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Portland Trips with Village Visits

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Live one of the below 4 unique Portland cultural experiences for 2024 or 2025. Visit villages and experience local cuisine with a local English speaking guide on your own private tour or small group guided tour. Discover unique local cultures on trips that include activities like small ship cruises, cruises, village visits, cultural, and land & sea exploration and cost from $6,640 for experiences of 8 to 15 days. Tell us about your ideal Portland cultural trip and our Portland experts will help you plan every detail of your next trip.
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Beautiful seascapes in Maine
$6,640
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Maine Coast & Harbors Cruise

Roundtrip Portland - 8 Day Itinerary aboard American Glory
  • Visit Bucksport
  • Visit Camden in Maine
  • Visit Bar Harbor
  • Visit Cape Elizabeth
Starts / Ends:
Portland / Portland
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits, Wildlife Viewing
Activity Level:
Relaxed
On this 8-day Maine Coast & Harbors Cruise roundtrip Portland aboard the American Glory, explore Maine's breathtaking coastline, framed by a backdrop of mountains teeming with native wildlife. Immerse in the region's maritime heritage in a trip past the grand homes of sea captains and …
Cruise Details
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Springtime in Boston
$7,350
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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
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Visit Portsmouth
$13,155
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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
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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
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