Portland City Tours

Travel made your way ™
Talk with an expert
Build your ideal East Coast of US trip. Call 800.344.6118
Start Planning My Trip
Choose from one of these 10 City Tours to Portland in 2027-2028 to explore the streets and take in the cityscapes of Portland on a trip seamlessly planned by the Portland experts at Adventure Life. Breathe in the culture, smell the local cuisine, and experience the people of Portland on one of these extraordinary small group or private tours. Your options will likely include walking tours, bus tours, and boat tours, all led by exceptional multi-lingual local tour guides. Select any the urban exploration tours below and customize it to fit your personal interests with the help of one of Adventure Life's expert Portland trip planners. 
Filter (10 Results)
  • Start Date
    Months
    Years
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Portland
Beautiful seascapes in Maine
from $5,240
Savings
EXPLORE

Maine Coast & Harbors Round-Trip Cruise

Portland Roundtrip - 9 Day Itinerary aboard American Independence
  • Explore Historic Portland
  • Discover Fort Knox
  • Explore Acadia National Park
  • Discover Maine Maritime Heritage
Starts / Ends
Portland / Portland
Activities
Village Visits
Activity Level
Variable
Explore Maine’s coast on a 9-day cruise from Portland aboard American Independence. Visit Bucksport, Bangor, Bar Harbor, Rockland, Camden, Boothbay Harbor, and Bath. Discover Fort Knox, Acadia National Park, maritime heritage, seafood traditions, and coastal communities across southern and midcoast Maine.
Cruise Details
0
Edgartown on Martha's Vineyard
from $7,180
EXPLORE

Charm and heritage of the North American shores

Halifax to New York - 9 Day Itinerary aboard L'Austral
  • See Lunenburg UNESCO historic town
  • Eastport Maritime Historic Site
  • See Newport Gilded Age mansions
  • Martha's Vineyard island escape
Starts / Ends
Halifax / New York
Activity Level
Variable
Explore Canada and New England on a 9-day cruise aboard L'Austral. Visit Halifax, Lunenburg, Yarmouth, Eastport, Portland, Boston, Oak Bluffs, Newport, and New York. Discover maritime history, UNESCO heritage sites, coastal landscapes, iconic landmarks, and charming seaside towns throughout the voyage.
Cruise Details
0
Visit Portsmouth
from $7,299
Save $500
EXPLORE

New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I
  • Explore Portland
  • Watch whales in Saguenay Fjords
  • Walk Old Quebec streets
  • Explore Charlottetown history
Starts / Ends
Portland / Toronto
Activity Level
Variable
Experience a 12-day cruise from Portland to Toronto aboard Victory I and enjoy coastal views, local cuisine, and relaxing days at sea. This immersive journey blends Canadian culture, maritime history, and scenic waterways for a unique small-ship cruising experience.
Cruise Details
0
Charming Quebec City
from $8,450
EXPLORE

Canada & New England Featuring Quebec City

Bayonne - Montreal - 12 Day Itinerary aboard Silver Shadow
  • Tour Newport’s Gilded Age mansions
  • Stroll Portland’s Old Port
  • Explore historic Boston
  • Discover maritime Halifax
Starts / Ends
Newport / Montreal
Activities
Archaeological Site Visits, Whale Watching, Urban Exploration, Wildlife Viewing
Activity Level
Variable
Take a 12-day Canada and New England cruise on the Silver Shadow from Bayonne, New Jersey, to Montreal. Tour the grand mansions of Newport, explore historic Boston, visit Halifax and Charlottetown, and spend a night in walled Quebec City before continuing up the St. Lawrence to Montreal.
Cruise Details
0
Stroll by the river running through Quebec City
from $7,299
Save $500
EXPLORE

Five Great Lakes + St. Lawrence Seaway: Portland to Toronto

Portland to Toronto - 13 Day Itinerary aboard Victory II
  • Cruise Atlantic Canada to Toronto
  • Wander UNESCO Old Quebec
  • Discover Charlottetown's history
  • Sail the Saguenay Fjord
  • Tour Old Montreal's basilica
Starts / Ends
Portland / Toronto
Activity Level
Variable
Embark on a 13-day cruise aboard Victory II and sail from Portland, Maine to Toronto, Ontario, calling at Nova Scotia, Prince Edward Island, Quebec City, and Montreal. This voyage links rugged Atlantic shores, a deep glacial fjord, and Great Lakes channels into one seamless passage across North American coastal waterways.
Cruise Details
0
Portsmouth, New Hampshire
from $9,899
Save $500
EXPLORE

East Coast: Halifax to Jacksonville

Halifax to Jacksonville - 16 Day Itinerary aboard Victory I
  • See Portland Head Light
  • Discover Provincetown galleries
  • Tour Newport's grand mansions
  • See Charleston's historic landmarks
Starts / Ends
Halifax / Jacksonville
Activity Level
Variable
Embark on a 16-day East Coast cruise aboard Victory I. Explore Halifax and Peggy’s Cove before visiting Portland, Portsmouth, Provincetown, Newport, and New London. Continue south to Norfolk, Wilmington, Charleston, Savannah, Brunswick, and Jacksonville. Experience New England’s coastal heritage, Southern history, and Atlantic scenery.
Cruise Details
0
Colorful sunrise at Portland Head Lighthouse in Maine
from $9,899
Save $500
EXPLORE

East Coast: Jacksonville to Halifax

Jacksonville to Halifax - 16 Day Itinerary aboard Victory I
  • Explore Jacksonville's waterfront
  • Tour Newport's Gilded Age mansions
  • Stroll Savannah’s historic squares
  • Discover Norfolk’s naval heritage
Starts / Ends
Jacksonville / Halifax
Activity Level
Variable
Sail from Jacksonville to Halifax aboard Victory I, visiting historic coastal ports in Georgia, South Carolina, North Carolina, Virginia, Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Nova Scotia. Explore waterfronts, museums, historic sites, mansions, naval landmarks, and lighthouses along the Atlantic coast.
Cruise Details
0
Visit Portsmouth
from $18,198
Save $500
EXPLORE

5 Great Lakes + St. Lawrence Seaway: Montreal to Jacksonville

Montreal to Jacksonville - 29 Day Itinerary aboard Victory I
  • Watch Saguenay Fjord belugas
  • Kayak Gaspe's Forillon coastline
  • Tour Halifax's hilltop Citadel
  • Admire Newport's Cliff Walk
Starts / Ends
Montreal / Jacksonville
Activities
Local Market Visits, Kayaking
Activity Level
Variable
Embark on a 29-day voyage aboard Victory I, from Montreal to Jacksonville, linking the St. Lawrence Seaway with the Atlantic Seaboard. Walk Old Quebec, watch beluga whales in the Saguenay Fjord, and explore Halifax, Yarmouth, and Newport, then stop in Brunswick, Georgia, before reaching Florida.
Cruise Details
0
Colorful sunrise at Portland Head Lighthouse in Maine
from $8,299
Save $500
EXPLORE

New England and Canada

Montreal to Portland - 13 Day Itinerary aboard Victory II
  • Walk Quebec City's Old Town streets
  • Saguenay Fjord sailing
  • Gulf crossing experience
  • Tour Halifax historic citadel
Starts / Ends
Montreal / Portland
Activity Level
Variable
Begin your 13-day voyage in Montreal with a hotel stay, then board Victory II and sail the St. Lawrence River to Quebec City, Saguenay, Baie-Comeau, and Gaspe. Cross the Gulf of St. Lawrence to Charlottetown, continue to Halifax and Yarmouth, and finish in Portland, Maine. Explore fortified cities, fjords, island capitals, and working waterfronts.
Cruise Details
0
Aerial View of Halifax Skyline
from $8,299
Save $500
EXPLORE

New England and Canada

Montreal to Portland - 13 Day Itinerary aboard Victory I
  • Visit UNESCO-listed Old Quebec City
  • Charlottetown historic charm
  • Learn Yarmouth’s Acadian heritage
  • Sail through Saguenay Fjord
Starts / Ends
Montreal / Portland
Activity Level
Variable
Begin the 13-day voyage in Montreal with a hotel stay, then board Victory I and cruise through Quebec City, Saguenay Fjord, Charlottetown, Halifax, and Yarmouth before ending in Portland, Maine. Sail the Gulf of St. Lawrence and Strait of Canso while exploring historic towns, coastal villages, and maritime landmarks across Atlantic Canada.
Cruise Details
0
1-10 of 10 Results
  • 1

Relax. We've got this.

Talk with an expert trip planner 800.344.6118

Plan My Trip
Mary Curry Adventure Life employee profile
Mary C.
East Coast of US

Chat Portland with a specialist

Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.

Let's Chat
800.344.6118

Where is your next adventure?

Contact Chat Call

Why Travel With Us?

More Value.

Receive personal attention and concierge-level service for the same cost as booking direct. Gain access to exclusive rates, perks, and insider expertise on how to maximize the value for your dollar.

Unbiased Cruise Expertise

We're not tied to any one cruise line, so you receive honest guidance on the best ship and itinerary for you—not a sales pitch.

Seamless Trip Planning

We guide you through every detail beyond the cruise—from flights to pre- and post-trip stays—so your journey feels effortless.

As Featured In

How it Works

Connect

No cost, no commitment. Talk with our experts about your dream trip.

Plan

Share your travel style—we match you with the right itinerary or create one just for you.

Book

Lock in knowing every detail is handled and you’re fully supported.

Travel

Enjoy a seamless journey—and unlock 5% off your next adventure.