Charter a bareboat to sail the Chesapeake Bay's magical coastal shores and other amazing locations.

The Naval Academy Dome and the Maryland Statehouse buildings show up centered in the Annapolis Skyline

The Chesapeake Bay, immortalized by so many writers, artists, sailors, and naturalists, is a truly magical destination along the coastal shores of the United States. It is by far the largest estuary with the most coastline of any other Bay within our lands. In fact, its 11,600 miles of shoreline is more than the entire coastline of the US. It drains 64,000 square miles across six states. And although it averages only 21 feet in depth, it has deep channels that run to 100 feet accommodating the passage of submarines and commercial traffic of every description along its 200-mile length. Its width varies from 4 miles at the Bay Bridge to 30 miles at the Potomac. It has more than 150 rivers and streams feeding its rich grounds, and as much variety along its shores as any cruiser would wish to find. So what’s not to like?

Yachts and boats in harbour of St Michaels on Chesapeake bay with heron

Perhaps the heat, stillness and stifling humidity that characterizes the middle of the summer. But in the Spring and Fall, with the nice long season, it is hard to beat cruising on the Chesapeake.

Advance planning a sailing vacation is always challenging. Unpredictable weather, wind direction, and strength, sometimes render advance planning impossible to adhere to. Please use this plan as a guide when creating your float plan. Also, be sure to allow some time either at the beginning or end of your charter to explore the Annapolis Harbor, in downtown Annapolis. Mooring balls and slips are available first come/first serve. Here you will find Main St and small side streets loaded with shops restaurants, galleries, and the market house. And if time allows, take a stroll through the US Naval Academy.

The Chesapeake is a seasonal cruising ground with the season opening in April and ending in October.

CHESAPEAKE BAY ITINERARIES

Advance planning a sailing vacation is always challenging. Please use this plan as a guide when creating your float plan.

Sailing South

North Winds

Day 1: Sail to Herrington Harbour

Herrington Harbour South and sister marina Herrington Harbour North are both located on the western shore of the Chesapeake Bay and offer overnight slips, several restaurants and lounges, and a wide range of amenities. Note: due to Herrington Harbour South’s popularity, it’s best to reserve a slip in advance 1-800-213-9438 Mango’s Bar & Grill: 410-257-0095 Beautiful waterfront dining in a classy but casual atmosphere.

Day 2: Sail to Oxford

Oxford is located on the Eastern Shore and bordered on three sides by the Tred Avon River and Town Creek. Oxford’s allure is the quiet small town where townspeople make visitors feel like old friends. Oxford works hard to maintain its serene, boater friendly atmosphere and boasts a small, easily walk-able downtown with enough shops, restaurants, and attractions to satisfy most visitors.

Day 3: Sail to Cambridge

Cambridge lies about 13 miles up-river from the mouth of the Choptank River. Cambridge is the county seat of Dorchester County, Maryland. Cambridge was settled in 1684 and is one of the oldest towns in Maryland. The elegant 19th century homes lining Cambridge’s shaded streets hail from a time when the town was an economic and social center—a heritage also proudly preserved in its maritime museums. Town attractions include several museums (Brannock Maritime Museum, Richardson Maritime museum, and Meredith House), the Skipjack Nathan,  Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample anchoring room for those looking for a protected spot to relax.

Day 4: Sail to St. Leonard’s Creek

Patuxent River (Anchor or dock at Vera’s) St. Leonard Creek, about seven miles upriver from Solomons, has been said to be the most beautiful on the Patuxent. This five-mile-long creek is on the river’s northern shore. The shoreline is a mix of marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek is Vera’s White Sands Beach Club. This fanciful place looks like a Polynesian island misplaced on the Chesapeake. Decorated with South Sea treasures culled from international voyages. Vera’s is a wonderful marina that welcomes all cruisers!

Day 5: Sail to Solomons (Solomons Island)

Solomons Island is picturesque island town nestled in the joining of the Patuxent River and the Chesapeake Bay in Calvert County Maryland. Once a renowned seafood packing house supported the local economy, but now tourism is its mainstay. Solomons remains a fishing village—alive with work-boats and an active charter fishing fleet—but it’s also a place to escape and to learn about the Bay’s past, present and future. Solomon’s mile and a half long town offers numerous dining options, shopping and special happenings. Be sure to visit The Tiki Bar:(410) 326-4075 The
first completely open air bar in Southern Maryland. The annual opening of the Tiki Bar has become a firmly entrenched Southern Maryland Tradition with crowds in excess of 10,000 people at the event. The house drink is the Mai-Tai, the potency of which has been known to cause people to react in a variety of ways.

Day 6: Sail to St. Michaels (anchor or dock)

St Michaels, Maryland is a quaint waterfront village on the Eastern Shore, situated on a picturesque peninsula between Tilghman Island, Easton, and Oxford. St. Michaels became an important shipbuilding center especially noted for its “Baltimore Clippers,” the fastest sailing vessels of their time. Today the town is better known as a popular yachting center and offers numerous things to do and see. Chesapeake Maritime Museum: On permanent display at the campus is the nation’s most complete collection of Chesapeake Bay artifacts, visual arts, and
indigenous watercraft. Interpretive exhibitions and public programs cover the range of Chesapeake Bay maritime history and culture including Native-American life, Anglo-American settlement, seventeenth and eighteenth-century trans-Atlantic trade, naval history, the Bay’s unique watercraft and boat building traditions, navigation, waterfowl, boating, seafood harvesting, and recreation.

Day 7: Sail back to Annapolis. Expect a sail time of between 5 to 7 hours.

Sailing North

South Winds

Day 1: Sail to Rock Hall

Rock Hall is a quaint fishing town that sits picturesquely on the eastern shore. As a top cruising destination, it offers a bevy of marinas, interesting shops, a variety of restaurants and a burgeoning artist colony. Waterman’s Crab House: 410-639-2261 Overlooking Rock Hall Harbor and the Chesapeake Bay, Waterman’s Crab House Restaurant and Dock Bar is well-known for its award-winning steamed crabs, jumbo lump crab cakes and barbecued baby-back ribs. Swan Creek has long been a favorite destination for cruisers because of its rural beauty. Located directly north of Rock Hall harbor, this well-protected creek offers a wonderful place to anchor.

Day 2: Sail to Baltimore Harbor

The harbor itself is actually the end of the Northwest Branch of the Patapsco River and includes any water west of a line drawn between the National Aquarium in Baltimore and the Rusty Scupper Restaurant. You’ll find a variety of things to see and do at Inner Harbor, all within walking distance. Baltimore’s Inner Harbor is one of the most visited features of the city. Distinct in function and form, Baltimoreans and visitors alike enjoy Baltimore’s Inner Harbor and the surrounding neighborhoods that offer a variety of fine dining, cultural experiences, and exciting nightlife.

Day 3: Sail to Chester River

The second-longest river on the Eastern Shore, the Chester River is bordered along much of its shoreline by beautiful, rolling countryside, and lovely estates. Nearly three miles across at its widest point, the Chester gradually narrows to about a quarter mile at Chestertown, with good navigating depths in a well-buoyed channel. Above Eastern Neck Island, the Chester fans out in four generous branches: Gray’s Inn Creek, Langford Creek, the main extension of the Chester that leads to Chestertown and the Corsica River. All are inviting.

Day 4: Sail to Mill Creek/Whitehall Bay

This quiet little anchorage lies between the Chesapeake Bay Bridge and the Severn River. Be sure to pay attention to the winding, well-marked channel and once inside you will find good depths for peaceful anchoring along with the famous Cantler’s Restaurant, known for some of the best steamed crabs in the area.

Day 5: Sail to St. Michaels (anchor or dock)

St Michaels, Maryland is a quaint waterfront village on the Eastern Shore, situated on a picturesque peninsula between Tilghman Island, Easton, and Oxford. St. Michaels became an important shipbuilding center especially noted for its “Baltimore Clippers,” the fastest sailing vessels of their time. Today the town is better known as a popular yachting center and offers numerous things to do and see. Chesapeake Maritime Museum: On permanent display at the campus is the nation’s most complete collection of Chesapeake Bay artifacts, visual arts, and indigenous watercraft. Interpretive exhibitions and public programs cover the range of Chesapeake Bay maritime history and culture including Native-American life, Anglo-American settlement, seventeenth and eighteenth-century trans-Atlantic trade, naval history, the Bay’s unique watercraft and boat building traditions, navigation, waterfowl, boating, seafood harvesting, and recreation.

Day 6: Sail to St. Michaels

Sail into the Wye River on the Eastern Shore The river—divided into three branches—embraces the Wye Island along 21 miles of shoreline. You won’t find supplies or public facilities anywhere on Wye Island but secluded anchorages and a rich historical heritage are among the charms of the Wye River. The western shore of the Wye River is well developed, but it’s eastern shore offer more secluded anchorages. On the Wye East, big old houses, many dating back to colonial days, stand on the banks, greeting cruisers at every turn.

Day 7: Sail back to Annapolis. Expect a sail time of between 5 to 7 hours.

Middle Sail Plan

Alternative Itinerary

Day 1: Mill Creek / Whitehall Bay – Quiet anchorage between the Bay Bridge and Severn River,
Cantler’s Restaurant is water‐accessible

Day 2: Rock Hall – Quaint marina town, marinas with waterfront restaurants

Day 3: St Michaels – Quaint tourist/boating town, marinas, Chesapeake Bay Maritime Museum,
shops, and restaurants

Day 4: Oxford – Small quaint tourist/boating town

Day 5: Solomons – Marina, fishing town, shops, and restaurants

Day 6: Galesville / West River Marina town/Rhode River Quiet anchorage off West River

Day 7: Return to Annapolis – Great restaurants, shopping, Naval Academy tour

PROVISIONING OPTIONS

A variety of breakfast and lunch options are available at these establishments and most everything on each menu is made from scratch! Premade crew meals consist of your choice of sandwich, chips, fruit and a drink. Pick them up before your charter and take the work out of lunch! Party platters of cheese, fruit and vegetables are also available. Ice is also available for purchase.

CHESAPEAKE BAY FLEET

Length

34'5"

Cabins

2

Bareboats

7-Day Low Rate

$5100

7-Day High Rate

$5100

Sleeps

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Location

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Length

38'4"

Cabins

4

Bareboats

7-Day Low Rate

$6440

7-Day High Rate

$6440

Sleeps

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Location

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Length

41'10"

Cabins

3

Bareboats

7-Day Low Rate

$4270

7-Day High Rate

$4270

Sleeps

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Location

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Length

42'

Cabins

3

Bareboats

7-Day Low Rate

$7000

7-Day High Rate

$7000

Sleeps

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Location

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Length

43'4"

Cabins

3

Bareboats

7-Day Low Rate

$4970

7-Day High Rate

$4970

Sleeps

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Location

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Length

44'

Cabins

3

Bareboats

7-Day Low Rate

$11550

7-Day High Rate

$11550

Sleeps

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Location

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Length

44'

Cabins

3

Bareboats

7-Day Low Rate

$4550

7-Day High Rate

$4550

Sleeps

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Location

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Length

46'

Cabins

3

Bareboats

7-Day Low Rate

$9100

7-Day High Rate

$9100

Sleeps

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Location

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Length

48'

Cabins

3

Bareboats

7-Day Low Rate

$11550

7-Day High Rate

$11550

Sleeps

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Location

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Length

50'5"

Cabins

3

Bareboats

7-Day Low Rate

$5775

7-Day High Rate

$5775

Sleeps

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Location

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Length

50'5"

Cabins

3

Bareboats

7-Day Low Rate

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7-Day High Rate

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Sleeps

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Location

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Length

53'

Cabins

3

Bareboats

7-Day Low Rate

$6230

7-Day High Rate

$6230

Sleeps

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Location

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Length

53′3″

Cabins

4

Bareboats

7-Day Low Rate

$6650

7-Day High Rate

$6650

Sleeps

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Location

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Length

58'4"

Cabins

3

Bareboats

7-Day Low Rate

$6650

7-Day High Rate

$6650

Sleeps

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Location

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