Boston Sailing Again
A local sailor’s guide

Find your way
onto the water.

Getting into sailing in Boston Harbor can feel like a maze. I’m sharing what I learned so you can spend less time researching and more time sailing.

Explore your optionsRead my story
A father and daughter sailing together in Boston Harbor, with the city skyline behind them
Boston Harbor · Back on the water
A little about me

Some things stay with you.

I first fell in love with sailing in Miami. After a long break, I found my way back in Boston.

I grew up sailing in Miami and fell in love with it the first time I went out. I learned on a Hobie 16, then moved on to fixed-keel cruising boats. My dad taught me what he knew, and we figured out the rest through trial and error.

When we moved to California, sailing mostly faded into the background, aside from a couple of races where I joined as crew. Then, after more than 30 years in Boston, the sailing bug finally found me again.

I started sailing again in August 2026. Figuring out how to get back on the water wasn’t straightforward. I spent a lot of time researching clubs, classes, memberships, and the different ways to access a boat.

I started this site to help other people find their own way onto Boston Harbor, without having to do all the homework from scratch.
Getting started in Boston

Four ways to learn.
Plenty of ways to sail.

There are four places to learn to sail around Boston Harbor, and each offers access to boats after you complete classes or demonstrate your skills. I’ve talked with all four and spent money with three, so I can share a useful, firsthand perspective.

01 / LEARN

Find the right starting point

Compare training paths, prerequisites, and what you’ll need to feel comfortable at the helm.

02 / GET ACCESS

Choose how you’ll sail

Understand the options for getting out on a boat after you’ve learned the basics or tested out.

03 / GO SAIL

Make the most of the season

Practical notes from a local sailor to help you spend less time figuring it out and more time underway.

Coming this winter

Be ready when spring arrives.

I’ll be putting together a dedicated guide to each of the four sailing organizations this winter, with firsthand insight into the classes, costs, and boat access. Check back before the season starts, and you’ll be ready to get out there.

Back to the top ↑