The First-Timer's Guide To Great Chartering

By Jeanne Craig

Why do many experienced boaters spend so much time running to and from the same ports season after season? Perhaps they don't know about the options available for great bareboat chartering? So many reputable companies operate reliable fleets of power and sailboats in some of the world's most spectacular cruising grounds. Four of those destinations — ideal choices for those venturing out of their home waters and onto a bareboat for the first time — are profiled here. Each spot can satisfy the desire to explore a new and beautiful place, yet these regions aren't so foreign that they'll challenge a skipper's seamanship skills or make the crew uncomfortable. In these beautiful coves and anchorages, it's easy to feel in command while exploring a new and exciting place.

The Inside Passage


The Allure:

For some boaters, cruising is all about the view, so if it's big, breathtaking vistas you're after, plot a course to the Pacific Northwest. Granted, steep tides, strong currents, and unpredictable weather can classify this region as a black-diamond run for boaters with no local knowledge, but some charter companies make those things less of an obstacle. Northwest Explorations, for instance, offers guided flotilla charters from the company's base in Bellingham, Washington, up the Inside Passage and as far north as Sitka. You can book one of the Grand Banks trawlers in the fleet and sign on for one or more legs of the journey. Guiding the flotilla is a boat crewed by a professional captain, naturalist, and deckhand.

Photo of a guided flotilla charter through the Northwest Passage

This type of charter is a good choice for the person who's ready for an adventure in a part of the world renowned for its raw, natural beauty and wildlife, but who also wants the security of running along with a fleet.

Don't Miss:

Glacier Bay is a star attraction on the Sitka-to-Juneau leg of the guided tour. "Because the tidewater glaciers in southeast Alaska are receding, it's only a matter of time before these natural wonders won't be around," says Brian Pemberton of NW Explorations. "Here you can nose your boat up to the tip of one, grab a chunk of 10,000-year-old ice, and put it in your scotch." There are few places in the world where you can travel in this type of wilderness, yet you're almost always in VHF contact."

Another top spot is Princess Louisa Inlet, where you can point the bow at lovely Chatterbox Waterfalls and leave the stern on the edge of an underwater cliff with a 1,000-foot drop.

Know Before You Go:

The crew of the lead boat will teach charterers how to read the tide tables, calculate currents when running through narrow passages, and make the most of the electronics suite onboard, which includes radar because chances are, you’ll run into fog. Even so, with the guidance of the company's local experts, newcomers to the area often feel secure traveling into the wilderness north of the San Juan Islands, as the run is done in mostly protected waters.


Cruises start at $2,550 during low season for a week aboard a 36-foot Grand Banks Sedan.

Pine Island Sound


The Allure:

Located in the southwest corner of the state, it's one of the finest cruising grounds in the country, and one of the most boating-friendly, thanks to the protected waters, relatively good weather year-round, and a sand bottom with no rocks or reefs. From Fort Myers, where the Southwest Florida Yachts bareboat fleet is based, you can run north to explore the barrier islands of Sanibel, Captiva, Cayo Costa, and Gasparilla, and never leave the safety of the sound to venture into the Gulf of Mexico. Here you'll find award-winning beaches, and you can see them from one of Southwest Florida Yachts' trawlers or motoryachts sized to 43 feet. The islands are close together, too, so you won't have to waste a day of vacation running long distances to get where you're going.

Photo of people enjoying the beach in Southwestern Florida

Deciding where to stay each night is part of the fun of cruising here. There are a number of first-class marina/resorts, as well as pretty anchorages that put you up close to herons, spoonbills, and other indigenous wildlife. "Many people out for a week-long charter do two nights on the hook and five in marinas," says Barb Hansen, vice president of Southwest Florida Yachts. "That's part of the flavor here. You tie up in the afternoon, head to the beach, then enjoy the marina's restaurants and amenities."

Don't Miss:

Boca Grande on Gasparilla is Old Florida at its best, or "stuck in time," as the locals say, a seaside village with a five-and-dime store and ice cream shop. For anchoring out, head to Pelican Bay on the backside of Cayo Costa. This secluded nature preserve attracts many of the 200 species of birds in the area. Cabbage Key is a popular stop for boaters, many of whom swap sea stories at the bar best known as "the place with all the money on the walls." The staff here has been serving cruisers for over 60 years.

Know Before You Go:

You can pass on the provisioning package when booking a charter here, as most marinas are close to grocery stores and other shops. Supplies are easy to come by, as are reasonable dockage fees. The average cost to tie up at a marina in Pine Island Sound is just $2 or $3 a foot per night.


A seven-day charter aboard a Grand Banks 32 in winter (Florida's high season) costs $2,631.

Grand Traverse Bay


The Allure:

Located on the eastern shore of Lake Michigan, boaters cruise here to enjoy the spirit-altering sunsets, beautiful coves framed by tall trees and anchor-friendly sand, and the clean water that's tinged teal near shore.

Although the area is most popular with Mid-westerners who keep boats here for the season, it's a good choice for a first-time charter crew because the bay is protected from the large waves that can build on Lake Michigan. Based on size alone, Grand Traverse isn't intimidating, especially when held up to the likes of Green or Georgian Bay, yet it ranks among the top cruising grounds in the Great Lakes. Plus, there are no tides and few navigational hazards. There are many good full-service marinas, too, along with some of the quaintest towns you'll ever find.

Photo of ballon rides over the midwestren countrysideWhen running to Charlevoix, you'll be exposed to Lake Michigan for a short time, so pick a big weather window when planning a cruise.

Bay Breeze Yacht Charters, with over 27 years in the charter business, has a fleet in Traverse City. From here, you can cruise to a number of lovely harbors in Grand Traverse, such as Suttons Bay with its fine municipal marina located in the heart of Michigan's wine country, or Elk Rapids, a small village with a big, sandy beach and incredible views.

Don't Miss:

"If you're looking to get off the grid, spend a night on the hook at Bowers Harbor," says Dave Conrad of Bay Breeze Yacht Charters. This quiet anchorage with a pretty beach is about seven miles north of Traverse City. Take a short walk away from the docks to the lovely vineyard up the hill. If you're feeling adventurous, head north to the end of the Grand Traverse Bay and into Charlevoix, a favorite stop for local and visiting boaters as there are many good marinas and marine services in this friendly town. Vintage mahogany boats are common sights and complement the all-American scene.

Note: When running to Charlevoix, you'll be exposed to Lake Michigan for a short time, so pick a big weather window when planning a cruise.

Know Before You Go:

Because the area is relatively compact, the charter operator can get to you quickly if you do have any problems — mechanical or otherwise. In addition, Bay Breeze Yacht Charters has midsize express cruisers in its charter fleet, which could be good news for the person not comfortable getting behind the wheel of a big inboard trawler or motoryacht.


Seven days aboard a 32-foot Catalina that sleeps four to six starts at $2,640. Chartering early or late in the season can get you a discount of up to 30 percent off some of the boats.

British Virgin Islands


The Allure:

One of the world's top spots for bareboat chartering, this island chain attracts as many first-timers as it does return visitors. It's one of those rare places where you can find seclusion on an impossibly perfect white beach as well as an incredible social scene, which plays out in the restaurants, beach bars, and fine resorts throughout the 50-plus islands and cays. It's a top-notch tropical paradise for boaters of all experience levels, but what makes it a great choice for the first-time charterer is the fact that it's so easy to get around. The wind, which typically heads west at 15 to 20 knots, is very predictable so you won't feel tense about the weather. In addition, navigation is line of sight, the water is deep, and most places have secure mooring systems, all of which mean it's easier for you to relax.

"Technically, you're in a foreign country, but it all feels familiar," says Gary Hendricks of The Moorings, which operates a reputable fleet out of Tortola. This company leases power cats that can cruise near 15 knots, which means you can cover a lot of territory in a single day. And because these islands are grouped close together in a relatively compact stretch of water, you can explore a good deal in the course of a seven-day cruise.

Don't Miss:

Most tourists head for The Baths on Virgin Gorda for an afternoon snorkel, but if you want to avoid the crowds, go to Sandy Cay off Jost Van Dyke. This tiny atoll has an incredible beach, plus good snorkeling. From here, it's a short run to Diamond Cay, home to the"Bubbling Pools," or natural rock formations that fill with water when the tide is up. For great evening entertainment, hit Cane Garden Bay on Tortola.

Know Before You Go:

The BVI are unique because there's so much to see and do. In addition to diving wrecks and snorkeling world-class reefs, there are cosmopolitan restaurants and crazy tiki bars. For that reason, don't arrive on the island and assume you'll get all the information you need at a skipper's meeting. Get informed before you go. Talk to the charter operator before you leave and request an itinerary. Some companies, like The Moorings, put them online so you can begin to plan the trip as soon as you book it.


A seven-day charter aboard a two-cabin Moorings 37.2 that sleeps six, in June 2012, cost $2,735 (at press time). 

— Published: June/July 2012

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