Charter

Specialty ChartersA warm breeze across the deck and an azure sea are enough for me, and it’s what I remember most when I’m not on the water. But for many sailors, a long-awaited vacation had better include more than tropical isles and quiet anchorages. That’s why charter ...read more

The Great Lakes have long gotten a bad rap for everything from cleanliness to the quality of the sailing there. But the days of burning rivers are ancient history, and while it’s true the lakes are not dotted with the same abundance of islands and bays as, say, the Eastern ...read more

Time was that mapmakers would append the designation “Here be dragons” to those portions of the globe still unknown to them. But the terrors of the unknown pale in comparison to the fog, tides and rock (and lobster pot!) strewn harbors of coastal Maine—or so I thought until I ...read more

My last day of a recent weeklong charter revealed an expensive lesson: when we gathered up all the leftover provisions, they covered the saloon table. I’m no newbie when it comes to provisioning, but I let this one slip as we were harried on departure day and multiple people ...read more

There’s a reason New England sailors are so dedicated; New England is simply one of the world’s best cruising grounds. The southern side of Cape Cod and its off-lying islands—Nantucket, Martha’s Vineyard, the Elizabeth Islands and Block Island—are a cruiser’s dream. The weather ...read more

It’s not every day you can run aground twice in the space of 10 minutes and extract yourself gracefully each time. Chesapeake neophytes, we were feeling our way into the picturesque harbor of Rock Hall, and as we discussed the approach to the marina the boat slowed ever so gently ...read more

Contrary to perceived wisdom, the Caribbean can be a delightful place to charter in the summer. It’s true that yearnings for sun-kissed isles and turquoise waters tend to be strongest in the winter, but a mid-year Eastern Caribbean cruise has many benefits and may just become ...read more

Thanks to Google, there’s very little you can’t find online these days. So why, you might ask, would you need an intermediary or agent to book a bareboat charter vacation? The answer is that you don’t need one. However, you may gain value by using one, depending on where, when ...read more

While skippering charters around the world, I’ve learned never to bypass the boat checkout or the chart briefing. While most charter-base managers are thorough with their briefings, be sure to ask about the following so that you’ll be armed with as much information as possible ...read more

I like to pay special attention during my charter checkout because from years of learning the hard way, I’ve come to realize that the time to figure out what will go wrong later is before you leave. Also, while I listen to what the base managers are telling me, I also keep an ear ...read more

I am not the first, nor will I be the last, to refer to peer-to-peer (P2P) boating as pier-to-pier—it’s irresistible. The proliferation of the sharing economy has birthed P2P boating and with it, more players in the field of direct boater-to-renter vessel chartering. So I wanted ...read more

“The last time I visited Baja, it was 1972. I was 18 years old and on a road trip from Rapid City, South Dakota, to Cabo San Lucas, Mexico. There were five of us in a four-seater Jeep with a spare tire on the roof. I was the youngest, so they gave me the ‘fifth seat,’ perched on ...read more

For years I’ve been hearing about the Spanish Virgin Islands, as they’re called, on the eastern edge of Puerto Rico: how they’re like the U.S. and the British Virgin Islands once were before being discovered by the charter and tourist trade, with their wide-open anchorages, ...read more

Chartering with people who have never done it before? No problem, so long as you consider their needs, interests, fears, budgets and passions. It’s also important to remember that it’s their vacation too. Even if you’re an old pro with multiple charters under your belt, new ...read more

I was feeling nervous as my mom, my brother and I walked to the baggage claim area at St. Thomas airport to meet my three best friends from college. Non-sailors all, Andrew, Alex and Wayne were joining us for a week’s bareboat charter in the BVI aboard a brand new Moorings 45.3. ...read more

The Cat Sailor’s Bucket ListHere are some ideas that will get you to some new cruising grounds that are guaranteed to make your twin-hulled excursion an adventure.Click here for details and links to these exciting travel destinationsby Zuzana ProchazkaMHS Fall 2016 ...read more

It’s time for a charter sailing vacation, so what’s the best way to go? You can go it alone with a bareboat, get a captain for a crewed experience or tag along with a group of sailboats in a flotilla.Here’s how each stacks up.BareboatThe most common way to get your sailing fix ...read more

When bareboat chartering with friends or family, it can be tough to be the captain. Not only are you ultimately responsible for navigation, anchoring and the safety of the vessel, but you also have to manage crew duties without coming off like Captain Bligh. Part of good crew ...read more

You don’t need a passport to enjoy a spectacular sailing vacation. There are plenty of great places to charter right here in the States. Whether you want to go north, east or west, you’ll find fantastic cruising areas just waiting to be explored.Here are five of them...San ...read more

Annapolis is a true hub of sailing activity A big and little body of water—all at the same time Looks can be deceiving on the Chesapeake. It’s a body of water than can be both intimate and absolutely enormous all at the same time: a cruising ground where you can enjoy a ...read more

I like to consider myself something of a professional charter sailor. I’ve booked dozens of vacations under sail for myself and for others, and have read and written numerous articles on making chartering better, smarter, cheaper and more fun. So what could a charter broker ...read more

Click on the locations below to learn more about them. Then, check out our in-depth directory of charter companies in all locations.The Chesapeake BayReplete with rich boating historyClose to home; affordable flightsNumerous and varied spots for gunkholing2. The AbacosSublime ...read more

Dear SAIL,Your charter stories in the March issue had my mind traveling afar, and I’d like to be a bareboat captain. How does a charter company know that someone is sufficiently qualified or experienced to charter its craft? Some sailors are extremely capable, but have no ...read more

Chartering Southwest Florida