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Top Sleepy Hollow Cruises & Trips

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Explore these 3 top Sleepy Hollow cruises for 2025 and 2026. Some of the most popular activities on our Sleepy Hollow trips include Archaeological Site Visits, Urban Exploration, Village Visits, Local Market Visits, and Wine Tasting. Discover with your expert local English-speaking guides who will show you the hot spots and the off-the-beaten-path hidden gems. We work with only the best small ships that carry under 500 fortunate guests, and we can give you unbiased advice to match you with the perfect ship and perfect cruise for your next vacation. Our Sleepy Hollow cruises start from $7,070 for cruises of 8 to 16 days. Contact one of Adventure Life's Sleepy Hollow cruise specialists for help planning a seamless trip.
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Vanderbilt Mansion National Historic Site
from $7,070
Savings
EXPLORE

Hudson River Fall Foliage

New York - New York - 8 Day Itinerary aboard American Glory
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.
  • Visit Sleepy Hollow landmarks
  • Tour West Point Academy
  • Discover Hyde Park’s history
  • Admire Vanderbilt Mansion
Cruise Details
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Eastern Point Lighthouse, Gloucester, Massachusetts
from $11,030
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Independence
Starts / Ends
Portland / New York
Activities
Urban Exploration, Archaeological Site Visits, Village Visits, Wine Tasting, Local Market Visits
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.
  • View Cape Elizabeth lighthouses
  • Discover Nantucket whaling history
  • Walk Portland’s Old Port
  • Visit Maine Maritime Museum
Cruise Details
0
Visit Portsmouth
from $13,285
Savings
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New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Glory
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.
  • Walk Portland’s working waterfront
  • Tour Newport’s seaside mansions
  • Walk at cobblestone streets
  • Visit Gloucester’s Maritime Museum
Cruise Details
0
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TrustScore 4.8 | 544 reviews
TrustScore 4.8 of 5
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Based on 544 reviews on
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2 hours ago
Erin seemed to know all about Galapagos locations and travel
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