Small but Mighty: The Case for the Day-Sailor Lifestyle

With changing lifestyles and landscapes, opportunities to enjoy simpler and more frequent sailing excursions can be had with an affordable day sailer. In regards to waterline length, complexity of systems, and financial commitment, experiencing the joys of sailing on a smaller scale may lead to more days on the water. So if you love the wind in your face as much as we do, this updated article from Bethany Whitley tells her story of the unsuspecting boat that found its way into her life and why she now swears by the day-sailor lifestyle. Get sailing!

The best boat I ever owned I bought for $500 at a charity boat auction, mostly for the really nice aluminum trailer it was resting on. The 19-foot O’Day Mariner 2+2 was a bit of an eyesore. The sails were dirty, the wood was begging for some love, and the chipping bottom paint was exposing layers like an onion. To top it off, its hull was a dazzling shade of guacamole. Not the delicious, freshly made guacamole, but more like a bowl of guacamole that has been sitting in the fridge a day or two past its prime.

Standing in line with our auction number to pay, I thought to myself that at least the money goes to a good cause. Meanwhile, my husband was going on and on about all the great things he could do with the shiny new trailer once we figured out a way to dispose of the sad, old fiberglass shell on top of it. Never in our wildest dreams did we think that we would fall in love with Wholly Guacamole and all the places she, and her trailer, would take us.

After owning and sailing our small but mighty vessel for several years, we were converted to the day sailor lifestyle. We preached its virtues to all our “big boat” friends with cult-like enthusiasm. We were absolutely sure that we had uncovered the secret that smaller boats are better in many ways! Here is a breakdown of how the day-sailer outshines its larger rivals and can be a great option for many sailors.


The single biggest obstacle to getting out and enjoying the sailing lifestyle is the cost of the boat and of maintaining all the systems and equipment necessary to sail it safely. Each foot you add to the boat exponentially increases the cost of sails, auxiliary power, spare parts, etc. Now multiply that by secondary costs such as insurance, haul-out fees, and slip rentals, and your relaxing hobby has become a stressful financial burden that can keep you from fully enjoying the sailing experience.

With a small, portable sailboat, you simply don’t have many of the financial stressors to begin with. Keeping the boat on a trailer eliminates slip fees. You are your own haul-out crew. The thought of insuring the boat doesn’t even cross your mind when the deductible is often more money than the boat is worth. With the excessive overhead out of your way, you will save thousands of dollars, if not tens of thousands of dollars, annually by owning a simpler, smaller, and mobile boat.

No matter how careful and competent you are with your boat, something will eventually break and it will need repair. Boatyards often charge for exterior work based on the length of the boat or by the hour, which is a direct reflection of the size and complexity of the vessel. If you are more of a do-it-yourselfer, you’re still talking significantly more time and more material costs with every foot and beam your boat increases. Used spare parts also become less available, and the tendency to need more of them increases with boats that are more than 25-feet long. Both money and associated stress are greatly reduced with every foot you loose from the length of the vessel, increasing your ability to enjoy the relaxing hobby you set out to master.

So the next time you’re at the yacht club and your buddy with the 50-foot foreign luxury yacht scratches its hull on the dock or has to call a diesel mechanic, reach deep into your pocket filled with cash, give him a pat on the back, and buy him a Dark and Stormy. He needs it a lot more than you do!


For many of us, time is our most valued commodity. So why devote more time to the things that don’t give us pleasure when a simpler answer–a day-sailer–is right in front of us?

Unless you are living on your yacht or taking it out four or more times a week (Good for you, you salty pirate!), a day-sailer makes it much easier to get out and enjoy time sailing and less time burdened with projects and maintenance. On a simple day-sailer, there are no hydraulic systems to fix, no instruments that need calibration, no electric winches to test, and the generator doesn’t need an oil change. Sure, it will take an hour to get the day-sailer’s rig and sails up and launched–and another hour to put it away. But that time pales in comparison to the time it takes to ensure that your yacht, and its multitude of systems, is in proper working order.

Beyond the time it takes to keep a sizable yacht maintained, there is also the time it takes to get somewhere. I helped a friend deliver a 60-foot ketch from northern Michigan to southern Florida. We took our time and stopped to visit friends and family along the way. I remember thinking to myself as we neared our destination several months after we departed that I could have driven the distance, pulling Wholly Guacamole, in less than 24 hours.


With a small, trailer-able boat, you are no longer confined to the body of water you call your home port. You don’t need weeks of vacation to get from one place to another. You can literally sail in Lake Michigan one day and Lake Winnipesauke the next, giving you more opportunities for exploration. A small boat with a reasonable trailer can be pulled by just about any four-wheel-drive car at speeds of up to 70 miles per hour! Can you imagine your boat traveling at those breakneck speeds?

Wholly Guacamole was especially good at creating opportunities for us because of her cozy cabin and swing keel. We could take her further than some day-sailers because her cabin gave us a moderately comfortable place for two people to sleep and keep our clothes and bedding dry in case of inclement weather. Because of the cabin, we made a habit of taking her camping all over the Great Lakes and sailing in beautiful and remote areas where we were often the only boat on the water.

The greatest thing about our boat, however, was the swinging keel. The ability to lift it up into the hull let us sail in shallow water and pull up on sandy beaches to go exploring. With no galley onboard, we could choose a secluded spot on a beautiful sugar-sand beach and cook our dinner over a flickering campfire. Walking down stretches of beach, laying in the sun, and exploring the land around us was always a great treat after reaching our destination.

The places and the opportunities this mighty vessel gave us truly convinced me that bigger isn’t always better. I had been sailing the Great Lakes for the better part of a decade before acquiring my day-sailer, but I had never felt so connected to the landscape and so in tune with nature as I did on the tiny boat that took me anywhere.


Owning my boat helped me become a better, more intuitive sea woman. Leaving behind all of the fancy gadgets we’d become accustomed to on larger boats was a wonderful sensation. Feeling how the boat maneuvered was much easier with a small sailboat, and it helped advance my skills in predicting wind shifts, balancing the boat, and gaining more control and confidence.

It makes sense to learn how to sail in a simple boat such as an Opti, Sunfish, or Butterfly. If you can master the fundamentals and understand the elements in these small, sensitive boats, then cruising or racing in larger boats becomes significantly easier. Applying the same principles and mechanics on a larger scale is all that’s needed once the essentials have been engrained in your brain.

I used to get a kick out of people’s reaction when we would bring our day-sailer into a marina or boat launch under full sail. People would watch us, sure that we were fools who had no idea what we were doing. They would break out their phones and get ready to record a You Tube fail video that was sure to go viral. I never could tell if the look on their faces was surprise at our skill or disappointment that we ruined their chances at Internet fame, but, as they sat there and watched us shift our weight and let out the sail to reduce our speed, executing a perfect full-sail landing to a dock, I realized again just how awesome and simply fun a day-sailer is.

Day sailers come in all shapes, sizes and budgets, so let’s just focus on getting you on the water and simple pleasures creating memorable experiences. Source your perfect day sailer like Bethany, refresh the tired sails, replace any crusty rigging, de-funk and clean your vessel, but more importantly enjoy the heck out of it and go sailing!

Request a quote

The Discussion

Rob Jones
Rob Jones

You've struck a nerve here. Wandering through the marina about 8 years ago [ to go out on a friends "big boat"], I spotted what I thought was the cutest, saltiest little boat I ever saw. It was a 1970 O'Day Mariner 2+2, and the same color as yours although quite sad looking as it was sitting forlorn and unloved for over 5 years. If "Thomas the Tank Engine" was a sailboat, it would be a Mariner. Many hours of labor later it's my pride and joy. Although I have a trailer, I keep mine in a slip on the Chesapeake, 20 minutes from home and 15 minutes from my office. Funny you mention towing a boat to Florida. 4 years ago my sailing buddy and I towed "Nunyet" to the Keys for a 2 week cruise. It was quite an adventure to say the least. But, no one was hurt, the boat didn't sink and the beers at sunset were cold... Love me some Mariner!

John Hoover
John Hoover

Thanks for the great testimony! My 1977 Mariner 2+2 is fully outfitted for cruising, including convertible galley! My son and I have take many Chesapeake trips from Annapolis to St Michael's and back, not to mention South and West Rivers. We trailed to Niantic CT from NJ for the Mariner 50th Anniversary Rendezvous Cruise to Mystic, infamous now for the storm we encountered that day on LI Sound.. 6 foot seas, driving rain and 35 Kt gusts (it was hard work). The Mariner performed incredibly well and we arrived to a washed-out but welcoming Mariner fleet and their captains! I'm always noticing how much more my sailboat is actually sailing versus sitting idly at the dock like so many big boys- waiting for what?

Terry Moulton
Terry Moulton

The Mariner also comes with a great association and website. Check it out at!

Stephen Baetz
Stephen Baetz

As an avid sailor of small boats i started with a foam and molded plastic boat my father bought to see just how serious his son was who'd just returned from Landmark School in Prides Crossing,Massachusetts and got to learn to sail on Gen. George Pattons famed "When and If" an Alden designed 3 master schooner. Since that lil boat, I've had a Sunfish, a Zuma and my favorite an 18 foot O'Day daysailer. I'd bought it used from a retired Attorney in Fairfield, CT. Hauled it home, and then the Refit began. Took a couple of months to complete, but what a sight to behold. I named her for my first wife's love of all animals "Marie's Mennagerie" she sailed out of Mitford Boat Works in Milford until we moved to NW CT where she sat until sold. Many fond memories sailing her on Long Island Sound during the summer's. Now I'm boatless but a New gf whose never sailed is intrigued by my love of all things of Sail

Thierry Humeau
Thierry Humeau

Great paper, you made all good arguments for trailer sailing. We had a 40 and 35 footer in past that never had time to sail much further than a few miles around Annapolis, MD. Intrigued by trailer sailers and their limitless possibilities, we decided to give it a try and last year, acquired an immaculate 1986 Siren 17. Over the course of the summer, we sailed on 4 or the Great Lakes and in December, we took Sundance all the way down to Florida and explore its coastal shores. Coming from larger boats with all comfort, it took some adjustments but as long time backpackers and campers, we are used to live out of a small footprint. We are about to begin our second season as trailer sailors and are definitely planning to head back to the Great Lakes, Lake Superior in particular which is quite a unique and very special experience.

Leland (Micky) Burkett
Leland (Micky) Burkett

Wow great story! My first Mariner was also a lucky find, it was a green 1970 2+2 that was advertised as a O'Day Daysailer which what I was looking for since I had had one and sold it and wanted another, the guy was moving that day and needed to get rid of it pronto, so I went ahead and bought it for $500 then I discovered doing some research that it was a very coveted and valuable boat with a great history and a great association to go with it. In short it cleaned up beautifully and I loved it, I mistakenly priced it to a guy ($3700) thinking it was high enough that he wouldn't buy it, but he did. I've had 5 Mariners since and have a project 1968 , and a nice 1976 2+2 now. I live in mid Missouri and can be on several lakes within an hour, My family (grandkids now) love to sail and we go an average about every 2 weeks, it's a great family activity. And your right it's very inexpensive to own a Mariner.