Our beautiful yacht is a classic. She’s a 1968 Islander sloop that is 37 feet long overall. She’s sloop rigged, fin keeled, and has a diesel inboard. She can sleep seven, has excellent standing headroom, and a very spacious cockpit.
More details about the model of boat can be seen at the Islander 37 Association web page. Not very many of these boats were made, so they are not often seen. They were succeeded by the Islander 36, which became a very popular model with hundreds sold.

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Hey guy,
My wife and I love your Wee Happy and Way Happy blogs. We are working out a plan to buy a boat and sail the Caribbean. We have found and Islander 37 and I am now curious about your thoughts on her abilities. I know she’s not a blue water boat, but would you consider her suitable for Caribbean cruising? What are some of the advantages and disadvantages of living and cruising on an Islander 37?
Thank you,
Jason
Hi Jason,
Sorry about the delay in responding to your message.
After living on an Islander37 for over a year, we still love her. It’s a great boat. We would recommend it to anyone. We have especially appreciated how well she goes to windward and how easy she is to sail.
The interior is a bit small for long term living aboard — there is a lot of storage but much of it is not conveniently accessible for day to day living. We lived on her while we were stopped working for too long. This is a boat that is better suited to actively cruising, not just living on!!
Yes, we would take her to the Caribean no problem, as long as the rigging, etc. was well inspected before heading out. That is what we need to have upgraded on ours before we take her to the Caribbean.
Good luck and happy travels!!
Lala and Capt K.