comparisons between sailboats that were both worthy of ocean cruising and praised as comfortable to live-aboard.

Dreaming Sailboats

My search, on the other hand, commenced on Pinterest—duh!

For me, searching was a lot like dreaming.  Scrolling through countless photos and clicking further to determine from where the sailboat photos originated captured my attention.

I created the board “Sailboat Dreams” even before we had bought Gem&I.  The board was to store the sailboat images of interiors and exteriors that had won a place in my heart.

My hope was that in the future, I could reference it when we would “one day” start the search for a bluewater boat of our own.

Sailboat show disappointment

The Annapolis Sailboat Show we had attended in the fall of 2014 and 2015 had no longer been the exciting exhibition we had been told it would be.  We were relentlessly disappointed time and time again, because the types of classic sailboats of yester-year that caught our eye and made our hearts skip a beat were never exhibited in the show.  The closest thing we ever got to what we wanted was a Hylas—and clearly that boat was reserved for the millionaires.

This was frustrating for us, because so many of our sailing friends were enamored with the new sailboats displayed at the show each year.  They oohhed and ahhed and wanted us to ooh and ahh about these production boats too.  Yes, they were grand. But far too modern for our liking.

A pirate ship.

Now that’s what we really wanted.

The motivation we needed

After our trip to Boston to help with the Hands Across the Sea book packing project, Damian and I had both felt the desire to take our searching to the next level and get a bit more serious about what we were looking for.

It was time.

Together, we sat down together and made a list of all of the boats that we admired and used that as a springboard to launch us in the same direction.

Sailboats we like (in no particular order):

  • Passport 40
  • Island Packet 40
  • Hans Christian 41
  • Hylas 44
  • CSY 33
  • Shannon 28
  • Valiant 32
  • Fuji 35
  • Alajuela 38
  • Tayana 37
  • Pacific Seacraft
  • Mariah 31
  • Westsail 32
  • Baba 40
  • Hinterhoeller Nonsuch 36
  • Ta Shing Tashiba 36
  • Contest 43
  • Formosa 51
  • Fairlie 55
  • Vagabond 39
  • Liberty 458
  • Hinckley Sou’wester 42

Which sailboat was the winner?

Based on our wants and needs described above, which of the sailboats on our list do you think we chose?  What makes you think that?  Comment below to get the conversation going!