Have questions? We're here.
Boston's skyline and harbor

Gloucester Urban Exploration Tours

Travel made your way
Talk with an expert
Build your ideal East Coast of US trip. Call 1.406.541.2677
Start Planning My Trip
Discover the historic charm of Gloucester, Massachusetts on our 3 enriching urban exploration city tours for 2025. Nestled on the Atlantic coast, Gloucester offers a blend of maritime history, art, and coastal beauty that will captivate your senses. Immerse yourself in the local art scene, stroll through quaint coastal towns, and uncover the region's rich history. Over 15 days, you'll have the chance to explore the picturesque landscapes and cultural heritage that define Gloucester. With prices starting at $10,835 to $24,635, join us on a journey to experience the best of this iconic New England destination. Contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (3 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Gloucester
Visit Portsmouth
$13,155
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 15 Day Itinerary aboard American Glory
  • Visit Portsmouth and Gloucester
  • Explore Martha’s Vineyard & Newport
  • Explore Sag Harbor
  • Discover Mystic Seaport
Starts / Ends:
Portland / New York City
Activities:
Adventure Options, Land & Sea Exploration, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Experience an adventure through New England's picturesque waterways, adorned with vibrant autumn hues. Encounter stunning natural scenery and historic shipbuilding traditions along Maine's coast, followed by exploration of iconic destinations like Martha’s Vineyard and Newport. …
Cruise Details
0
Visit Plymouth
$13,940
Savings
EXPLORE

Grand New England Cruise

Roundtrip Boston - 15 Day Itinerary aboard American Patriot
  • Explore Portland iconic lighthouses
  • Discover Bath historic shipyards
  • Explore Bangor Victorian mansions
  • Discover Portsmouth architecture
Starts / Ends:
Boston / Boston
Activities:
Local Market Visits, Urban Exploration, Village Visits
Activity Level:
Variable
Embark on a 15-day cruise to and from Boston aboard the American Patriot. Explore historic waterways, uncovering America's rich past. Visit seaport towns like Portland and Newport, explore iconic shipyards, and enjoy a traditional Maine lobster bake. Experience the charm and history of New …
Cruise Details
0
Eastern Point Lighthouse, Gloucester, Massachusetts
$10,835
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 15 Day Itinerary aboard American Independence
  • Visit Portsmouth and Gloucester
  • Explore Martha’s Vineyard & Newport
  • Explore Sag Harbor
  • Discover Mystic Seaport
Starts / Ends:
Portland / New York City
Activities:
Adventure Options, Land & Sea Exploration, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Experience a 15-day New England Fall Foliage Cruise from Portland to New York aboard American Independence. Through New England's picturesque waterways, adorned with vibrant autumn hues. Encounter stunning natural scenery and historic shipbuilding traditions along Maine's coast, followed by …
Cruise Details
0
1-3 of 3 Results

North America Travel Guide

Favorite North America North America All Trips

Top North America Travel Destinations

North America Trips by Departure Date

Top Experiences in North America

North America Trips by Duration

North America Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By