Things to Do in Portland, Maine
Most lists of things to do in Portland, Maine focus on landmarks. This guide focuses on how to experience the city well.
Written by locals, this page highlights walking, van, and harbor experiences that help visitors understand Portland’s neighborhoods, history, and coastline—without rushing or over-planning. Whether this is your first visit or a return trip, these experiences help the city make sense.
All Portland Explorer tours depart from the Portland Beer Hub, making it easy to plan your day without a car or complicated logistics.
This guide is especially helpful for first-time visitors, travelers without a car, and anyone looking to experience Portland beyond a checklist.
Explore Portland on Foot
Portland’s compact peninsula makes walking one of the best ways to experience the city. Neighborhoods, historic streets, and the waterfront are closely connected, and moving at walking pace reveals details that are easy to miss otherwise.
Much of Portland’s history lives at street level—from repurposed warehouses to working wharves that still shape daily life. Walking allows visitors to see how past and present overlap, rather than experiencing the city as a series of disconnected attractions.
Walking experiences are especially helpful for first-time visitors, travelers without a car, and anyone who wants to get oriented early in their stay.
Experience Portland from the Water
Portland’s harbor is not a backdrop—it’s a working part of daily life. Fishing boats, ferries, and island communities continue to shape how the city functions and how it has grown over time.
Seeing Portland from the water provides perspective that’s difficult to gain from land alone. From the harbor, the city’s layout makes sense, and its maritime history becomes tangible rather than abstract.
Harbor experiences pair naturally with walking and van tours, helping visitors understand Portland from multiple vantage points.
Why the harbor matters to Portland
When to Visit Portland, Maine
There’s no single “best” time to visit Portland—each season offers a different version of the city.
Summer is lively and energetic, fall is calmer and deeply local, winter feels cozy and authentic, and spring brings renewal as the city wakes up. Choosing when to visit often comes down to how much activity, space, and structure you prefer.
Understanding seasonal differences helps visitors plan experiences that feel natural rather than rushed.
See Beyond Downtown
While Portland’s downtown is highly walkable, some of the region’s most iconic sights sit just beyond the peninsula. Lighthouses, coastal viewpoints, and quieter stretches of shoreline are an important part of understanding the city’s relationship with the sea.
Guided van tours make it possible to explore these areas comfortably without navigating unfamiliar roads, managing parking, or coordinating logistics. For visitors without a car—or those short on time—van tours offer an efficient way to see more of the coastline while learning how geography shaped Portland’s development.
Van tours are especially popular with first-time visitors and guests who want a broader sense of place beyond downtown.
Food & Drink, the Local Way
Portland’s food and drink scene is defined less by trends and more by proximity—to the water, to local farms, and to the neighborhoods that support it.
Restaurants, breweries, and neighborhood bars often double as gathering places for locals. Experiencing this side of Portland with context helps visitors understand why the city’s culinary reputation developed organically rather than through hype.
Food and drink experiences work best as part of a walking route, where stops feel connected to the neighborhoods around them rather than isolated destinations.
First-Time Visitors
For first-time visitors, Portland can feel deceptively small. There’s a lot packed into a compact area, and understanding how the city fits together early can make the rest of the trip more enjoyable.
Many first-time guests find that starting with a guided experience—on foot, by van, or from the water—provides helpful context and confidence. Once oriented, exploring independently feels easier and more intentional.
CHECK IN LOCATION
Portland Beer Hub
320 Fore St, Portland, ME 0410
Your tour will begin at the Portland Beer Hub, the home of Portland Explorer and the best craft beer bar and retail shop in Maine. Enjoy the following amenities as you comfortably wait for your tour to begin.
- Air conditioning
- Clean bathroom
- Comfortable seating
- Water
- Beer, cider, and gluten-free options
- Snacks