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Our Portland Trips & Vacation Packages

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Discover the vibrant city of Portland, Maine, with our 7 diverse tours for 2024. Join us on one of these top-rated trips and vacation packages to explore this charming coastal destination. From indulging in the local food scene to exploring the picturesque lighthouses along the rugged coastline, there is something for every traveler in Portland. Immerse yourself in the rich maritime history, enjoy whale watching excursions, and stroll through the cobblestone streets lined with boutique shops and art galleries. Whether you're interested in cultural experiences, food & wine tours, or outdoor adventures like hiking or kayaking, Portland offers a perfect blend of activities. With tours ranging from short day trips to longer adventures, there is an option for every schedule. Don't miss the chance to experience the beauty and charm of Portland, Maine, with Adventure Life. Contact one of our tour specialists for help planning your next seamless trip.
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    • Portland
Beautiful seascapes in Maine
$6,640
Savings
EXPLORE

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:
Variable
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
0
Explore beautiful Montreal
$7,399
EXPLORE

New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I
  • Explore Portland
  • Explore Charlottetown
  • Sail on the Gulf of St. Lawrence
  • Enjoy whale watching near Tadoussac
Starts / Ends:
Portland / Toronto
Activities:
Archaeological Site Visits, Small Ship Cruises, Village Visits, Whale Watching
Activity Level:
Variable
Embark on a 12-day cruise from Portland to Toronto aboard Victory I. Begin with a stay in Portland, exploring the historic Old Port district, or visit the nearby town of Kennebunkport. Sail along the Atlantic Ocean, stopping in Halifax to enjoy its vibrant waterfront. Navigate through the Strait of …
Cruise Details
0
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
Golden light over the Chicago skyline
$4,999
EXPLORE

Montreal to Portland

10 Day Itinerary aboard Victory I
  • Explore Montreal's European charm
  • Visit Halifax’s Citadel Hill
  • Stroll Portland’s historic streets
  • Enjoy a scenic whale-watching
Starts / Ends:
Toronto / Portland
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Whale Watching
Activity Level:
Variable
Embark on a 10-day cruise from Montreal to Portland aboard the Voyager I. Experience Montreal’s European charm, featuring historic architecture and vibrant arts. Explore landmarks like Mount Royal Park and Notre Dame Basilica. Visit Quebec City, a UNESCO World Heritage site known for its …
Cruise Details
0
Explore the parks around Quebec City for a view of the city
$7,399
EXPLORE

New England and Canada

Toronto to Portland - 12 Day Itinerary aboard Victory II
  • Explore Toronto's landmarks
  • Visit Quebec City's historic sites
  • Go on a whale-watching adventure
  • Visit Halifax’s historic waterfront
Starts / Ends:
Toronto / Portland
Activities:
Archaeological Site Visits, Small Ship Cruises, Village Visits, Whale Watching
Activity Level:
Variable
Embark on a 12-day cruise from Toronto to Portland aboard Victory II. Begin with a hotel stay in Toronto, and explore iconic sites such as the CN Tower and the Royal Ontario Museum. Board the ship and set sail across Lake Ontario. Explore Montreal's rich culture and cuisine, then cruise the St. …
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
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