Things to consider when buying your first sailboat

Things to consider when buying your first sailboat

Searching for a sailboat

It all started right after Hurricane María hit Puerto Rico, September 20, 2017, or maybe a little bit before that for me. Looking into old Affirmation and Planning documents I keep writing once in a while, I found that back in 2015 and 2016 I was already visualizing myself owning a sailboat.

But Hurricane María made it real.

For the past ten years, I've been renting apartments in San Juan and I've moved six times during that period. It was important to me to have a place where to live with my daughter, who moved with me when she started college, and my youngest son that stays with me every chance we get.

 Hurricane María damage to apartment

Hurricane María damage to apartment

When Hurricane María hit, I lost the living room window of the 17th floor apartment I was renting in front of the beach. When the owner of the apartment came to see the damage, she expressed to me the desire of fixing and moving back into the apartment.

For some reason, the message came loud and clear and my first thought was to purchase a sailboat. It was going to be cheaper than buying an apartment I thought. I want ahead and started out my search. Of course, that meant doing a Google Search: Sailboats for Sale.

Searching for a sailboat for sale online

It was all new to me. Not knowing how to price a sailboat or how to tie brand, year, size and price together, it was not an easy task. I started to look into local sales and my base price at that time was $25,000 and from 1985 onwards. I was way off. I went to see some boats on that price range. It was clear I had to raise my price range and year of manufacture.

I continued looking for the best option. After some research online, I was clear I wanted a Beneteau or a Jeanneau. After reading reviews and all sort of data, they came out as winners. Also, I decided that I wanted it to be within 37 and 45 feet to accommodate a spacious and livable live aboard sailboat comfortable enough to fit my family if they wanted to stay over.

Getting real about the price and condition of the sailboat

 Beneteau 411 Galley (Cool Change)

Beneteau 411 Galley (Cool Change)

Suitable options started to come along, but the price was significantly higher than the starting price. Besides, this was after Hurricane María and there were a lot of options, including salvage and damaged boats. Also, it was unclear what to find in what conditions. Everyone was trying to get rid of their damaged boats, specially if covered and paid by insurance. I expanded my search to the Leeward Islands in the Caribbean to Florida and the Northeast.

Again, even though I was ready to work on the boat and fix whatever it needed fixing, I laid some ground rules as to what to look for in amenities and comfort:

My Sailboat minimum requirements



  1. 3 staterooms
  2. 2 heads (bathrooms)
  3. Air Conditioner
  4. Working Refrigerator/Freezer
  5. Good Sails
  6. Working Stove
  7. Water Heater


  1. Autopilot
  2. GPS
  3. Dinghy with Engine
  4. Solar Panels

In February I found it. And it had all the minimums, plus the extras and then some. It was impeccable. It had a scratch on the port side hull caused during the Hurricane, but besides that, it was perfect. The owner wasn’t ready to sell until April and I did look at other boats, but I had my sights on this one already and I was sure it was going to be mine.

Making the sailboat dream real

It all materialized in April 2018. I bought it without taking it out of the water. The owners were from Puerto Rico, but living in the Mainland. The boat was documented with the US Coast Guard and I kept that. It was an easy transition. I submitted the paperwork and it took about three and a half months to get the Documentation Paperwork under my name. I of course requested the decal from CBP and subscribed to Sea Tow for any unforeseen situation. I did a Survey for the Insurance and everything has worked out fine since.

Four Months living on the dream sailboat

Four months into it I am certain I made the right decision and I’m enjoying my new life at sea. I commute to San Juan every weekday now after my youngest started school and soccer practices, but I try to stay at the Marina and the boat as much as I can and I’m always looking for crew to sail with me during the weekends.

Don’t give up on your dream. Do as your heart desires, weight the pro’s and con’s, just a bit, and follow through.

Happy Sailing!