Can I book the trolley for private events?

Yes, Portland Discovery Tours offers private charters perfect for weddings, parties, and corporate outings.

How long is a typical trolley tour?

Most tours last between 1 to 3 hours, depending on the route and stops selected.

Is the trolley accessible for everyone?

Yes, the trolley is accessible for guests with mobility needs; please request accommodations when booking.

Are refreshments allowed on board?

Outside food and beverages are generally not permitted, but inquire about special arrangements for private bookings.

What areas does the trolley cover?

Routes can be customized to include Portland’s historic districts, waterfront, and cultural neighborhoods.

Is there a minimum group size?

Group sizes vary; contact Portland Discovery Tours for tailored quotes and availability.

Charter Trolley | Boat Tour in Portland | Trolley | Boat Tour

Portland, Oregon, is a city full of vibrant neighborhoods, historic sites, and eclectic streets that beckon to be seen in style. One of the most charming ways to get an authentic feel of the Rose City is aboard the Charter Trolley from Portland Discovery Tours. This experience isn’t just about transportation; it transforms a simple ride into an event, perfect for special gatherings, celebrations, or private tours. Whether you're organizing a wedding shuttle, a corporate outing, or a fun day with friends and family, the trolley offers a memorable way to traverse the city’s diverse attractions. The trolley’s classic design, combined with friendly commentary, makes it a standout choice for storytelling and sightseeing. Imagine cruising down the historic streets, passing by landmark bridges and iconic neighborhoods, all while enjoying the comfort of vintage-style transportation. The business’s tailored experiences ensure your group can customize stops and routes, making each journey uniquely your own. Portland has long celebrated its colorful history and progressive culture, and this vehicle offers a fresh, engaging way to connect with that vibrant spirit. The trolley is more than a ride — it’s a moving piece of Portland’s story, perfect for exploring the city’s lively districts and hidden corners. What sets Portland Discovery Tours apart is their dedication to creating flexible, personalized adventures that bring people together through shared experiences. Ideal for groups seeking a fun, accessible, and distinctive way to see the city, the Charter Trolley makes any outing special. Whether you're celebrating a milestone or just craving a different perspective on Portland, this trolley provides a distinctive, cheerful ride that’s as much about memories as it is about sightseeing.

About Portland Discovery Tours

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.