Things to do in Portland
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Portland Maine: 3 Lighthouses & City Tour with Local GuideYou ride in a shared van through Portland's downtown, waterfront, and three lighthouses with a guide who knows the city's actual history, not just the script. The tour includes Portland Head Light (where you get time to explore), views of two other lighthouses, Victorian mansions, Civil War memorials, and the Old Port's shops and restaurants. You're dropped at the starting point on Commercial Street 10–15 minutes before departure, and the whole thing takes 1 hour 45 minutes.Is it for me?Book this if you want Portland's main sights and three lighthouses covered in one afternoon without renting a car or figuring out the route yourself — the shared van and fixed schedule are what make it possible to hit all three lighthouses and the downtown highlights in 1 hour 45 minutes.
Portland Maine: Trolley Tour & Portland Head LightYou board a narrated trolley that covers Portland's historic peninsula — Victoria Mansion, Longfellow's childhood home, the Portland Museum of Art, and the waterfront — then stops for 20-30 minutes at Portland Head Light, Maine's oldest operational lighthouse. No driving, no planning, no deciding which sights to skip.Is it for me?Choose this if you want to see Portland's main sights and the lighthouse without arranging transport or deciding which stops matter most — the trolley and narration handle both.
Portland Maine: 3 Lighthouses & Coastal Tour with HistoryYou ride in a climate-controlled van through Portland's historic Old Port, stop for photos and walking time at three working lighthouses — Portland Head Light, Spring Point Ledge, and Portland Breakwater — and learn the maritime history of each from your guide. Water and an umbrella are included. Comfortable walking shoes matter, especially at Fort Williams Park where you'll spend the most time. The tour picks up less than half a mile from the cruise ship terminal.Is it for me?Book this if you're docked in Portland or visiting for a few hours and want to see Maine's most famous lighthouses without renting a car or figuring out three separate trips — the van handles the driving, your guide handles the history, and you handle the camera.
Vintage Fire Truck Tour Portland Maine: 50-Minute SightseeingA 50-minute sightseeing tour of Portland, Maine aboard a vintage fire engine, with a live English-speaking guide covering the city's lighthouses, Civil War forts, historic mansions and neighborhoods. The tour departs from 180 Commercial Street and runs on a fixed schedule; arrive early because tours leave promptly and refunds are not issued for late arrivals. Infants sit on an adult's lap; service animals are welcome.Is it for me?The live guide speaks English, so the tour works for anyone comfortable following commentary in that language. The 50-minute length fits a morning or afternoon slot without taking a full day, which makes it easy to pair with other Portland activities or attractions nearby.
Portland Harbor Cruise: 4 Lighthouses & Civil War FortYou board a harbor cruise that circles past four operational lighthouses and a Civil War-era fort in Casco Bay, with close views of Portland Head Light and the shipping channel islands. The boat includes a bar and restrooms, and the full cruise takes around two hours without requiring any walking or climbing once you're onboard.Is it for me?Book this if you want to see Portland's lighthouse collection and Civil War fort without arranging a separate boat or timing your own route — the fixed course covers all four lights and the fort in one loop, and you stay onboard the whole time.
Portland Maine: Hidden Histories Walking Tour with Local GuideYou walk Portland's Old Port and downtown for two hours with a local guide who knows the city's overlooked stories: Wabanaki diplomacy, 19th-century maritime life, changemakers left out of official histories, and the complicated people behind the Victorian buildings. The tour includes a water-tour discount and a donation to a historic Black church. You'll climb some stairs and walk uphill, but the pace is steady and the stops are frequent.Is it for me?Pick this tour if you want Portland's real history—the stories about people and power that don't make it onto official plaques—and prefer a guide who actually lives here over someone reading from a script.
Portland Old Port Walking Tour & Local History StoriesYou’ll wander Portland’s Old Port on foot, hearing stories about poets, sea captains, and fires that shaped the city. Expect small surprises: a sweet treat at the end, local color along Commercial Street, and moments where history feels close enough to touch. It all leaves you wanting just a bit more time in those old streets.
Portland: Old Port Food Walking Tour with Local TastingsYou’ll walk Portland’s Old Port with a local guide, tasting everything from chowder to maple sweets while hearing stories behind each dish. Expect laughter, unexpected flavors, lunch-sized portions across several stops—and a sense of Maine’s real character by the end.
Portland Maine: Casco Bay Lighthouse Cruise & Fort ViewsYou’ll feel Maine’s maritime history come alive as you cruise Casco Bay for an hour, passing four lighthouses including Portland Head Light and Fort Gorges. With stories from your local guide and a snack bar on board, you’ll spot seals and seabirds while soaking up salty air and city views—leaving you with more than just photos.
Afternoon Windjammer Cruise: Casco Bay Sailing in PortlandAn afternoon windjammer sail on Casco Bay in Portland, Maine, where you board a historic wooden schooner and spend two hours under sail past lighthouses, seals, and seabirds. The crew is there to answer questions about what you're seeing, but this is not a narrated tour—you set the pace by how much you want to engage. Life jackets are provided; you bring your own food and drink.Is it for me?You're sailing an actual historic schooner through Casco Bay's lighthouses and seals—the crew answers questions, but the experience centers on the vessel, water, and coastline.
Portland Maine: Sunset Lighthouse Cruise Casco BayYou board at dusk and spend 105 minutes cruising past five historic lighthouses and military sites in Casco Bay, including Portland Head Light and Fort Gorges, with a narrated guide explaining the history of each stop. The boat has a restroom, moves at a relaxed pace suitable for all fitness levels, and returns as the city lights come on. Book if you want the main Portland waterfront landmarks without planning a route or timing yourself.Is it for me?Book this if you want the main Portland lighthouses and bay history without renting a car or planning stops — the fixed departure time and narrated route handle both, and the slow pace means you actually see the landmarks instead of rushing past them.
Portland Tall Ship Cruise on Casco Bay: Sail Maine SchoonersA two-hour sailing cruise on Casco Bay departing from Portland aboard one of three historic Maine schooners—Bagheera, Wendameen or Timberwind—where you can help raise the sails, take a turn at the wheel, or simply sit back and watch the Maine coast slip past. All three ships are wooden windjammers listed on the National Register of Historic Places, certified by the U.S. Coast Guard, and built in Maine. Life jackets are provided for all ages.Is it for me?Meet fellow sailors on a shared schooner cruise, or book privately to have the ship and your departure time entirely to yourselves.
Portland Walking Food Tour: Skip-the-Line Donuts & HistoryA 90-minute walking food tour through Portland's Old Port where you skip the line at The Holy Donut and two other local bakeries, sample six Maine potato and artisanal donuts, and hear a local guide's stories about sea captains, Prohibition, and the immigrant sailor credited with inventing the modern donut. Small groups, water included, all fees covered.Is it for me?If you land in Portland with a free afternoon or a couple of hours between plans, this tour solves the problem of not knowing which donut shop is actually worth the line or what the city's history actually is. The guide does the routing and the timing, so you taste the best of it without building the day yourself.
Portland Maine: Sunset Windjammer Cruise & Casco Bay LighthousesYou board a working wooden schooner and sail Casco Bay for two hours, passing lighthouses, seals, and the 1858 Fort Gorges while Portland's fishing wharves slip behind you. Bring your own food and wine, ask the crew what you want to know, and let the sails do the work. No narration, no schedule—just the water and the boat.Is it for me?Right for anyone wanting to be on the water without a guided tour script—you get the boat, the sails, the lighthouses and seals, and two hours of quiet time with a drink and a meal. The boat works for all ages and fitness levels, though expect to be outside on deck the whole time.
Portland: 5 Lighthouse Bike Tour & XL Lobster Roll LunchYou’ll cycle along Portland’s rugged coast with locals guiding you past five historic lighthouses, pausing for stories and sea views. Expect salty breezes, laughter over an XL lobster roll lunch from Bite into Maine (with all diets welcome), and a relaxed pace that lets you soak up every detail — right down to sand between your toes.
Portland, Maine: Black History Walking Tour & StoriesYou’ll walk Portland’s oldest streets with Dugan, hearing stories of Black Mainers who shaped the city’s soul—from secret signals in barbershops to bold choices on the waterfront. Expect laughter, pauses for thought, and moments when history feels suddenly close. It’s not just facts—it’s voices you can almost hear under your feet.
Old Port Seafood Walking Lunch Tour: Maine Lobster & WaterfrontThis 3-hour walking tour of Portland's Old Port and Waterfront District pairs a progressive lunch—lobster roll, New England clam chowder, local craft beer and a Maine whoopie pie—with stories about Maine's lobster industry and the people who work the boats. You'll stroll roughly 1 to 1.5 miles, stop at local restaurants and markets, and taste a couple of surprise seafood bites along the way. A live English-speaking guide leads the group; minimum age is 21 to drink alcohol, though younger travelers are welcome.Is it for me?The tour is a steady 3-hour walk with food stops built in, so it suits someone who wants to eat well and learn something without a demanding pace—bring comfortable shoes and a moderate level of fitness, since you're on your feet the whole time moving between neighborhoods.
Portland Lighthouses: 3-Hour Bike Tour with 4 StopsYou ride 3 hours on a dedicated pathway, stopping at four working lighthouses, with your bike provided and lunch sourced from a local vendor. The final stop is Portland Head Light, the iconic 1791 structure in Cape Elizabeth. You're back by early afternoon.Is it for me?A good fit if you want to see multiple lighthouses without driving between them and have moderate cycling fitness. The 3-hour pace means you're moving steadily, which is what lets you fit four stops into one morning.
Portland Maine: Sunset Sea Kayak Tour Casco BayYou paddle a two-hour route on Casco Bay timed for sunset, with a professional guide steering toward seals, lighthouses, and Fort Gorges depending on conditions and your group's interests. All kayaks, paddles, lifejackets, and a dry bag are included. Expect to be on the water in cooler air than on land, and plan to arrive ten minutes early for check-in.Is it for me?A good fit if you want to see Casco Bay from the water at the moment it looks best, without arranging your own kayak or worrying about navigation — the guide handles the route and timing so the sunset lines up with your paddle back. Expect two hours of steady paddling in cooler air than on land, which is what makes the full tour possible in the time you have.
Portland Maine: Lighthouse Cruise & Casco Bay with WineYou board Ruth at the Portland waterfront and spend ninety minutes drifting past five lighthouses, Fort Gorges, and the working islands of Casco Bay while seals and seabirds move around you. Bring your own picnic and wine. The boat does the work; you just sit there and let the 1935 wooden hull carry you through water that's been doing this since before the lighthouses were built.Is it for me?Right for families and groups who want to see Maine's lighthouses without a guided narrative — just a slow boat, salt water, and time to talk or sit quiet. The ninety minutes is short enough for restless kids but long enough to actually feel like you've left the city.
