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

Gloucester

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
Select one of the below 3 best Gloucester trips for 2024 and 2025. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Gloucester. Our Gloucester trips for 2024 feature small ship cruises, cruises, village visits, cultural, and land & sea exploration, and start from $7,350 for trips of 11 to 15 days. Contact Adventure Life's Gloucester trip planning experts to start planning your next seamless trip.
Filter (3 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Gloucester
Springtime in Boston
$7,350
EXPLORE

New England Explorer

Boston Roundtrip - 11 Day Itinerary aboard American Constitution
  • Experience Portland’s craft wines
  • Take a ride to Acadia National Park
  • Explore the Gloucester City
  • Visit Fort Adams
Starts / Ends:
Boston / Boston
Activities:
Small Ship Cruises, Village Visits
Activity Level:
Relaxed
Set sail on an 11-day New England Explorer cruise roundtrip from Boston aboard American Constitution. Explore Boston's Revolutionary history, cruise past the iconic Portland Head Light, and discover charming Camden with a local historian. Indulge in a traditional lobsterbake luncheon by the …
Cruise Details
0
Visit Portsmouth
$13,155
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, Village Visits
Activity Level:
Relaxed
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
Eastern Point Lighthouse, Gloucester, Massachusetts
$10,835
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, Village Visits
Activity Level:
Relaxed
Experience a15-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

Gloucester Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By