All Boat Types
All Crew Types

Chesapeake Bay Yacht Charter

So how do you get to know America’s largest estuary? For an out-of-town visitor, the Chesapeake can be overwhelming. The bay is nearly 200 miles long and anywhere from three to 30 miles wide. Its shoreline, depending on who’s measuring, is over 11,000 miles. About half of the bay’s 8,100 square miles of watery surface is in Maryland and half is in Virginia, and it is filled with rivers and creeks as it spills from the Susquehanna River source down to the Atlantic.

See Yachts in Chesapeake Bay

Chesapeake Bay Overview

Cruising the Chesapeake is like learning to ski. No matter how long you’ve done it, only a fool would call himself an expert because there’s always more to do and learn.

Tourists come by land and by bay to visit the outstanding Chesapeake Bay Maritime Museum in Oxford.

So how do you get to know America’s largest estuary? For an out-of-town visitor, the Chesapeake can be overwhelming. The bay is nearly 200 miles long and anywhere from three to 30 miles wide. Its shoreline, depending on who’s measuring, is over 11,000 miles. About half of the bay’s 8,100 square miles of watery surface is in Maryland and half is in Virginia, and it is filled with rivers and creeks as it spills from the Susquehanna River source down to the Atlantic.

The coffee-colored Chespeake wetlands function as nature’s filter, cleaning the water with each tidal change, and they also serve as a giant nursery for young creatures of all kinds. Saltwater marsh flats are home to raccoon, opossum, water snakes and fiddler crabs among many other animals. Great Blue Heron, red-winged blackbirds, osprey, kingfishers and ducks are frequent visitors too.

With just a few feet of elevation, the salt marsh changes to a brackish or freshwater habitat where woody plants and wildflowers join a variety of rabbits, squirrels and muskrats. Spring and summer are the busy seasons when the marshes turn green as the cordgrass begins to grow and many birds return to the area to nest. Winter is the quietest season as critters burrow to wait out the cold.

Locals with the luxury of cruising the bay all summer have a favorite anchorage or frequently visited bit of river like the Little Choptank, but a visitor wishing to hit the highlights has to have a plan. The distances are long and there’s much to do in every cove.

Whatever your chartering approach, the four places listed below are well worth a visit. And be absolutely sure to make time for your departure city, Annapolis, before or after your cruise. Take a tour of the Naval Academy, visit the museums, or check out the annual sail and power boat shows. Without a thorough inspection of Baltimore, Maryland state’s capital, your Chesapeake experience is simply incomplete.

St. Michaels is a walkable town oozing with history.

St. Michaels
On a recent mad crisscross of the bay, we started in Annapolis and headed south to St. Michaels, a seaside resort approximately 25 miles away on Maryland’s eastern shore. Quaint sounds cliché but it’s accurate; St. Michaels is a must-see for history buffs and crab lovers. It’s also a great spot for amateur photographers 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. So you won’t be alone anchoring out on the Miles River in 15-30 feet of water. The town occupies one square mile, about 10% of which is water. It was chartered in 1804 but has been a settlement since the early 1600s. Today tourists come by land and by bay to visit the outstanding Chesapeake Bay Maritime Museum, which has eighteen acres of campus exhibits and restored boats on display.

Beyond the waterfront, the town is a collection of well-preserved Colonial, Victorian and Federal style houses, many of which are now bed and breakfast inns or restaurants. St. Michaels has been everything from tobacco trading post to shipbuilding center, as well as a seafood processing town when most of the population was employed in some aspect of oyster tonging and crabbing. It wasn’t until the 1970s that tourism became the mainstay of the local economy. Today, there are very few summer weekends when you won’t find some sort of festival, expo or event in town.

St. Michaels came under attack by the British in the War of 1812. Legend has it that folks, forewarned of the British progress toward their area, hung lanterns high up in trees and dimmed their own lights, which caused the British to overshoot in the night. St. Michaels gained the moniker “the town that fooled the British.” Who knows if it’s true or just a charming marketing tidbit, but regardless this compact waterman town is both walkable and oozing with history. Don’t forget your camera.

Dawn in Oxford, one of Maryland's oldest towns

Oxford
Around Tilghman Island and up the Tred Avon River is Oxford, one of Maryland’s oldest towns. There is a self-guided tour of historic houses including Bratt Mansion, once a part of the Maryland Military Academy, and Grapevine House which has a grapevine that was planted in 1810 and is still growing.

The Oxford-Belvue ferry, the oldest privately operated ferry in the country, has been running since 1683 and drops you (and your bike) off across the river in the flat countryside that leads back to St. Michaels. For bibliophiles, Mystery Loves Company is a great bookstore specializing in whodunits. After browsing, stroll the shady streets with a camera to capture the picturesque inns with their colorful signs.

There are lots of wonderful bistros and restaurants like Schooners and The Masthead, but save room for dessert, because you can’t leave Oxford without stopping at Scottish Highland Creamery. This ice cream shop is hardly more than a window-front but serves homemade frozen concoctions that we later deemed the best ice cream on the Chesapeake.

Inside the Calvert Marine Museum in Solomons Island

Solomons Island
Across the bay and south lies Solomons Island, another former boatbuilding and seafood packing town that today is a tourist magnet. Jutting out between Back Creek and the Patuxent River, Solomons is connected to the mainland by a long causeway. Less than 1½ 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; there you’ll find the Drum Point screwpile lighthouse and narrated tours on a 1899 bugeye boat. In the 1880s more than 500 locally built boats made up the Solomons fishing fleet. By the 1930s the town specialized in building wooden pleasure yachts.

Rent a Segway to get around Back Creek to Annmarie Garden, a 30-acre sculpture park.

Anchoring in Back or Mill creeks is easy and there are dinghy docks everywhere, especially at the many waterfront restaurants like Stoney’s Kingfisher Seafood House, where the no-filler crab cakes are the size of softballs.

Reedville has a menhaden fishing operation that has been in business since 1874.

Cockrell’s Creek, Virginia
If you have time, stretch down across the Virginia state line to Cockrell's Creek in the town of Reedville, where in 1874 Elijah Reed started a menhaden fishing operation that is still functioning today. The factory’s giant blue purse-seining ships can be seen casting nets out on the bay. You don’t want to be downwind of the factory when they’re “cooking” or processing the fish into oil. The smell is enough to make it worth re-anchoring if you mistakenly first set the hook downwind of the smokestacks.

The Fisherman’s Museum here is great, as are the vessels out back at their docks. To get there, walk along Millionaire’s Row and admire the Victorian mansions, built by those who made their fortunes in the menhaden industry. Afterward, grab lunch at the Crazy Crab which has both a dinghy dock and great fresh seafood. You can tank up at the fuel dock nearby on either gas or diesel, though the bathrooms are reputedly the scariest on the whole bay.

Another Chesapeake must is Tangier Island, where apparently time has stood still for quite a while. We tried to get there to but grounded in the shallow eastern entrance. Next time, we’ll be smarter. And next time we’ll also have a whole new itinerary of can’t-miss spots that will get us a little closer to being well versed—if never experts—on this terrific cruising playground.

Read more:

Cruising the Chesapeake: Baltimore by Boat

The Moorings Launches New Chesapeake Base in Annapolis

Northern Chesapeake Cruising

View yachts for charter in the Chesapeake

Chesapeake Weather

The Chesapeake is the largest estuary in the United States, with a watershed area of 64,000 square miles supporting over 450 different species of fish, shellfish, birds, mammals, reptiles, and amphibians. Along its shores, you’ll discover thriving cities, major military installations, and quaint towns. But when you visit these waters will have a huge impact on your experience here.

A fisherman's perspective of the Chesapeake Bay Bridge, which divides the upper and lower Bays.

The transitional seasons of spring and fall provide for the best mix of wildlife, but they also bring unpredictable and sometimes violent weather. Luckily, the Chesapeake is riddled with well-protected rivers, harbors, and creeks. While winds in excess of twenty knots are relatively common at these times of year, waves in the bay rarely exceed four to five feet. With an average depth of merely twenty feet and few portions deeper than a hundred feet, waves that grow any larger will break. But don’t think that makes for a smooth ride—these waves can also stack up on one another, and the Chesapeake is well known for a short, tight chop that locals say can “bang your teeth out”.

There’s also a bright side to this area’s underwater geography: the vast majority of the bay’s bottom is made up of sand and mud, so groundings are rarely damaging. And since the area is densely populated (particularly along the bay’s western shore), if you do encounter problems, help in the form of a tow boat or repair facility is never far away.

Spring can bring with it an additional danger of flotsam, if heavy rains fall in March and April. Since water enters the bay from upstream locations as far away as New York State, rainy springs bring floating logs, tree branches, and other potentially damaging items. On the other hand, spring also marks the beginning of the largest annual migration of striped bass along the entire east coast, drawing anglers from across the nation.

Summer is, unquestionably, prime-time for boaters on the Chesapeake Bay. From June through September the weather commonly settles into a predictable pattern: several days of calm, interrupted only by the passing of a front once or twice a week or the occasional afternoon thunderstorm. At this time of year you can expect daily highs in the upper 80’s and lower 90’s, with night-time lows in the 60’s and 70’s. But be forewarned: fair weather here coincides with mosquitoes, and on breezeless evenings, sitting at anchor can be a painful experience.

Winter, of course, is bug-free—but it’s not commonly thought of as a time to cruise in these waters. Below-freezing temperatures and heavy winds are the norm, and most local boats are pulled and blocked from late November or early December through February. This is the time when commercial boats rule the waters; gill netters, hardy oystermen working their tongs, and big “ro-ro” ships (roll-on, roll-off), full of Hondas and Toyotas that make their way up the channel to unload in Baltimore.

Regardless of which season you cruise through these waters, you should expect moderate currents and tidal changes at the mouth of the bay which gradually grow less and less dramatic as you move northward. At the very head of the bay they increase again, thanks to the flow of the C & D Canal. Throughout the bay, it’s rare to have tidal range of more than a foot or two.

Whether you cruise here to enjoy the spring run of stripers, the summer blue crabs, the fall arrival of Canada geese, or the winter oyster harvest, one thing is for sure: the Chesapeake offers a rich diversity of maritime pleasures that boaters of all ages and types will enjoy.

Chesapeake: Five Maritime Museums

For history buffs and maritime museum geeks like me, there’s nothing better than a trip up and down the Chesapeake.

On a recent charter, we visited five museums that added a touch of local color to our cruise. We found small and intimate treasures focused on the immediate area, as well as serious educational destinations. All were run by people who are knowledgeable and passionate about their exhibits, so our visits were not only informative, but fun.

The Chesapeake Bay Maritime Museum in St. Michaels dedicates 18 acres to preserving maritime history.

Chesapeake Bay Maritime Museum
There is absolutely nothing small or provincial about the Chesapeake Bay Maritime Museum in St. Michaels. This spectacular 18-acre institution is dedicated to preserving maritime history and has a functioning restoration yard and professional educational opportunities.

The museum stretches across multiple buildings, and nearby are three examples of typical Chesapeake boats including the bugeye Edna Lockwood, the skipjack Rosa Parks, and the buyboat Mr. Jim. Indoor and outdoor exhibits are dedicated to the maritime heritage of the area: waterfowl hunting, boatbuilding, and seafood processing. You can tour a lighthouse, take a boat ride, or learn about oyster tonging, a method of digging oysters off the bottom with nothing but long-handled tongs.

The most prominent display is the Hooper Strait lighthouse, a typical Chesapeake screwpile lighthouse that was decommissioned after 75 years of service on Tangiers Sound and transferred in 1966 to its present location. The cottage-style building was used to house lighthouse keepers while anchored to the muddy bottom on pilings that were “screwed” in.

This museum deserves a multi-day visit to take in all it has to offer. For your lunch break, try the nearby Crab Claw restaurant.

Hooper Strait lighthouse has been in its current location since 1966.

Calvert Marine Museum
The jewel of Solomons Island (besides the scenery) is the Calvert Museum with its mini estuary, extensive permanent exhibits, boat rides, and typical screwpile lighthouse. The main facility houses nearly 30,000 square feet of exhibits on local life, types of bay boats, and old-time outboard engines.

Outside, there are a couple of playful otters running around and a marsh boardwalk that shows the plant and animal life of salt and freshwater habitats. A 6,000 square foot outbuilding houses a small craft collection that puts the various styles of bay boats in perspective; anywhere else, this building would qualify to be a museum in its own right.

When the kids get tired of museum touring, take them on a narrated river cruise on the Wm. B. Tennison. Afterward, it’s time for some crab and a glass of wine on a waterfront dock at one of the nearby restaurants.

The Calvert Marine Museum is the jewel of Solomons Island.

Crisfield Historical Museum
The J. Millard Tawes Historical Museum is a tiny, two-room museum that is surprisingly informative. From here you can arrange a day trip to Tangier Island if your boat has a deep draft and you’d rather not risk grounding in the narrow entrance. It was in this museum that I found simple, photocopied pamphlets full of information on the life of the blue crab, data on the size of the Chesapeake, and Maryland state trivia including the state dance (square dance) and sport (jousting).

Outdoor exhibits include blue crab cages and oyster tonging equipment. If you read every exhibit, the museum will take you an hour. That leaves time to find some Smith Island 10-Layer cake at the Sweet Shop bakery up the street.

Reedville Fisherman’s Museum
Reedville’s Fisherman’s Museum is a short walk from the Crazy Crab restaurant where we left our dinghy. We walked up Millionaire’s Row, which is one mile of ornate Victorian homes and gardens that are designated a National Historic District.

The museum campus includes the main building and gift shop and the William Walker House, which was built in 1875 and restored by volunteers. You can tour it to see how a well-to-do family lived just over a century ago.

Two vessels are moored at the docks here, the skipjack Claud W. Somers and the deck boat Elva C, both of which are in the National Register of Historic Places. The museum also hosts a number of activities: the annual blessing of the fleet in May, the Antique and Classic Boat Show in September, and an oyster roast in November.

The small Deltaville Maritime Museum has lots of photographs and a small library that helped bring local history to life.

Deltaville Maritime Museum
Of all the museums on our itinerary, the Deltaville Maritime Museum surprised me the most. Deltaville is small and half of it had blown away in a tornado a month earlier, so when we pulled up in front of a well-kept lawn with a museum sign, I didn’t have high expectations.

We had to wait a half hour until it opened, so we wandered the neatly kept grounds of the Holly Point Nature Center. Nicely painted boats were surrounded by flowers and covered with butterflies. We also found a replica of Captain John Smith’s barge moored at the docks, and then stumbled into an outdoor sculpture garden complete with piped-in music.

Once inside the main museum building, the multiple rooms did an excellent job of detailing the differences in the variety of bay boats. There was also a sizeable exhibit on the restoration of the F.D. Crockett buyboat, which was moored out back. Lots of photographs, a small library and an eager docent helped this place come to life.

Other noteworthy museums include the Annapolis Maritime Museum with its tours to Thomas Point Shoal lighthouse, and Baltimore Maritime Museum with historic vessels and Seven Foot Knoll lighthouse.

Chesapeake: What to Do Ashore

On the Chesapeake, an hour’s cruise can take you from cities like Norfolk Virginia, Washington DC, and Baltimore Maryland, to untouched salt marshes or sandy beaches.

Blue crabs are easy to catch in Chesapeake country—home of the crab feast!

City culture can be a welcome change for long-distance cruisers transiting the bay, and just about every city heading up the coast has its own flavor. In Norfolk/Hampton Roads, travelers who time their arrival with the July Fourth holiday will discover Harborfest, known as the “biggest outdoor dock party” on the eastern seaboard. Festivities include live music, fireworks, wine samplings, parades, and visiting tall ships.

Half way up the bay, no matter when you visit, Washington DC provides visitors with a nearly endless choice of attractions ranging from the Smithsonian to the White House. Slightly farther north, Annapolis is a must-see for sailors, with such points of interest as the US Naval Academy and the Maritime Museum. Power-hungry boaters will enjoy “Ego Alley” in the center of town. In this canal, the greatest status symbol is gleaming fiberglass armed with obscene amounts of horsepower.

The northernmost large metropolitan area on the bay, Baltimore is a prime place for boaters to enjoy night-life with a historical twist. Fell’s Point has been packed with restaurants, pubs, and taverns since its establishment in the early 1700’s, and today you can find a mix of Irish pubs, market stalls, and cobblestone streets—where launching clipper ships was once a way of life.

In all of these cities and their surrounding areas, there’s one thing every out-of-towner should experience: a crab feast. This area is well-known for its blue crabs, and as any local will tell you, “real” Maryland-style steamed blue crabs can’t be found anywhere more than a few miles from a Chesapeake shoreline. Come prepared to get messy from smashing shells and picking the sweet white meat out of crab shells for hours on end. Here, eating crabs is thought of as an activity rather than a mere meal.

The faint of heart can opt for crab cakes instead, and let the locals do the picking for them. But beware: due to the blue crab’s popularity and a shortage of local hand-picked meat, many traitorous establishments use imported Asian crab in their cakes. So before you order, ask if it’s local.

Cruisers in search of a destination offering quaint yet high-quality shopping should head for St. Michaels on the eastern shore. Artists' and artisans' shops, clothing stores, and nautical-themed shops all are within walking distance of the dock, and all are unique—this is one place where you won’t find a Starbucks or a Wal-Mart.

Looking for a waterborne adventure? Aside from the obvious exploits like fishing for Chesapeake Bay striped bass or blue fish, consider following the John Smith Water Trail. This is America’s first official national water trail. Download your free trip itineraries and trail guides, and follow the historic route of explorer John Smith from 1607 to 1609.

Or maybe you’d rather blaze a new trial across the Chesapeake—however you decide to explore these waters, you’ll discover that they hold a wealth of interest for boaters of all types.

Annapolis, Maryland: Insider View

by Lenny Rudow

If you’re taking your bareboat charter to or from Annapolis, or you’re just passing through, there are plenty of restaurants, landmarks, and shops to see. But if you stay locked into the downtown area, you’ll miss out on some of the Chesapeake experiences that locals love, and tourists rarely find.

annapolis maryland

The view of Annapolis, Maryland, from the harbor. There's plenty to see and do within walking distance of these docks, but venturing a bit farther from the center of town has its rewards.

Food – There are dozens of good restaurants within walking distance of the downtown moorings, which a water-taxi will be happy to shuttle you to and from. Excellent sushi (try Joss, two blocks up on Main Street), great French cuisine (the Treaty of Paris on Church Circle), and simple casual dining (the Dock Street Bar and Grill, which is naturally located on Dock Street). But for a real taste of Maryland, drop the mooring, and head up Mill Creek to Cantler’s Riverside Inn. Pull into their docks, walk up the concrete steps, and you’ll be in for home-cooked Chesapeake seafood at its best.

Steamed crabs are, naturally, the local favorite. But don’t forget to order a bucket of “steamers,” clams that you rinse in broth then dip in drawn butter. Rockfish (the local name for striped bass) stuffed with crab imperial is another hometown favorite.

Night Life – The downtown area is not at all short on night-life, as anyone who’s ever tried the “Pain Killers” (a concoction consisting mostly of rum) at Pussers, or visited McGarvey’s Saloon, can attest. A bit farther from the harbor, however, this town has a lot more to offer. One place out-of-towners might miss is the Ram’s Head on West Street, about a 10 minute walk from the harbor (stroll up the hill to Church Circle, turn left, then turn left again at West Street). The Ram’s Head is unique for its Ram’s Head On Stage musical events, which include surprisingly well-known bands and soloists playing in an extremely up close and personal venue. Time your arrival right, and you might even be able to catch O’Mally’s March, the Celtic Fusion band led by the Governor of Maryland, Martin O’Malley.

Other Attractions – Naturally, visitors often go to the Annapolis Maritime Museum, on Second Street. Those with kids aboard may also want to stop by the Chesapeake Children’s Museum, with its live animals, nature trails, and the “help yourself” visual art workspace. But another site of interest is the Chesapeake Bay Foundation’s Phillip Merrill Center, one of the world’s most energy-efficient buildings, which houses the offices of the Foundation. (Tours must be scheduled ahead of time by contacting CBF, and you will need to take a 10 to 15 minute cab ride to get there). Another local point of interest is the Naval Academy, an American icon rich with history, which has a visitor center and guided walking tours.

steamed crabs

The local favorite, steamed crabs, may look a bit odd to a first-timer.

Okay, it’s time for a bit of full disclosure: I’m a local, and have been living on the outskirts of Annapolis for over two decades. So yes, I may look at this town with rose-colored glasses. But I know from talking with countless visitors that this is a great place to visit, and it makes for an excellent charter destination. So the next time you’re in town, make sure you take the time to see some of our local highlights—and make sure you order the steamed crabs.

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.