Want to Retire on a Sailboat? The Brutally Honest Must Read Guide

So you want to retire on a sailboat?

You can taste the margaritas and visualize the sunset from your luscious spot in the Caribbean, the Mediterranean or the South Pacific.

You love the idea of throwing the mooring lines and setting off somewhere new once a place has lost your interest.

But is it as laid back and as easy as it sounds, or is it more problematic?

You may have heard many good things about living on a boat– the freedom, the laid back lifestyle and being part of a vibrant community. Even if living on the ocean is not for you there is always life on a narrowboat instead.

You may have also heard the horror stories of people getting hurt, things breaking, and bouts of bad weather. Or of the couples whose dreams of sailing the globe, sink rapidly into divorce.

The reality is that living in a condo also has its downsides. Things break, they can leak and there are many condos full of bored, miserable people.

So what is the truth? How much of the lifestyle is just romantic fiction?

How can you decide if the potentially treacherous waters of a liveaboard retirement are for you?

We chatted with Mike and Gigi McFarlane (who have been sailing the Caribbean for the last four years) whom we met in Bequia in July 2019 to get the true picture.

The result, is a warts and all insight into what living aboard in retirement is really like

Let’s cast the line and explore the world of a live aboard Retirement.

What made you choose to retire on a sailboat?

Having chartered the Caribbean and the Med during our vacations from our jobs for over 25 years, we knew we wanted to live on a boat full time in retirement.  We wanted to do it when we are still active because at some point, we will not be able to live this lifestyle.   I’m 59 and my husband is 67, so it was now or never.  

How long have you been doing it and in what areas?

While on a charter in Greece, Gigi decided she wanted to be able to be captain herself, so she trotted off to Maine for sailing instructions.  As a result she achieved the ability to charter a yacht up to 60’.  We immediately put that to use to sail the British Virgin Islands, an easy sailing location that allowed us to get our sea legs. 

The following years we chartered as Captain and crew in Greece, Turkey, St. Vincent and the Grenadines, Antigua, Croatia, Sardinia, and we revisited the BVI’s over 10 times during our chartering years.  We have also sailed the St. Martin, St. Barths, Anguilla area over 4 times. I know I am missing a few places.

We bought our boat (Last Tango) four years ago in Florida.  Our goal was to sail the Caribbean, but we didn’t want to miss out on anything on the way down.   To get there, we sailed to the Bahamas, Turks and Caicos, Dominican Republic, Puerto Rico, Virgin Islands and over the last couple of years, have spent time at just about every island in the Caribbean.  We are currently in Grenada for hurricane season.

What are your typical monthly costs and what are your expenses? Any tips to manage costs?

A typical sailing budget can cost less than living on land.   It’s all based on how much can you entertain yourself, how often you go out to eat, what condition you want to keep your boat, and many other factors. But it is similar to living anywhere else.   In our case it is less, as we no longer have property taxes, pool maintenance and general upkeep of the house. We have no water or electric bills as we have a water maker and use solar power.   

We stay anchored out (‘on the hook’) so we do not have marina fees.   Clothing expenses go way down.  Since we no longer have a car, we no longer have gas and car expenses.  We don’t have a TV, so we no longer have cable or Netflix expenses. 

Grocery expenses fluctuate from country to country.  On Martinique and the other French islands, many of the products are subsidized by France, so it is possible to fill a grocery cart to the brim, including wine and beer, for less than $150 USD.

Everything in the sea is subject to quite a bit of corrosion, so things break more often than living on land.  A rule of thumb is to expect to pay 10% of the value of your boat on maintenance on an annual basis.  Phone and internet costs used to be extremely high for us.  Now they have laid fiber optic throughout the Caribbean, the costs have gone down significantly.  

 We meet so many sailors that are living on budgets of far less than $2000 a month, to Mega Yacht owners that spend far more than we can imagine on a monthly basis.  It’s all based on how much you can entertain yourself, what condition you want to keep your boat, and many other factors. It also depends on where you are sailing.  Panama is very inexpensive, as is Costa Rica.

How much of an investment is needed for setting yourself up with your own boat? What are the minimum requirements to be comfortable living aboard?    

 Most cruisers we know paid cash for their boats.  Again, the range is all over the board in what you would expect to pay; it’s all about creature comforts.  Having a watermaker and solar power contribute greatly for us to be comfortable living aboard.   We don’t have to lug water around on a regular basis, and solar power allows us to live off the grid without using a generator.  When we purchased our boat, we created a spreadsheet of all the items we wanted included in a boat, for example, number of cabins, number of heads, etc. that will greatly impact the price of the boat. 

Do you need to have prior knowledge of sailing?

Some liveaboard cruisers we know started out knowing zilch, and figured it out along the way and have been successful.  I wouldn’t suggest that approach, as the learning curve in the first two years can be quite steep.  I would recommend joining a sailing club, taking classes, attending boat shows, and getting as much experience as you can to make sure you are as prepared as possible for the transition.   

Taking classes in weather forecasting, engine maintenance and electrical systems helped prepare us. But no matter what you know, the boat is going to stretch your knowledge and understanding for the task at hand.

What are the key factors in determining if this lifestyle would be right for you? 

You have to be extremely flexible as you are dependent on the wind and weather to sail to the next port of call.  The mistake some cruisers make is trying to meet a deadline, such as meeting a friend at the airport on a certain date.  The weather may not be in your favour. 

You must possess excellent troubleshooting skills and not be afraid of work.  When you are out at sea and something breaks, you don’t have the luxury of calling your mechanic or plumber.  There is an often quoted saying that cruising is all about “fixing things in exotic places”.

What’s the best thing about the lifestyle and conversely what’s the worst?

The sunsets are spectacular.  Watching dolphins and whales swim by and jump out of the water, is amazing.   Getting to know and understand the people and the culture of the locals is truly rewarding.  On a daily basis, life looks like a picture perfect postcard with its white sandy beaches.  I have read there are 10,000 active cruisers worldwide. There is a camaraderie that exists between sailors that brings people together from all over the world and crosses all socio-economic barriers that makes sailing the great equalizer.

The get togethers and sundowners with new friends and those we have met in a previous ports result in what I know will be lifelong friendships.  It’s never “bye”, it’s always “Sea Ya later”!

On the other hand, it gets hot and humid in the Caribbean, especially in September and October.  Without a car, you have to walk or find public transportation to anyplace you want to go.  Walking to the grocery store and back with bulky items in tow, then stowing them in a hot boat is not really my idea of a fun time. 

Having things go wrong or break at the most inopportune time can get really annoying, as the entire boat gets turned upside down to gain access to the “part” needed to fix the problem.  Wanting to adhere to a schedule can be a major pain as you are totally dependent on the weather forecast. 

Is there anything that you now know that you wish you had known before committing to being liveaboards?

The learning curve and adjustment during the first year or two of being cruisers was extremely steep.  As charterers, we would pick up a clean, maintained boat and be on our way.  As cruisers, you need to know and understand all systems in your boat and how they interface with each other.

In addition, living in extreme close quarters with your spouse, especially when you are both learning, well, tempers flare.  Since we had both just recently retired, getting used to living with each other 24/7 was a challenge.  Getting used to living on the boat really took us about 2 years before it became second nature. 

What essential skills or aptitudes are required to retire on a sailboat?

There is really nothing that says you need to know X,Y,Z before you go cruising.  It’s all about resume building in terms of sailing.  Having troubleshooting skills to fix things as they break is key, and being flexible about life in general is required.

What do you miss the most about living on land?

Hot showers, flushing toilets, a car, and a fully-stocked kitchen you can cook in are the primary things I miss most living on the boat.  Not being able to walk off the boat while anchored out is very limiting and can make you feel claustrophobic.

Is there a difference between the reality of liveaboard as opposed to the romantic notions of life on the water?

Yes.  As charterers, we knew what we were getting into for the most part as it related to sailing.  We didn’t have the romantic notion most people conjure up.  But we had no clue how steep the learning curve and adjustment to living on the boat required.  

We’re still out here four years later, we have survived without any major mishaps, and we’re still enjoying ourselves.  I suppose just that statement in itself attests to the fact that this is not an easy lifestyle and becoming a cruiser should be carefully considered.

Can you live a satisfying life when you retire on a sailboat?


Just be sure you understand your motivations for wanting to cruise, and understand that you will be “fixing things in exotic locations”.

It will take you about a year to get adjusted to life aboard!  But you can’t beat the picture postcard views, sunsets, the camaraderie of other sailors, and the locals you meet along the way.

Mike and Gigi McFarlane decided to retire on their sailboat “Last Tango” and have been sailing the Caribbean for the last four years.  Their website and more photos of their beautiful home can be found at www.thetangotimes.com.




Meet the Author

Yvonne Bauche

Born in the UK, with what must be more than a dash of Romany blood in her veins, Yvonne loves to travel. Yvonne’s other passion is writing, she now follows her bliss and combines the two as a blogger, travel writer and author.

2 comments… add one
  • Toni hodgkins Nov 23, 2021, 1:56 pm

    I note that no mention at all about health care cover as abroad you are on your own, a policy for two over 70 would be $10000 to $20000 less deductibles and excess, and could be a game changer to most, regards Toni hodgkins

  • Toni hodgkins Nov 23, 2021, 1:52 pm

    I am a retired British have lived on my 50′ schooner full time for 3 years in the uk and 6 months of each year of the last 6 years in the UK, and 6 months of each year in our home in cambodia, but in the UK health care not a problem, but sailing abroad is and once over 70 not easy to get multiple health cover, this particular item has been completely ignored which supprises me somewhat, as a policy to cover two people yearly would be in excess of $10000 to $20000 dollors depending on deductibles and level of cover, so that bit is a game changer for some who want to retire on a sail boat, how ever fit they think they are, regards skipper of the two master schooner Elinor.

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