Is Boat Life Right for You?

Jim and Judy Brown’s 55-foot sailing yacht. Photo: Javierto Mar

By Jim and Judy Brown 

While the world around us gets more crowded, more hectic, and more stressful, worldwide yacht sales are increasing. Many people are fleeing a traditional life on land for a more intimate and simple boating life. Imagine a life of fresh air, spectacular sunrises and sunsets, beautiful landscapes, remarkable cultural experiences, and never-ending adventure.

The #boatlife movement is growing rapidly thanks to the increased popularity of the tiny home/alternative lifestyle options propelled by a pandemic tailwind.

For the past few years, we have been living in the Caribbean, cruising crystal blue idyllic waters and exploring the vibrant sun-drenched islands with our guests—many of whom sail with us to take the boat life for a trial run. For us, living on the water and exploring the world by the power of the wind has been life-changing.

However, it’s not for everyone. There are many advantages and disadvantages to consider if you are thinking about this lifestyle.

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Jim and Judy Brown. Photo: Javierto Mar

Why We Chose This Lifestyle

In 1995 we bought a Farmette in Western Loudoun County, Virginia, at the foothills of the Blue Ridge and built our first home, and raised our family there. After successful careers as landscape architects, we became empty-nesting retirees and began thinking about our next big adventure.

We both love the water and began dreaming about what it might look like to travel the world sustainably.

Since we had both learned to sail as teenagers and Jim had become a licensed yacht captain, living aboard a luxury sailboat seemed like the perfect next chapter for our lives. Since we also love to entertain, the idea evolved into becoming owner/operators of a charter yacht, Dauntless.

On October 18, 2017, our 31st wedding anniversary, we untied the lines and headed offshore into the North Atlantic, put Dauntless on a fast port tack, and began this incredible adventure. So far, we have sailed more than 6,000 nautical miles with our guests, visiting 13 countries and territories in the Caribbean.

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Photo: Javierto Mar

Advantages of the Liveaboard Lifestyle

If you love to travel without schedules or itineraries, boat life may be for you. You can travel to wherever the wind takes you and discover exciting destinations you may have never heard of before. Sailing to charming islands and experiencing fascinating cultures can enrich your life in ways you may have never imagined.

The most significant advantage and extremely appealing is living a simple life. As Americans, it’s easy to get trapped in the “rat race” with a focus on all the “stuff” we can accumulate through the years. An enormous burden can be lifted by downsizing.

Another great perk is discovering things you never thought possible. Seeing places from the water is entirely different than seeing them on land. There is nothing quite like the feeling of making landfall in a new harbor to which you have safely navigated under the power of the wind.

Disadvantages of the Liveaboard Lifestyle

Of course, some disadvantages are important to consider. When traveling by sailboat, you are at the mercy of the weather—potential strong winds, rough seas, or no wind at all to push you forward can dismantle your plans. It is important to be smart, wait for a favorable weather window, and be patient.

In addition, depending on your location, access to proper medical care can be a real challenge, so it’s essential to be prepared with a good supply of all required medications and supplies. For many boaters, seasickness is also a substantial disadvantage.

Lastly, there is a misconception about the cost of living full-time on a boat. Food is more expensive in most remote places—although the rum is generally cheap. Dockage, mooring, and customs fees, along with continuous boat maintenance, can get costly.

We believe and can attest that boat life can be very stressful during times of bad weather. While this can be a great confidence builder when surviving a storm, it is best to try to avoid sailing in bad weather if at all possible.

For the most part, it is very relaxing to glide along the sea powered only by the breeze, but we highly recommend sailing training before taking the step to set sail without experience.


Photo: Sail Dauntless

Try Before You Buy

When considering adopting the liveaboard lifestyle, there are three questions one must honestly answer to consider this life-changing adventure.

  1. Do you have the self-confidence to step away from your comfort zone, give up good Wi-Fi, and take on a new, exciting, and challenging lifestyle?
  2. Do you have the required physical strength, patience, and essential good health to thrive in a challenging and demanding environment?
  3. Do you have the financial means to sustain this adventure to the level and quality of life and expectations to which you are accustomed?
  4. If the answer is “Yes” to these three complex questions, you may be ready for the next step.

However, it’s still a good idea to try before you buy. We advise our potential guests to get soaked and go sailing for a week with a seasoned crew. Enjoy some offshore and island-hopping itineraries and experience first-hand the eye-popping rewards and realities of the liveaboard lifestyle.

Our industry offers either direct, hands-on experiences or the opportunity to sit back and relax. Another advantage is experienced interaction with island locals for the best things to do at the best prices.

Trying a charter before purchasing a yacht helps you to live the realities of life at sea—the advantages and the disadvantages. Living aboard a boat, regardless of size and budget, is a big adjustment, so it’s important to consider everything before making the decision.

Some may struggle with the limited hot water for showers or poor Internet connection. Others may struggle with the idea of downsizing or giving up some luxuries of land life.

Boating is a life-changing event, so take your time, do your homework, and don’t rush into the decision. Like us, you will know if and when the time is right.


Photo: Javierto Mar

Why this Lifestyle is Perfect for People Over 50

We touched on some of the attributes this lifestyle offers and concerns regarding health, fitness, and confidence. The highlights are many. This active lifestyle provides ample opportunities to meet fellow cruisers, guests, and locals from all around the world. Many are retired and “living the dream.”

Sharing stories and life experiences provide knowledge, perspective and build community. The relationships with other liveaboards and locals have enriched our lives more than we could describe.

Another highlight is the constantly changing sea and how each day presents a new view and interaction with nature. In addition, this lifestyle will keep you moving as there is always something to do onboard or a new island to explore.

Those considering this lifestyle change should be honest with themselves and check it out to see if it is right for them. Dismiss the “hype and trends” and discover whether this lifestyle will truly light that fire from within, as it has for us.

Jim and Judy Brown are owners/operators of Sail Dauntless, a luxurious 55-foot sailing yacht based out of The Hamptons (Long Island, New York) and Newport, RI. For more information, visit
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