Cruising 101: Your Guide to Taking the First Step
Date Posted: August 26, 2025
Source: Scho & Jo

So you're interested in becoming a cruiser, but you don't know where to start? We cruised over 10,000 miles over the course of two and a half years, and this is how we wished we had started. We didn't take a first step; we took a "put a blindfold on and leap." Although we don't regret how we started, we do believe that with these three steps, our transition into cruising would have been smoother and more enjoyable. We're sharing actionable tips to learn from our mistakes and go from dreamer to cruiser.

 

 

Cruising up the Cumberland River, in Tennessee



To begin your journey to becoming a cruiser, first define your trip. Where will you be cruising? A circumnavigation, a season in the Bahamas, and the Great Loop all have very different cruising experiences. For example, on America's Great Loop, unless you break it up into sections, you'll be cruising for a year on average, and you'll have access to marinas most days. We've heard from friends cruising the Bahamas that they mostly spend time on the hook and have much longer provisioning cycles. Also, how long do you plan to cruise? Do you have a particular trip or route planned, or do you plan to "go all in"? Each of these requires totally different research and planning. Another key factor in planning is determining your budget. We created a budget calculator for the Loop, but there are other ways to budget your cruising lifestyle as well - the biggest categories will be fuel, marinas, and food (groceries and restaurants).

 

Our boat, PIVOT, docked in Jacksonville, Florida, off the St. John's River



 

Now that you have your trip in mind with clear goals, it's time to learn the basics of cruising. I'll break down cruising into two different categories: seamanship and lifestyle. The seamanship here is not any different from what you may have experienced on the water already, and this includes skills like boat maintenance, anchoring, reading the weather, etc. We recommend starting with American Sailing classes as well as taking Coast Guard Auxiliary boating safety courses to build your foundation. Join your local yacht club and start crewing for friends to just get out on the water. Once you have your own boat, hire a captain to show you what your boat is capable of. Learning seamanship takes time, but if you approach cruising with a learner's mindset, you'll get there. 


For the lifestyle of cruising, that's even easier to learn. Interacting with online forums, watching your favorite YouTubers, and attending boat shows and rendezvous are all fantastic ways to hear from other cruisers and get a glimpse into the lifestyle. It's not all margaritas and sunsets; there are challenges in the lifestyle that you'll want to be prepared for before you start your journey. To give you some concrete examples, here are some of our highs and lows of cruising. Some highs were the slower pace of life, stunning places to park our home, and the wildlife that you're immersed in. Some lows were being dependent on the weather, groceries, and laundry were always an adventure, and finding it hard to connect with family and friends.

 

 

PIVOT anchored on the Illinois River.



The final prerequisite to stepping into cruising will be finding your vessel. This is where steps one and two above are crucial - different boats will be best suited for different adventures. Keep in mind that there is no perfect boat - buy the boat that serves your needs and your cruising plans now, not the boat that may serve other plans. Every decision will have a trade-off, whether that's comfort vs speed or space vs maneuverability. We had a 34' Marine Trader for our Great Loop, and it was fantastic for that journey. It was a perfect combination of being small enough to easily bring in and out of various locks and shallow anchorages, large enough for us to comfortably live in, and being extremely fuel-efficient for our tight budget. However, if we were to plan seasons in the Bahamas, we'd look at getting a sailing vessel, as that would better fit the type of cruising we would want to do there. 

 

 

Sailboats in Penobscot Bay, Maine



If you have the opportunity and desire to become a cruiser, then go for it. The life lessons that living on the water taught us are irreplaceable - but be sure to keep a few things in mind as you step through the process of becoming cruisers. We're sure that by keeping these three considerations in mind, you'll have a smooth transition into the first few steps as a cruiser!




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