Charter America

This summer, go explore America’s best cruising grounds on a bareboat, crewed charter or cruise-and-learn experience. Over the past few years, charter fleets have been growing and new fleets are springing up at yacht dealerships and sailing schools where you can actually spend a week aboard a new boat you might be considering buying for your own.

From the northern regions of Maine to the shallows of southwest Florida, to the cool clear waters of Georgian Bay and the pine and rocky shores of the Pacific Northwest, North America has amazing places to cruise. Out there sailing, you can commune with eagles, orcas and manatees. You can swim in pure clear waters and hike along untamed shorelines. You can become human again.

The beauty of chartering is that you can fly or drive to a new cruising area, step aboard a well maintained boat, sail away for a happy vacation and then return the boat, hand over the keys and head home with special memories and without a worry in the world.

Most charter companies offer a variety of charter options and the long weekend charter has become increasingly popular. Four nights aboard and three days of sailing from Thursday to Monday is a great way to have a sailing vacation without taking off a whole week from work. And if you make long weekend charters a summer project, you can be in Maine one wTeekend, then escape to the Chesapeake Bay on another, and finish up with a tour of the San Juan Islands of the Pacific Northwest.

But if you have the time, then a week or 10 day charter is the way to really get to know a new charter area. Plus you will have the time to truly relax and get into that special cruising state of mind that so clears your head of the clutter of the work-a-day world.

Whether it is a weekend or a week away chartering, bareboat or crewed, there is nothing like the restorative powers of sailing in special places. Here’s our annual look at Chartering in America.

Portland Head Light in Maine, New England
Portland Head Light in Maine, New England


From June through the end of September, New England is a coastal cruising paradise that offers sailors a wide variety of anchorages, famous harbors and wildlife delights. Your choice will be to charter in Maine or along the southern coasts of Cape Cod, Rhode Island and Connecticut. Maine will take you into the wild. Southern N.E. will open the gilded doors of Newport and Nantucket, Bristol and Edgartown and all of the lovely anchorages and harbors in between.


You can pick up charter boats in Portland, Rockland-Camden, Castine and Southwest Harbor. From any of these homeports, most cruisers will head to Penobscot Bay and the islands of the mid-coast.

There are few marinas in Maine where you will overnight. Instead you will mostly be seeking out protected harbors where you can swing on your hook peacefully and there are hundreds if not thousands of suitable spots to discover. You can flock to the famous summer colonies at Booth Bay, Camden, Northeast Harbor and Bar Harbor where the restaurants are excellent and the nightlife fun. Or, you can seek out the places where the eagles breed and the mussels grow thick on the rocky shores.

Either way, a long weekend or a week or more chartering along the coast of Maine will be a memorable experience. Here you will find coastal schooners sailing on the morning breeze, lobster boats coughing and spluttering as they retrieve their catches, and fleets of summer folk racing their handsome gaff headed small boats as they have for generations. In early summer, you might find fog that will drive you up the bays to clear air. In late summer, you will feel the sharp edge of fall when the wind turns northerly and the sky goes dark blue. Whichever end of the season you sail in Maine, you will be immersed in a wild and wonderful world.

Long Weekend Itinerary – Starting in Rockland, Maine

Day One: Sail east to North Haven Island and spend the night in Pulpit Harbor.

Day Two: Sail up Penobscot Bay to Buck’s Harbor at Eggemoggin Reach.

Day Three: Visit Pond Island then spend the night in Smith Cove, Castine.

Day Four: Back to Rockland.

Seven Nights, Six days – Starting in Rockland, Maine

Day One: Sail east to Vinalhaven Island. Spend the night in Winter Harbor.

Day Two: Sail east through Merchant’s row with a stop at Stonington for lobster. Tuck in behind Camp Island for the night.

Day Three: Sail east to Mt. Desert Island. Anchor in Southwest Harbor.

Day Four: Sail west to Blue Hill Bay. Anchor in Blue Hill and enjoy this artists’ colony.

Day Five: Sail west Through Eggemoggin Reach to Buck’s Harbor.

Day Six: Back to Rockland.


The hub of sailing in southern New England is Newport, R.I. and Narragansett Bay. Many charters originate here and the choices of areas to explore over a long weekend or a week are almost endless. You can head west to Block Island and Long Island Sound and the amazing beaches and quaint summer colonies. Block Island in summer is a cruisers’ Mecca with the crowds that go with that status. You can venture into Mystic, Conn. to soak up maritime history. And you can hang out in Stonington to enjoy the seafood and the classic Yankee ambience.

But to the east of Newport, you have the Elizabeth Islands, Martha’s Vineyard and Nantucket beckoning on the horizon. Cuttyhunk at the tip of the Elizabeths is a favorite island among cruisers. Eastward you have Vineyard Haven and Edgartown on Martha’s Vineyard to savor and where you can rent bikes to explore this famous island.

Nantucket sits well out into the Atlantic and has a remote ambience even though it is a very elegant summer colony for the CEO class. The harbor is large and has many expensive moorings. Ashore is perhaps the quaintest village in America.

Long Weekend Itinerary – Starting in Newport, Rhode Island

Day One: Sail east to Cuttyhunk and pick up a mooring. Lobsters ashore.

Day Two: Catch the tide to Edgartown and pick up a mooring. Great restaurants.

Day Three: Heading back to Newport, anchor off the beach at Menemsha. The fish markets here are the best in New England.

Day Four: Back to Newport.

Seven Nights, Six Days – starting in Newport, Rhode Island

Day One: Sail southwest to Block Island.

Day Two: Head east to Cuttyhunk and pick up a mooring.

Day Three: Sail on the tide to Edgartown for a night out.

Day Four: Head east to Nantucket for a shot of quaintness.

Day Five: Head west to Vineyard Haven. Pick up a mooring.

Day Six: Catch the tide and head back to Newport.


chesapeake skipjack

From the Sassafras River in the North to Hampton, Virginia in the south, the Chesapeake Bay is one of the most varied and interesting bodies of water on the planet. It is the largest salt water estuary. It is also host to many of the earliest European settlements and farming communities at the birth of the nation. It is famous for crabs, oysters and shrimp and has supported a lively fishing industry for 400 years.

Ships that plied the American coasting trade often called the Chesapeake home and Norfolk, at it’s southern end, remains one of the country’s largest naval bases. The bay is famous for its sailing oyster draggers and for a wide range of innovative early sailing canoes and smacks. But if you are looking for the sailing capital of the bay, then you head to Annapolis. For those going on a charter, you most likely will begin and end your cruising in Maryland’s charming capital city.

The bay is a perfect place for a weekend or weeklong bareboat charter. Although quite shallow, the channels are well marked and there are hundreds of good harbors, rivers and gunkholes where you can drop the hook. The historic towns of the Eastern Shore make fun and interesting destinations and Solomons Island provides a glimpse into what the bay was like 100 years ago.

The best seasons for charting on the bay are spring and fall. Summertime can be hot and windless and the water littered with jellyfish. Not so good for swimming. But from April to June and September to Thanksgiving, the days can be warm, the breeze fresh and the nights at anchor cool and refreshing.

Sailing from Annapolis you can choose to head north to the head of the bay and the Sassafras River. Or, you can head south to Oxford, St. Michaels and Solomons Island. Here are sample itineraries that make for interesting cruises.

Long Weekend Charter:

North from Annapolis

Day One: Sail north from Annapolis under the Bay Bridge and head up the Chester River to Chestertown.

Day Two: Leisurly start and then a short sail to Rock Hall.

Day Three: Head north and make for the idyllic Sassafras River.

Day Four: Back to Annapolis.

Seven Nights, Six Day;

South from Annapolis

Day One: St. Michaels and a tour of the famous Chesapeake Bay Maritime Museum.

Day Two: Tilghman Island and a chance to see sailing oyster draggers and osprey.

Day Three: Oxford and a dinner ashore.

Day Four: Solomons Island and a lay day.

Day Five: West River and Galesville.

Day Six: Back to Annapolis.


FLBush Key and reefIf you want to get as close to Caribbean cruising as you can without leaving the confines of the United States, then the charter-friendly Florida Keys are the answer. With warm trade wind breezes, excellent diving and snorkeling, and a fun, vibrant island atmosphere, the Keys are an accessible paradise waiting for your next sailing vacation.

Fly into Ft. Lauderdale or Miami and choose from a number of places to start your charter. The Florida Keys are a long chain of islands looping southeast towards the Gulf of Mexico with outer reefs and a few sandy beaches. The prime cruising season is in the winter, but late spring—just before hurricane season—can be excellent as well.

Key West is the largest town in the chain and offers a funky, fun place to anchor or stay for a night in a marina. The nightlife here is legendary. Plan to visit a variety of famous restaurants and bars along Duval Street and the adjacent avenues and you won’t be disappointed.

But the gem of the keys is truly the Dry Tortugas. Known as one of the most remote National Parks in the U.S., the Dry Tortugas are 60 miles west of Key West and offer a truly wild sailing destination that ends with gorgeous water and beaches. If you’re going to spend a week chartering in the Keys, the Tortugas are worth the effort.

Long Weekend —

Upper Florida Keys starting in Ft. Lauderdale

Day One: Sail south to Miami and anchor or choose from any number of great marinas.

Day Two: Continue south to Biscayne Bay. Stop for a swim and snorkel at Elliott Key. Spend the night anchored at Pumpkin Key.

Day Three: Sail into Hawks Channel to snorkel at Craysfort Reef, and then sail back north towards Miami for the night.

Day Four: Depart in the morning for a leisurely sail back to Fort Lauderdale.

Weeklong — Lower Keys & Dry Tortugas

Day One: Leave Marathon and sail to Key West. Spend the night at anchor and get ready for the hop to the Dry Tortugas.

Day Two: It’s 60 miles from Key West to the Dry Tortugas and you want to arrive in daylight in order to see the entrance and anchorage. Therefore, either depart Key West very early in the morning or wait until that evening to leave so you arrive in the Tortugas the following morning in daylight.

Day Three – Five: Arrive at Garden Key in the Dry Tortugas and tour Fort Jefferson National Monument. Allow for a few flex days in the middle of the schedule so you can wait for good weather to get back to Key West if necessary. In the meantime, snorkel and explore Loggerhead and Hospital Key. Depart the Dry Tortugas and sail 44 miles back east to the Marquesas for the night.

Day Six: Set sail from the Marquesas towards Key West and stop to snorkel on the way. Anchor in Key West or get a slip in Key West Bight Marine. Go out for dinner and enjoy Key West’s famous nightlife.

Day Seven: Get underway from Key West as early as the night before will allow and sail to the anchorage at Bahia Honda. Spend your last night aboard on the hook at one of the best anchorages in the Keys.

Day Eight: Leave Bahia Honda for Marathon with enough time to clean up and turn the boat back over.



San Francisco Bay is famous for its consistent sea breeze that you can literally set your watch to. This makes planning a cruise easy, as you can enjoy an exciting or leisurely sail around the bay before stopping at an abundance of interesting harbors for the night. With a number of charter options and nearby airports, the San Francisco Bay is a perfect place to fly in and grab a boat for a few days and nights. You can head out for a long weekend charter in San Francisco Bay proper or into adjacent San Pablo Bay.

Some of the best winds for sailing in all of North America will have you cruising to iconic bayside towns such as Sausalito, Redwood City, Benicia, plus the lively city life of San Francisco’s Pier 39 or South Beach. You can sail year-round on the bay, but fall is considered an excellent time for great weather and fewer crowds.

If you’re looking for a longer charter, extend your time on the bay or charter farther south out of the Los Angeles area to explore Catalina Island and Channel Islands National Park where you’ll find a destination that is both wild and vibrant. You can charter a boat from various points along the Southern California coast and the islands are just a short hop offshore.

Channel Islands National Park includes Santa Cruz Island, Santa Barbara Island, Anacapa Island, Santa Rosa Island and San Miguel Island. Fantastic hiking is one of the major draws to the islands, but the snorkeling, scuba diving and kayaking is superb as well. There is also a significant seabird and sea lion population to keep an eye on, and if you come in the winter there’s a good chance you’ll see Gray whales. Each season has its own pluses when visiting the islands, but summer and fall are considered the best for sailing.

Long Weekend Charter — San Francisco Bay starting in Alameda

Day One: Pick up the boat and sail north to Benicia, Petaluma or Napa. Or, sail to the northwest corner of the bay to the quaint town of Sausalito.

Day Two: After a morning ashore, head to Angel Island and anchor in Ayala Cove for the night.

Day Three: Sail to San Francisco’s Pier 39 to enjoy the famous Fisherman’s Wharf and the city’s nightlife.

Day Four: Set sail back towards the Bay Bridge and Alameda.

Weeklong — Catalina and Channel Islands from Newport Beach (itinerary by Sail Newport Beach)

Day One: Sail from Newport Beach to the west end of Catalina Island. Isthmus Cove is the more popular spot but if you have done “Two Harbors” too many times, consider a mooring in Emerald Bay, which has beautiful clear water as the name suggests.

Day Two: Head from the west end of Catalina Island north to Santa Barbara Island. You’ll likely be the only boat in the anchorage and the only people on the island. This is also a huge sea lion rookery.

Day Three: Santa Barbara Island to Santa Cruz Island. This is the best of the Channel Islands and is home to the world’s largest sea cave, which is big enough to drive a sailboat into.

Day Four: Sail around Santa Cruz Island.

Day Five: Santa Cruz Island to Marina del Rey. Get a guest slip for the night and walk to a restaurant after being in the wild for five days.

Day Six: Marina del Rey to Newport Beach with a stop to check out the Palos Verdez Peninsula on your way down.

Option: Spend an extra day (Day Five) at Santa Cruz Island and get home on the seventh day.


PNW Doe BayCruising the islands, fjords and sounds of the Pacific Northwest is an unmatched experience in North America. British Columbia’s Desolation Sound will have you sailing through a mountainous playground where peaks rise strait from sea level to over 6,000 feet. Quaint towns and villages in Washington State’s San Juan Islands and BC’s adjacent Gulf Islands will introduce you to the population’s notoriously laid-back lifestyle. And there is a very good chance you’ll be sharing your time with whales, eagles, seals and other marine life that call the Salish Sea home.

The best time to go is July through September, but late spring and fall can also be excellent with no crowds and more wind. And for truly hearty mariners, cruising the PNW in the winter can be idyllic.

In the Pacific Northwest there is a charter itinerary for everyone—sail or power.


Long Weekend (from Bellingham):

Day One: Fly into Bellingham or Seattle and make your way to Squalicum Harbor to checkout your boat. Or, spend the night in a local hotel and get the boat the following morning.

Day Two: Get underway and sail to beautiful Sucia Island Marine State Park where you can pick up a mooring ball for $15 or anchor. Located just north of Orcas Island, Sucia has multiple anchorages, great hiking trails and several beaches.

Day Three Set sail from Sucia Island and head south around the southwest corner of Orcas Island to Deer Harbor. Deer Harbor has a gorgeous, protected anchorage and Deer Harbor Marina is a welcoming spot with a fun crowd of boaters in the summer. Walk around the small community, take a swim in the pool or borrow the marina’s van and take a tour of the island (they’ll seriously let you if it’s not in use).

Day Four: After breakfast, cut the dock lines and head east through Harney Channel to Obstruction Pass. Make a lunch stop at Obstruction Pass State Park on one of the mooring buoys and go ashore to stretch your legs on the beach or hiking trails. From there, transit Obstruction Pass and continue east across picturesque Rosario Strait. Alternatively, make your lunch stop at Doe Bay Resort on the southeast end of Orcas Island to relax in the outdoor soaking tubs while enjoying one of the best views in all of the San Juans. Spend the night tucked in at Inati Bay on Lummi Island, which is just a stones throw from Bellingham but seems much farther away.

Day Five: Inati Bay is only eight miles from the charter base, so enjoy a pleasant sail across Bellingham Bay. Turn the boat in by noon and then grab lunch at one of the great restaurants or breweries in town before heading to nearby Bellingham International Airport or to Seattle to catch your flight home.


Seven-day Charter (from Comox, BC):

Day One: Spend the night aboard in Comox, BC, located on Vancouver Island, just across Georgia Strait from Desolation Sound. Complete your chart-briefing, checkout your boat, top up on provisions and grab a bite to eat in town. Ready for a hop across the Strait, your first full day takes you to Cortes Island’s popular anchorage at Squirrel Cove.

Day Two: Enjoy breakfast aboard then head ashore to explore. Scenic hiking trails will take you north to Von Donop Lagoon, west to Von Donop Inlet and south through Klahoose First Nation land to the tiny community around the Squirrel Cove public wharf. Then, get back underway and sail east to anchor in Tenedos Bay.

Day Three: Sail northeast while enjoying views of giant mountain peaks towering all around you. From Homfray Channel and Prideaux Haven, take your pick between anchoring in Melanie Cove or Laura Cove to enjoy more incredible mountain views.

Day Four: This middle section is a tossup. Choose any number of spots up Waddington Channel between West and East Redonda Islands including Roscoe Bay, Walsh Cove, Pendrell Sound (with water in the summer that can get to 75 degrees), or Bunsen Cove.

Day Five: Start working your way south to the quaint fishing village of Lund to get in a good position to make the hop back across Georgia Strait the following day. Make sure to check out Nancy’s Bakery for coffee and pastries.

Day Six: Sail back across Georgia Strait. Anchor in Henry Bay on Denman Island for the night or spend it at the charter base where you can shower, enjoy a meal ashore and get your things together for departure.

Day Seven: Turn the boat back in at the base in Comox and head for home.

Charter Companies in the Pacific Northwest

United States:

Anacortes Yacht Charters Anacortes, Washington (Anacortes Marina)

San Juan SailingBellingham, Washington

Ship Harbor Yacht Charters Anacortes, Washington (Skyline Marina)


Nanaimo Yacht Charters Nanaimo, British Columbia

Island Cruising Sidney, British Columbia

Desolation Sound Yacht Charters Comox, British Columbia


Lighthouse in Lion´s Head port on Huron lake, Canada
Lighthouse in Lion´s Head port on Huron lake, Canada


Considered by cruisers who have explored the world to be one of the best cruising and charter regions in America, the North Channel and Georgian Bay at the top of Lake Huron offer hundreds of anchorages amid a wild untrammeled wilderness.

You can start from charter bases in Michigan or travel to Manitoulin Island in the North Channel. From the former you will need a week or more to get to the North Channel and back. For shorter cruises, it makes sense to start in the islands themselves.

The natural beauty of the islands, particularly the Benjamins, is legendary. Plus you will be sharing the harbors with eagles and osprey and along the shore you might catch a glimpse of deer or a bear or two.

On summer nights, you will be stunned by the brilliance of the stars since there is so little man made light around and because the air can be so dry and clear. You will enjoy meteor showers in August and the Aurora Borealis when conditions are right.

Villages at Little Current and Killarney will offer shore-side entertainment and groceries. The culture of the folks in these parts is all about the outdoors and life on the lake. Be sure to sample the local fish and don’t forget to bring along powerful bug spray.

It can take a whole summer to really explore the North Channel and Georgian Bay, so you may well have to plan multiple charters in the years ahead.


Lake Superior’s Apostle Islands, not far from Duluth, Minn., are one of the cruising wonders of North America. Twenty-one of the 22 islands that make up the archipelago are part of the Apostle Island National Seashore and thus protected from commercial development. The cruising here is wild and raw.

The only year round settlement is on Madeline Island, which is not in the park. Here you will be able to pick up basic supplies and chat with locals who are known for their doughty charm.
Out among the islands there are anchorages of all shapes and sizes that offer protection from the various winds you may experience. The prevailing breeze will be westerly but summer sea breezes can fill in from all directions and you may get the occasional summer easterly. The water between the islands is deep and clear but most often you will find sandy bottoms when anchoring closer to shore.

The islands are inhabited by deer and smaller northern mammals. Eagles nest in the taller trees and in summer you may see eaglets trying out their new wings as they master their trade. Bears are fairly common so you need to be vigilant when walking ashore and be sure not to leave food anywhere.

Whether you cruise the Apostles for a long weekend or a full 10 day charter, you will find them beautiful, wild and as close to pristine as any islands in the U.S.

North Channel Long Weekend

Day 0ne: Set Sail for the Benjamin Islands

Day Two: Explore ashore, swim in the crystal water and discover a new anchorage.

Day Three: Head to Little Current for a little North Channel culture.

Day Four: Sail back to the charter base.

North Channel Weeklong Charter

Day One: Sail to the Benjamins and find a perfect anchorage.

Day Two: Explore the Benjamins and uncover yet another flawless anchorage.

Day Three: Sail to Killarney and explore the village.

Day Four and Five: Sail back to the Benjamins and hang out looking for eagles.

Day Six: Sail to Little Current for an evening ashore.

Day Seven: Sail back to the charter base.

Apostle Islands Long Weekend

Day One: Sail from the charter base to the islands. Anchor in a secluded cove.

Day Two: Hike ashore and swim before sailing on to another secluded cove.

Day Three: Sail to Madeline Island for an evening ashore.

Day Four: Sail back to base with a lunch stop along the way.

Apostle Islands Weeklong Charter

Day One through Four: Explore the islands and soak up the solitude and the pristine wilderness. Count birds and keep an eye out for bear.

Day Five: Sail to Madeline Island for an evening ashore.

Day Six: Sail back to your favorite, isolated anchorage.

Day Seven: Sail back to the charter base.





Author: Blue Water Sailing