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Living On A Sailboat

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Last Updated on February 2, 2024 by Carolyn

Living On A Sailboat
Living on A Sailboat

Have you ever wondered what it would be like to live on a sailboat? Not just take a trip but actually call your sailboat home? We are lucky to have Jill Bockenstette creater of the blog moneyformangos.com , share with us her and her husband Scott’s recent experiences of selling all to pursue life living on a sailboat.

Meet Jill and Scott

Jill was born in Detroit, MI and grew up in New Baltimore, MI northeast of Detroit. Scott is from Ohio and attended the US Coast Guard Academy where he learned to sail and navigate the high seas and then spent 6 years on various US Coast Guard ships.

Over the years Jill’s occupation has evolved from training dolphins and sea lions when she graduated from college to being a training manager at Airbus’s US manufacturing facility where they assemble the A320 and A220 aircraft.

And now, she’s pursuing a new career since her training job can’t be pursued remotely:

“I am now spending time building my blog, moneyformangos.com, where I write about our travels and hope to help others out thinking about doing the same”.

Jill and Scott

 Jill’s Pastimes and Loves

It was no surprise when I asked Jill if she was a beach or mountain person , that she responded definitely a beach person, but she did admit that spending time in the mountains is great too!

Jill loves to read, and cited her favorite book is “Facing Fear” by Lisa Blair, the first women to sail solo around Antartica. Facing Fear is Lisa Blair’s memoir of that incredible voyage.

When docked Jill loves to stretch her legs and run. Jill and Scott can often be found on their boat playing a lively game of cards-lively as they both are competitive! They also enjoy walking with Mangaux ( pronounced “Mango”), their little adopted dog.

Jill’s favorite food? Homemade Chex Mix.

Favorite music: Appropriately for a sea lover, Jimmy Buffett is one of Jill’s favorite artists. She also enjoys Kenny Chesney, country music in general, 90s rock music, and Dropkick Murphys.

Why Would You Choose to Live on a Sailboat?

Downsizing is one thing, but selling almost all of your belongings and choosing to live on a boat is a totally different ball game. 

What inspired you to choose this lifestyle?

Per Jill: “I grew up near the water, and have always been interested in being out on the water. My husband Scott was in the USCG and is very comfortable being out on the water. We both love to travel and explore new places, so the idea formed from our interests.”

“We wanted to have the freedom to travel around to various places and not be tied down to one location.”

How long was the process from the day you decided to live aboard to actually moving aboard?

“We came up with a 6-year plan from when we decided to live aboard and sail full time to actually sailing away.”

“We knew that we didn’t want to work until we were retirement age. We lived well within our means and put any extra money each month into savings.

Jill and Scott were able to achieve their goals by spending intentionally, saving every extra dollar that came their way and making that money work for them.

Lifeaboard A Sailboat

How long have you called your boat home?

“We sold our house in July 2021, and moved from it to our boat, so we have lived fulltime on our boat for a little over 2 years.”

Where do you hang your hat now? Do you even have a home base?

Home is where the anchor drops. We lived in Mobile, AL for approximately 10 years, and left Mobile in January 2022. We sold our house, vehicles and our belongings, so we are not tied to any specific place on land.

Home is Where the Anchor Drops, today it’s at Meeks Patch

What were your first impressions of life aboard a boat when you set sail for the first few weeks?

“We set sail in January and honestly, the first few weeks were tough with frequent cold fronts and strong winds. Our second night out we were at anchor in 45+ knot winds. Our first overnight passage, was very rough with sustained winds over 35 knots. We had waves crashing over the bow while winds were coming out of the north. We both knew that it had to get better and kept pressing on. “

What do you enjoy most about living aboard a boat? What have been some of your favourite experiences?

I enjoy all of the different places we get to see and explore, and all of the different people we get to meet from all walks of life. Some of our favorite experiences include hanging out at anchor in the Bahamas with great groups of sailors.

What do you dislike most about living aboard a boat? Do you miss anything from your terrestial life?

Logistically, it can be a challenge at times to get back home to visit our family, or even get the dog out to shore for a walk. The thing I miss most from terrestrial life would be refrigerator space! We have a good size fridge for a boat, however, you have to move things around, and really dig to find what you are looking for.


What are the biggest adjustments you have had to make settling into life aboard a boat? 

“The biggest adjustment is that everything depends on the weather. Where you anchor, when you move from one location to the next, etc. We also must be conscience of our power usage and water usage.”

Social Life

Is life aboard a boat only for those who enjoy a solitary life or are there social opportunities?

“The sailing and cruising community is great! We have met the most amazing people out here. Everyone is eager to lend a helping hand, spare part, suggestions, etc. and look out for one another.”

Do you tend to sail alone or in the accompany of others?

“Both, it really depends on when and where we are going. When we got to the Bahamas, we met a couple who we ended up sailing with for about 6 weeks and became great friends with them. We went our separate ways, but met up with them again along the intracoastal waterway several weeks later.”

About Your Boat

Can you tell us about your boat and why you selected it for life aboard? Can you share the approximate cost?

“We live on Pelagia, a 1998 Hunter 450 Passage. My husband is 6’3” tall and one of the reasons we selected this boat is that it is a center cockpit, and he can stand up with clearance in the salon and aft cabin (our bedroom). It also has a great layout, separate fridge and freezer, a separate stand-up shower (with a mini tub!) and a lot of storage space. We paid $130,000 for her in 2020.”

Are there any features it doesn’t have that you wish it did?

“There are always things you would like to upgrade! Ha! We have a watermaker on board, but it only makes approximately 5 gallons per hour. I wish we had a more powerful watermaker on board. With a more powerful watermaker on board, we could also justify installing a washing machine  (our boat is actually plumbed for it, but we do not have one). “

Daily Life Aboard

Having never spent a night aboard a boat, I had questions on how some day to day tasks are completed on a boat:

How does one do things like laundry on a boat? Or is that done at a laundromat when you dock?

Some people actually have a washing machine on a boat, however, we do not. We either do laundry when we are “docked” at a marina, or in the Bahamas, we simply washed our clothes in a bucket.”

Bathing: Do you have a shower on the boat? How much water do you carry? 

“Yes, we have a great shower on our boat, that is separate from the toilet. Our boat carries 200 gallons of fresh water.”

What transportation means do you use when you go shopping for provisions? How often do you have to do groceries?

“One of the things we look for when choosing an anchorage or marina it its proximity to a grocery store. Often times we will walk to the grocery store (typically ½ mile to 2 miles away). We have a collapsible wagon that we use for grocery shopping. Some marinas have a courtesy shuttle that will drive you to and from the grocery store. We do large provisioning trips when we have a ride, such as a courtesy shuttle, or in Miami when visiting with Scott’s dad. Then we stock up on fresh foods about every week or two.”

How much time do you spend on the boat each week?

All of the time as it is our home ?.”

Do you dock most nights? How do you arrange that?

“We try to limit staying at marinas, due to cost. However, we stay at them mainly for protection from severe weather. We call the marina a day or two in advance to book a slip.”

Traveling the High Seas

Swinging over the sea
Swinging at Green Turtle C

Where have you sailed? 

“We left out of Mobile, AL, and sailed the Gulf of Mexico down the west coast of Florida to the Florida Keys. From there we sailed up the keys and over to the Bahamas for 2 months. We then sailed back from the Bahamas and up the east coast to the Chesapeake Bay, where we are hanging out for hurricane season.”

Where do you plan on sailing in the future?

“In October, we plan to sail south along the east coast to Miami where we will spend Thanksgiving with Scott’s dad. From there, we plan to sail to the Bahamas, then down to the Dominican Republic, Puerto Rico, and the Caribbean chain with hopes to spend next hurricane season in Grenada.”

As of the time of this post, Jill and Scott had sailed 3008 nautical miles since leaving Mobile, AL in January.


Cost of Living on A Sailboat

I was interested to know how much it costs to live on a sailboat. To my joy, Jill has kept a very detailed budget and tracked expenses.

Jill and Scott set a budget for a total of $4,750 a month to cover all spending. Below is their monthly budget and actual average monthly expenses for the first 6 months.

Monthly Cost of Living on a Sailboat
Monthly Cost of Living on a Sailboat

Did you Stay on Budget?

“We did a 6-month checkup and we were slightly overbudget for the first 6 months. The main expense that we went over budget on was marinas. We also realized we did not budget for boat upgrades (we only budgeted for typical boat expenses). We made a few upgrades this summer to our house battery bank, composting head, and internet (Starlink) that we did not budget for, so we expect our next 6 months will be over budget as well.”

Health care

Always a concern for retirees is healthcare costs. Per your budget, you are keeping those costs very manageable. What solutions have you found for affordable healthcare?

“My husband has healthcare available to him through the VA, however, I am not eligible. The cost of U.S. based healthcare for me was approximately $1,000/month which would exceed our budget, therefore I opted for a Christian-based cost sharing program that is working out very well for me. With our plans to stay in the Caribbean next year, I plan to look into purchasing global insurance.”

Pets On Board

You have a dog, how do you exercise your dog on a boat? And where does it relieve itself

“Our dog Mangaux is 10 years old. We try to get him to shore for walks at least twice a day for exercise and bathroom breaks. I’ve been trying to get him to use the bathroom on the boat for when we undertake longer passages, however, I have not had any luck, so we try to stick to shorter 1-2 day passages.”

Mangaux on Manjack Cay Ocean Beach

Do some places require any extra paperwork to admit the dog ( other than proof of vaccines)?

“Yes, each country has their own rules and paperwork requirements for admitting a dog into their country. Other than proof of vaccines, several countries require a rabies titre test, and health certificates signed by veterinarians within a specified timeframe of arrival into their country.”

Personal experiences 

Can you share any particular memorable experience since you’ve been living aboard?

“One of the most memorable experiences would be a calm day at anchor in Northern Eleuthera in the Bahamas. The water was crystal clear, and there were several of us anchored in this anchorage. We spent a lot of time hanging out, snorkeling, paddle boarding and having a bon fire at the beach (with the pigs!) enjoying getting to know each other and spending time with like-minded sailors.”

What is one tip you’d give someone contemplating a similar life?

“Just go for it! Boat work will never end and your boat will never be fully ready or fixed up. You will never have “enough” money saved up. But we are only growing older and have one life to live and explore this beautiful planet.”

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