Things to do in Portland
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Portland Sunset Harbor Cruise & Local Craft BeerYou board the Elizabeth Grace at Portland's harbor, cruise past Maine's oldest lighthouse and a 19th-century island fort while sipping included local craft beer, watch for seals in Casco Bay, and take in the sunset from the water before the city's nighttime skyline lights up. The whole thing takes 1.5 hours, small groups stay under control, and you're back on land before dark.Is it for me?Book this if you want the Maine sunset and the lighthouses without arranging your own boat—the fixed departure time and included drink mean you show up, board, and the rest happens on schedule.
Portland Maine: Ghost Tour & Historic Haunted MansionsYou walk Portland's historic district for 75 minutes with a lantern-carrying guide, stopping at Victoria Mansion, the Fire Museum, the McLellan Mansion, and five other haunted landmarks. You hear stories spanning from the city's first European settlement through the Great Fire of 1866 to present-day paranormal reports. Photos and video of each stop are included, and the guide answers questions at the end.Is it for me?Book this if you want Portland's real history—the fires, the families, the rise and fall—without arranging your own walking route or missing the details; the ghost stories are the hook that keeps you paying attention to the actual buildings and what happened inside them.
Fort Scammel Tour Casco Bay: Boat Cruise & Island ExploreA two-hour private boat tour from Portland to Fort Scammel on House Island, where you explore a historic 19th-century stone fort with underground passages and French architectural details. The boat departs from SeaPortland, includes a local craft beverage or non-alcoholic drink per person, and operates with a live English-speaking guide for groups of four or more. The fort itself has been privately owned and closed to the public until now, making this the only way to access it in Portland.Is it for me?At two hours, the tour leaves your morning or afternoon open for other plans in Portland — you're not committing a full day. The four-person minimum means you need a small group, but that's also what keeps the experience genuinely private and the fort from feeling crowded.
Portland Old Port Ghost Walking Tour: 2-Hour Haunted HistoryA 2-hour guided walking tour through Portland's Old Port explores haunted history tied to the waterfront's seafaring past, with a live guide leading small groups through sites of reported apparitions, psychic phenomena, and local maritime legends. The tour is wheelchair accessible and suitable for all fitness levels, with public transportation nearby.Is it for me?Book this tour if you have a free evening in Portland and want to explore the Old Port's darker history with a guide who knows the stories and the sites. The small-group format and live narration work well for a first-time visitor curious about local legends without needing to research them beforehand.
Portland Lighthouse Bicycle Tour: Two Lighthouses, One MorningA 2-hour guided bicycle tour from South Portland follows the Greenbelt Pathway to Portland Breakwater Light (built 1875) and Spring Point Ledge Light (built 1897), with a live English-speaking guide, helmet and bike included. The tour departs at 9 am or 3 pm and returns to the bike shop after visiting both lighthouses and the historic Fort Preble site.Is it for me?Pick this if you want a guided route along the Greenbelt Pathway to two lighthouses and prefer a set itinerary over planning your own; the 9 am or 3 pm start fits a half-day schedule.
Casco Bay sea kayaking: Island-hopping with seals and lighthousesA four-hour sea kayak in Casco Bay where you paddle through an island-dotted archipelago, spot seals and seabirds, and stop on an island beach for a break. The route shifts with weather and tides, so no two trips are identical. Small groups, tandem kayaks (solo available on request), all paddling gear and a licensed Maine guide included; children from age 12 welcome, though ages 12–15 paddle tandem with an adult.Is it for me?Small groups suit this trip—you're paddling with a handful of other people, not a crowd, which keeps the pace relaxed and the guide able to point out seals and landmarks without shouting over an engine. Book this one if you want to actually paddle instead of watch, and if you're comfortable spending four hours on the water with some moderate physical effort.
Portland Peninsula Bike Tour: Eastern Promenade & WaterfrontA 2.5-hour guided bike tour of Portland's peninsula covers the Eastern Promenade waterfront path, the Back Cove loop, and the brick buildings along the water. The tour includes a helmet, bicycle, and a live English-speaking guide. Minimum age is 12; the tour suits all fitness levels.Is it for me?This is a shared, guided tour at a set pace, so it works best if you want someone else to navigate and explain the route rather than exploring on your own. The 2.5-hour window suits a morning or afternoon slot without eating your whole day.
Casco Bay Morning Windjammer Sail: Historic Maine SchoonerA two-hour morning sail on Casco Bay in Portland aboard one of Maine's historic wooden schooners, with views of Fort Gorges, Bug Light Park, and the Portland waterfront. The crew answers questions about the harbor and its sights as you move through the bay; life jackets are provided for all ages. Bring your own food and drink to enjoy while sailing.Is it for me?The schooner departs from Portland's waterfront, so no car is needed if you're staying downtown or can reach the wharves by public transit. The two-hour morning window fits easily into a day of exploring the city, leaving your afternoon free.
Sea kayaking in NW Casco Bay: Oyster farm & tastingSea kayaking in NW Casco Bay combines a guided paddle to a working oyster farm with an island tasting of oysters you'll shuck yourself, led by a Master Maine Guide. The tour starts with on-land instruction for all skill levels, includes all kayaking gear and a choice of sauces for the oysters, and runs three hours from a launch point in Brunswick. Weather or tidal conditions may shift which of two farms you visit, and the guide takes candid photos along the way.Is it for me?The early 8:15am start and three-hour paddle suit travelers who are comfortable on the water and ready to move their own kayak. If you prefer to stay dry or need a slower pace, a motorized boat tour of the same farms would work better.
Casco Bay Cruises: Private sunset tour among lighthousesYou board a private boat for two hours exploring Casco Bay's 14 islands, passing Maine's oldest lighthouse and secluded coves where seals rest on rocks. The boat carries blankets and water; you choose between morning, afternoon, or sunset departure. Groups stay under six people, so the captain can slow down when something catches your eye.Is it for me?Right for small groups or families who want the Maine coast without a crowded tour boat, and who can handle two hours on the water with wind and motion. The sunset departure books fastest, but morning and afternoon cruises give you the same islands and lighthouse with fewer people.
Sea Kayaking in Brunswick: Island paddle with guideSea kayaking in Brunswick launches from Mere Point for a three-hour morning paddle through Northwest Casco Bay with a Master Maine Guide. You'll learn the basics on land first, then paddle south to the end of Mere Point, cross to an island for a break with homemade muffins and tea, explore the shoreline, and return by a different route. Single and double kayaks are available; no experience is needed, and the guide adapts the route to conditions and your ability.Is it for me?The guide speaks English and adapts the paddle to your ability and the group's comfort, so paddlers of all ages and fitness levels—including families with children—can enjoy the bay without prior experience or worry about keeping pace.
Portland Ghost Tour: Haunted Waterfront & Historic SitesThis one-mile ghost tour of Portland's historic waterfront runs nightly year-round, led by expert local guides who connect documented history and local folklore to real sites—Bell Buoy Park, Andy's Old Port Pub, the Portland Harbor Hotel, and a section of the Berlin Wall. The tour takes about an hour and covers locations tied to maritime tragedies, mysterious deaths, and unexplained activity. Service animals are welcome; moderate fitness is needed for the walking distance.Is it for me?Book this if you're staying downtown or using public transit—the Old Port meeting point is walkable and the nightly schedule lets you join any evening that fits your plans.
Portland Sunset Powerboat Cruise Casco Bay & LighthousesYou board a Maine-built powerboat in South Portland and spend two hours on Casco Bay as the sun sets, passing Portland Head Light and four other lighthouses while watching seals, seabirds, and working lobster boats move across the water. The captain shares local history and ecology; you bring your own food and drinks, use the onboard refrigerator, and wrap up in lap blankets as the light changes. The boat holds up to six guests, keeping the experience intimate and unhurried.Is it for me?Book this if you want a quiet evening on the water with a small group and don't want to arrange your own boat—the fixed two-hour window and private boat mean you get the lighthouses and the working harbor without the crowds or the logistics.
Portland Jetport to Hotel: Private Round-Trip TransferYou get picked up at the jetport with a nameplate, tracked flight arrival, and door-to-door service to your Portland hotel. The return transfer is included, with the same fixed price and professional driver. Child seats, luggage help, and free Wi-Fi are part of the package. Book it once and both legs are arranged.Is it for me?Book this if you want to skip the taxi queue and arrive at your Portland hotel without arranging transport or worrying about timing — the driver tracks your flight and the return is already booked, so both directions are handled before you land.
Portland Jetport to Hotels: Private Arrival TransferYour driver meets you at baggage claim with a name sign and handles your luggage and route to your Portland hotel. The vehicle is air-conditioned and equipped for any weather; child seats are available on request. You pay a fixed price with no hidden fees, so the transfer costs what you agreed to before you boarded the plane.Is it for me?Book this if you land at Portland Jetport and want to skip the taxi line and ride-share negotiation — the fixed price and scheduled pickup mean you know exactly what you're paying and when you're leaving the terminal.
Portland ME to PWM Airport: Private Hotel Pickup & TransferYou get picked up at your Portland hotel at a time you choose, driven directly to PWM airport with your luggage handled, and dropped at the terminal. The driver meets you by name, tracks your flight, and the price is locked in before you book — no negotiating at the curb, no waiting for a shuttle, no parking stress.Is it for me?Book this if you want to skip the parking lot, the shuttle schedule, and the uncertainty of timing — a fixed pickup time and a driver who knows where you're going means one less thing to manage on the morning you leave.
Portland Port to PWM Airport: Private Transfer & Luggage HelpYou get picked up at the cruise terminal with a nameplate, travel in a private air-conditioned vehicle with luggage assistance, and arrive at Portland International Airport (PWM) on a fixed schedule with no hidden fees. The driver handles the route while you relax, and the service works for groups up to 15 passengers.Is it for me?Book this if you want to avoid the taxi queue and shared shuttle wait after disembarking — the fixed pickup time and door-to-door route mean you're not managing transport logistics, just getting to the airport on schedule.
