At a glance
- Duration:
- 7 Days
- Start/End:
- Round Trip Baltimore
- From:
- $3,425
- Time of Year:
- March - December
Embark on a captivating 7-day Chesapeake Bay cruise, sailing roundtrip from Baltimore, MD, and immersing yourself in the region’s rich history and culture. Departing from Baltimore’s vibrant harbor, journey to Yorktown, Williamsburg, and Jamestown—together known as the “Historic Triangle.”
Your adventure begins in Yorktown, where you’ll explore historic battlefields and well-preserved colonial homes. Wander the charming, time-honored streets of Colonial Williamsburg, a living history museum reflecting life as it was during the early English settlements. In Jamestown, delve into the story of America’s first permanent English colony.
Continue to Crisfield, a once-modest fishing village now celebrated as “The Crab Capital of the World.” Experience maritime tradition firsthand with a sail aboard an authentic skipjack in Cambridge. In Annapolis, ride a trolley through picturesque streets as a local expert guide shares fascinating tales from the city’s 350-year history.
Chesapeake Bay Cruise Highlights
- Baltimore, MD
- Yorktown/Williamsburg, VA
- Crisfield, MD/Tangier, VA
- Cambridge/Oxford, MD
- St. Michaels, MD
- Annapolis, MD
Chesapeake Bay Cruise Details
Day-to-Day Itinerary
Pre-Cruise: Baltimore, MD
Enhance your cruise experience with our Signature Pre-Cruise Package at the luxurious Four Seasons Hotel Baltimore. Situated in the vibrant Harbor East district, this 5-star hotel offers a premier stay just steps from the waterfront, renowned restaurants, and top attractions.
Begin your journey in style with a one-night stay, indulging in world-class amenities and breathtaking harbor views. On the morning of your cruise, savor a delightful breakfast at the Four Seasons before embarking on our Baltimore City Exploration shore excursion. Discover the iconic Inner Harbor, historic neighborhoods, and notable landmarks, including the Star-Spangled Banner waving proudly over Fort McHenry, before concluding your tour at the ship.
To take advantage of this exclusive package, reservations must be made at least 30 days before your cruise departure.
Day 1: Baltimore, MD
Baltimore is a vibrant maritime city, rich in colonial history and bustling with energy. Immerse yourself in its storied past as you step aboard historic ships and stroll along the cobblestone streets of the picturesque Inner Harbor. Discover Fort McHenry, the site that inspired Francis Scott Key to write The Star-Spangled Banner, and experience the enduring spirit of this iconic waterfront destination.
Day 2: Yorktown/Williamsburg, VA
Journey to a town that helped shape a nation’s history. Yorktown is renowned for its pivotal battlefields, historic colonial homes, and rich heritage. Explore museum exhibits, walk through recreated Continental Army camps, and visit beautifully restored homes from the 1700s. Continue your adventure in Colonial Williamsburg, once the political and economic heart of the Virginia Colony and now the world’s premier living history destination.
Day 3: Crisfield, MD/Tangier, VA
Founded in 1608 by Captain John Smith, the picturesque island of Tangier offers a glimpse into a bygone era, where traditions endure, and time seems to stand still. On a personalized guided walking tour, wander through the quaint village, past historic crab shanties, charming shops, and distinctive homes in the heart of the “Blue Crab Capital of the World.”
Day 4: Cambridge, MD/Oxford, MD
Cambridge is a quintessential Chesapeake town, celebrated for its deep history, stunning architecture, and thriving arts scene. Set sail on an authentic skipjack or explore the Blackwater National Wildlife Refuge, home to diverse wildlife and an array of shorebirds. Just a short journey away, visit Oxford, one of America’s oldest coastal villages. Steeped in maritime heritage, Oxford boasts historic homes from the late 1600s, intriguing museums, and the storied Oxford-Bellevue Ferry, the nation’s oldest privately operated ferry in continuous service.
Day 5: St. Michaels, MD
Wander along the scenic waterfront of St. Michaels or browse the quaint gift shops and boutiques along the tree-lined Talbot Street. Dock at the Chesapeake Bay Maritime Museum, set in a historic shipbuilding village, and step back in time to experience life as it was in the 1800s.
Day 6: Annapolis, MD
This 18th-century port town beautifully preserves its Colonial American charm. With streets lined with thousands of historic buildings showcasing diverse architectural styles, Annapolis is often referred to as a “museum without walls.” This lively city is also home to the United States Naval Academy, a prestigious National Historic Landmark.
Day 7: Baltimore, MD
Spend the day exploring Baltimore, one of America’s most vibrant cities. Choose from a variety of excursions, many highlighting the city’s rich maritime heritage. Don’t miss the chance to visit the renowned National Aquarium and the Baltimore Civil War Museum for an unforgettable glimpse into the city’s history.
