There’s no question that sailboats require a lot of kit, and that reality often makes gift giving for the sailors in our lives as easy as a trip through the latest gear catalogue or a clean sweep of the specials at the fall shows. But the best gifts are about doing stuff, rather than getting stuff, about experiences rather than material goodies. Giving someone the opportunity to become a better sailor or spending time on the water with people we love are two of the best gifts you can give or get, and we’ve focused on short-term chartering and sailing education as two great ways to make those things happen during this gift-giving season. Often, the two go hand in hand, as many charter operations are linked to sailing schools in which people can learn the basics and then try them on a charter. What follows is by no means an exhaustive list, but it’s a good place to start getting inspired.
Most people hear “charter” and immediately think bareboat in blue water, island time, BVI, or pick your exotic, faraway destination. Which is all great, of course, but trips like these do require a commitment of time, money, airplanes, and logistics that make it harder to knock one out as a surprise gift. What if you could find a closer-to-home charter option that’s easier to plan and carry out and doesn’t hit the wallet as hard? Turns out, there are many possibilities.
“Most of our people don’t go to BVI; they’re coming here to relax. They want to take some family time,” says Lana Lohe, head of customer service at Dream Yacht Charter’s Annapolis base. Boats available for charter here include monohulls from 40 to 46 feet and multihulls up to 50 feet. “We get a lot of people from New York, DC, Virginia—people who are tired of being in the city, and they just want to be on a boat and chill out.”
While Dream Yacht offers charters of a week or more on the Chesapeake Bay, for many people, arriving on a Thursday afternoon for a “sleepaboard,” then heading out first thing Friday for three days of sailing to return on Sunday is just the ticket, she says. They can easily hit popular mid-Bay destinations like St. Michaels or Baltimore. “It’s easy for them to get here; they don’t have to pack a big suitcase.”
Likewise, at Dream Yacht’s base in Warwick, Rhode Island, people can charter catamarans or monohulls (Bali, Lagoon, Fountaine Pajot, and Jeanneau) for a few days and have all of Narragansett Bay at their fingertips, says base manager Jim Limoges.
“They just stay in the Bay—Newport, Jamestown, Bristol, and back to East Greenwich, and it’s awesome,” he says. “They take it easy. There’s so much to see.” Cost varies based on boat size and type, but on a 41-foot monohull in either base, a Friday-to-Sunday charter with sleepaboard on Thursday starts at about $2,750, including fees and taxes.
Haven Charters in Rock Hall, Maryland, offers a minimum two-night stay on any of 22 boats ranging from 32 to 51 feet, says Jacki Appleton, who has owned the business with her husband, David Fife, for 20 years. The cruising area is limited more by time than mileage; Baltimore is an easy day half-day sail right across the Bay, Annapolis not much farther.
“The majority of folks who charter with us know where they want to go, but some want us to offer advice,” she says.
In mid-Chesapeake Bay, Sail Solomons also makes two-day minimums possible on their fleet of bareboat monohulls ranging from 32 to 45 feet, says Jeff Carlsen, who’s co-owned the business with his wife, Cami, since 2015.
“We’re not a chain, we’re a family operation,” he says. “Our boats are in exceptionally good condition. The owners sail them on a regular basis, so they’re well used and maintained.”
Sail Solomons is one of the many charter operations that also teach classes as an ASA sailing school. Many of their guests start gathering skills with the ASA curriculum, then do their first charters there. The Chesapeake’s relatively forgiving nature as a sailing ground makes it a great place to start, he says.
“Everyone wants to get certified and go to the BVI, but wouldn’t you want to try a first charter here where it’s closer to home?” Carlsen says. “There’s more flexibility in time, location, itinerary. Our sailing area is one of the finest in the Bay…You can go north and visit small towns, go south and visit more rural parts of the Bay.”
Prices vary based on the type of boat and duration, but a three-day weekend, their most common charter, runs about $2,200 for a three-cabin 39-footer, he says.
Bluenose Yacht Charters based in Safe Harbor New England Boatworks in Portsmouth, Rhode Island, is another example of a combination ASA school and charter company, says owner Glenn Walters.
“It’s an excellent transition to chartering and ownership and that’s one of the reasons why we’ve added it,” he says. Operating charters May 15 through October 15, Bluenose offers mostly new Jeanneaus ranging from 34 to 51 feet, as well as an Excess 11 catamaran. Minimum charters are three days, and from Portsmouth, that allows for a great cruising ground including Narragansett Bay, Block Island, and even over to Cuttyhunk and the Elizabeth Islands in Massachusetts.
“The vast majority are typically in the southern New England waters from the Cape, Nantucket, sometimes Long Island,” he says. Shorter-term charters are prorated; for one of the larger boats in the fleet, it would be about $1,300 per day, less for a smaller boat. “We also have a winter base that is in the Abacos, and some of our boats go there as well,” he says.
Further north, NorthPoint Yacht Charters offers bareboat charters based mostly out of mid-coast Maine, including Rockland and Camden, but also Down East in Mount Desert and Bass Harbor, says owner Larrain Slaymaker, who’s been running the business for 40 years. NorthPoint requires a minimum of one week for a bareboat, but Slaymaker says that more people are requesting captained and crewed charters, which can be booked for shorter terms of two nights and three days.
Hope Swift, owner of Swift Yacht Charters in South Dartmouth, Massachusetts, helps people find charters and says most bareboats require a four-day minimum. “I bring clients to charter companies and I help them pick the vessel,” she says. “It gives people a wider choice with knowledgeable advice and more concierge service.”
Maybe northern waters aren’t your thing, or you want to plan something warm for wintertime. Waypoints Yacht Charters based at Vinoy Resort and Marina in St. Petersburg could be a good place to start (they also offer training as an ASA sailing school).
“We definitely recommend a long weekend in St. Pete, I would say at least three days” says Chelsea Houpt, charter sales and customer service manager. “It’s a really unique cruising ground because there’s something for everyone…There are lots of barrier islands to explore. And on any given day you can anchor or pick up a mooring ball or also dock for the evening and check out some of the local bars and restaurants off the beaten path.”
Waypoints has a fleet of 37- to 47-foot monohulls and Fountaine Pajot catamarans up to 45 feet in Florida. At their Annapolis base, they also offer long-weekend chartering on the Chesapeake in a similar fleet of boats. As an example, a four-day weekend (three nights, four days) on a new Dufour 430 is about $3,300 to start—about $1,000 a day with taxes, extras, and fees.
“The ideal itinerary is a three- to four-day weekend in Annapolis that gives them enough time to really explore the area and not feel rushed,” Houpt says. “We have guests from families to people having bachelorette parties to friends having a reunion.”
If you really want island time as part of your charter gift and don’t wish to go too far to get it, Cruise Abaco offers minimum four-day bareboat charters out of their base at Boat Harbor Marina at Abaco Beach Resort in Marsh Harbor, says Emily McGhee, co-owner with her husband, Chad.
“Wheels up from Miami or Fort Lauderdale, it’s about 45 minutes from Florida to Marsh Harbor,” she says, which makes a shorter-term charter very feasible for people leaving from the southeastern U.S. “If you left in the morning, you’d be here just after noon and have time to provision before check-in at 3.”
Cruise Abaco has 25 boats ranging from monohulls in the 40s to a range of multihulls from 40 to 51 feet. For shorter trips, she says, it’s a simple matter of choosing whether to go 30 miles south or north, based on weather. Navigating cuts is optional but not necessary, and the Sea of Abaco generally isn’t affected by the swell offshore, which makes it pleasant for those who prefer calmer conditions.
“A lot of people find it super easy,” she says. “We also have a ‘Captained by Day, Bareboat by Night’ set-up, meaning the captain doesn’t stay on board. If you have a three-cabin boat you can use all three cabins. This makes sharing the trip more affordable.”
Horizon Yacht Charters doesn’t have a base in the Bahamas, but they act as a broker to offer primarily bareboat charters in the Abacos and Exumas, says Christalen Ambrose-Thomas, global reservations manager. She says that more monohull chartering options exist in the Exumas, and she agrees that the Bahamas are a great quick getaway destination for chartering.
“It’s actually become, over the last three years, easier to get there with the different flights that have come onboard,” she says. “It’s reachable, it’s attainable.”
Learning by Doing
If you’re not ready to jump right into a charter, there are lots of educational opportunities that still offer plenty of time on the water with the added support of an instructor who can help you solidify the basics, hone your racing skills, get offshore, and more.
When you start researching sailing schools, you’re going to see one name come up a lot: ASA, or the American Sailing Association. Their certification courses are popular and available at over 300 different sailing schools across the country and around the world. The certifications cover everything from 101: Basic Keelboat Sailing, to 104: Bareboat Cruising, and 107: Celestial Navigation, to 108: Offshore Passagemaking, plus five endorsements that focus on specific skill areas like marine weather and radar usage. Depending on the certification and sailing school, the courses range from one day to multiple weeks, and you can expect to pay anywhere from $500 to multiple thousands.
According to David Pyle of Blue Water Sailing School in Florida, the typical student in their ASA certification courses “is someone who is interested in learning to sail for two main reasons: first, to do bareboat charters with their families, and second, to buy a boat for long term cruising. Many times, these overlap—someone wants to charter now and then buy a boat for cruising once they retire.”
As the name Blue Water Sailing School suggests, they specialize in liveaboard cruising courses, and it’s not uncommon for ASA sailing schools to have some kind of specialty in a particular topic, like San Diego’s West Coast Multihulls, which is a great opportunity to learn the ins and outs of catamaran sailing, or Narragansett Sailing School in Rhode Island, which has a thriving women’s program led by their five female ASA instructors. The latter has three locations for its program, which goes beyond the typical ASA curriculum to include DIY classes in diesel, electrical, sewing, splicing, sailmaking, and winter commissioning. These classes help sailors save money doing their own preventive maintenance and small fixes and communicate better with the pros when it’s not a simple fix.
“People comment that they pick our school because it offers not only sailing classes but also classes to troubleshoot things that may come up when chartering or renting a boat,” says Narragansett Sailing School owner Mary Goff.
Specialist courses aside, for many people the location is the main factor in what sailing school they get a certification from. Fortunately, there are plenty of options including Puget Sound Sailing School in Washington, Great Lakes Sailing Co. in Michigan, Florida Yachts Charters in Key West, and Norton Yachts in Virginia, just to name a few. The ASA provides a useful tool for looking up the location nearest to you: asa.com/find-sailing-school.
“From a practical point, many insurers require some proof of sailing competence, and they often will accept the ASA certifications as that proof,” says Pyle. “Many charter companies, especially in the Med, also require some certification to charter, and they usually accept ASA certifications.”
But ASA is far from your only option. The Colgates and their venerable Offshore Sailing School offer courses taught with trusted US Sailing curricula in gorgeous warm-weather destinations. The company, which will begin celebrating its 60th anniversary into 2024, has taught more than 160,000 people how to sail, race, and bareboat charter.
Offshore Sailing School’s most popular course is Fast Track to Cruising, available in the Caribbean from Scrub Island, BVI, and in St. Petersburg and Captiva Island, Florida, but they have plenty of other offerings as well. Prices are in the $2,000-$6,500 range plus accommodations.
“Students can arrive with no sailing experience. We include resort accommodations for the first three nights of the course while students learn to sail aboard a Colgate 26 for two full days,” says Sales and Marketing VP Beth Oliver. “Then students move aboard a 40- to 50-foot cruising monohull or catamaran for five nights and six days, living and learning how to handle a big yacht with up to four students and the instructor.” Families are welcome, including kids 12 and older.
Let’s say your sailor leans more towards racing than cruising. North U might be a good option. The program, which has been partnering with the ASA since early 2023 to provide elite racing training to ASA members, offers online courses as well as pop-up racing clinics in gorgeous locales, coinciding with other racing events for “Performance Race Weeks.” This allows for a unique opportunity to train with sailors from across the country, have a coach onboard, and debrief at the end of the day with video footage before participating in a race or regatta like St. Thomas Performance Race Week or similar events in the States. Sailors come to these programs with a range of abilities but should be prepared for a demanding week of in-depth, personalized training. Performance Race Weeks will cost around $2,500.
For anyone who loves adventure and Andy Schell’s “At the Helm” column, you cannot go wrong with a trip with 59° North. Though Schell and his team are probably most well known for their high latitude adventure sailing, the 2024 schedule includes two Atlantic crossings, a stint in Caribbean, and quick jaunt above the Arctic Circle.
“There is no better way to earn seamanship skills than by sailing with professional instructors on a real ocean passage with real stakes on a properly equipped boat,” says Schell. “59° North teaches seamanship in the real world, with the added bonus of getting to experience the magic of a long ocean crossing.”
Schell says the crews come from all walks of life, and since last year, 59° North has guaranteed at least two women’s places on each passage. They nearly always sail with mixed gender professionals.
“Some participants are circumnavigators who have since sold their own boats and get their offshore ‘fix’ with us, others are preparing their boats for long voyages and looking to gain experience, and many understand they’d rather sail offshore on someone else’s boat to save the cost and hassle of doing it themselves!” Though these programs can be pricey, running between $5,000 and $7,200, it’s a lot cheaper than owning and prepping your own boat for a similar passage.
That’s all pretty big commitment stuff, and maybe you’re looking for something a little bit more chill (or less expensive). You might consider SailTime, a program that allows you to become a member of a certain boat in their fleet and book time on it, allowing you to get out on the water without having to own or maintain the boat yourself. Prices vary, and they have 30 sailing schools from Anacortes to Alabama that teach ASA and RYA curricula.
“Our goal is to have an offering for everyone,” says Paul Sullivan, owner of SailTime Boston. And, he adds, “If you join SailTime Boston, but you’re traveling to the Chesapeake or California or Florida, if there’s another SailTime base nearby, you can reach out to one of those bases and use one of their boats.”
And finally, if you’re looking for something fun, low key, and close to home, why not gift a summer of small boat sailing with a membership to your local community sailing center? Especially if you’re used to a 50-foot LOA, a small boat is an excellent teacher. You have to hone your sense of wind and current without instruments, and your heel angle and sail trim matter more than usual. These programs maintain their own fleets of boats and often have classes, racing opportunities, and great social scenes. These vary in price but will probably be a couple hundred dollars for the season.
Plan a Staycation
If travel isn’t in the cards and there’s not a local option, consider an online course. They’re typically taught by top industry leaders at a fraction of the cost of an in-person session. You can expect these to run you anywhere from free to a couple hundred dollars.
For those getting started, NauticEd is a great launch point with free baseline courses all the way up to more advanced topics. One benefit of these courses is that after completing them, students can also attend one of their in-person sailing schools to gain hands-on experience.
For sailors looking to flex their DIY muscles, Nigel Calder’s Boat Electrics 101 course might be the place to start. Or, on the Sailing Channel, you can also find courses from other notable names like Gary Jobson, Don Street, and Lin Pardey, who recently launched her Storytelling for Sailors course discussing how to make the sailing life pay.
North U also has an online course catalogue for the racers out there, and ASA members get discounts on their programing.
And finally, SAIL’s parent company, Active Interest Media, produces Boaters University, which covers a number of boating safety and practical topics like medical emergency management, weather basics, and a deep dive into navigational rules. SAIL readers can use coupon code SAIL to get 20% off these courses.
Dream Yacht Charter
Annapolis 410-268-2140; Rhode Island 401-996-1099
Bluenose Yacht Charters
NorthPoint Yacht Charters
Swift Yacht Charters
Waypoints Yacht Charters
Horizon Yacht Charters