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Work Hard, Play Hard – Designing a Boating Lifestyle

sailing lifestyle



From life aboard work boats at sea to his regatta and offshore long-distance sailing, Chris Hefferan is living his boating lifestyle to the fullest [Podcast]

Anchors AweighAnchors Aweigh Boating Podcast is a podcast for all boaters, from aspiring to experienced. Featuring in-depth conversations with boating experts and industry leaders, and packed full of tips, tricks, gear, and industry info, boaters of all levels will come away with new skills and knowledge each episode.

When we think of boating careers, we often think of building and selling boats, working at marinas and boatyards, maybe commercial fishing. But there are whole other industries that rely on boaters and skilled workers and provide a great living an opportunity to live and work at sea.

I really enjoyed recording this Anchors Aweigh podcast episode, as the guest is a friend who I have been fortunate to have a lot of fun on the water with.

Chris Hefferan currently helps manage Subsea Fleet Support for Noble, a leading offshore drilling contractor for the oil and gas industry. The company owns and operates one of the most modern, versatile and technically advanced fleets in the offshore drilling industry. Chris has been with Noble since 2011 and has traveled the world maintaining their fleet, doing rotations of up to 90 days living aboard the ships.

Chris grew up sailing with his father off the coast of Massachusetts and attended the Massachusetts Maritime Academy where he concentrated in Marine Engineering and was a member of the varsity sailing team.

sailing lifeWhen he’s not at sea for work, he is at sea for fun aboard his C&C 41 Leverage, which he purchased at the age of 25 to fully dedicate himself to the boating lifestyle.

Chris has extensive regatta and offshore long-distance sailing experience – for instance he has completed 7 round trip sails from New England to the Caribbean, including multiple trips with just himself and one crew, and just as many Figawi races from Cape Cod to Nantucket.

I have had the pleasure of being a guest on Chris’s boat many times including a week in the BVI, many of the previously mentioned Figawi races, sails in Newport, RI and Boston, MA, and more. Chris is a first rate captain and I am truly indebted to him for helping create some of my all-time favorite memories on the water.

This is a really fun interview with some great stories from sea including an incredibly harrowing tale of foul weather way off shore around the 16-minute mark, working on 90 day rotations off shore, and his ambitious sailing goals he’d like to accomplish before the age of 40.

This is jam packed with too many stories to write so give a listen, and if you’re in the market for a sailboat, check out his listing. Enjoy!

Be sure to click on links to listen to the full podcast interview at the end!



His sailing start

I started out sailing when I was young. My dad had smaller sailboats off the coast of Massachusetts. As I progressed I went to Mass Maritime Academy and joined their sailing team. From there I ended up doing some off shore racing and sailing and the play part came when I purchased my own boat at 25 years old. I bought that before I ever bought a house.

Getting into racing

Racing didn’t come until I went to college. I actually got cut my freshman year first semester. I had sailed and had plenty of experience but I didn’t have the gear or terminology down. I tried out the next semester and did make the team. The dynamics of sailing are the same, I always tried to make the boat go as fast as possible so that part was easy. It was more the tactics against other boats and trying to position yourself ahead of them or in the right spot to make sure you can stay ahead and beat them ultimately.

Some of his favorite college races

We raced from Maine to Annapolis. They had quite a program down at the Naval Academy. They had 44 foot sailboats all of the same kind. That was a lot of fun having a one-design sailboat so you didn’t have to rely on any kind of rating system to keep the playing field level.

Deciding to attend Mass Maritime

My dad knew that I liked to be outside and work with my hands, and being close to the water. I went my sophomore year and looked around, and all the beaches and water was intriguing to me. They had an engineering program and all the boats around. I applied early and got in early and never looked at another school.

The inspiration for buying his own boat

When I went to Mass Maritime, I met quite a few people who didn’t go to school there and one of them introduced me to the off shore sailing aspect. I did a few off shore deliveries with him on other people’s boats, moving them from Massachusetts to the Caribbean.

I did one delivery on a Swan 48.We sailed 9 days straight to the Caribbean and I remember approaching the islands and seeing the clear waters and blue colors and that’s when I decided I needed my own boat that could go offshore, I could handle by myself, and something that I could live on so that I could reach those places on my own terms and own schedule.

DIY work around the boat

The reason I do the work myself is it saves me a lot of money. It’s hard to find marine technicians. And I like to know all the ins and outs of my boats, especially doing trips off shore where I am completely reliant on the boat. If something fails I know where it is and how to fix it, I think that’s the most important part of DIY work.

boating lifestyleHis favorite places to sail

In New England, my favorite place is Nantucket. Everyone is on vacation there. It is completely relaxing and fun and has beautiful beaches.

Bermuda is a wonderful spot as well. Not only do they have incredible waters, flight-wise its only two hours from Boston. The people are friendly, it’s a very protected island, and in the way of off shore sailing it was put in a perfect place to be a harbor of refuge between New England and the Caribbean.

I started off sailing in the BVI when I took my boat down the first time and that is a beautiful area. I know they were recently hit by two devastating hurricanes and it’s a different landscape from when I last saw it, but the beauty is still there and the people are friendly. The water is the same temperature as the air and the wind is always blowing perfectly.

What he is looking for in his next boat

I want the strength of the current boat that I have, I like the speed for its size. But I’d like more tankage, and a couple more cabins so that families and friends can join us wherever we sail off to next. Ultimately the goal is to cross the Atlantic from New England before I’m 40 and see some of the Mediterranean, then down to the Caribbean and come back up, the great Atlantic Loop (Ed note: I think Chris made this term up, but I like it and what a great goal!).

I’m looking for a boat strong enough to do that, 50-60 feet. There’s a wide range of boats out there. I’ve looked at modern boats, classic cruising boats. I’m excited for the next chapter.

Sail versus power

I’m partners in an old 18 foot bass boat, a 1956 Palmer Scott built in New Bedford, MA. It currently needs a bit of work before we put it in next year. But when it comes to sailing the distance, I prefer to use the wind instead of fuel to get across oceans.

Life aboard the work boats

I did about five years on oil tankers running between Alaska and if we got lucky down to Hawaii. I used to do 75-90 day rotations and that got a little old. I looked for something shorter and decided to move to drill ships and became an engineer on a drilling rig. It floats in about 10,000 feet of water using thrusters to keep itself on location and drilling into the earth as deep as 40,000 feet. Since then I’ve shifted into Subsea engineering. We maintain the blowup preventer and all the associated equipment.

The best boating advice received

The best advice is have your ducks in a row when it comes to safety. That was always drilled into my head and now that I skipper my own boat I would never want to hurt anybody on board and think about what I could have done differently. Other than that it’s being comfortable on the water. To have a nice day on the water you have to be relaxed and comfortable with your boat and what you’re doing and that goes out to everybody else’s attitude and affects them to positively have a nice day.

Essential equipment

Life jackets are a basic, simple thing to have on board but that’s a great start right there. I have an EPIRB on board and that gives me a lot of comfort knowing wherever I am in the world I can activate that and help is on its way. I also carry a life raft when I go anywhere off shore, it would be foolish not to.

As I mentioned, there’s a lot more packed into this half hour, so give a listen and let us know what your boating goals and dream destinations are!

Listen to the full Podcast:

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Listen on iTunes: Chris Hefferan – January 26, 2018 (free)


Listen on Google Play: Chris Hefferan – January 26, 2018 (free)


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Matt O’Hara is the owner, along with his wife Rebecca, of Freedom Boat Club Lake George and operator of Beckley’s Marina. After a 10-year career in media sales in Boston, MA Matt and Rebecca decided to relocate and open their own Freedom Boat Club, where they could share their love of boating and Lake George by helping others get on the water. Matt has combined his background in media with his move to the boating industry to launch Anchors Aweigh, a podcast for boaters.

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