Learn to Sail & Cruise


Last Updated on August 22, 2020 by Amy

When David and I met, David had been out sailing once as a child. Now, we’ve completed a world circumnavigation together and we are both experienced and skilled skippers.

In the years between meeting (2008) and taking off sailing (2014), we were lucky to have a lot of opportunities to learn to sail.

We recognize that not everyone is as fortunate as we are. Here are some great ways EVERYONE can learn to sail before buying their own boat.

Sailing Blogs & Vlogs

Just like us, there are tons of people out there living the dream right now! Once David started to think about cruising in our future, he turned to the internet and absorbed himself in some fantastic blogs.

Here are some of our favorites:

  • Bumfuzzles – this couple started sailing around the world in 2003 for a 4-year circumnavigation. Since then, it’s been one adventure after another, and they’re currently back cruising in a powerboat.
  • The Sailing Family – in 2009, the Hynes started the first sailing vlog when they took off on S/V Honeymoon and sailed across the Pacific. Now, they’re back cruising the Pacific on their Outremer, Archer.
  • Sailing Britican – this couple has been cruising the Meditteranean and are now in the Caribbean. They have a ton of great resources on their blog to learn how to sail.
  • Sailing Totem – Behan and family have just completed a 9-year circumnavigation. She is the go-to resource for cruising as a family.
  • The Boat Galley – A resource for budget cruising and all things galley related.

As far as vlogs, they weren’t as popular back when we started (we started our sailing channel the same week as La Vagabonde!). However, there are tons of great channels out now (other than ours, of course!).

If you have a particular brand of boat you are interested in, try to find sailing channels specific to that boat. For example, there are several Fountaine Pajot sailing channels.

Sailing Magazines

We have been pouring through our magazines to learn a lot and to clear them out of our stuff! Our main magazine is Cruising World. This magazine is really helpful. We had about seven years’ worth of back issues before we went cruising, and we read through them all! Now, I’m a contributor to Cruising World Magazine, as well as a regular reader. In particular, I really enjoy reading Cap’n Fatty Goodlander’s articles. He’s been cruising for so long and has a great sense of humor and a wonderful relationship with his wife. Some CW back issues are available on Google Books.

We have sporadically read a few other magazines such as Sail and Blue Water Cruising, but not enough to develop an opinion on the magazine.

Cruiser’s Forum

David and I have spent a lot of time reading through Cruiser’s Forum and asking questions of other cruisers. Cruiser’s Forum is by far the most popular, and we’ve held long conversations with several people, as well as connected with other Helia owners.

Facebook Groups

There are some really terrible Facebook groups out there, so it’s very clear when you find a good one. Women Who Sail is an amazing group! It is incredibly active, with tons of new posts every day and over 16,000 members. The members vary from ladies who are dreaming of boats to coastal cruises to circumnavigators to professional experts such as Beth Leonard and Carolyn Shearlock.  Topics vary to sailing as a woman, to kids on board, to repair and maintenance, and everything in between.

I presented at the 2018 Women Who Sail Australia Gathering on the Bay.

Boat Shows

Before buying our boat we attended several boat shows. You can read about our Annapolis Boat Show tips and our experiences and advice for the Miami Boat Show.

Best Books to Learn About Cruising

Onboard Starry Horizons we have dozens of reference books about boats on hand. It’s a great idea to buy and read in advance – you can learn a lot!

There are also tons of memoirs out there. Here are a few to check out that were written fairly recently:

Join a Sailing Club

If you live near the water, local yacht clubs are often full of opportunities for someone to learn to sail. They usually have a weekly race, and many boats need hands to crew. See if you can volunteer.

Hitchhike on a Boat

There are many places throughout the world where cruising boats wait – for the right weather, or, maybe, for the right person. Many boats take on an additional crewmember or two for longer passages, and there are plenty of ways to find those openings. Check out how to Boat HitchHike.


I went on charters with my family when I was a kid, but when David and I started thinking about cruising, we knew we needed some more time on comparable boats. We did two charters – the BVIs and St Martin – before we bought our boat.

After circumnavigating the world, we have some thoughts on the best sailing destinations where you can charter a boat.

Sailing Courses

For someone looking to recreationally sail, there are many options available. ASA and NauticEd both have in-person courses and online courses (some are free).

Why didn’t we take a course? We owned our own boat and had extremely capable captains that worked for us.

Looking for a more advanced class? Sailing Virgins‘ curriculum includes a Performance Catamarans course.

Mariner’s Learning System

David and I both wanted to become licensed captains for the business, so we purchased a course through Mariner’s Learning System. As a result, we both have our USCG Master 100 Ton licenses, with Sailing Endorsements.

The class was done entirely online until the test. Then it was just a matter of applying to the USCG!

Now, that is not how to learn to sail, but it will build up your confidence in knowing the rules of the road, manual navigation, and a host of other topics.

Our Boating Histories

Amy’s Childhood

It all started back in the 1950s…with my grandfather. Grandpa started a company called State Boat, which operated offshore supply vessels. The company grew to over 40 boats around the world during its lifespan. I have pictures of myself and my parents aboard the boats. Some of them are still in operation today under different companies and names.

Tom with State Swan
Dad with the State Swan.

Next up is my Uncle Jim. In the 1980s, Jim bought his sailboat, Requisaire, a Hinkley Bermuda.  Jim traveled the east coast and Caribbean for a few years and then settled into life as a lawyer back in Houston. But he still has Requisaire, and she’s now kept in Camden, Maine, where Jim and his wife Melinda spend their vacations. They are the reason we went to Maine on Starry Horizons.

Amy and Jim at Requiescere 1988 (2)
Jim and I with Requiescere in 1988.

Next, we have my parents. Both my mom and dad went to Texas A&M at Galveston. My dad graduated with a degree in Maritime Transportation, and my mom with a degree in Marine Science. They both spent a lot of time on the Clipper, the crew ship of TAMG, where they got to travel the world. They met at A&M, and after graduation, moved to Louisiana, where Dad went to work for State Boat. That’s where they had me! When I was a baby, Dad attended Maine Maritime, and we lived there for a while.

Dad worked for State Boat until it was closed in the late 80s. From there, my dad started his own company – Star Fleet. This is the business I bought when my dad passed away.

Amy and Tom in the Pilothouse of the Star Gazer August 17 1997

When I was a pre-teen, my dad chartered a sailboat in the Bahamas, and then in high school, I went for a week in the BVIs with my best friend Bronwyn (who you may remember from Bermuda) and her family.

BVIs Sailing Trip 2000 (5) - B and Amy at the helm

In high school, my parents (mom and step-dad) had a monohull, Utopia, that we would take out for day sails as a family with our friends. I have great memories of sailing Galveston Bay with my high school friends, with Mom packing a picnic.

When I was in college, my dad started to really get into sailing. He bought a Hobie Cat, and pushed the boundaries of its utility. Dad created a suitcase with solar panels on the outside, that would open up to navigation equipment in the inside. He would pack a sleeping bag and tent and set it up on the trampoline of the Hobie to camp out. One time he left without filing a float plan – and the CG sent a chopper out to look for him.

A few years after buying the Hobie, Dad upgraded to a Maine Cat 30 – named Star Cat. Again, Dad sailed beyond what was really expected of this coastal cruiser. Dad single-handed the boat for most of the trip to the Bahamas and back. I joined him for about 3 weeks, crossing the Gulf Stream, enjoying Nassau and Eleuthera, and then coming back with him through the Okeechobee waterway.

Doesn't Dad look like a Salty Sailor?
Doesn’t Dad look like a Salty Sailor?

David’s History

Now we get to David. David had only sailed a handful of times when he was a kid, although both his grandparents had boats. About 6 months after we met, my dad wanted to celebrate his birthday by taking us out for a sail after work. We sailed the Star Cat to Alena Island, grilled dinner, and sailed back. That’s where David’s spark was lit. As most future cruisers do, David started gorging himself in sailing videos and cruising blogs, and then the idea was formed that we would take off and go cruise around the world.

When Dad died six months after that first sail with the three of us, I took over the business, which consisted of four passenger boats and the Star Cat. David and I started really learning to sail, thanks to Captain Nick, and adventuring out on the Star Cat.

Sailing on our honeymoon in Roatan, Honduras.

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  1. We have Hull # 89 which is due to splash on Dec 13. We are putting her into charter in the USVI for 4-5 years but there is some additional commissioning at La Rochelle by Uchimata before she is transported to St. Thomas. We plan on meeting her in the USVI when she arrives in Feb. Heard good things about Uchimata so your experience will be valuable.

  2. Reading your posts for the first time. What a great adventure! My wife and I are in the middle of ordering our own Helia 44 and your posts have been very helpful. We live in Severn and have our own coastal cruiser in Annapolis. Heading to the Annapolis Sailboat Show so if you are going, my wife and I would love to meet the two of you. In any case, fair winds and following seas. Soon-to-be owners of the Big PapaLulu, Allen & Linda Dobbs

    1. Hi Allen!

      Thanks for following and the compliments! We will not be attending the Annapolis Boat Show this year as we will be in La Rochelle picking up Starry Horizons! When do you plan on picking up your Helia and where will you keep it?

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