by Kim Kavin | April 1, 2024

Come Sail Away: Explore the Best Boating Experiences in Florida

A guide to Florida's best on-water experiences for beginners and experts alike.

Launch your own Jet Ski from the No Matter What Sanlorenzo SX88 chartered yacht. Photography courtesy of Superyacht Sales and Charter

Barb Hansen has owned boats, sold boats, chartered boats, been frustrated by boats and deeply loved boats alongside her husband, Vic, pretty much every day for the past four decades. She has spent more time than most people thinking about why a private boating experience can make such a memorable impression. As the owner of Southwest Florida Yachts just inside Glover Bight in Cape Coral, Hansen has seen countless people learn to sail, operate a powerboat or just head out with a captain for a long weekend of relaxation on the water. The unbridled joy that so many of these people describe, she says, boils down to the authenticity that a boating experience offers: “It’s like Disney, but it’s cheaper, and it’s the real world. It’s not trained dolphins. It’s the real thing.”

Travel adventures aboard all types of vessels in Florida and the neighboring islands of the Bahamas are endless, and the possible itineraries to explore are as varied as the styles of the boats themselves, from luxurious and fast to simple and slow. In some cases, no prior boating experience is required. In other cases, a boating resume is a must—with quite a few qualified educators around the Sunshine State ready to help anyone who wants to learn. The Chapman School of Seamanship in Stuart offers recreational classes for everything from boating essentials and powerboat handling to Bahamas crossing insights. The American Sailing Association lists more than three dozen locations where people can learn to handle a helm all around the state. 

It’s private. It’s quiet. It’s peaceful under the stars. It’s no noise, no nothing.
—Kimber Tracy

And, in many cases, Florida’s boating adventures can be booked in some of the most pristine waters on the planet. 

“All the waters of the Florida Keys are national marine sanctuaries,” says Kimber Tracy, owner of Florida Yachts Charters in Key West. “Most Americans don’t have a clue that this is in their backyard, and they don’t even need a passport.”

Here’s a look at a few of the best on-water experiences that are available aboard different kinds of boats at varying price points in Florida and the Bahamas. 

A Beneteau Swift Trawler 52, similar to what you might find in the fleet at Southwest Florida Yachts. Photography by Barb Hansen.

Sailing in the Florida Keys

The Florida Keys, at the far south of the state, are home to the third-largest barrier reef in the world. All of that coral makes for great fishing, snorkeling and some truly outstanding boating experiences. 

Nestled between the reef and the islands of the Florida Keys is Hawk Channel, which runs from Biscayne National Park all the way south to Key West. This channel creates an oasis where boaters can cruise in calm, protected waters, even if Mother Nature is kicking things up to a steady spin cycle out beyond the reef in less-protected waters.

“It’s fabulous. It’s beautiful,” Tracy says, adding that the waters in this part of Florida also tend to be far less crowded than in boating hot spots such as the British Virgin Islands. “The difference between the BVI is that it has 1,500 charter boats, and you have to fight for a mooring ball and be up at 6 a.m. to get it. Here, there might be two or three other boats, maybe. It’s private. It’s quiet. It’s peaceful under the stars. It’s no noise, no nothing.”

Tracy was born and raised on Oahu, Hawaii, where her sailor parents had her on boats at age 7. Surfing and scuba diving followed, along with sailing expeditions in faraway places like the Baltic Sea, the Seychelles and Alaska’s Inside Passage. As the owner of Florida Yachts Charters, Tracy is a franchise partner of The Moorings, a global boat-charter company that uses her business to fulfill its bookings for bareboats out of Key West. The term bareboat can be confusing to people thinking about booking a nautical vacation for the first time because the word sounds like it means a stripped-down vessel, but that’s not the case. The boat itself can be filled with flashy amenities, but the difference is a bareboat has no crew or captain. The opposite is called a captained boat or fully crewed boat. In short, you are your own captain, crew and chef when you book a bareboat.

The bareboats available at Florida Yachts Charters are built by some of the most venerable companies in the world. The base, headquartered south of the Overseas Highway on Stock Island in the Florida Keys, is home to 38- and 44-foot Jeanneau monohull sailboats that offer classic sailing experiences such as raising the mainsail and feeling the boat heel over when it picks up a brisk breeze, as well as 40-,  42- and 46-foot sailing catamarans built by Fountaine Pajot, Lagoon, Leopard and Bali that stay flatter to the water (no heeling over for the more timid sailors) while letting guests spread out and relax across bigger outdoor deck areas. 

Aboard those boats, guests can watch the sun set from a cozy settee as the captain drops anchor in a private cove. Or charterers can stand at the helm themselves, check the weather report and charts and then set a waypoint for whatever destination they please just over the horizon. Kids can get in on the fun, too, learning the basics of tying off lines to a cleat at the dock or figuring out how to peer through the water to spot coral heads and shoals. 

Florida Yachts Charters offers bareboat, captained and crewed charters, as well as private liveaboard educational courses. The base is an American Sailing Association school, which means the certifications students earn will be accepted at most other boating locations worldwide. 

“Usually, people who want to learn to sail are doing it because they want to start bareboat chartering,” Tracy says.

The Moorings’s fleet of catamarans offer comfort and style inside their cabins. Photography courtesy of The Moorings.

Sailors who want to try their hand manning a bareboat without a captain need to meet a high standard of experience in the Florida Keys, she adds, because the destination necessitates a lot of anchoring out. It’s different from locations where boaters can tie up at a marina slip or hook up a line to a pre-positioned mooring ball in most of the harbors. In the Florida Keys, you have to be able to anchor in conditions that can be challenging. Even people who have owned boats their entire lives, or who have chartered extensively in other locations, can still lack the requisite experience to book a bareboat in the Keys. 

“Probably 50% of the people who apply for bareboat charter captain are not qualified,” she says. “The general qualifications are that you have sailing certifications from a known body: ASA, US Sailing, RYA (the Royal Yachting Association in the United Kingdom). We want to see that you have learned to sail. We would also like to see previous bareboat charter experience. You have to have sufficient and up-to-date experience on boats of a similar size and type. If you’ve only sailed monohulls, we’re not going to give you a catamaran.”

Pricing for a week of bareboating starts at about $5,900 a week for the monohull sailboats and about $5,450 a week for the sailing catamarans. “If somebody wants to do a captained charter for just the weekend, we do that, too,” she says. 

It opens up a whole other world of vacation options versus the same old thing.
—Barb Hansen

Where can they go? She says to the west of Key West is the region’s wild side with no services of any kind: no fuel, no water, no restaurants, just uninhabited, nature-preserve islands. “It’s beautiful with the beaches, the turtle preserves and the bird preserves,” Tracy says. “You anchor out and take the dinghy to the beach and just enjoy being in nature. Just a six-hour sail from Key West, you’re off the grid with no cell service. The stars are outrageous because there’s no ambient light.”

To the east of Key West, she says, is more civilized, with cell service, restaurants and cities such as Marathon, which has The Turtle Hospital and the Dolphin Research Center as available activities ashore.  

“You have Looe Key and Sombrero Key, and they’re arguably the best snorkeling sites in the Keys. Woman Key is probably one of the best beaches in the Caribbean. There’s a dolphin playground, and you can snorkel,” Tracy says.

The team at Florida Yachts Charters prides itself on being able to direct boaters to places the locals like to go, especially to uncrowded spots that are the antithesis of prepackaged typical tourist experiences.

“These are wild beaches,” Tracy says. “There’s not some machine out there cleaning up the seaweed on the sand every day. This is nature. That’s the thing that’s so beautiful about it—and it’s not all covered with people.”

Cruise the Florida Keys on the Mooring’s 4000 Catamaran. Photography courtesy of the Moorings.

Cruising on Florida’s Gulf Coast

Hurricane Ian’s cleanup continues in Southwest Florida, where the Category 5 storm wrecked an enormous number of boats and waterfront businesses. Southwest Florida Yachts was among them; Hansen says the 15-foot storm surge at the marina left all the charter and instructional boats from her fleet in a snarling pile of destruction. 

But it’s hard to keep a good charter company down. While Southwest Florida Yachts has been accepting reservations since October 2023, the business won’t fully reopen with charters and classes until March 2024. It’s restarting with three motor yachts available for bookings—a Fountaine Pajot MY4.S, a Fairline Phantom 46 and a Silverton 43, which are considered midrange motor yachts in the wide, wide world of boats. These motor yachts, more like cozy floating cottages, are not as glamorous as bigger luxury yachts, but offer a surprising amount of creature comforts and certainly far more comforts than the  smaller, open powerboats that most people grow up messing about on. Midrange motor yachts have enclosed spaces with seating and dining out of the weather, true beds and bathrooms for a good night’s sleep and galleys with the kind of appliances you’d find in just about any well-appointed Airbnb ashore with a kitchen. Hansen says she plans to start with these three motor yachts, and then add more boats of various kinds back into the fleet as they become available for cruising around Sanibel, Captiva, Useppa Island, Cabbage Key and Boca Grande. 

“Everything is open again,” Hansen says. “Fort Myers Beach, the Pink Shell is open, Useppa, ’Tween Waters.”

Southwest Florida Yachts offers instructional classes as well as captained and bareboat charters. The charter boating experiences are limited to six people. “It’s not a tour boat,” Hansen says. “This is a private cruise where you can spend a few days to a week with a captain and dine out at the restaurants while island-hopping.”

In general, she says, it’s often a husband’s idea to book a charter. “He wants to buy a boat, and he wants to get his wife interested, so he wants it to be a really, really nice time. If that’s your goal, we can do that,” Hansen says. “It’s also a great area for families. Kids can fish, learn about history and learn about boats. The captain will teach them as much as they want to learn if they’re little sponges. They can put down the video games and be in the real world.”

Depending on the boat, Hansen says, she estimates that it costs about $4,000 to $8,000 per week for all six people, not including meals, gratuity or the $250-per-day fee for a captain. 

“Our thing is that we’re very personal,” she says. “We have a cruising concierge service. We ask what they like, what do they not like. Do they want to be at the beach, go to upscale restaurants, go to casual restaurants? We can tailor the float plans around what they want to do.”

A float plan is another way of describing a boat’s itinerary. It can be a two-day plan, a two-week plan, a two-month plan or more, and it can be changed along the way. 

The Golden Ours is equipped with state-of-the-art navigational technology, including an upgraded Sonos A/V system. Photography courtesy of Superyacht Sales and Charter.

For instance, perhaps the initial idea is to stay at marinas with only one or two nights anchored out on the hook. If the clients decide they love the privacy of anchoring out and want to do it every night, then the float plan can be changed to add more of that experience. By contrast, maybe the clients realize they love to be out having fun in the sun all day, but  prefer to relax on shore at night at casual restaurants with live music and dancing. That client would want a completely different float plan than the privacy-seekers who point the bow toward quiet anchorages. Whatever the preferences are, the float plan can be built to accommodate them.

You’re getting a $150,000 crew experience on an 86-foot yacht.
—Jeff Shaffer

And with the instructional charters, Hansen adds, the bonus at the end is that graduates can learn about all kinds of destinations that are available to boaters. Often, charters are available in places that people cannot access any other way, in regions of Florida and well beyond.

“It opens up a whole other world of vacation options versus the same old thing of going to a hotel and sitting by the pool,” she says. “That’s nice, but sometimes people are a little more active than that, and they’re looking for more adventure in their vacation. This really opens up the door for a lot of that, all around the world.”

Become Your Own Captain

The classes that Southwest Florida Yachts offers are for power or sailboats, and people can sign up with zero boating experience. Classes run from three days to a week, so the options work with many budgets and time allowances. 

“We can customize that to their needs, too,” Hansen says. “And they’re all liveaboard classes, so you really get the feel of whether boating is right for you,” she adds. “Can you and your spouse live on a 36-foot boat for a week? This gives you a real taste of what that’s like.”

In fact, she says, quite a few people who sign up for classes at Southwest Florida Yachts want to learn more about a particular type of boat than they can figure out just walking through it at a boat show. She also sees more than a few boat owners signing up for classes so they can develop better skills behind their own helm.

“The first thing they do when they get to Florida is buy a house on the water, and then they buy a boat. They think it’s like driving a car, but it’s not,” she says. “We take people from knowing nothing to being cruisers. This doesn’t teach you everything you need to know about boating; this is your first step. This gets you moving toward that goal.”

The No Matter What Sanlorenzo SX88 accommodates up to eight guests. Photography courtesy of Superyacht Sales and Charter.

Five-Star Charter in the Bahamas

If you have a bit more cash in the vacation fund—OK, maybe more than a bit—then another option is a crewed luxury yacht charter. This segment of the marine marketplace starts with yachts around 80 feet long and weekly base rates around $55,000 for eight guests, and it goes all the way up to billionaires’ superyachts that charter for more than $1 million per week.

Yes, it’s a big jump in price from some other options for a boating vacation, but a charter party of guests can be couples or families who share the cost, making this kind of top-level experience achievable for a larger number of people. 

And, there’s the proverbial reality that you do get what you pay for. On many of these yachts, the crew are liveaboard teams who have honed the guest experience in ways that rival five-star, big-city hotels. 

“This is a luxury yacht,” says Jeff Shaffer, charter management director at Superyacht Sales and Charter in Fort Lauderdale. Shaffer has spent years traveling the world to see and inspect yachts in the Mediterranean, the Caribbean and more, all with an eye toward making sure the boat and crew he offers are providing top-notch amenities and services that can compete on a global scale. “The crew is looking after your needs. It’s not just a for-hire captain. They’re going to pay attention to the tiniest details. You have a culinary-trained chef preparing your meals. The captain has knowledge of the cruising areas and local contacts to enhance your experience.”

A few of the offerings in Shaffer’s fleet are considered entry-level luxury charter yachts. While they may get regular maintenance in South Florida, the base for charters in the Bahamas. It’s much easier and more comfortable for clients to fly to meet the yacht in Nassau or Bimini, and begin a charter there, instead of cruising with the crew across the Gulf Stream, which can get rough. 

Enjoy the spoils with a full crew and personal chef aboard the No Matter What. Photography courtesy of Superyacht Sales and Charter.

This approach is particularly advantageous when considering vessels in Shaffer’s fleet like the 86-foot Golden Ours, a Sunseeker motor yacht that charters with eight guests and three crew members. Its weekly base rate is $55,000. In the luxury crewed marketplace, the term base rate means only the yacht and crew. Food, drinks, fuel, gratuity and other expenses can add 25% or more to the listed base rate, depending on how the charter party chooses to use the yacht. 

Guests fill out what’s known as preference sheets prior to the charter, and the chef stocks the galley with exactly the types of foods and drinks the clients want. Menus are prepared in keeping with everyone’s personal tastes and dietetic needs. Everything from spa cuisine to vegan and classic French are among the options. Pretty much anything goes as long as the chefs have advance notice so they can provision the galley accordingly.

What else do charter clients get for this kind of coin? Amenities such as king- and queen-size beds, ensuite bathrooms, luxe woods, marbles and fabrics in the decor, high-tech audiovisual systems, and all kinds of tenders and toys that the crew can teach guests of all ages to use. Fishing? Sure. Snorkeling? Absolutely. Want to give stand-up paddleboarding a try? No problem at all. The board will be in the water and waiting off the yacht’s swim platform with a member of the crew standing by to help. 

“One thing that’s really great about Golden Ours is that Capt. Jamie and his wife, Sarah, she’s our chef, come from a larger-yacht mentality,” Shaffer says. “They’ve worked on yachts over 150 feet long, but they wanted to be on a yacht the size of Golden Ours. They take things up a notch. You’re getting a $150,000 crew experience on an 86-foot yacht.”

The yachts that Sunseeker builds are known not only for their high-quality amenities but also for their impressive speed. Golden Ours lists a cruising speed of 20 knots, which gets the charter guests from point A to point B much faster than, say, a sailboat that can only hit about 8 to 10 knots in a stiff breeze. 

Other luxury yachts are best known for their design. As an example, two of the yachts in Shaffer’s fleet are newer models from Ocean Alexander, which has been making a push toward building yachts with enormous windows in the primary guest areas. In some of the onboard spaces with yachts like the 88-foot Almost Done (weekly base rate: $85,000 for 10 guests with four crew members including a chef), the windows go almost from the floor to the ceiling in spaces like the main salon. 

Imagine that view when the yacht is anchored all by itself in a harbor with pristine aquamarine waters, sandy white beaches and wildlife all around. 

“It’s like bringing the whole outside in,” Shaffer says, “and they have balconies.” 

He means foldout balconies, as in a piece of the yacht’s side folds right out of the hull and creates a platform with a safety rail where guests can sit and have a cocktail, read a book or simply enjoy the view. These balconies allow for such a unique and private experience, they have become staples aboard much larger yachts that A-list celebrities and titans of industry charter from St. Bart’s to St. Tropez.

Charter Golden Ours, a one-of-a-kind 2019 86-foot Sunseeker. Photography courtesy of Superyacht Sales and Charter.

The indulgent ways to pass the time onboard are endless. Relax with a glass of champagne in the sundeck hot tub. Enjoy an ocean breeze while lounging on a sun pad up front at the yacht’s bow. Or choose from an armada of water toys at your disposal off the swim platform back aft. In Shaffer’s fleet, one toybox extraordinaire is aboard the 88-foot No Matter What (weekly base rate: $85,000 for eight guests with four crew members). It’s a yacht that charters with a 27-foot tender plus a smaller jet tender, a surfboard, tow toys such as floats and wakeboards, stand-up personal watercraft, sit-down personal watercraft, bicycles and more. 

“That boat’s loaded with water toys,” Shaffer says of the superyacht. “It’s insane.”

When asked how he sums up a luxury crewed charter for anyone new to this type of vacation, Shaffer offered just two words that say it all: “Pamper yourself.”