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Top East Coast of US Trips & Tours in May 2026

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Discover East Coast of US in May 2026 on one of these 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2026 as you enjoy Urban Exploration, Archaeological Site Visits, Wildlife Viewing, Local Market Visits, and Whale Watching. Prices for trips in May 2026 range from $4,380 to $12,545 for a vacation of 8 to 11 days. Choose any of the below 6 itineraries in May 2026 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
Sailing in Boston
from $6,640
Savings
EXPLORE

Yankee Seaports

Boston - New York - 8 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 8-day Yankee Seaports 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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Deans Blue Hole
from $4,380
EXPLORE

West Caribbean Cruise

Belize - Fort Lauderdale - 11 Day Itinerary aboard SH Vega
  • Witness Bahama's pinkest flamingo
  • Swim with nurse sharks in Exuma
  • Snorkel vibrant coral reefs
  • Visit Cockscomb wildlife sanctuary
Starts / Ends
Belize City / Fort Lauderdale
Activities
Wildlife Viewing, Snorkeling, Rainforest Exploration
Activity Level
Variable
Embark on an 11-day SH Vega cruise through the Western Caribbean. Explore Mayan ruins in Belize, relax on Grand Cayman's beaches, snorkel Montego Bay’s reefs, and visit Jamaica’s mountains. Enjoy birdwatching at Great Inagua, swim with sharks in the Exumas, and marvel at Nassau’s beauty.
Cruise Details
0
Mackinac Island, Michigan
from $6,799
OBC
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
  • Visit car-free Mackinac Island
  • Sail through the Soo Locks
  • Explore the Henry Ford Museum
  • Visit Niagara Falls
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise aboard Victory II, visiting iconic cities such as Chicago, Detroit, and Toronto. Discover scenic wonders like Mackinac Island and Niagara Falls, exploring rich history and culture along the way.
Cruise Details
0
Golden light over the Chicago skyline
from $7,299
OBC
EXPLORE

All Five Great Lakes

Toronto - Chicago - 11 Day Itinerary aboard Victory I
  • Discover the diverse food scene
  • Enjoy the vibrant nightlife
  • Visit Niagara Falls
  • Explore Niagara Peninsula
Starts / Ends
Toronto / Chicago
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard Victory I, exploring vibrant cities and stunning natural landscapes. Enjoy historical tours, and scenic sailing on this unique cruise through the heart of North America.
Cruise Details
0
Detroit, Michigan at Dusk
from $6,799
OBC
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
  • Explore Toronto
  • Experience Niagara Falls
  • Visit Henry Ford Museum
  • Enjoy a horse-drawn carriage tour
Starts / Ends
Toronto / Chicago
Activities
Urban Exploration, Archaeological Site Visits
Activity Level
Variable
Set sail on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard a Victory II. Explore Toronto, Niagara Falls, Cleveland, Detroit, and Mackinac Island, experiencing unique landmarks and vibrant cultures.
Cruise Details
0
Boston's skyline and harbor
from $5,145
Savings
EXPLORE

Yankee Seaports

8 Day Itinerary aboard American Independence
  • Visit the Massachusetts Maritime
  • Explore the Mystic Seaport Museum
  • Travel to Old Saybrook
  • Stroll around Sag Harbor
Starts / Ends
Boston / New York
Activities
Local Market Visits, Whale Watching
Activity Level
Variable
Join this 8-day Yankee Seaports cruise from Boston to New York aboard American Independence. 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
0
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