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How to gain nautical miles as a sailor?

Sailing has a reputation: it is expensive, intimidating, and difficult to gain experience without owning a boat. So, how do you do it?


Take a Sailing Course

The first thing we recommend you do is take a sailing course. Courses will teach you not only how to become a valuable crew member, but also when and where it's most safe and fun to sail. For those of you just getting started or getting back into sailing—consider Cruiser’s Academy's summer sailing lessons in Lake Tahoe. Sailors with more experience can check out our offshore sailing school in Mexico where we move past the foundations and level up in a bigger boat environment. Students learn about weather and navigation, boat systems, night passages, cooking and cleaning, and other cruising tools and trades. 


Get involved in your local sailing community

Fun fact: sailors LOVE Facebook. A quick search for groups in either your local area, or an area you are interested in sailing in, will show you just that. Wherever there is a sailable body of water, there will likely be a sailing Facebook group! You may also find groups tailored to types of sailors: female sailors, Catalina owners, catamaran cruisers, and so on. So join, make an intro post, offer to help with boat work or as crew, and see what happens. 


Beyond Facebook groups, places with big enough bodies of water are often home to “yacht-clubs'' or sailing clubs of some kind. A quick google search should help you discover if that’s the case. These clubs can vary in size and cost; while high end yacht clubs may cost thousands and offer more socializing than sailing, smaller clubs are usually more affordable and may offer sailboat rentals. Many clubs will also have a racing program with weekly races where teams are often in need of more crew to join as “rail-meat” (literally people that are needed to add weight to the boat!). While this might not seem like the hands-on learning you were hoping for, it does get your foot in the door. You’ll start rubbing elbows with the right people and gain a front seat to the action. 


Don’t discount dinghy TRAining

Many people believe that dinghy sailing is just for kids. They want to move straight to 40+ feet boats. But having taught hundreds of people to sail, we promise that sailing smaller boats is without a doubt the best way to become a good sailor. The smaller the boat, the more reactive it will be to weather which will train you to act faster, master the fundamentals, and develop a sense for conditions. The larger the boat, the more unique it will be, the more confusing the rigging, and the higher the risk when making a mistake. Smaller boats have the added benefit of being far more affordable, accessible in smaller bodies of water, and more easily transported by trailer. To check some out, start with these dinghies: optis, lasers, sunfish, and Catalina Capris. You may decide that owning one of these and emssing around will be the fastest way to learn.


Join Crew Sites to Gain Miles 

Once you’ve taken a course and are feeling comfortable on smaller boats, start to think bigger. There are several websites that link crew with boat owners who are planning to make a passage and need a helping hand. But beware: this is the Internet connecting people, and you HAVE to do your due diligence. 


Here are a list of sites for finding crew:  


This site is probably the largest boat and crew network. You first choose between "Find a Crew" or "Find a Boat" and then pick a location you’d want to start from. When clicking through boat profiles you can read about the boat, the owners, and plans for trips to come. At the bottom, previous crew may also provide reviews.


Unlike Find a Crew, when you first enter this site you pick between if you want a professional or recreational experience and if you are looking for a boat or crew. Then, each boat is listed with a few high-level details to scroll through. More details on the skipper, the vessel, and the positions will pop up in a separate page once you click on a profile. 


CoBoaters and Crewseekers are two others that connect you to boats or crew based on your preferences. The Facebook group, World Sailing Hitchhikers and Crew Connection, functions similarly. People looping for boats or crew make posts detailing what they are looking for and then members of the group can respond to connect with them. (Note: if you search “boater seeking crew on sailboats” or “crew seeking sailboat” in Facebook, you can find other groups as well). 


Once you've found the experience you're interested in you'll want to connect with the captain to learn more. Here is a list of questions you should ask:


  1. Get to know the captain: How much experience do they have? Sailors usually sum up their experience in nautical miles. For a frame of reference, sailing an entire lap around Earth at the equator is equivalent to about 24,000 nautical miles. Most ocean crossings are 2,000-3,000 nautical miles. While many of the most accomplished sailors don’t have any official qualifications, it definitely doesn’t hurt if someone is a licensed skipper (through the RYA, IYA, and ISST most commonly). So ask about it.  

  2. Know the boat: What size is it? What’s the cabin/bunk arrangement? Is there a water maker? Is there refrigeration? Do you use autopilot? When was the rigging done last? Are there any leaks or other issues etc? Do you have any major boat projects coming up? Read up on the boat and ask about the specifics so you can get an idea as to what it's like to live aboard and what you may expected to help with (first).

  3. Ask about safety: What safety equipment do you have on board?  Will we be doing man overboard drills and other safety checks before we leave the dock? NEVER go offshore in a sailboat that does not have a functioning EPIRB, a recently serviced life raft big enough to hold the entire crew, and adequate PFD’s. If your captain doesn’t give you an adequate safety briefing, leave. 

  4. Get to know your crew: Who else will be crewing? What do you usually buy when you provision? Do you drink/smoke? Do you have any dietary restrictions or preferences? You'll want to make sure, to some extent, you know what kind of person you'll be working with.

  5. Know what you’re paying for: What is the exchange of the money/work? It is important that you know what work is expected of you before you commit. There are three typical variations of how this may work, depending on your experience sailing: 

    1. You're less experienced so you pay the skipper in exchange for your time onboard. 

    2. Your work as crew is traded in exchange for your time onboard. Or, possibly, you contribute a small amount towards provisions (or other things). 

    3. You are paid crew helping on a passage (you will need a fair amount of experience to land this gig).

  6. Know the plan: What is your schedule and how tightly do you intend to stick to it?  The thing about sailing is plans are often fluid and changing which can be fun, except if your entire three week vacation is spent in a boat-yard when you thought you’d be island hopping. 

  7. Ask to meet: Can we do a video call? Again, it’s the internet so make sure people are who they say they are!

  8. Ask for references: Do you have any past crew references? Some of these websites already offer this function but it's good to hear the captain's response to this question.

  9. Share expectations: What do you expect of me as a crew mate? Can I share what I expect of you as a captain or what I hope to get out of this experience? Safety aside, this is the most valuable thing you can communicate. Remember, you are about to be living in a small space in, at times, stressful situations. 


This ones for the ladies…If a situation sounds too good to be true, it just might be. I wish I could say I haven’t heard stories about men with boats using these crew sites as dating sites, but I’d be lying. There is nothing wrong with being honest and upfront that your intentions are to learn to sail, not to explore romantic opportunities. Can’t quite feel the situation out? Try dropping the word “boyfriend” and see how that goes down…


The absolute GOLDEN RULE is that you should always be okay with leaving the boat. Always have enough money to get a ticket back home or be okay with the chance that your month-long sailing trip might turn into hanging out at the beach if something doesn’t feel right. If you ask these questions and are getting pushback on answers, it’s probably a red flag. If you join a boat and anything feels unsafe, LEAVE. If you join a boat and the people give you a bad vibe, LEAVE. You could be saving your life!


Partake in a Regatta

There are several annual regattas that take place around the world. We’ll share a couple examples here, but encourage you to research other options based on where you want to sail. These regattas are a great way to get some miles in a relatively safe set of circumstances. Each regatta will have its own safety regulations, support crew, and by a matter of sheer numbers, less risks involved.


Here are a few (of many) choices which will differ based on the type of boat, the difficulty of the route, the distance, and whether it is coastal or off-shore:



If you’re interested in getting paid to crew, check out our blog about “How to be a Yachtie”. Even if you don’t want to make a full fledged career out of sailing, the blog will give you some ideas on courses you can take that will make you stand out from the herd. 


For more hands-on experience, check out our Sailing Fundamentals Course in Lake Tahoe or our Offshore Cruising Courses in Mexico!




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