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Select one of the below 4 best Maryland trips for 2026 and 2027. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Baltimore, and Chesapeake Bay. Our Maryland trips for 2026 feature Archaeological Site Visits, Urban Exploration, Wildlife Viewing, Local Market Visits, and Village Visits, and start from $4,610 for trips of 8 to 16 days. Contact Adventure Life's Maryland trip planning experts to start planning your next seamless trip.
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Sunset casts a golden glow over Maryland’s Chesapeake Bay Bridge
from $4,610
Savings
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Chesapeake Bay Cruise

Baltimore, MD Roundtrip - 9 Day Itinerary aboard American Independence
  • Explore Baltimore Inner Harbor
  • Visit Jamestown Settlement museum
  • Learn Maryland distilling tradition
  • Explore the U.S. Naval Academy
Starts / Ends
Baltimore / Baltimore
Activity Level
Variable
Cruise the Chesapeake Bay on a 9-day cruise aboard American Independence, sailing from Baltimore to Yorktown, Williamsburg, St. Michaels, and Annapolis. Explore colonial streets, museums, battlefields, maritime towns, wildlife-rich waterways, and historic harbors through guided tours and scenic cruising.
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Visit historic Baltimore
from $4,925
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Potomac River & Chesapeake Bay Cruise

Washington to Baltimore - 9 Day Itinerary aboard American Independence
  • Visit Yorktown battlefield site
  • Tour Jamestown Settlement museum
  • Cruise Chesapeake Bay waters
  • Discover Annapolis landmarks
Starts / Ends
Chesapeake Bay / Baltimore
Activity Level
Variable
Sail from Washington to Baltimore on an 9-day cruise aboard American Independence. Explore Revolutionary War sites, historic seaports, and Chesapeake Bay wildlife. Visit Yorktown, Williamsburg, Cambridge, St. Michaels, and Annapolis. Enjoy onboard enrichment, local excursions, and scenic cruising through America’s historic heartland.
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Visit historic Baltimore
from $12,460
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Celebrating America's 250th: An Exploration of History and Culture

Halifax - Baltimore - 8 Day Itinerary aboard L'Austral
  • Talks by Martin Luther King III
  • Explore Boston’s Freedom Trail
  • Visit Newport mansions or sail bay
  • See New York’s Statue of Liberty
  • Explore Philadelphia historic sites
Starts / Ends
Halifax / Baltimore
Activities
Archaeological Site Visits
Activity Level
Variable
Discover the 8-day Celebrating America's 250th Eastern Seaboard cruise on L'Austral from Halifax to Baltimore, featuring history-focused talks by Martin Luther King III and Arndrea Waters King. Highlights include Boston’s Freedom Trail, Newport’s Gilded Age mansions, New York’s Statue of Liberty, 9/11 Memorial, and Philadelphia’s Independence Hall.
Cruise Details
0
Visit historic Baltimore
from $11,570
Savings
EXPLORE

East Coast Inland Passage Cruise

Baltimore, MD to Amelia Island - 16 Day Itinerary aboard American Liberty
  • Explore Baltimore’s Inner Harbor
  • Visit Jekyll Island landmarks
  • See Savannah’s Civil Sites
  • Visit Chesapeake Bay Museums
Starts / Ends
Baltimore / Amelia Island
Activities
Urban Exploration, Wildlife Viewing, Local Market Visits, Village Visits
Activity Level
Variable
Embark on a 16-day East Coast Inland Passage cruise aboard American Liberty. Explore coastal towns like Charleston, Savannah, and Beaufort. Enjoy guided excursions to historic sites, maritime museums, and Civil War landmarks. Discover lighthouses, plantations, and preserved Southern architecture across 14 ports along the East Coast.
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