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Colorful sunrise at Portland Head Lighthouse in Maine

Top East Coast of US Trips & Tours in May 2027

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Discover East Coast of US in May 2027 on one of these 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2027 as you enjoy Archaeological Site Visits, Urban Exploration, Local Market Visits, Village Visits, and Wildlife Viewing. Prices for trips in May 2027 range from $4,925 to $46,995 for a vacation of 9 to 15 days. Choose any of the below 6 itineraries in May 2027 and customize it when you contact one of Adventure Life's expert East Coast of US trip planners.
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    • East Coast of US
Tour colorful, historic Charleston, South Carolina
from $7,415
Savings
EXPLORE

Southeast Sea Islands Cruise

Charleston to Amelia Island - 9 Day Itinerary aboard American Liberty
  • Tour historic Charleston homes
  • Explore Beaufort’s Cypress Wetlands
  • Visit Mighty Eighth Museum
  • Walk Savannah’s historic district
Starts / Ends
Charleston / Amelia Island
Activities
Village Visits
Activity Level
Variable
Cruise the southeastern coast on a 9-day voyage from Charleston, South Carolina to Amelia Island, Florida, aboard American Liberty. Explore Savannah, Beaufort, Hilton Head, and more.
Cruise Details
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Sunset casts a golden glow over Maryland’s Chesapeake Bay Bridge
from $4,925
Savings
EXPLORE

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.
Cruise Details
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Sailing in Boston
from $6,350
Savings
EXPLORE

Northeast Harbors Cruise

Boston - New York - 9 Day Itinerary aboard American Glory
  • Visit the Massachusetts Maritime
  • Explore the Mystic Seaport Museum
  • Travel to Old Saybrook
  • Stroll around Sag Harbor
Starts / Ends
Boston / New York
Activity Level
Variable
Join this 9-day Northeast Harbors cruise from Boston to New York aboard American Glory. Explore historic Boston before visiting picturesque Plymouth, MA, and the grandeur of Newport. Dive into maritime history in New London, Mystic, and Essex, CT. Lastly, enjoy an evening cruise around New York Harbor.
Cruise Details
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Visit historic Baltimore
from $4,925
Savings
EXPLORE

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
Activities
Urban Exploration, Archaeological Site Visits, Local Market Visits, Wildlife Viewing
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.
Cruise Details
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Relax on the shores of the Great Lakes
from $6,799
Save $6600
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
  • Cruise all five Great Lakes
  • Visit Niagara Falls up close
  • Tour Cleveland’s museums
  • Visit Mackinac Island
Starts / Ends
Toronto / Chicago
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise aboard Victory II and explore cultural hubs like Cleveland and Detroit, visit Niagara Falls, and relax on car-free Mackinac Island. Enjoy scenic days on Lake Ontario, Erie, Huron, Michigan, and Superior.
Cruise Details
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Door Peninsula, cliffs, forests, and clear Lake Michigan waters
from $13,995
EXPLORE

Great Lakes Collection

Canada to Minnesota - 15 Day Itinerary aboard Viking Great Lakes
  • Cruise Niagara Falls
  • Explore Mackinac Island
  • Kayak Killarney’s turquoise waters
  • Enjoy Sleeping Giant hike views
Starts / Ends
Toronto / Duluth
Activities
Wine Tasting, Hiking, Kayaking, Citizen Science, Biking, Fishing
Activity Level
Variable
Set sail on a 15-day voyage aboard a Viking Great Lakes cruise ship, starting in Toronto and exploring North America’s inland seas. Visit Niagara Falls, Detroit, Mackinac Island, and enjoy scenic hikes, vineyards, and optional excursions like helicopter rides on this enriching cultural voyage.
Cruise Details
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