What’s The Best Cruising Sailboat – 10 Strategic Steps

If I told you that there was one particular monohull or catamaran cruising sailboat that is absolutely perfect for cruising, would you want to know which one it is? Unfortunately, there is no ideal cruising boat that suits everyone, and there’s no one-size-fits-all answer about what you should do with your life. Different people have different likes, dislikes, preferences, budgets, dreams, and aspirations.

One person’s perfect cruising boat will be another person’s very worst nightmare.

When helping our Sailboat Buying Guide readers select a future cruising boat, we first ask them to put aside any solid ideas they have regarding a particular boat. 

Sure, it’s possible that the boat you currently like best is right for you, but what if it’s not? What if the boat you’re considering doesn’t best suit your plans?

What Will The Best Cruising Sailboat Give You?

Defining YOUR Big Picture is the first step to finding the right cruising boat. People often mistakingly think that getting the boat is the end goal. It’s actually not the boat – it’s what the boat will give you. Many people want freedom, an ability to see the world, and perhaps a way to escape/retire from the rat race.

Interestingly, I know many people who have bought a boat and failed to find freedom, were too afraid to leave the dock, and transitioned from the rat race to an equally unfulfilling situation on a boat. 

Unless you define what the boat will give you – the big picture – it’s almost impossible to find the RIGHT boat. By defining where you want to sail, who you want to sail with, what sailing conditions are preferable, and what you want to spend your time doing once you have the boat, you can work backward.

How Wrong Can Things Go?

I met a Canadian guy in Antigua on a 38-foot light displacement monohull. He sailed the boat down from Toronto. He said that once he got into the Atlantic Ocean, he realized that the boat was not big and heavy enough to handle the seas. During his journey, he determined that he loved sailing, but he got the wrong boat for the seas he wanted to sail in. He’s since sold the boat and is looking for a larger heavy displacement boat.

Another example is a retired couple who decided to sail around the world. They were sold a boat that was far too large for them to handle. The broker said they’d easily manage a 62-foot bluewater cruising boat. The broker was wrong. The couple’s requirement was that they could sail and maintain the boat themselves, but in the end, they bit off way more than they could chew. They quite quickly had to hire an extra crew.

While anchored in Puerto Rico, I met a British-flagged sailboat that stopped over for a drink. I couldn’t believe it when they told me they were heading for America’s Intracoastal Waterway. The plan was to spend the season off the ocean and in the comfort of the calm inland waterway system.

I felt terrible breaking the news to them that it wasn’t going to happen. Their mast was too high to make it under the bridges, and their keel was too deep to manage most of the waterway. It was the wrong boat for what they wanted to use it for.

Advice For Getting The Right Cruising Sailboat

As I say often, if you don’t know precisely what you want and why you want it, a boat broker will sell you what they have (convincing you that it’s what you want). 

There are excellent boats that are more suitable for the Bahamas than others. There are other boats that are better for cooler regions and of course, there are boats best suited for the tropics. There are boats that are more stable for people that are less mobile and there are certainly boats better for big oceans. Let’s not forget the performance cruising sailboat, either.

Once you determine the big picture for your cruising sailboat, it is time to understand what type of boats best fit your requirements.

Then, it’s a matter of evaluating a variety of specifications. It’s important to consider as many boat elements as possible to determine what will be best for you and your crew.

For example, rigging style is a massive consideration. Do you want to be able to set sails and reef them (reduce the size) or pull them in from the comfort of the cockpit, or are you okay with going up on the deck? What about pulling a sail down on the foredeck in a storm?

Other considerations include deck material, cockpit placement, galley layout, comfort factors, and keel type. The more you understand which options are available and how each choice impacts your big picture, the easier it is to make a tick list that suits your needs.

Make sure to purchase a copy of my Sailboat Buying Guide here. The guide provides an easy-to-follow 10 Steps To Buying A Sailboat outline, including:

• Step 1: Understand Your Big Picture (12 Questions and loads of options to help you define EXACTLY what you’re aiming for)
• Step 2: Prioritizing Your Requirements For The Right Boat (35+ variables to consider that will make your boat the RIGHT cruising boat)
• Step 3: Understand Boat Ownership Costs (A list of over 90 potential cost areas broken down into costs to buy the boat, costs to get the boat ready for cruising, and finally, costs to maintain and service the boat. It’s an excellent help for budgeting and making the unknown costs known.)
• Step 4: How To Study Different Sailboats & Cruisers (from home)
• Step 5: The Importance Of Getting Out Sailing & Gaining Experience
• Step 6: Finding Potential Boats To Buy & The Important Questions To Ask (At least 10 questions you should ask about the boat before spending any time making plans to view the boat)
• Step 7: Create A Strategy On Boats To Buy & View Them (A 50-point checklist on what to look at and why you’re looking at it)
• Step 8: Sea Trial & Survey (What to do during your sea trial)
• Step 9: Negotiating The Terms Of Sale (Don’t ever offer asking price!)
• Step 10: Buy The Boat (The process involved in taking possession of your new baby).

Visit our shop to get more information on our Sailboat Buying Guide

Are you planning to sail in the Caribbean?

Make sure to read Top 10 Must-Haves: The Best Boat For Cruising The Caribbean