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Historic Chesapeake Bay Cruise

10 Days, 9 Nights | Price Starting at $3,109.00

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Explore America’s largest estuary by small ship on a 10 day cruise that takes you back in time. Celebrate some of the most environmentally rich and protected shorelines along this region of the United States. Step back to a different era, where freedom is new and liberty prevails. Scenic shores, architectural gems and historic sights are not to be missed. 

Known as one of the most historically dynamic regions in the US, you may opt to tour museums or former battlefields in Norfolk and Yorktown. Enjoy sight-seeing along the Potomac River or while walking the streets in Philadelphia. Optional excursions may take you to Washington, DC or the US Naval Academy in Annapolis. 

Historians rejoice! For those who study history and those who live it, your ship has finally come in! 

Ports Visited

Waterways Navigated


Philadelphia, PA

Best known as the first city of the colonists, Philadelphia is often called the “Cradle of Liberty” for being one of the country’s most historic cities. Revolutionary and Civil War buffs can enjoy exploring heritage trails and museums.

Saint Michaels, MD

The “Heart of the Chesapeake,” was named for the parish that established here in 1677. By the War of 1812, this was an established shipbuilding town known for producing fast schooners. These ships adapted to evading blockades and outrunning pirates at sea! Today, visit the idyllic harbor with tastefully restored buildings and interesting waterside museum.

Oxford, MD

Tiny Oxford is home to parks that run to the bay, where every promenade produces incredible views of the sea. This tiny town is one of the oldest in Maryland and was one of two ports of entry for all of Maryland in 1694. 

Cambridge, MD & Crisfield, MD

Settled by England colonists in 1684, Cambridge is one of the oldest colonial cities in Maryland. Then visit Crisfield, “Crab Capitol of the World” and southern most city in Maryland, witness the local ‘farming’ communities along the Chesapeake Bay.

Norfolk, VA

Home to the world’s largest naval base, Norfolk remains a stopping-off point for nearly 30,000 naval personnel destined for ships and stations overseas each year.

Yorktown, VA

Site of the final battle of the American Revolution in 1781, the Battle of Yorktown was successfully lead by General George Washington. Today, it is a charming riverfront town offering boutique shopping. You may opt to tour Colonial Williamsburg, the world’s largest living history museum.

Mount Vernon, VA & Alexandria, VA

President George Washington lived on this stunning plantation. Overlooking the Potomac River, you can explore the out-buildings, museums and final resting place of George and Martha Washington. Also, explore Alexandria, a bustling city just minutes from Washington, D.C. Travel back in time to Old Town where over 2,000 buildings predate 1899 or enjoy a tankard of ale at the famed Gadsby’s Tavern where the Founding Fathers would arrange meetings.

Annapolis, MD

Situated on the Chesapeake Bay at the mouth of the Severn River, Annapolis is a genteel city of elegant mansions and stately parks. Here, the Maryland State House has been in continuous legislative use since 1772. You may also opt to visit the prestigious U.S. Naval Academy.

Baltimore, MD

The cultural and economic hub of Maryland and hometown to the legendary Babe Ruth, scout out the Inner Harbor and renowned National Aquarium. A visit to Fort McHenry and the USS Constellation may also be available!


Category I
Category II
Category III
Category IV
Category III Singles
Port Charges



Optional sightseeing tours are at an additional cost. All itineraries including ports, activities and routes are subject to change based on availability, weather, river, water levels and sea conditions.

Departure Dates

Embark: Philadelphia, PA
May 19, 2019
Disembark: Baltimore, MD
May 28, 2019
Embark: Baltimore, MD
May 30, 2019
Disembark: Philadephia, PA
Jun 08, 2019

The Ship Grande Caribe

Your small ship adventure is a personal and casual one- like cruising on a friend’s yacht.

Hover over the cabin to view the room layout

Deck Plans

Category I Cabin

Category II Cabin

Category III Cabin

Category IV Cabin

Cabin Bathroom

Includes shampoo, conditioner, body wash, hair dryer, fresh towels daily

Building in Alexandria, VA
Old-time car and restaurant in Alexandria, VA
Baltimore Harbor in Maryland.
Battleship Wisconsin docked in Norfolk.
Cannons at Fort McHenry
Washington Monument in Washington, DC
Knoll Lighthouse on the Chesapeake Bay
Naval Academy Chapel in Annapolis, MD
President George Washington's home, Mount Vernon
A passenger and veteran observes the ships in Norfolk
World War II submarine docked in Balitmore

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