Some of us see retirement as an opportunity to change our lives and fulfill big dreams. In the fall of 2017, Ronna Benjamin and her husband Mike did just that. They sold their home of 30 years and most of their possessions, moved onto their 49-foot sailboat and headed south.

Their first major trip was a 12-day passage from Hampton, Virginia, to the island of Antigua in the company of 20+ other boats. They’ve cruised the Caribbean Islands, the coast of Colombia, the San Blas Islands off Panama, the Honduras Bay islands, Belize, past Mexico and to the Dry Tortugas, and are still on board, planning new adventures.

I wanted to learn more about Ronna’s decision to spend her retirement living on her boat, so I spoke to her recently on one of their infrequent stateside trips (her husband was getting a knee-replacement).

Before we talk about your cruising, Ronna, tell us about your working career and profession.

I graduated from Boston College Law School in 1983 and worked as a real estate attorney for twenty-eight years. Most of that was full-time work with a big law firm in Boston. Later, when my three kids were growing up, I worked part time for my father’s real estate firm. But I never had a passion for it. What I did have a passion for was writing.

I retired from the law in 2011. A friend told me about a then-new website, Betterafter50founded by Felice Shapiro, and I contacted her and began writing for the site. I became her partner but then scaled back to just writing after we moved on the boat. I haven’t been involved since 2018 but it’s going strong under Felice’s leadership.

How did your decision to go cruising come about?  Was there a eureka moment when you knew you were definitely going to do this?

My husband and I always knew that we would do this someday. We’d been sailing for years. All our family vacations were sailing vacations, chartering boats all over the world.

There wasn’t one eureka moment, but there were a number of things that coalesced in 2017 to make us know that it was now or never. Our kids were grown and settled, there were no grandkids, I had successfully undergone breast cancer treatment the previous year, my husband felt it was a good time to quit his job, and between us we had one living parent who was healthy. Nobody needed us. We had bought this boat in 2014, had a dream of sailing the world and knew that this was our time.

We researched the cruising life, read tons of books, and every book said, “don’t be tied to land.” So, we sold our house, my car, most everything we owned and moved onboard Exodus, a Hylas ’49, in October 2017.

How did it feel to leave your work life behind? Is there anything you miss about working?

At first it was bittersweet. I loved writing and collaborating with Felice, and some days I do miss the intellectual stimulation. But I have no regrets at all, even when we have a miserable passage, or it seems like all we’re doing is repairing broken boat parts.

How do you spend your time now that you are living aboard?

This is the age-old question that people ask cruisers: “So… what do you do all day?” They just can’t imagine how we spend our time.

The mechanics of daily living are different on a boat—there are always boat chores (fixing broken things, cleaning, polishing chrome, checking the weather, provisioning, doing laundry, planning passages). We tend to do those in the morning and have our “fun time” in the afternoon—swimming, snorkeling, paddle boarding, fishing, reading, writing, exploring our surroundings.

Then social hour begins around 5:00 p.m. The cruising lifestyle is normally very social, and boaters get together in the evenings around cocktails and games. COVID has changed that considerably, though. We don’t meet as many new people and we’ve formed our own “pods” with friends on other boats. If any of us have visitors, we quarantine before we get together again.

How has cruising affected your relationships? How do you stay connected to your land family and friends?

When I’m on the boat, I feel a little bit disconnected from my friends, family and community from land. We usually have cell phone service and call them often, and we make trips home every few months to reconnect. Our family is mostly in the Boston area, and we bought a condo there so that we have a place to stay. Of course, COVID has made it difficult for people to come visit us on the boat.

When we’re cruising far away, I miss my kids terribly, but all have thrived in my absence. What has been hardest about keeping relationships from home strong are the instances when you cannot be there to comfort a family member or friend—a brother with cancer, a friend whose parent has passed away. Those are the moments that are most difficult for me.

What’s been the biggest challenge in your cruising life? The biggest reward?

The biggest challenge has been the long passages. Our first long passage, from Virginia to Antigua, took 12 days and so many things broke along the way. That was the worst passage ever. And we had a second long passage where we had three days of terrible weather and lightning all around us. Every day is a journey, and I have never been bored, although every once in a while I am terrified.

Although we’re good sailors, we were newbies to the cruising life and that first 12-day passage taught us that we had to be self-sufficient in every way. It was so bad that we had serious discussions about quitting and going back home. But the cruising community takes care of each other, and we leaned on (and learned from) more experienced boaters and decided to continue.

There are lots of rewards—arriving at our destination, the closeness of the cruising community, our many cruising friends. I love that it is an outdoor life—that we are living in nature.

What are your plans for the future?

Our immediate plans revolve around where we’re going to go this summer. We’d like to cross the Atlantic and go to the Mediterranean. But that’s dependent on what happens with COVID and the vaccine. Our Plan B is to go to the Bahamas and then cruise north into Canada, maybe up to Nova Scotia or even Newfoundland.

Long term, we’d like to continue as liveaboards for as long as we can. This lifestyle keeps us young, but it is physically demanding. At some point, as we age, we will probably move away from a sailboat and to a powerboat.

I say I’d like to do this forever, but I know that if/when grandkids come along, I’ll want to spend time with them. We talk about maybe living six months on land and six months at sea so we can be part of their lives.

What have you learned from this adventure? What advice would you give to someone considering retirement?

I’ve learned respect for the sea and that I love an outdoor life. I’ve learned many new skills and am especially interested in weather and forecasting. Most of all I’ve learned humility—how much I don’t know and how much I can learn from others.

I’ve also learned that plans get derailed and you have to be able to roll with things and adjust. We cruisers say, “Plans are made in the sand at low tide.”

My advice to others in their retirement is to follow your passion and take a chance when the time is right. Don’t wait for the “perfect” time to follow your dreams because “perfect” never happens.

Oh, and one other thing I’ve known, and been happy to confirm, is that women are often running their own boats. I’ve met many skilled and totally bad-ass women captains, and they are simply fantastic sailors.

 What dreams do you have for your retirement? How do you feel about Ronna’s advice to not wait for “perfect”? Please share!