“These boats have a very high “look back” factor, meaning upon leaving the boat you keep looking back to enjoy her lines. A key indicator if you should buy the boat.

Calypso, Sabre (Sail) 36’

Interview with the Captain – Peter Fein

About Boating 

Why did you choose to buy a Sabre?
I was looking for a sailboat in the 34′-36′ range for New England cruising, day sailing and occasional club racing. The Sabre 36′ was love at first sight. These boats have a very high “look back” factor, meaning upon leaving the boat you keep looking back to enjoy her lines. A key indicator if you should buy the boat.

What other kinds of boats did you consider before buying this particular model (and how did they compare)?
I shopped a bunch of different boats but after being aboard a few Sabres I focused exclusively on them. The Sabre quality of construction is well above the typical 80’s / 90’s production sailboat.

How did you come to find/locate her before purchasing (and what’s the boat’s history if you know it)?
I found her on YachtWorld and contacted the listing Broker. She was down in Stamford, Connecticut on a private dock and had been lightly sailed on Long Island Sound her entire life under two previous owners. She was well maintained and had a nice cruising equipment list. We had a flawless three day trip home to Marblehead in early May 2013 and I knew I had a special yacht.

Who first introduced you to boating/sailing?
When I was quite young my father used to take me sailing with his Aunt and Uncle who had a 33′ sailboat out of City Island, NYC. I have very fond memories of those times. Later on with minimal experience I joined my college sailing club and got the bug. After graduation I started sailboat racing as much as possible. Shortly after I bought my first sailboat and have really enjoyed ownership and maintenance as well. While sailing is my passion I love being on the water and have owned a few powerboats as well.

What boats have you previously owned?
Pearson Triton, Pearson 26, Evelyn 25, Cape Dory 25, Pursuit 2320 (Power)

What are the features you like most about your boat?
She is a great all around boat in this size range. She has good light air performance which is important for Marblehead summer conditions. Her keel / centerboard design only draws 4’4″ with the board up which allows gunkholing into the quietest of coves when cruising. 

What features/improvements have you added or do you plan to add?
Calypso is equipped for extended coastal cruising and performance sailing. She has a B&G autopilot, large battery bank, refrigeration, a full set of canvas, new sails and a custom v-berth mattress. Future improvements include a cabin heater and updated electronics.

Do you belong to a yacht club or other boating organizations (and what’s your homeport)?
I am a member of the Boston Yacht Club and Storm Trysail Club. Home port is Marblehead, MA.

What is the biggest challenge you have in servicing your boat?
I am a DIYer and do most of the service and upgrades myself. Marblehead Trading has handled hauling, launching and rig storage since I bought her.

Do you have any advice for those looking to buy a Sabre like yours?
With beautiful all wood interiors, these boats require above average level of maintenance to keep them looking bristol. Always be on the lookout for water intrusion and deck leaks must be dealt with quickly.

What’s the story behind the boat’s name?
She has always been known as Calypso and we decided to keep this classic name.

Click the gallery below for more photos and information about Calypso!  And be sure to check out her socials as well!
Instagram @pbfein