Chesapeake Bay Cruise
Baltimore, MD to Baltimore, MD
Set sail on a cruise from Baltimore’s historic harbor and journey through Chesapeake Bay, heading to the renowned "Historic Triangle" of Yorktown, Williamsburg, and Jamestown.
In Yorktown, walk the historic battlefields and visit authentic colonial homes that hold stories of the past. Meander through the preserved streets of Colonial Williamsburg, virtually unchanged since the era of the first English colonists. In Jamestown, uncover the beginnings of the first permanent English settlement in the Americas as you explore Virginia’s coastal waterway corridor.
Visit St. Michaels, home to the acclaimed Chesapeake Bay Maritime Museum, offering a glimpse into the region’s seafaring past in Maryland’s Eastern Shore region. Enjoy a trolley tour through the enchanting streets of Annapolis, where our expert local guide will share fascinating narratives of its 350-year history in Maryland’s capital city.
As you explore the treasures of Chesapeake Bay, enjoy fresh, local seafood to find out why the area is famed as "The Crab Capital of the World" throughout this iconic Mid-Atlantic estuary.
Ask about our Current Savings and our Hotel Upgrade, which includes a 1-night stay at the luxurious Four Seasons Hotel Baltimore, MD, concierge luggage service from the hotel to the ship, and, on the morning of embarkation, enjoy breakfast, a curated city experience, and transportation to the ship.
Upcoming Dates & Fares
Itinerary & Excursions
*Exact itinerary & excursions will vary by cruise date
Map & Itinerary Overview
This 9-day riverboat cruise takes guests to the "Crab Capital of the World," visits the U.S. Naval Academy in Annapolis, and many other historic ports, including Jamestown, VA, and Williamsburg, VA, that define our Chesapeake Bay cruises.
Day 1 - Baltimore, MD
Before your cruise, treat yourself to a 1-night stay at the Four Seasons Hotel in Baltimore. This vibrant waterfront destination is known for its bustling Inner Harbor, where tall ships, world-class museums, and lively shops and restaurants create a welcoming atmosphere for visitors along the Patapsco River, which flows into the Chesapeake Bay. The city played a key role in American history, notably during the War of 1812, when Fort McHenry inspired Francis Scott Key to write “The Star-Spangled Banner.”
Today, Baltimore blends its maritime heritage with a thriving arts scene and renowned institutions like the National Aquarium and the American Visionary Art Museum, making it a captivating stop on any Chesapeake Bay cruise through the Mid-Atlantic region.
Hotel Packages must be reserved at least 30 days before your cruise date. Please call 800-460-4518 for pricing and availability.
Day 2 - Day of Cruising Chesapeake Bay
Step aboard and receive a warm welcome from our crew. It's the perfect opportunity to meet your fellow travelers as we begin our journey along the legendary Chesapeake Bay’s historic waterways. Spend the afternoon cruising past celebrated shorelines. Take in panoramic views of Maryland’s Eastern Shore landscapes, iconic lighthouses, and passing working waterfronts. Throughout the afternoon, keep watch for graceful herons, playful ospreys, and other Chesapeake wildlife that thrive in this renowned estuary.
Day 3 - Yorktown / Williamsburg, VA
Williamsburg, Yorktown, and Jamestown collectively comprise Virginia’s renowned "Historic Triangle," each site echoing pivotal moments in American history.
Led by an expert guide, explore Colonial Williamsburg’s preserved 18th-century district. Stroll through the narrow, time-worn streets that have preserved their colonial character. Engage with blacksmiths, cobblers, and other artisans practicing their crafts just as the first English colonists did.
Step back in time at the Jamestown Settlement, a comprehensive museum that brings to life 17th-century America. Here, you can uncover the story of America's first permanent English colony, founded in 1607, through meticulously recreated environments and detailed exhibits. Board the Yorktown Trolley, making convenient stops at Yorktown’s most significant sites, including the Yorktown Battlefield, where the final major conflict of the American Revolution unfolded.
Visit the American Revolution Museum, which tells the story of the nation’s founding, from the twilight of the colonial period to the dawn of the Constitution and beyond.
Day 4 - Cruising Chesapeake Bay
Bask in the beauty of Chesapeake Bay’s winding tidal waterways as you cruise along serene and picturesque landscapes. From the comfort of your private balcony, enjoy the opportunity to spot birds, dolphins, and other marine life native to Maryland’s estuarine coastline.
As we voyage, onboard specialists will enrich your journey with insights into the local culture and heritage. Come evening, mingle with other guests and revel in the talents of some of the region's best entertainers.
Day 5 - St. Michaels, MD
The port of St. Michaels is a scenic harbor on Chesapeake Bay, well-known as a keystone locale in colonial history, serving as a trading post for farmers in the region.
Docking at the Chesapeake Bay Maritime Museum, once a famed shipbuilding village, get a glimpse of what life was like in the 1800s. Explore the museum’s variety of exhibits, including historic boats, artifacts, and interactive displays that highlight the area's maritime culture, shipbuilding, and environmental issues.
Visit the Classic Motor Museum, dedicated to appreciating and preserving America’s heritage of automotive innovation. Later, stroll along the waterfront of St. Michaels or explore the quaint gift shops and boutiques on the tree-lined Talbot Street.
Day 6 - St. Michaels, MD
Spend an additional day exploring St. Michaels on Maryland’s Eastern Shore. On a guided walk, visit the Historic District as you learn about 350 years of shipbuilding, classic homes, and the famous Battle of St. Michaels from the War of 1812.
In the afternoon, board The Patriot, a replica of a 1930s steam ship, for a cruise on the Miles River. The captain will be your guide as you keep an eye out for the vibrant wildlife that calls this serene landscape home, from graceful herons to playful otters.
Add some flavor to your experience as you uncover the artistry behind one of Maryland’s most celebrated craft distilleries. Gain insight into the meticulous craftsmanship of their premium spirits and be treated to a tasting.
Day 7 - Annapolis, MD
Let your Colonial-attired guide lead you through a vivid narrative spanning 350 exhilarating years, revealing Annapolis' stories and captivating tales. Walk in the footsteps of George Washington, where, in 1783, inside the State House, he resigned as commander-in-chief of the Continental Army. Continuing through the downtown area, pass many 18th-century mansions and learn about the significance of their beautiful architecture within Maryland’s historic capital district.
Later, visit the U.S. Naval Academy. Experience “Life on the Yard” as you explore the Academy campus with a certified guide who highlights its past and present. Or, view the Academy from the water aboard the classic Harbor Queen for a narrated cruise along Annapolis Harbor on the Chesapeake Bay.
Day 8 - Baltimore, MD
From the cobblestone streets of Fells Point to landmarks like Fort McHenry, where the national anthem was born, Baltimore offers something for everyone.
Take a narrated cruise through the Inner Harbor, learning about the renaissance of Baltimore's waterfront as well as its fascinating maritime history, and Maryland’s Chesapeake Bay port communities.
Visit The National Aquarium, home to thousands of marine species, including sharks, dolphins, and sea turtles. Learn about animals from all over the planet, from the depths of the ocean to the canopy of the rainforest, and discover the connection they all share with water.
For a deeper understanding of Maryland’s history, explore the city’s History & Culture Center with a vast collection of artifacts and artworks. A visit to Baltimore wouldn’t be complete without indulging in its famous seafood, especially the famous Maryland crab cakes.
Day 9 - Baltimore, MD
Your captivating Chesapeake Bay cruise through time wraps up in the lively city of Baltimore, where it all started. Have one last breakfast aboard the ship before you disembark to either start your journey home or to extend your stay for further exploration in Maryland’s historic harbor city.
Our Chesapeake Bay cruise itinerary offers an upgraded hotel package in Baltimore, making it effortless to join your cruise and explore the local sights. Enjoy a comfortable overnight stay at this top-rated five-star hotel, complete with breakfast. Follow this with a lively Baltimore City Exploration that takes you directly to your ship.
Board a motorcoach for a scenic ride through the historic gems of Baltimore. As you travel, immerse yourself in the city’s rich heritage as you view iconic landmarks such as the Inner Harbor, Fells Point (the oldest neighborhood in the city), and Little Italy. Visit Lexington Market, the world’s largest continuously running market, and the USS Constellation, a historic naval vessel. Discover the Hippodrome Theatre, which opened as a vaudeville venue in 1914, and pay your respects at the grave of Edgar Allan Poe.
Explore Fort McHenry, the site of the heroic defense in 1814 that inspired Francis Scott Key to write the words to our national anthem. Stop at the Maryland Center for History & Culture, where you can explore fascinating artifacts, documents, and artworks that tell the story of Maryland’s history, from its colonial roots to the present day.
Hotel Packages must be reserved at least 30 days before your cruise date. Please call (800) 460-4518 for pricing and availability.
As you board the ship, be welcomed by the crew who will ensure that every detail of your journey is seamless. Take the time to meet fellow travelers, share stories, and immerse yourself in the relaxed atmosphere of small-ship cruising.
From panoramic deck views to thoughtfully designed lounges, every corner of the ship offers a chance to relax, socialize, and prepare for the memorable adventures that await.
Travel along the Colonial Parkway, which connects Williamsburg, Yorktown, and Jamestown, to witness beautiful views of the York River and the Virginia countryside without the obstruction of commercial traffic or signage. Upon arrival in Colonial Williamsburg, enjoy a guided walking excursion through this 18th-century city followed by free time to explore at your leisure.
Activity Level: Medium | ADA Accessible: Partial
Enjoy a walking and trolley exploration of Historic Yorktown. Led by our knowledgeable guide, visit the Yorktown Victory Monument. Walk down Main Street and learn about the history and significance of Yorktown during the American Revolutionary War. Continue to the Gallery at York Hall where local artisans display their work, before boarding the Trolley for the return to the ship.
Activity Level: Moderate | ADA Accessible: Yes
Explore the Jamestown Settlement and discover the story of the people who founded this historic town. Learn about the Native Americans of Virginia they encountered, through film, gallery exhibits, and living history. Visitors can board replicas of the three ships that sailed from England to Virginia in 1607 and explore life-size re-creations of the Colonists’ fort as well as a Powhatan village. In the outdoor areas, costumed historical interpreters describe and demonstrate daily life in the early 17th century.
Activity Level: Medium | ADA Accessible: Yes
The American Revolution Museum at Yorktown tells the story of the nation’s founding, from the twilight of the colonial period to the dawn of the Constitution and beyond. Exciting indoor galleries feature period artifacts, immersive environments and films, including “The Siege of Yorktown,” with a 180-degree surround screen and dramatic special effects.
Activity Level: Moderate | ADA Accessible: Yes
Board the Yorktown & Co. Steamer Wagon for a guided evening ride through the Historic Village and hear the many ghost stories that have occurred over the years. Allow your guide to connect historically correct information to recurring ghostly experiences in original buildings still standing from before the Revolutionary War. Hear past and present tales of paranormal activity, unmarked graves, footpaths that led Enslaved People to auction, and places locals will not go at night. Pass by the most haunted building in Yorktown, the Cole Digges House c.1726 (now Mobjack Coffee and Petite Café). Finish your riding tour by visiting the Yorktown Monument with a nighttime scenic view of Chesapeake Bay.
Activity Level: Low | ADA Accessible: Partial
This is a Signature shore excursion and should be reserved in advance. Please call (800) 894-8570 for information.
Board a Yorktown & Co. open air historic steamer wagon at the Somerwell House c 1692, now Little York Confectionery. Delight in a narrated exploration by a National Park Certified Guide. Witness the site of the last major battle of the American Revolution. Walk to a viewing station at Surrender Field, where you can see original cannons from the Revolution displayed to commemorate America’s victory. Ride alongside the vast fields where the make-shift hospitals cared for the wounded, soldiers camped, and cannons and ammunitions were stored. Cross the stream to the location of George Washington’s camp headquarters, bow your head at site of the French Cemetery, or simply ride along and feel the weight of these hallowed grounds as you follow the timeline of battle and victory at Yorktown. Stop at the National Park Service Visitor Center Museum where you will see one of George Washington’s campaign tents, exhibits depicting the 1781 siege of Yorktown, Revolutionary War artifacts, and the campaign table used by General Cornwallis. After enjoy exploring Main Street, Little York Confectionery, Historic Mobjack Petite Café, as well as local Art Galleries and shops.
Activity Level: Low | ADA Accessible: Partial
This is a Signature shore excursion and should be reserved in advance. Please call (800) 894-8570 for information.
Beginning at the River Walk Landing, this trolley makes convenient stops at Yorktown’s most significant sites, allowing you to explore at your own pace and comfort. Travel back in time at the Yorktown Battlefield, where the final major conflict of the American Revolution unfolded. Visit the Yorktown Visitor Center to see fascinating exhibits and learn about the pivotal events that shaped our nation. Stroll along historic buildings, where the stories of 18th-century life are brought to life through well-preserved architecture and cobblestone streets. Take time to browse boutique shops and galleries offering locally crafted goods, art, and souvenirs.
Activity Level: Moderate | ADA Accessible: Yes
There are a variety of activities scheduled on board when the ship is underway, which vary depending on the itinerary and scheduled date. Enjoy destination-focused enrichment programs with special guest speakers who present topics related to the region and ports of call, including Art Classes, App-titude Classes (Tech Made Easy), Cooking Demonstrations, Mixology (practice of making great cocktails,) Trivia, Game Shows, and more.
This 18-acre waterfront museum, which is dedicated to furthering the understanding of the maritime heritage of the Chesapeake Bay area, features 10 exhibit buildings, a historic lighthouse, and a working boatyard. Docking right in the heart of the museum, American Cruise Lines’ guests can enjoy a private exploration of this fascinating museum.
Activity Level: Low | ADA Accessible: Yes
The Classic Motor Museum is dedicated to appreciating and preserving America’s heritage of automotive innovation. Explore the museum to learn the history of motoring, from its earliest days to the current state of transportation. View everything from a Ford model T to today's Porsche 911 Turbo.
Activity Level: Low | ADA Accessible: Yes
Enjoy a guided motorcoach ride exploring the landscape surrounding the childhood home of Underground Railroad Conductor Harriet Tubman. Led by a guide, view the setting of her escapes north. Explore Harriet Tubman State Park and the onsite museum at your leisure. You will also see the Brodess Farm and the Bucktown General Store, the site of her first known act of defiance.
Activity Level: Low | ADA Accessible: Yes
Enjoy a guided walking exploration of historic St. Michaels, a charming waterfront town, named as one of the Top 10 Best Small Coastal Towns in America by USA Today. Explore the picturesque harbor front on Maryland's Eastern Shore, lined with bustling marinas and ornamented with boats of all shapes and sizes.
Stroll through St. Michaels' famed Historic District, as we rediscover 350 years of shipbuilding, classic historic homes, and the famous battle of St. Michaels from the War of 1812. Our exploration concludes along the community's quaint Talbot Street shopping district, lined with one-of-a-kind boutique shops, fabulous eateries, and towering church steeples.
Activity Level: Moderate | ADA Accessible: Yes
Discover the artistry behind one of Maryland’s most celebrated craft distilleries, steps from Chesapeake Bay, during this exclusive experience at Lyon Rum. Delve into the rich history of American Rum, guided by founder Jaime Windon herself, a pioneering leader in the spirits industry and a proud example of the growing number of women shaping the future of craft distilleries across the country. Enjoy a clear view of the production room and gain insights into the meticulous craftsmanship behind Lyon Rum’s premium spirits. Next, unwind in their newly finished Golden Hour Tasting Room, a beautiful and inviting space designed for comfort and relaxation, to indulge in a hand-crafted cocktail or three 2-oz Rum samples.
Activity Level: Low | ADA Accessible: Yes
Soak in the sights along an eight-mile cruise on the Miles River. Your knowledgeable captain will be your guide, sharing fascinating stories as you glide past stunning 200-year-old mansions that reflect a bygone era. Keep on the lookout for the vibrant wildlife that calls this serene landscape home, from graceful herons to playful otters.
Aboard The Patriot, a charming replica of a 1930s steamship, enjoy a unique blend of nostalgia and comfort. Sip on your favorite drink from the full bar, with an array of beverages and delightful snacks available for purchase.
Activity Level: Low | ADA Accessible: No
Enjoy a leisurely afternoon in Easton as you explore the charming downtown district at your own pace. Browse fashionable apparel, fine jewelry, antiques, and eclectic art galleries while discovering the town’s rich heritage and distinctive local culture. You’ll also receive complimentary access to the Talbot Historical Society, where engaging exhibits offer a fascinating glimpse into the region’s storied past, and the beautifully maintained gardens provide a peaceful place to stroll and relax.
Activity Level: Low-Moderate | ADA Accessible: Yes
A Colonial-attired guide will lead you through Annapolis' historic district and into the Maryland State House. Walk in the footsteps of George Washington, where in 1783, inside the State House, he resigned as commander-in-chief of the Continental Army. Continuing through the downtown area, pass many 18th-century mansions and learn about the significance of their beautiful architecture. Throughout your exploration, your guide will share Annapolis history with you, including stories of the famous statesmen that built these magnificent structures.
Activity Level: Moderate | ADA ACCESSIBLE: Yes
Step aboard the classic Harbor Queen for a narrated cruise along the Annapolis Harbor and the banks of the U.S. Naval Academy. Hear the history of the Academy, discover Annapolis' role as a historic seaport, and learn about the region's waterways. Along the way, catch a glimpse of the Chesapeake Bay Bridge.
Activity Level: Low | ADA Accessible: Yes
Founded in 1845 by Secretary of the Navy, George Bancroft, the Academy was started as the Naval School at Old Fort Severn. Experience “Life on the Yard” as you explore the Academy campus with a professional, certified guide. The excursion highlights life at the U.S. Naval Academy past and present and includes Lejeune Hall, Bancroft Hall, Tecumseh, Herndon Monument, Main Academy Chapel (when open), and the crypt of John Paul Jones, Revolutionary War hero.
Activity Level: Low | ADA Accessible: Yes
Ride through the streets of the Annapolis Historic District as an experienced and knowledgeable colonial-attired guide provides historical anecdotes and narration throughout your journey. Pass Maryland's Governor's Mansion and the Historic State House, the country's oldest state capitol in continuous use. Other sights include Hammond-Harwood House, St. Mary's Church, and Charles Carroll House, as well as St. John's College, originally a young men's school that educated George Washington's grandsons. Enjoy a stop at the Maryland WWII Memorial which overlooks the scenic Severn River and the U.S. Naval Academy for an opportunity to stretch your legs and take photos.
Activity Level: Low | ADA Accessible: Yes
Baltimore is a fascinating and beautiful city to view from the water. On this narrated cruise through the Inner Harbor, learn about the renaissance of Baltimore's waterfront as well as its fascinating maritime history. Highlights include the iconic Domino Sugar sign, Fort McHenry, the Key Bridge, Fell's Point, Under Armour, and more.
Activity Level: Low| ADA Accessible: Partial
One of the largest attractions in Maryland, The National Aquarium boasts several exhibits including the Upland Tropical Rain Forest, a multi-story Atlantic Coral Reef, an open-ocean shark tank, and many more. Learn about animals from all over the planet, from the depths of the ocean to the canopy of the rain forest, and discover the connection they all share with water.
Activity Level: Low | ADA Accessible: Partial
Visit this center, which offers a wide array of exhibits that showcase Maryland’s past and cultural legacy. Enjoy a guided tour of The Unfinished Revolution exhibition, which explores the chaos, confusion, and conflicts of the early United States as it fought to defend its newly attained freedoms. Learn about impact the French and Indian War, the American Revolutionary War, the Quasi-War, and the War of 1812 had on Maryland, and the political and economic growth of the state and the nation thereafter. Take time to explore the center’s extensive collection on your own, including artifacts, documents, and artworks that provide a deeper understanding of Maryland’s history.
Activity Level: Low | ADA Accessible: Yes
Begin your journey at the Star-Spangled Banner Flag House, where Mary Pickersgill stitched the flag that inspired the national anthem. Enjoy a guided tour of the historic home and museum, then explore the gift shop before continuing to the Francis Scott Key Monument, a striking tribute to the anthem’s author and a perfect photo opportunity. A short drive brings you to Federal Hill Park, offering sweeping views of Baltimore’s harbor and a glimpse into the city’s storied past. Along the way, your guide will highlight the home of Charles Carroll of Carrollton, the last surviving signer of the Declaration of Independence, completing a rich exploration of Baltimore’s iconic sights and enduring legacy.
Activity Level: Low | ADA Accessible: Yes
If you choose to extend your stay, a number of great excursions are available, including the Fort McHenry National Monument and Historic Shrine, Civil War Museum, and the city's many art museums.