Have questions? We're here.
Buzzling New York

Top New York Trips & Tours in September 2025

Travel made your way ™
Talk with an expert
Build your ideal United States trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Discover New York in September 2025 on one of these 9 tours hand-selected by the travel experts at Adventure Life. Explore the best of during September 2025 as you enjoy Urban Exploration, Archaeological Site Visits, Local Market Visits, Village Visits, and Wildlife Viewing. Prices for trips in September 2025 range from $7,070 to $34,100 for a vacation of 8 to 16 days. Choose any of the below 9 itineraries in September 2025 and customize it when you contact one of Adventure Life's expert New York trip planners.
Filter (9 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • New York
Vanderbilt Mansion National Historic Site
from $7,070
Savings
EXPLORE

Hudson River Fall Foliage

New York - New York - 8 Day Itinerary aboard American Glory
  • Visit Sleepy Hollow landmarks
  • Tour West Point Academy
  • Discover Hyde Park’s history
  • Admire Vanderbilt Mansion
Starts / Ends
New York / Catskill
Activity Level
Variable
Embark on a scenic Hudson River 8-day cruise from New York to Albany aboard American Glory. Visit historic sites in Sleepy Hollow, West Point, Kingston, Hyde Park, and Catskill. Enjoy scenic views, onboard enrichment, and cultural landmarks. Experience the beauty and history of the Hudson River on this unforgettable journey.
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $7,899
Save $6600
EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I
  • Discover Michigan's Upper Peninsula
  • Explore Detroit's Henry Ford Museum
  • Stroll Chicago’s Navy Pier
  • Visit Niagara Falls up close
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day Great Lakes cruise from Chicago to Toronto aboard Victory I, exploring cities, islands, and historical sites. Enjoy scenic sailings and unique excursions.
Cruise Details
0
Visit historic locations along the shores of the Great Lakes
from $7,899
Save $6600
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 Escanaba's lighthouse
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 $7,899
Save $6600
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
Activities
Local Market Visits, Biking
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
Eastern Point Lighthouse, Gloucester, Massachusetts
from $11,030
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Independence
  • View Cape Elizabeth lighthouses
  • Discover Nantucket whaling history
  • Walk Portland’s Old Port
  • Visit Maine Maritime Museum
Starts / Ends
Portland / New York
Activities
Village Visits, Wine Tasting
Activity Level
Variable
Cruise the New England coast on a 16-day cruise from Portland to New York aboard American Independence. This journey delivers history, culture, and natural beauty through iconic destinations, guided tours, and onboard enrichment—all while experiencing the region’s fall colors and crisp sea air.
Cruise Details
0
Visit Portsmouth
from $13,285
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Glory
  • Walk Portland’s working waterfront
  • Tour Newport’s seaside mansions
  • Walk at cobblestone streets
  • Visit Gloucester’s Maritime Museum
Starts / Ends
Portland / New York
Activity Level
Variable
Sail the coast of New England on a 16-day New England Fall Foliage cruise aboard American Glory, visiting historic cities and scenic harbors from Maine to New York. This cruise blends history, coastal charm, and iconic landmarks with smooth sailing and guided excursions.
Cruise Details
0
Aerial view of New York City at dusk
from $8,600
EXPLORE

Montreal to New York, NY

Montreal - New York - 12 Day Itinerary aboard Silver Shadow
  • Discover Montreal’s landscape
  • Explore Quebec City historic charm
  • Experience Saguenay’s wilderness
  • Stroll Charlottetown’s streets
Starts / Ends
Montreal / New York City
Activities
Urban Exploration, Wildlife Viewing, Kayaking, Whale Watching
Activity Level
Variable
Embark on a 12-day cruise from Montreal to New York on the Silver Shadow, exploring Canada's Atlantic coast and New England's charm. Highlights include Quebec City, Prince Edward Island, and excursions like hikes and heritage walks, offering a blend of culture and relaxation.
Cruise Details
0
Detroit, Michigan at Dusk
from $7,899
Save $6600
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
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
Enjoy the scenery of the Great Lakes
from $7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Chicago - Montreal - 13 Day Itinerary aboard Victory I
  • Visit Willis Tower in Chicago
  • Explore the Henry Ford Museum
  • Visit Rock and Roll Hall of Fame
  • Discover Toronto's culture
Starts / Ends
Chicago / Montreal
Activities
Archaeological Site Visits
Activity Level
Variable
Sail from Chicago to Montreal on a 13-day cruise aboard Victory I, exploring iconic cities, engineering marvels, and natural wonders. Scenic lake crossings offer time to unwind between dynamic destinations.
Cruise Details
0
1-9 of 9 Results
  • 1

United States Travel Guide

Top United States Travel Destinations

United States Trips by Departure Date

Top Experiences in United States

United States Trips by Duration

United States Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By

Angie Broeckel Adventure Life employee profile
Angie B
Plan My Trip
We love travel, talk with an expert 1.800.344.6118
GOT IT!
We use cookies to give you the best experience on our website. Continue browsing the site if you're ok with this. For more info, please see our privacy policy.