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United States Yacht Charter

United States yacht charters offer every type of harbor, scenery, and boat. The best time of year for yacht charter in the US is from April to October, though Florida and Southern California offer a pleasant climate year-round.

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United States Overview

The double bridge crossing Chesapeake Bay connects Annapolis with the Eastern Shore.

The double bridge crossing Chesapeake Bay connects Annapolis with the Eastern Shore.

The United States offers an incredible variety of charter opportunities. The Southeast ranges from the opulence of South Florida to the remarkable estuary of Chesapeake Bay. The Northeast stretches from the rugged coast of Maine south to the charming ports of Cape Cod and Newport, RI. The West Coast offers stellar scenery from the Pacific Northwest to San Francisco and San Diego.  The lengthy Gulf coast offers great beaches and fantastic fishing.  The five fresh water Great Lakes are sometimes referred to as the North Coast.  And in the middle of it all is the rich sailing tradition of the Midwest.

You can charter any boat imaginable in some of these destinations: classic America's Cup winning yachts, superyachts, event boats,  privately owned sailboats, sport fishing boats, and  motorboats of all sizes.

Choose a specific USA region for more detailed information:

Southern US and Gulf Coast
West Coast
Pacific Northwest
Great Lakes

Chesapeake Yacht Charter: One and Two Week Itineraries

Chesapeake Bay’s immense size means it would be possible to spend the rest of your life cruising here and most likely not see it all. A vigilant lookout is necessary, and navigating marker to marker is important. The maximum depth is around 200 feet, but the average depth is 25 feet and in many areas you could get off your (now grounded) boat and walk for quite a distance.

Dawn departure on a windless Chesapeake Bay

You’re likely to encounter crabs, oysters, dolphin and a vast variety of birds which makes the area entertaining and educational, especially for kids. Distances can be long, certainly for sailboats, so consider getting to know a couple areas well rather than rushing from one anchorage to the next.

Seven Days: Annapolis-Solomons-Annapolis

Day 1: Annapolis to St. Michaels
After checking out on your charter boat, head for the quaint town of St. Michaels about 27 miles south and east. Get oriented and plan your next day’s activities.

Day 2: Exploring St. Michaels
A bustling little town with a fantastic maritime museum, St. Michaels can provide enough activities for a week, much less a day.

Exploring ashore in St. Michaels, you might discover this church.

Day 3: St. Michaels to Oxford
Head down around the southern tip of Tilghman Island and up onto the Trent Avon River. Oxford is about 30 miles from St. Michaels.

Day 4: Oxford to Solomons
Cross the bay to the western shore and head over to Solomons which is about 35 miles. Anchor in Back or Mill creeks.

Day 5: Solomons
The Calvert museum is the highpoint of this area and well worth a visit.

Day 6: Solomons to Cambridge
Solomons will be your southern-most point on this itinerary so it’s time to head north and break up the trip with a stop in Cambridge with its nineteenth century homes and shaded streets.

Day 7: Cambridge to Annapolis
This will be a long day, nearly 40 miles to Annapolis, so start early.

Fourteen Days: Annapolis-Southern Maryland and Virginia-Annapolis

Day 1: Annapolis to St. Michaels
If you’re checked out near noon, you’ll be able to reach St. Michaels in time to anchor, stroll and have a great crab dinner.

Day 2: St. Michaels
There’s much to do in St. Michaels so take a day to explore. Wine tasting, museums, antiquing—there are lots of options.

Day 3: St. Michaels to Oxford
Get an early start so you have time to explore Oxford after a 30 mile trek. Don’t miss the ice cream at Scottish Highland Creamery.

The dock in front of the Deltaville Museum

Day 4: Oxford to Solomons
Cross the bay and anchor in one of the nearby creeks. Get the lay of the town and enjoy a relaxing happy hour at one of the many restaurants.

Day 5: Exploring Solomons
The Calvert Marine Museum with its screwpile lighthouse can’t be missed. Then shop for some fresh seafood for dinner aboard.

Day 6: Solomons to Crisfield
Crisfield is a quiet little town with plenty of room in a modern marina. Try Watermen’s Inn for dinner.

Day 7: Crisfield to Reedville
Today you’ll cross into Virginia. Don’t spend much time downwind of the menhaden ships in Reedville but do make time for the museum and the Claud W. Somers and Elva-C, historic vessels moored out back at their docks.

Day 8: Reedville to Deltaville
A two hour run south will put you into Deltaville, where you can get a slip at one of the modern marinas. Tie up and take a very short taxi ride to the museum, its docks, and the wonderful sculpture garden in the woods.

Day 9: Deltaville to Urbanna
A short hop up the Rappahannock River and you’re in the tiny town of Urbanna, with its antique shops and a self-guided walking tour.

Day 10: Urbanna to Tangier Island
Tangier can serve as a good stop on the way back north to Annapolis. Tangier is a town lost in time. Call ahead to reserve a slip and watch the shallow entrance. Depending on your draft, you may or may not be able to make it in.

Day 11: Tangier to St. Mary’s City
To break up the trip back north, stop in St. Mary’s City. St. Mary’s River is the second tributary on the northern shore of the Potomac. There’s a good breeze and plenty of easy anchorages.

Day 12: St. Mary’s to Cambridge
You’ll need to double back a bit and then cross the bay again but at a very narrow point. Enjoy the bay as this will be a long sailing day.

Day 13: Cambridge to Annapolis
Rise early and get a head start on this 40 mile trip north, giving yourself plenty of time to tie up in Annapolis.

Day 14: Annapolis
Return your boat early and head into town. Take a tour of the Naval Academy or explore the many shops and restaurants.

Pacific Northwest: One Week and Two Week Itineraries

There are lots of destinations to explore in the islands of the Pacific Northwest. From the southern Sun Juan Islands to the northern end of Desolation Sound is about 160 miles, with countless islands and miles of coastline in between. These waters include the San Juans, the Canadian Gulf Islands, Victoria, Vancouver, and Princess Louisa Inlet. Strong currents and significant tidal ranges make tide and chart tables a must. And be sure to invest in a recent cruising guide to get the local flavor as well as some safety information.

A sculpture in Roche

There are many good chartering companies in these islands and boats book up fast. If you’re thinking of chartering here, you should start planning an August adventure by February of that year—even earlier if you want your choice of vessels.

If you have guests who come late or need to leave early, they can take advantage of the extensive ferry network that connects various towns. Or send them home via one of the many float planes, which will add the bonus of a thrilling aerial view.

One Week – San Juan Islands

Day 1: Anacortes to Lopez Island

Just 12 short miles from Anacortes is Spencer Spit State Park, with 130 acres of great hiking. Good anchoring nearby.

Day 2: Lopez to Friday Harbor, San Juan Island

A bustling little town with great restaurants and galleries, Friday Harbor has guest dockage for over 100 yachts.

Day 3: Friday to Roche Harbor, San Juan Island

Head down around the southern tip of San Juan Island and out into Haro Strait where you might spot a pod of orcas. You may even find some wind to set sail, before cutting through Mosquito Pass to picturesque Roche Harbor.

Day 4: Exploring Roche

Take an extra day to hike the area, visit the sculpture park or maybe even take in a little outdoor theater on a summer’s evening. Don’t miss the sunset flag ceremony.

Day 5: Roche to Rosario Resort, Orcas Island

Grab one of the moorings outside the mansion and take a tour. Make sure you call ahead to check times for the organ concert that is not to be missed. Afterward, stroll around the beautiful grounds where deer wander freely.

Day 6: Rosario to Deception Pass

Transit south to a narrow pass between Whidbey and Fidalgo islands. At times other than slack tide, this can be a wild ride with ripping currents like a river. Anchor or dock at Cornet Bay.

Day 7: Anacortes

After returning the boat in Anacortes, explore the many galleries, marine stores and restaurants that serve up good local seafood.

Two Weeks – San Juan & Gulf Islands to Desolation Sound

Day 1: Anacortes to Friday Harbor, San Juan Island

If you’re checked out near noon, you’ll be able to reach Friday Harbor for dinner. Call ahead to secure a spot at the dock.

Day 2: Friday to Victoria, B.C.

Cross Haro Strait into Canada. Make sure you secure a permit to take the charter boat out of the country and check into Canadian Customs. Secure a dock in front of the majestic Empress Hotel.

Day 3: Victoria, B.C.

The food, the museum, the bagpipers and the shopping – there’s so much to do. Take a day to explore this European style capital.

Day 4: Victoria to Sidney Island

Head north up the Haro Strait which will give you another chance to look for orcas and grab a mooring at Sidney Island Marine Park. A mile-long loop makes a nice walk through a dense forest.

Day 5: Sidney Island to Nanaimo

This will be a long day so plan ahead as you go north to Nanaimo, a busy town with all sorts of yacht provisioning and excellent restaurants.

Day 6: Nanaimo to Egmont

Plan on an early departure across the Straits of Georgia to Egmont. Dock at the government float or the marina and then hike to Sechelt rapids where the current can run 14 knots.

Day 7: Egmont to Chatterbox Falls

Head up Jervis Inlet to Chatterbox Falls where the hardy (or crazy) can take a bracing dip in one of the pools beneath the 120-foot falls.

Day 8: Transit to Cortes Bay

You’ll have nearly 70 miles to cover today to make good progress north, so get an early start. Good anchoring can be found east of the Seattle Yacht Club outstation.

Day 9: Cortes to Prideaux Haven

Explore this area that has lots of oysters on the warm beaches. It’s one of the prettiest spots in Desolation Sound.

Day 10: Prideaux to Pender Harbor

Pender is on the Sunshine Coast and has ample anchorage as well as a fuel dock. Enjoy the local pubs and shopping.

Day 11: Pender to Telegraph Harbor

Cross the Georgia Strait to Telegraph where resorts host pig-roast barbeques.

Day 12: Prevost

Ideal day at leisure with a short transit (16 miles) to Prevost and its beautiful sunsets.

Day 13: Prevost to Roche Harbor

Clear U.S. Customs at Roche and take a slip at the beautiful marina. Have a camera handy for the spectacular scenery and the sunset flag ceremony.

Day 14: Roche to Anacortes

Wind your way through Harney Channel and Obstruction Pass back to Anacortes.

San Juan Islands: Photo Tour