Sailing for Seniors: Can an 83-Year Old Woman Handle a Week on a Catamaran?

by | Feb 8, 2024

Views of the blue water surrounding Virgin Gorda in the British Virgin Islands.
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Last updated on May 10th, 2024

Featured image: Is sailing for seniors possible? Diana Eden says YES! | Photo by Diana Eden

How a sailing trip to the British Virgin Islands took me out of my comfort zone

by Diana Eden

When I decided to go on a week-long sailing trip on a catamaran in the British Virgin Islands, I wasn’t sure if my 83-year-old body could handle such an adventurous excursion. There are certain trips I KNOW I can’t do (climbing Mount Everest is one), but this one was on the cusp. 

At my age, would a small cabin on a boat 50 feet long be comfortable enough for me? Could I share a cabin and bathroom with a stranger? Would rough days at sea climbing waves and crashing down be doable with my painful back problems brought on by scoliosis?

Now that the trip is over, I can report that I CAN and DID make such a trip, and it was marvelous!

Getting out of my comfort zone

I met Joy Sherman of JoyRide Charters at the Women’s Travel Fest conference in March 2023 after speaking at a panel on solo travel over 50 hosted by JourneyWoman CEO Carolyn Ray.  

Joy grew up on boats in the Bahamas from a young age and was sailing herself by age 10. Then, she was not encouraged much, being a woman, but later, her father was completely behind her transition to making it a full-time occupation. Her transition to boat captain happened after a career managing her father’s car dealership and before retiring from the Oncology department at Yale. 

As a late bloomer in the sailing world, she wants to encourage women to get out of their comfort zone. 

“Women tend to shut down as they age, and it is important to counter that with new experiences,” she says. “There is so much of the world to see!”

When I looked at the waiver for the sailing trip, the only requirements on the waiver form were ‘can you swim?’ (yes, I can) and ‘can you climb into a dinghy?’ (yes, I can, albeit gingerly.) 

Well, the good news came in stages. First, it turns out that Carol, my 80-year old younger sister, was able to be my cabin mate. We last shared a bed when I was nine and she was six. 

Making new friendships

There were three boats that sailed together. Our boat had 8 women between the ages of 60 and 83 from all over the US and Canada. We had on board two retired dentists, one retired firefighter, a former pastry chef, a realtor, a television director, a still-working IT project manager, and me, a retired costume designer. 

One evening, we sat out on the deck and just talked; on another, we played games. One night, we played charades, and I laughed harder than I have laughed in years! That alone was worth the price of admission for me.

Diana Eden sits on the catamaran on a sailing for seniors trip

Diana enjoys the sunshine on board the sail boat / Photo by Carol Moore-Ede

A rainbow over a catamaran in the British Virgin Islands

A rainbow stretches over a catamaran / Photo by Diana Eden

A group of friends pose in front of the Bitter End sign on a sailing for seniors trip in the British Virgin Islands

New friends enjoying drinks and food at The Bitter End / Photo by Diana Eden

Is a sailing trip right for you? 

Once on board, our usual schedule was to wake up leisurely and have a delicious breakfast (we took turns helping prepare) and then do about a three-hour sail to our next island, snorkeling spot, or bay, where we would dinghy in for lunch and swim. 

Our destination was largely dictated by the winds, our night spot by the availability of mooring balls. Our shore excursions were to enjoy a drink or a meal at a beach restaurant or take a tour, as we did on Virgin Gorda. 

A large van took us up over the crest of the mountain in Virgin Gorda, where the views were dramatic in all directions, and then down the “The Baths,” where we were able to hike (a short or a long route) down the beach and massive boulders that are famous for appearing in the movie The Flintstones. Lunch was back up at the top at Hog Heaven!

Sailing for seniors: Having the courage to say yes

A sailing trip on a small boat is not for everyone. If you crave a king-size bed with high-count linens, fresh towels daily and lots of free shampoos and lotions in the bathroom (and there’s nothing wrong with that), this might not be for you. If you want lavish sit-down 3-course dinners every night, you won’t find them here. 

Joy wants women to know that it really is not that difficult to do a sailing trip like this, especially with her cruises in Europe (Greece, Sicily, and Croatia) or Thailand. The catamaran is docked every night rather than moored so that you can walk right off the boat. On most of Joy’s charters, there is a dedicated hostess or cook, and on the Thai charter in April, she will provide a well-known local Thai cook.

“It is especially gratifying when I hear from women considering going on a solo trip and then choosing to come with me,” she says. “I know that for those women who find themselves alone in life, maybe from divorce, widowhood, or by choice, and have the courage to say yes, I am here to support them in their journey and to watch them develop newfound confidence. I have always loved sharing the experience of sailing with others, hoping they would feel the same peace, tranquillity, and power of the ocean I have felt throughout my life.”

A sense of balance is an asset for all boaters, but railings are everywhere to hang on to. We were instructed in the “three points of contact” method for climbing ladders, decks, or stairs.

Jost Van Dyke island in the British Virgin Islands

Jost Van Dyke island / Photo by Carol Moore-Ede

Boulders at The 'Baths' Virgin Gorda

Boulders at The ‘Baths’, Virgin Gorda / Photo by Elizabeth Wright

Turquoise water at The Baths, Virgin Gorda

Turquoise water at The Baths, Virgin Gorda / Photo by Diana Eden

What to bring on a sailing trip

The weather was 82 degrees every day, except the one day we had rain when it dropped to 79 degrees. We didn’t bother with raincoats; we mostly had windbreakers and stayed under cover. We were just so grateful to be out of January’s cold temperatures in most of the US. We delighted in sipping a fair number of rum drinks as we sat at the beach bars in our bathing suits!!

Joy sent a comprehensive suggested packing list months before we departed with items I might not have considered, such as a dry bag, water shoes, reef-safe sunblock, plastic bags, hat keepers to attach to clothing in case of strong winds, etc. I was asked to bring a quick dry towel for the beach to not bring sand back on the boat. The islands are very casual, so there was no need to pack dresses or jewelry. 

As spaces are tight for storage on the boat, luggage needs to be soft-sided, like a duffle bag. Although Joy provides a paddle board and snorkel equipment, guests need to bring their own inflatable “water toys” and floats.

A group of women enjoying happy hour at a beach bar in the British Virgin Islands, on a sailing for seniors trip.

Enjoying happy hour drinks at a beach bar in Virgin Gorda / Photo by Diana Eden

Getting to the BVI and arriving in Tortola

This sailing trip starts from Nanny Cay on the island of Tortola. Most people flew from their origin cities to Miami, Orlando, San Juan, or Puerto Rico, where they connected to the smaller planes to the islands. Some connected through St Thomas, USVI, and took the ferry over (one hour, $60). Cabs on the island are plentiful and available, though be prepared for bumpy roads and lots of speed bumps!

Find a flight here. 

Disclaimer: Diana Eden did not receive any compensation from JoyRide Charters and wrote this article to inspire women over 80 to seek new adventures!  

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Diana Eden is a Contributing Writer for JourneyWoman magazine, focused on travel for women over 80. She was born in England, raised in Toronto, lived and worked in New York, Los Angeles, and now Las Vegas. She is a former dancer, actress, Emmy-nominated costume designer, and now author. She recently published her memoir, "Stars in Their Underwear: My Unpredictable journey from Broadway dancer to costume designer for some of Hollywood’s biggest stars."


  1. Sandy Daniels

    thank you inspire me to venture out
    and to be more adventurous!!!
    loved the photographs

    • Carolyn Kemp

      I am 83 and ready to travel..loved your article about another 83 year olds adventure. Às I have grown older I have become fearful of traveling alone and its encouraging about people my age traveling.
      Thank You

  2. Dee Johnson

    What a wonderful narrative about your recent sail in the BVI’s with Joyride Charters. I have learned so much about sailing from Joy both in our singles sailing club over the years and also while in the BVI’s. I commend you on your energy and travels and wish you continued good health.

  3. Diane Nazarko

    Thank you for this warm dose of inspiration and lovely photos. I have been thinking of joining one of the wonderful trips Captain Joy has planned, but fear and life’s circumstances has held me back. You mentioned the small cabins and bunks, nothing about the toilets (heads) – a major factor for me.

    I know it will be an adventure of a lifetime. On my bucket list!

    Safe and happy travels to you and I look forward to reading more of your stories.

    Diane N.
    Shoreline Sailing Club, Connecticut USA


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