Charter Sailing in North America

With most international travel postponed for now, American sailors have taken the opportunity to rediscover amazing charter destination closer to home.

October 28, 2020
Island Packet 420
An Island Packet 420, available from Anacortes Yacht Charters, plies the waters of Washington’s San Juan Islands. Courtesy Anacortes Yacht Charters

Remember the good old days, when all you talked about was going out on charter, or taking sailing lessons so you were qualified to do so? Now, like just about everything else in a pandemic era, the times have demanded new labels for recreational sailing and instruction.

Staff at Club Nautique on San Francisco Bay, like many others in the industry, immediately heeded the call: Socially Acceptable Independent Leisure (SAIL) became their go-to slogan. “We offered a basic keelboat and basic cruising package of instruction to families,” says Don Durant, chief executive officer. “We’d tried it a few years ago with no success, but in 2020 the timing was right. It’s been extremely rewarding, and the families love it.”

Slogans aside, Marcus Abbott, general manager of Anacortes Yacht Charters in Washington state, sums up current affairs this way: “People want to get out on the water. This pandemic has ended up being good for business.” By any name you call it—staycationing, quaranteaming, family adventuring, safe social bubbling, notching another checkmark on the bucket list—sailing in America is booming again.


RELATED: Buying a Charter Sailboat

After a bleak spring 2020 of lockdown due to COVID-19, sailing schools and chartering outlets across the country are enjoying a silver lining from customers venturing mostly closer to home. Instead of flying to the Greek isles, they’re driving to the Great Lakes. And to coastal towns in established sailing regions, from New England to the Chesapeake and Florida on the East Coast; from the Pacific Northwest down through the Mexican border on the West Coast.

Record numbers are joining sailing clubs, signing up for coursework offered by US Sailing and the American Sailing Association teaching affiliates, taking crewed charters if they’re nonsailors, or booking bareboat charters and buying boats if they are. Companies have scurried to hire instructors and skippers, add to new- and used-boat inventories for sales and charter, create standby lists for classes, and lengthen sailing seasons for clients who just want to get away—for a day, overnight, a few days, or a week or two.


This crop of new participants and old salts has much to look forward to as they fulfill their dreams and discover—or rediscover—remote anchorages, stunning scenery and pleasant weather in their beautiful backyards on the water.

Two Steps Back, Leaps Forward

Before the phones rang off the hook and the emails poured in, companies and schools had to adopt cleaning and safety protocols for workers and vacation sailors. It was anything but easy, yet in the end, they report that the efforts paid off, and clients, via their wallets and feedback, support the changes.

What transpired at Great Lakes Sailing Company and ASA school in Traverse City, Michigan, is a vivid example: “In May, we were frustrated that we couldn’t open our industry even with strict safety standards in place,” says company president Dave Conrad.


Great Lakes Sailing, which had developed its own guidelines with help from a medical doctor with the Centers for Disease Control and Prevention COVID-19 Task Force, wound up getting involved with the Michigan Boating Industries Association and state senators to create industrywide standards. “It was one of those situations where we realized that the governor’s office was overwhelmed with trying to develop guidelines for every industry to safely reopen,” Conrad says. “It really shows what good can happen when people stop complaining and get involved.”

The changes ushered in include digital practices that will likely have staying power for clients and ­students who seek to explore the freshwater paradise of northern Michigan in 2021: “We changed our charter briefings so clients could better familiarize themselves with the boat before arriving,” Conrad says. “They receive digital information on where every mechanical and safety component is on the boat, and we digitized our chart briefings.

“We found that the client was arriving already familiar with the boat, and we could do a majority of the mechanical, systems and chart briefings in the open air of the cockpit. We’ll keep these procedures in place because it’s not only a timesaver for us and the client—it doesn’t skimp on the process. The client is actually better-informed.”


Not only are clients better-informed by the time they show up at the base, but their “asks” reflect pandemic-inspired trends. Those who shun dockage and restaurants are asking for dinghies and grills. Some clients, especially those coming by car, want the sleep-aboard service the night before the charter starts. “For the most part, people are driving to our base,” says Susan Restauri, charter manager with Cruise Annapolis and the Waypoints network in Maryland. “I get more inquiries out of Washington, D.C., than I’ve ever gotten before.”

If there’s any tip for American ­vacation sailors, it’s this one: Book your charter now, whether near or far—2021 is filling up already.

Aside from experienced sailors booking charters a week or longer, the newbies are jumping aboard quickly. “Many of the new charter clients don’t even know what a monohull is,” Restauri says. “So the key is matching them with the size boat that would meet their party size and allow accommodations for a skipper. They would also reduce their group size just to get whatever boat is available.”

Other types of clients are also driving the activity. “We’ve had birthdays, daysails, bachelorette parties and a wedding,” Restauri says. “In 2020, family is what it’s all about.”

Families are definitely evident on the instruction side of the equation—similar to what worked for Club Nautique. Here’s what’s in demand at Offshore Sailing School in Florida: “We are doing more private courses—just for a couple who want to learn together without any other strangers aboard except the instructor, and for families who live together back home,” says Doris Colgate, president. Singles are also welcome, with one cabin going to the instructor and a maximum of three cabins filled by others, whether singles or couples.

Sail Nautique
Sail Nautique’s learn-to-sail ­program has been a popular choice for ­families looking to get out on the water safely during the pandemic. Courtesy Sail Nautique

“It turned out to be a family adventure rather than just a sailing course,” Julien Grascoeur says of his family’s experience with Club Nautique. “Once COVID-19 is under control, we’ll start expanding our horizons and see where the wind brings us. Isn’t that what sailing is all about, after all?”

As crewed charter client Maureen Fox sees it: “We always wanted to go sailing and have talked about it for decades. The pandemic pushed us to do it. It was time to check this off the bucket list.”

Fox, her husband, and another couple hired a captain and spent the Labor Day holiday sailing Chesapeake Bay with Cruise Annapolis. The weekend trip included an overnight off the town of St. Michaels, Maryland. “The best part of the trip was being back on the boat,” Fox says. “We grilled off the stern, and I was surprised at how easy that was. We watched the sunset and the moonrise. It was so beautiful and quiet. We couldn’t get over the silence. This was a very different experience for us—sailing is really relaxing. We’d do it again.”

Book It!

If there’s any tip for American vacation sailors, it’s this one: Book your charter now, whether near or far. A number of factors contribute to this advice from companies and schools. In the face of the pandemic, companies adjusted policies, usually giving clients a year grace period to rebook, so 2021 is filling up already. Others have offered partial or full refunds.

Read the fine print of your contract and know exactly what you’re paying for, as well as rebooking and reimbursement limits. Stay up to date with quickly changing travel-refund policies offered through credit-card companies and insurance agencies. Cancel for Any Reason policies, or CFAR, which are receiving attention now, carry stiff premiums but eradicate most risk up to 48 hours before scheduled departure.

Bali 5.4
This Bali 5.4 is one of the boats available from Dream Yacht Charter’s base in St. Thomas, US Virgin Islands. Courtesy Dream Yacht Charter

The Moorings created a Travel with Confidence program, accessible through its website, to educate clients about safety measures, base reopening ­schedules, and refund and rebooking policies. “We’ve been extremely flexible the whole time,” says Josie Tucci, vice president of sales and marketing for Travelopia, owner of the Moorings. “A lot of ­customers are booking into 2021, and availability is limited due to rebooking. With all the policies in place, go ahead, get your vacation booked. Flexibility is key, so don’t wait too long. You can always postpone and change.”

While its partnership with Sailing Florida in St. Petersburg opened up a domestic tropical option for Moorings clients, US customers are still planning getaways in popular and as-yet-off-limits ­destinations such as the British Virgin Islands and other Caribbean locations, as well as in the Bahamas. “There is so much pent-up demand for chartering and travel in general, it doesn’t even matter which Caribbean destination opens up,” says Ian Pedersen, marketing manager at the Moorings. “People gravitate to what is open first. Lack of demand is not a concern for next year; sailors will go, one way or another.”

Funneling some of those bookings are the r­­ecord-breaking numbers of sailing-school students working toward bareboat certification. “When you look at what our clients write, as far as their plans go, nearly all intended to bareboat-charter in no more than two years from the time they graduated,” says Colgate, of Offshore. “Most, within the year.”

Destinations 2021

While Offshore has a full slate of Colgate Sailing Adventures Flotilla Cruises planned into 2021, Dream Yacht Charter is working to keep clients satisfied with expanded domestic and international locations.

In 2019-2020, Dream added to its 60 global ­destinations by taking on partners Navtours and Virgin Islands Yacht Charters. The expanded US footprint includes bases in Burlington, Vermont; Newport, Rhode Island; Annapolis, Maryland; Key West, Key Largo, and Miami, Florida; and St. Thomas in the United States Virgin Islands. Navtours and Dream are also partners at a base in Nassau, Bahamas. “The breadth of our company’s destination portfolio is critical to accommodate rescheduled bookings,” says Dan Lockyer, Dream vice president of global tourism. “Flexibility and clear rescheduling options are going to be key for customers unable to travel as planned due to COVID-19 disruption. We recently surveyed our customers and found continued demand for US-based sailing in 2021, plus much interest in the Caribbean and Bahamas.”

Cruise the ­dramatic coast of California aboard a catamaran. West Coast Multihulls offers lessons, ­charters and flotilla adventures. Courtesy West Coast Multihulls

Access to the USVI has definitely helped with demand. “With the BVI being closed, we have definitely had some converts to sailing in the USVI waters,” says Kristi Query of Virgin Islands Yacht Charters. “The US Virgin Islands have always been used as a jumping-off point for the BVI, and charterers rarely take the time to explore here. So many of our guests have come back to the base so excited about their charters, asking, ‘Why have we not done this before?’”

While some companies hint at additional US base openings, like Dream, West Coast Multihulls is ­reaping the benefits of just doing it. ­With its ­headquarters in San Diego, the company recently expanded its Sea of Cortez operations, accessible by car or a two-hour flight from Los Angeles. Options include crewed and bareboat catamaran charters in San Diego and from the Baja California peninsula in Mexico. Bases at Marina Puerto Escondido in Loreto, as well as the new site at Marina Palmira in La Paz, offer Fountaine Pajot and Leopard sailing catamarans. The company also teaches ASA sailing lessons in all locations, specializing in catamaran certifications.

“Flexibility and clear rescheduling options are going to be key for customers unable to travel as planned due to COVID-19 disruption.”

While the three locations have peak seasons, all West Coast Multihulls bases can offer charter and instruction year-round. Custom trips themed around blue whale and gray whale migration ­seasons, ­swimming with whale sharks, surfing, spring wildflower blooming, diving, yoga, and health and wellness spa treatments are available.

For those with a hankering to head offshore from the East Coast, Cruise Abaco offers multiple dates for a 160-nautical-mile Gulf Stream crossing with a licensed captain from Port Canaveral, Florida, to Abaco, Bahamas. ASA instruction and certification on the passage are also available. Dates in November and December 2020 as well as June 2021 are available.

Sorting through the options, it’s important to keep an open mind to the possibilities of SAIL. “We’ve ­experienced one of the best charter seasons we’ve had in over 15 years,” says Cindy Kalow, owner of Superior Charters in Bayfield, Wisconsin. “Our sailing-certification school has trained twice as many people as the previous year, and we’ve experienced a significant number of new customers as they travel from all over the Midwest to come sailing in the Apostle Islands.

“It’s hard to predict what 2021 will bring. Because we are pretty remote—four hours from the nearest major metropolitan area and major airport—we’ve always struggled with getting people to come here. Yet, in summer 2020, a number of new customers returned to sail a second or even third time. Once we get people to experience true wilderness cruising in the Apostle Islands, they want to come back!”

Elaine Lembo is a CW editor at large.


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