Explore Portland, Maine on two wheels with a private bike tour designed just for you. Discover hidden local spots and stunning waterfront views while getting some fresh air and exercise.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for beginners to moderate fitness levels; riders should be comfortable on a bike and able to maintain a steady pace.
Wildlife
History
Portland’s rich maritime heritage shaped its growth as a key shipping and shipbuilding hub in New England.
Conservation
Local organizations actively maintain bike lanes and green spaces to promote eco-friendly tourism and protect Portland’s coastal ecosystems.
Portland Discovery Tours
Explore Portland, Maine on two wheels with a private bike tour designed just for you. Discover hidden local spots and stunning waterfront views while getting some fresh air and exercise.
Portland Discovery Tours operates in Portland, Maine, offering guided trolley tours, scenic cruises, and charter options that showcase the city's maritime history and coastal landmarks.
The company’s fleet includes heated trolleys with open windows for fresh coastal breezes and comfortable boats with enclosed cabins and covered decks for all-weather cruising.
Tours focus on iconic sights around Portland and Casco Bay. The Peek at Portland Tour is a 60‑minute classic trolley experience with knowledgeable guides. The Portland City and Lighthouse Tour is a 105‑minute trolley route that includes a 30‑minute visit to Portland Head Light and highlights such as Victoria Mansion and Henry Wadsworth Longfellow’s childhood home. The Guardians of the Harbor trolley tour stops at three lighthouses, visiting Bug Light Park, Fort Preble, and Portland Head Light while exploring shipbuilding and harbor history.
Boat experiences include the Port‑City Lights Cruise, a 60‑minute narrated scenic cruise past lighthouses and historic forts; the Harbor Lights and Sights Cruise, a 1 hour 45 minute tour of Portland Harbor and Diamond Pass; and the 105‑minute Sunset Lighthouse Cruise, a fully narrated dusk voyage around inner islands and lighthouses. Seasonal and special-event departures include a July 4th Fireworks Cruise. Charter options are available for private boat trips and for trolley rentals suitable for events or group transportation.
Tours emphasize narrated interpretation, close-up lighthouse views, and comfort features that make visits to Portland’s coastal attractions accessible and memorable. Activities accommodate families, dog owners on select cruises, and groups seeking private charters or event transportation in Portland.
Tours & Cruises
10
Diverse trolley and boat experiences
Boat Options
Multiple
Enclosed cabins & covered decks
Tour Durations
60–105 min
Short, narrated local excursions
Private Charters
Trolley & Boat
Available for events and groups
Secure seats on narrated lighthouse cruises, family-friendly harbor tours, and private charters — limited availability for peak dates and special events.
Wear a Helmet
Safety first—always wear a properly fitted helmet to protect your head during the tour.
Bring a Refillable Water Bottle
Stay hydrated by carrying water, especially during warmer months when the ride may get sweaty.
Be Aware of Traffic Signals
Portland has many dedicated bike lanes, but pay attention to traffic signs and pedestrian zones for a safe ride.
Dress in Layers
Portland’s weather can change quickly; wearing layers helps you adjust for comfort throughout the tour.
Helmet
Protects your head and is required for safety during the tour.
Water Bottle
Keeps you hydrated throughout the ride, especially in warmer months.
summer
Light Rain Jacket
Useful for spring showers and unpredictable weather.
spring
Layered Clothing
Allows you to stay comfortable as temperatures vary during fall rides.
fall