Boating Guide

Boat & Boating Guide – History, Types and Nautical Style

“A bad day on the water is better than a good day on land” – Unknown

Whether traveling by sail or motor, gentlemen around the world have always had a fascination with being on the water. While a proud few have the ability to own a private yacht, the ability to charter is something that might be slightly less costly than you would imagine.

Obviously, yachts are not for everyone. Some people prefer personal watercraft which can range from submersibles to Sea-Doo’s or even paddle boats, canoes and kayaks.

One topic I’ve had the privilege of writing about is super yachts and I’m always interested in hearing the stories behind the boat.

History of Sailing

Since the dawn of man, boats have been an integral part of the development of new civilizations. As long as man has lived near water, experts agree that he has utilized a boat in one fashion or another. Whether it be tying some logs together to make a raft or digging out a log to form a canoe, we have these historic watercraft to thank for the civilizations we call home.

Dugout Boat

Dugout Boat

For many years, archaeologists have spent careers finding and scavenging for historic ships of all sizes. Since boats have served us as transportation for thousands of years, we have continued to uncover new information that points to some of the oldest inventions in nautical history.

With findings that date back over 900,000 years ago, historians have had difficulty pinpointing the very first watercraft, but believe it to have been created sometime during prehistoric times. The earliest boats were believed to be logboats, but the eldest found to date have been dugouts which date as far back as 10,000 years. Today, historians consider the holy grail of boats to be a Pesse canoe made of a hollowed Pinus sylvestris tree trunk believed to have been made sometime between 8200 and 7600 BC. Currently and exhibit at the renowned Drents Museum in the Netherlands, other dugouts have also been recovered and can be found on display, but none quite as old as the Pesse.

With watercraft being found each decade, most experts agree that the first boats were primarily used in the Indian Ocean.

With the ocean known at the time for his inclement weather and raging currents, despite being so unforgiving, settlers continued to brave the water in an effort to develop civilizations and engage in commerce between Mesopotamia and the Indus Valley Civilization.

Christ in the Storm on the Lake of Galilee by Rembrandt

Christ in the Storm on the Lake of Galilee by Rembrandt

What’s rather interesting, is that evidence shows us that not all boats were the same, and despite the lack of knowledge at the time, ship builders were constantly managing to improve their designs. A prime example of ingenuity is the Uru which was built in the small village of Beypore in southwest India. It was an enormous wooden ship for the times constructed from teak and capable of carrying a whopping 400 tons. Used as a trading vessel, it was an important part of the import and export between the Greek and the Arabs.

One of the biggest advantages of traveling by water was that it afforded man far greater mobility, capable of traveling faster and farther than they could by land. In addition to being used for trade, these ships also acted as a transportation hub and offered a defense against foreign acts of war. The earliest documentation found is a small painted disc that was unearthed in Kuwait which clearly shows a sail boat. While sails were a modern convenience in comparison to the first dugouts, this disc has been dated as far back as 5000 BC illustrating the remarkable advances man had managed to achieve in times of strife and hardship.

With the development of sail technology, it allowed Arab, European, Indian and Chinese explorers to travel further by a natural propulsion that didn’t necessarily require backbreaking labor by the sailors. This offered settlers the opportunity to battle extreme weather patterns like never before. With sails, masts and rigging continuing to improve, navigation was made easier and maps were drawn in an effort to educate other vessels and decrease the chances of being stranded or lost at sea. By the end of the 15th century, European ships were making regular runs through the Pacific Northwest, traveling further north and remaining at sea for far longer intervals, even managing to explore the western Arctic.

Now that boats were considered “seaworthy”, explorers had the ability to chart course for new land, which is how, among many others, Australia was discovered.

Maritime exploration soon became an organized industry, with the first reference found dating back to the Mauryan Empire from the fourth century BC.

An English Ship with Sails Loosened Firing a Gun by Peter Monamy

An English Ship with Sails Loosened Firing a Gun by Peter Monamy

It’s widely believed by historians that it was the Ancient Egyptians who first began to understand the science behind sailing and aerodynamics as first documented by the Greek historian Herodotus. It is said that once the science of sailing was understood, the Phoenicians managed to successfully sail from the Red Sea to the mouth of the Nile in just three short years. Despite Herodotus being uncertain of the legitimacy of his own claim, most historians take that account to be factual and it is something that can be seen in many history books.

Sailing only continued to become more advanced, resulting in many famous explorations by some of history’s most profile navigators. Almost every independent country was located via nautical exploration and explorations via sea are a sure way to become a part of history.

Even today explorers are rampant in the world’s water. While we have found the majority of land on this planet, explorers have turned to new opportunities and now use vessels to located everything from new sea life to sunken treasure and ships.

Types of Watercraft


Technically just about anything can be classified as a boat if it floats. From the manmade rafts of the bygone era to canoes and kayaks dug by hand. Here are just a sampling of the types of vessels that are in operation today.

Technically there are two types of watercraft, from which all other categories are formed. The two are sailboats and motorboats, the first of which is operated by sails and uses the wind and current to move, and the latter of which is propelled mechanically. Some boats fall in to both categories leaving the crew with the option of sailing or motoring to their destination.


In North America bow riders are the most popular boats for private use. Typically they’re used for very short tours whether it be for relaxation, exploration or water sports. Many will offer a variety of features from built in bar fridges to storage for scuba gear. Today, most also come standard with a stereo system and are available in a variety of sizes from many builders. These boats are ideal for cabin use by small families who enjoy a variety of water based activities. They are often referred to as sport boats and runabouts.

Cabin Cruisers

A cabin cruiser is a way to describe a larger bow rider that can be used for personal use. Often people will purchase cabin cruisers with the intention of using them as you would a bow rider. They range in size from small to medium in size offering an enclosed cabin, often with sleeping and living quarters which include a galley (kitchen) and bathroom.

Center Consoles

Center consoles are a type of fishing boat typically used for commercial purposes. They are designed to undergo a beating and capable of challenging rough waters while hunting for fish.

Cuddy Cabins

A cuddy cabin is another term for a day cruiser. Similar to bow riders, they can be used for a variety of purposes from water sports and touring to swimming in the open water.


A deck boat is very similar to a bow rider but offers a larger deck (floor plan) for more passengers. They can be incredibly fast and are ideal for water sports and pleasure cruises.


Dinghies are very small watercraft designed for use in shallow water near the beach. They are very popular since they’re so light and can often be transported on the roof of your car, rather than behind with a trailer.

Fishing Boats

While even the largest super yachts can be fished from, actual fishing boats are vessels specifically designed for the purpose of catching fish or other sea life. The vast majority of these boats are quite small and used for short trips of a single day. These boats can be made of a variety of materials and for the most part are propelled by motor, with some smaller crafts operated by hand rowing.

High Performance Boats

A high performance boat is the Lamborghini of the sea. Often used by adrenaline junkies, these fast boats are very popular for water skiing among other sports. In addition to being an excellent choice for personal use, they have come under fire in recent years as they are used by criminal organizations to quickly transport drugs and weapons, most notably from Cuba to Miami and vice versa.


Growing up I always dreamed of living on a house boat. A house boat is exactly what it sounds like. It’s a watercraft that is designed for permanent or seasonal living. Very popular with bachelors and couples without children, they can be docked permanently in a marina or can navigate the water while providing comfortable accommodations. While houseboats have been around for many years, they surged in popularity after being featured in a number of hollywood movies in the 1980s.

Inboard Ski Boats

Designed specifically for the fast and the furious, these boats have inboard motors and are mean’t for water skiing and wake boarding.


This is a very broad category as inflatables can be rowed by hand or even have a motor to propel them. They range in price from under $100 upwards of thousands and can be used in shallow water for a variety of purposes.

Jet ski

Jet ski

Jet Boats

These are virtually identical to the bow riders we discussed above but with one major difference. Their motors are located inside the hull.

Personal Watercraft

Fast and affordable, these are the jet skis that can be used for a variety of fun and exciting purposes. In addition to being popular for use by waterfront home or cottage owners, they are also very popular with yacht owners wanting to speed off on their own or race with friends.

Pontoon Boats

Pontoons are slower wide boats that are great for families looking to float about. Often used for dining or swimming they are ideal for use on small lakes and rivers.


From the compact whitewater kayaks to team row shells designed for racing, these boats are hand propelled using oars.

While there are many other types of boats and multiple styles within each category, this should give you a basic understanding of the most popular types of watercraft.


Ranging in size, sail boats are non-mechanical vessels that are propelled by the wind being caught in the sail. They can often gain considerable speed and are very popular with a loyal following. Unlike many motorboats, sailboats take a considerable amount of training to operate and require a highly experienced captain who’s familiar with aerodynamics and other sciences.


Often used by commercial fisherman, these boats are great for families as well with onboard accommodations for short excursions lasting a couple of days.


Yachts are the granddaddy of the boat world and are designed for private use by those wishing to travel in the most luxurious way possible. Ranging in size, some of the larger super yachts in this category can easily rival commercial cruise ships both in size and capabilities. Often costing millions of dollars to buy, they can be chartered for a fraction of the price.

Purchasing vs. Chartering

If you love the water but don’t have the experience on a boat, it can often be a daunting task trying to find one. Most medium to large boats can be either bought or chartered (rented) and it can sometimes be tough deciding which option is best for you.

My first inclination is to suggest chartering since it costs a fraction of the price in comparison to purchasing, while giving you a glimpse into the lifestyle you think you want to live. Even the largest super yachts of the world can be chartered and it saves you the hassle of ownership and maintenance.

One billionaire I once interviewed for an article on yachts told me the best piece of advice he could give is to never buy. Whenever you purchase a boat, it becomes almost a second job. Like a cabin, unless you’re self employed or live on the shore, chances are you’ll have very limited use of it. For larger yachts that require a crew, you also have to worry about hiring and you need to pay them. Many new millionaires often make the mistake of buying not realizing that the operating costs of ownership can quickly drain a bank account. From the cost of maintenance, fuel, cleaning and outfitting to having to rent space in a marina, it’s an investment that quickly adds up. If you only plan on getting a bow rider or another small speed boat, buying is probably worth it, but unless you have money to throw down the drain, consider chartering if you want a yacht.

Even smaller watercraft down to jet skis can be rented and it’s kind of nice to just dock the boat and be able to leave after.

Private Yacht

Private Yacht

A third option is buying shares of a boat. This can be done through companies or privately with a neighbor or close friend. By owning a percentage of the boat, you decrease your costs and workload by half and still have the ability to say it’s yours. Obviously schedules aren’t as flexible as they are if you’re the sole owner, but it’s a viable option to consider if you don’t plan on using it daily.

If you do happen to decide you want to own, the best piece of advice I can offer you is to hire a broker. While smaller boats can be purchased from a dealer or builder directly, having a third party broker ensures you’re not sold a lemon or something that doesn’t fit your lifestyle. Boat Brokers like Realtors work with your interest in mind and while some will work off a flat rate, most simply charge a commission. The biggest benefit to hiring one is that they’ll guide you through the entire ownership process right down to selecting a crew and arranging the lease of a dock at a marina.

Top Recommended Brokers

Below are a few of my favorite brokers I’ve personally dealt with for one or more articles on yachting. They have each proved to be exceptionally knowledgable and very quick to return phone calls. Each of them comes with years of experience and usually represents a significant chunk of the yachts currently for sale on the market.

Denison Yacht Sales in Fort Lauderdale Florida

Curtis Stokes (private broker) from Fort Lauderdale, Florida

Worth Avenue Yachts (my top pick) located in Palm Beach, Florida

McManus Supersports / Apache Powerboats in Fort Myers, Florida

While you’ll notice many brokers are in Florida, for the most part they all work globally, traveling anywhere their clients need them to be. For smaller vessels, you ideally want to deal with a local authorized dealer which usually operates similar to that of a car dealership. If you’re set on a specific boat, visit that company’s website to find recommended sellers.




The cost of chartering boats can vary dramatically based on the size of the vessel, the crew (if any), the location (is it in Miami or Monaco) and the season. When it comes to smaller boats, in most cases the cost of the rental is just for the boat itself coming pre-fueled. Like renting a car, it’s your responsibility to refill the boat before returning it. Most domestic and international marinas do offer boat rentals, whether it be directly through the marina, or privately through the owner of the boat. For day cruisers and smaller sailboats, you can usually rent them hourly, half-days, daily or for many days at a time.

One tip I always like to offer is that if you happen to be renting a property in the area, try and find properties that come with the rental of the boat. Many oceanside residences and quaint lakeside cottages do have private docks and this is something that can often be negotiated into the rental, saving you the additional expense of renting the boat separately.

For those people interested in the luxury market and wanting to rent a yacht or super yacht, the prices also vary based on similar factors. Yachts can range in price from a few thousand dollars a day to upwards of a few million each day. Typically, they are rented for a minimum amount of days and many yacht owners or brokers will only allow guests to charter them for a week or more at a time.

When you are chartering a yacht, the prices can also increase if you happen to be competing with other prospective renters or with the owner himself.  Many owners utilize their yachts as an investment so they’re keen to rent them. Unfortunately, if you are looking to charter on a specific day the owner has intended to go out himself, you could be looking at a hefty premium if you really are set on that particular yacht.



If you do manage to rent a yacht, unlike most small vessels, yachts will typically come all inclusive. The rental rate usually includes everything from food, alcohol, fuel and even the cost of the crew. One yacht in particular, the Mi Sueno which was just sold by Worth Avenue Yachts, previously enjoyed many charter trips with one of the top crews in the world. One reason it was so popular was because the crew was unusually accommodating, working by the motto that provided it’s not illegal or unsafe, they’ll do it. Unfortunately, now that the ship has sold, it’s distinctly possible the new owner may keep it as their private sanctuary.

Chartering a boat or yacht is quite simple. There are many websites that offer valuable information on it and even just Googling “Yacht Charter” will generate a number of worthwhile hits. Of course, like everything on the internet, one must do their own research before committing to such an expensive purchase.

Once you do decide to buy or charter a boat, you’re going to want to look the part.

Nautical Style & Clothing

Traveling on the water is something that is popular around the world, but for many living in America, the art of sailing is a lifestyle as much as a hobby. From the rowing teams of the ivy league who race crew to the retiree summering in Nantucket, nautical interests amongst Preps are often a part of their every day life on and off the water.

Even for those who don’t own a boat, many preps will surround themselves with nautical memorabilia. From the model sailboats in wood paneled offices to the anchor bracelets and boat shoes worn in the Hamptons, enjoying life on the water isn’t exclusive to those who own boats.

Many of the most diehard preps will surround themselves with friends and associates for the purpose of having access to a boat. They may have no idea how to sail but so long as they know someone who can they’re happy. Clothing and style has long been influenced by sailing and vice versa. In almost every American coastal city or town, it’s not difficult to spot the nautical influence and leisurely style that is more in vogue than anywhere before. Even if you don’t own a boat or have the finances to afford one, you can easily showcase your interest in the nautical lifestyle through your clothing and lifestyle.

Recommended Clothing Companies influenced by Coastal Culture

Boat Shoes – boat shoes are an integral part of a boating outfit. Take a look at our extensive guide.
Anchored Style
Bird Dog Bay
Brooks Brothers
Collard Greens
Country Club Prep
High Cotton
Knot Belt Company
Lemon & Line
Ralph Lauren
Smathers and Branson
Social Primer
Southern Proper
Starboard Clothing Co.
Vineyard Vines
Onward Reserve


The amount of information one needs when venturing into sailing is extensive. Stay tuned for the next article in this series where we’ll break down the types of boats and go over some of the top sellers as well as my favorite boats. In addition, we’ll focus more on coastal culture and preppy style with features on clothing, accessories and the top Cities to dock at.

What are your favorite boats and boating accessories? Did we miss anything on our list?

Boat & Boating Guide - History, Types and Nautical Style
Article Name
Boat & Boating Guide - History, Types and Nautical Style
Learn more about boating, different kinds of boats, how to charter a boat , what companies to use and how to dress when you are on a boat.
8 replies
  1. Elliot Nesterman says:

    A wise man once said, “Never go out on the water without a knife.”
    God forbid there should be a life-threatening situation, but it is not inconceivable that you may in an emergency need to cut a line or cut yourself or someone else out of a tangle. A good sharp knife ready to hand can prevent an injury or even save a life.
    It needn’t be a fancy or expensive piece of nautical cutlery, so long as it has a sharp blade and is in easy access. A stout clasp knife, preferably with a serrated or partly serrated blade, is an essential part of any sailor’s or boater’s kit.

  2. Guillaume Helary says:

    Hi, I do like your site and the article makes a decent introduction to the boating lifestyle, but I believe it missed where is most of the glamour that resonates with the purpose of the Gentlemans Gazette.

    I grew up in the West of France by the shore, where the culture was very focused on the sea both at the level of the hobbies practiced, but also workers (yachting, fishermen and navy essentially, commercial fleet and shipyards to a lesser extent)
    Myself I sailed from young age and while I live now far from the sea (Prague in central Europe) I still hop on a boat whenever I can.

    I can’t comment in details on the US version of boating and sea culture, but I can comment on the European one (I know a bit of UK, Ireland, Spain, Portugal and Greece versions)
    First your introduction goes into too much details on motor boats compared to sailing boat, at least from all the Marinas and ports I’ve been in the split is 50/50 or in favor of sailing boats, including in rich people places like Monaco.
    The reason is easy, boating is never cheap and can be hugely expensive very quickly. One said once, “Sailing is like tearing up 100$ notes under a cold shower”. A motor boat will suck up petrol (or diesel) at alarming speed – on the picture above the dinghy has a total of 8 – 250HP engines, so 2000 HP in total. What it’s mile to the gallon. To give another example, my father witnesses the other day a 12m motor boat (hardly a “big” yacht, not even close to a super yacht) getting a refill on its 1000L tanks, the cost: 1800 € (that’s 2500 dollars) from another source I heard that such a boat can burn 500€ of oil a day (that was 10 year ago)

    From that perspective, sailing on similar sized boats is much cheaper, you use the engine only when there is no wind or to maneuver in ports. At my place, it was also much more highly regarded, “real” sailor know how to sail. To a large extent the knowledge gained while operating a boat with sail (dealing with wind, but also the waves and streams) this is the reason why most Naval academies strongly encourage competitive sailing or have 19th century style work boats (like clippers) to train students.
    Overall the whole boating as a mean of transportation is rarely the fastest way to go from point A to point B, even on a speed boat (compared to car or plane I mean) On a long distance (say from France to Ireland or Italy to Greece) Motor boats are not that much faster than a performance multi-hull sail boat (not race, just not a floating caravan) as the first cannot cover the distance full speed on their tank. This is even truer on trans-ocenanic trip.
    The comfort on similar priced sail and motor boats are similar as well. (we could enter on endless debate here)
    For a non-professional use, motor boats only make sens
    Overall you will never look very cool if you show-off in a motor boat, but you would also be a joke trying to operate a sailboat not knowing a thing about it.
    For a beginner who attracted by all the romanticism and coolness of boating.
    – Get a pro to tour you on the type of boat that makes your eye shine, see if you like it.
    – If you like it, get lessons, one week full time will get you the basics, one year of weekly sessions somehow autonomous (depending on the medium) after that it many year to really master the craft like all crafts.
    – If after that you love it, lease (you can lease boats without a crew)
    – Wait for 10 years before buying even if you have the money. Sailing (or boating) takes a lot of time, your significant other may not share the enthusiasm.
    – After 10 years, you’ll know how much time you’d have, and you’d what you want to buy (although, many sell a couple year later to buy bigger, until they don’t have the capacity to maneuver it on their own anymore and have to rely on friend who won’t have as much time)

    If you don’t have a lot of money. Sail dinghy is about cheapest point of entry to boating and the best school – there are competitive series presented to the Olympic games like Laser (solo) or 470 (crew of 2) A couple of grand would buy you one in decent shape and counting half a grand a year to maintain (this is a minimum) Those can be operated on lakes and are an excellent learning experience before going on the big inhabitable yachts. It is much easier to “feel” things on the smaller boats than on the bigger ones.
    Inhabitable boats are expensive to buy and expensive to maintain and require often a crew. if you made your classes, then you can try to hop in as a crew member, skipper are often on the look for new crew members for competitions, and this is definitely the cheapest way to spend time on a boat.

    Now this blog entry is also talking about lifestyle and clothing. If I have one advise to give: Like for trekking, never cheap out on your equipment. Get a set of technical gear adapted to the conditions you’d be in, even if you are trying it for only a few days. It is very easy to get dangerously cold at sea, even in what seem to be a mild climate.

    Competitive yachting can be a very posh experience with crew wearing uniforms and ceremonies with mandatory blazers and ties, I’ve seen some form of affectation to distinguish the “real” sailor from the tourist imitating the style, typical example is not cleaning the traces of salt on your boat shoes (it damages the leather but hey that mean that you got your feet wet in hot maneuvers)
    Avoid like plague poseur brand (that have only imitation of traditional) like Ralf Lauren, it has no “street” cred (sea cred?)
    Avoid also the memorabilia like the bacelet above. It screams tourist (even if you’re one) Sailor have a long tradition of decorative knots. It is easy to go to a shipchandler and by a few meters of rope, a small stainless steel shackle (or bronze) and get it done by yourself. This is how I’ve always seen it done.

    In terms of knife, my father also swear by Opinel. I do prefer Swiss knifes or Leathermans, but that a matter of taste.

    Brands that are popular in France (I know that some are also distributed in USA)
    Traditional (but can actually be used on a boat)
    – Saint-James (official provider of France’s Royale) Great pullovers and pea-coats
    – Le Glazik – Pea coats and traditional fishermen wear
    – Armor lux – Sweaters, cotons clothes

    – Aigle (shoes, boots and clothing)
    – Guy Cotten (clothing)
    – Le chameau (boots)
    – Helly Hansen (clothing)
    – Henry Lloyd
    Most of the technical brands, have a “casual lifestyle” line (meaning you can use it in mild weather, but cotton is the last thing you want to wear in a cold humid night)
    In France at least, the Dockside Sebago is considered to be the original boat shoe.

    Currently I own a Laser (small monotype series) that is rotting at my parent’s as life carried me away from the sea. My father owns a 10m sailboat (30y old Centurion from Wauquiez) and is just finishing a 3 month trip from Brittany to Madeira and back.

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