Close to Home Charters


Interesting, educational and fun places to charter around or near North America  (published March 2016)

So you want a boating getaway but don’t want the travel headaches including long flights, currency issues, minimum charter time commitments and language barriers? That’s easy—just charter close to home. Whether you’re looking for small town charm, abundant sea life, white sand beaches with swaying palm trees or rugged scenery and challenging sailing, you don’t have to go far to experience a three to 10 day charter that’s out of this world.

Friday Harbor Marina
Friday Harbor Marina

Just off the coast of Washington state in the Salish Sea, lie the beautiful San Juan Islands that are compact cruising grounds easily covered in a weeklong charter. You can get boats in Everett or Anacortes and provision along the way in any small town. The weather is variable and the high season is July to September. Because the window is so short, you’ll need to book by the beginning of the year for the following summer. Fog is frequent so get a boat with radar.

These islands provide a unique experience with lots of sea life and great hiking among pine trees, sometimes with deer. Winds here are light and the weather changes quickly so sailing may be sporadic but you can always charter a powerboat (gasp). The people are friendly and the seafood is as fresh as can be. Bring your passport if you’ll be visiting Victoria, British Columbia, Canada.

View from Rosario
View from Rosario

Anacortes—This small town has charm to spare. Most charter companies are based here and it’s close to the center of the best cruising grounds.
Friday Harbor—Another quaint village with fun galleries, coffee shops with live music and a true PNW vibe.
Roche Harbor—Eat at McMillan’s, an excellent restaurant at the historic Hotel de Haro (1886) where tradition dictates that all activity cease for the duration of the striking of the colors at sunset. The 377-slip marina offers full facilities. Stroll through the outdoor art park or catch a weekend performance at the al fresco amphitheater.
Rosario Resort on Orcas Island—Call ahead for show times so you don’t miss the organ concert at the Moran Mansion, sometimes accompanied by the black/white movie  Phantom of the Opera with Lon Chaney.
Deception Pass between Whidbey and Fidalgo Islands—For a wild surf through the pass, arrive well before slack tide. Passing through to Cornet Bay is like a roller coaster in the water but keep your engine on and sails down because it’s not for the faint of heart.
Haro Strait between U.S. and Canada -This stretch of water is perfect for a day sail due to a more steady breeze and a likely place to spot a pod of orcas.

There are two major destinations off the coast of Southern California: Catalina Island for a quick three to five day hop and the Northern Channel Islands for more challenging sailing.

Aerial view of boats parked on Catalina Island California
Aerial view of boats parked on Catalina Island California

Only about 30 miles west of Los Angeles, Catalina Island is a step back in time. Shaped like a bowling pin, the island has its main town of Avalon on the southeast bottom tip and the Two Harbors settlement at the neck of the pin. There are over 1,100 moorings in the major harbors around the island that are available to the public for a fee and plenty of room to anchor for free.

Catalina is a perfect charter destination for a week or even a long weekend any time of year. August is exceptionally busy and January to March can have unsettled weather while October is sublime for hiking, kayaking, diving, and snorkeling. Buccaneer Days, on the first weekend of October, is a madhouse festival as costumed swashbucklers drink the signature Buffalo Milk cocktail at Two Harbors’ only restaurant and bar, Doug’s Harbor Reef.


Two hours away, Avalon is a charming town, often passed off as Monaco in commercials. The 50-minute tour of the Casino and a visit to its museum are chock-full of historic information. A bus tour to the “Airport in the Sky” (with its DC3 mail service plane that still flies) is a good way to see the interior of the island and catch a glimpse of buffalo—the offspring of beasts that were brought to the island for a 1924 movie.

Two Harbors (Isthmus)—This is a locals’ hangout most any time of year except for late summer when it gets busy. Great biking, kayaking and snorkeling are everywhere and all equipment may be rented on the pier. One bar and one restaurant serve the tiny settlement but it’s all you’ll need.
Avalon—Rent a golf cart, go zip-lining, SCUBA off Casino Point or while away the afternoon with a cocktail at one of the many waterfront restaurants.

For rugged scenery, check out the Northern Channel Islands. You can visit Anacapa, Santa Cruz, Santa Rosa and San Miguel islands in a week if the weather cooperates. Chartering is available year-round but best times are from May to October and best places for departure are Oxnard, Channel Islands Harbor and Santa Barbara.

Channel Islands
Channel Islands

Bring your water shoes because there are no docks for dinghy landings and prepare yourself for a remote adventure. Be sure to get a landing permit from the Conservancy to go ashore (free online). In 1542, Juan Cabrillo was the first European to visit San Miguel Island and some say he is buried here. The uphill hike from the beach to his monument offers spectacular views and a good workout with about a thousand steps (or so it to feels). With prior arrangements with the Park Service, you can hike to the Caliche Forest, a petrified forest formed by wind, sand, calcium deposits and plants. Visit Point Bennett to see the sea lion rookery. Pack a snack as the hike is 14 miles round trip!

Dolphin, whale, seal and sea lion sightings are common. Provisioning has to be done on the mainland as there is no shopping on the islands. Have your anchoring skills down because there are no moorings and some areas require fore and aft hooks.

Anacapa Island—Set a lunch hook to visit nesting seagulls in spring.
Scorpion Bay—Anchor in crystal clear emerald-colored water and spectacular scenery.
Santa Cruz Island—Hike between Prisoner’s Harbor and Pelican Bay and arrange for someone to pick you up by dinghy for the return trip.
Painted Cave—Keeping the big boat outside and attended, take the dinghy into Painted Cave on Santa Cruz Island for a close-up of sea lions perched on the cave shelves. This is a good weather excursion only.
San Miguel Island—Cuyler Harbor can’t be beat for remote beauty and elephant seal sightings.

Chesapeake Bay
Chesapeake Bay

America’s largest estuary is nearly 200 miles long and anywhere from three to 30 miles wide. Its shoreline is over 11,000 miles divided between Maryland and Virginia. Best time to charter is July to October. Winds are variable with perfect sailing days interspersed with dead calm motoring conditions. Lots of shoals require a close eye on the chartplotter and lines of crab pots demand a good lookout. A weeklong charter should cover at least Annapolis itself where many charter companies are based, and St. Michaels, approximately 25 miles southeast of Annapolis. Two-week excursions allow an investigation of unique towns in the southern portion of the bay. Maritime museums abound and add much history and context to any visit.

St. Michaels, a seaside resort on Maryland’s eastern shore, is a must for history buffs, crab lovers and amateur photographers looking to feel like pros because this place never takes a bad picture. In the summer, the population of St. Michaels swells beyond its 1,500 residents and getting a guest dock is like winning the lottery but you can anchor nearby. The outstanding Chesapeake Bay Maritime Museum is world-renowned with its 18 acres of exhibits and restored boats.

Oxford—On Tilghman Island and up the Tred Avon River, this is one of Maryland’s oldest towns. For bibliophiles, Mystery Loves Company is a great bookstore specializing in whodunits.
Solomons Island—This is a former boat building and seafood-packing town that today is a tourist magnet. Less than 1 ½ miles long, and in parts just the width of a two-lane road, the island has a long wooden boardwalk that takes you up to the Calvert Marine Museum with its Drum Point screwpile lighthouse and narrated tours on a 1899 bugeye boat.

Virgin Islands
Virgin Islands

For a warm weather break close to home, a short flight will bring you to the Virgin Islands—either U.S. or British. The cheapest flights are to St. Thomas where you can charter a mono- or multihull and visit neighboring St. John (USVI) or take a ferry to Tortola (B.V.I.) for more charter outfits.

Because St. John is a part of the USVIs and only about six miles from St. Thomas, your cell phone will work and you don’t need to check into the country when visiting from the States. Most of St. John is a national park that enjoys a nine-month tourist season (12 if you want to risk a hurricane). There are plenty of moorings to keep your anchor from damaging the underwater park and red and green markers signify dinghy trails to shore. Stretch your legs on one of the many hiking trails and remember there are no privately owned beaches in the USVIs. There are also no marinas so the whole island has a relaxed atmosphere.

Caneel, Maho, and Francis Bays
Beautiful northern spots for good anchoring in certain weather.
Leinster Bay—Offers great snorkeling and the ability to dinghy in and visit the Annaberg Sugar Plantation ruins.
South side anchorages Salt Pond or Lameshur Bays, Hurricane Hole, or Coral Bay have laid back locals and funky bars.
Cruz Bay—This cove offers the best shops in the Caribbean (visit Mongoose Junction) and a variety of restaurants from gourmet to ethnic grub.

The B.V.I.s have been referred to as Chartering 101. The Leeward Islands of the Caribbean generally serve up smaller swells, consistent winds of 10-20 knots, temps in the 80s and short distances between idyllic islands. You’ve most likely heard of many of the places already including Foxy’s, Pusser’s and the incomparable Baths on Virgin Gorda.

Anchoring is easy in 20-40 feet of water with sandy bottom and there are lots of bars and small shops to keep everyone entertained. Distances are short, restaurants and bars are plentiful and the party never ends in the B.V.I.s.

Anegada—The 11-mile island’s appeal is its remoteness. Anegada’s surrounding 18 mile long Horseshoe Reef is a notorious boat eater but today, buoys clearly mark the entrance. Anegada Reef Hotel is a romantic spot for a lobster feast or Potters by the Sea next door is more lively with a wild band and a bar serving up endless pain killers, which can result in quite a bit of pain the next day.
Top of the Baths—This is a nice spot to grab lunch after tunneling through the Baths below.
Wreck of the Rhone-This easy wreck dive lies in 30-80 feet of water off Salt Island.
Willy T’s—A raucous floating bar on an old schooner, this place serves up deadly drinks until the wee hours. Nudity used to be encouraged.
Foxy’s Tamarind Bar-On Jost Van Dyke, this is an institution where a pina colada is de rigeur. Dinner and lunch is also served but come early as moorings are gone before noon.
Bubbly Pool—Around the corner from Foxy’s and between Jost Van Dyke and Little Jost Van Dyke is the Bubbly Pool, a small cove where rolling waves, washing through rock formations, make it feel like you’re swimming in a washing machine.


The Bahamas are an amazing chain of over 700 islands but the most compact place to cruise (and seemingly the only place to charter) is the Sea of Abaco. The Sea offers protected water, no matter what the Atlantic is cooking up on the outside, and dozens of interesting coves and harbors in a tiny area. The best months are April-June and again October-November. Winds are usually 10-20 knots. Although there are no coral heads, there are coral flats that love keels so watch the plotter. Taxicab rates are astronomical while moorings are only about $20 per night. Also, beware the no-see-ums that defy bug spray. Otherwise, bring a swimsuit and a book and settle in for a glorious tropical week.

Man-O-War Cay
This is a small and tightly knit community with families who have been here since the settlement was established in the 1700s. Visit Albury’s Sail Shop where handmade canvas bags have been created for three generations.
Hope Town—A camera-friendly harbor where Sherwin Williams must send all the crazy colors of house paint they don’t sell anywhere else. The 130 year-old candy stripe lighthouse is one of only two manned, kerosene-fueled lighthouses still in operation in the world. A trek up the 200-plus steps inside is a must-do, if only for the fantastic views from the top.
Little Harbor—This is a quiet teardrop-shaped harbor at the southern tip of the Sea on a pointy outcropping of Great Abaco Island. Dolphins and stingrays visit regularly and have no fear. Pete’s Pub and Gallery sells cast bronze mementos and they ship the art anywhere in the world.
Great Guana Cay—For a cheeseburger in paradise, Nippers on Great Guana is the place. The colorful bar even has a pool or you can shoot down to the windward side beach to catch some waves.

Zuzana Prochazka is a veteran cruiser and freelance writer. She is based in Southern California.

Author: Zuzana Prochazka