Things to do in Portland
The unmissables
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Portland Maine: 3 Lighthouses & City Tour with Local Guide★ 4.96 (1,665) · 1h 45m
Top rated
Portland Maine: 3 Lighthouses & Coastal Tour with History★ 4.90 (1,010) · 2h
Best value
Portland Maine: Trolley Tour & Portland Head Light★ 4.77 (1,278) · 1h 45m
Recommended (7)
Vintage Fire Truck Tour Portland Maine: 50-Minute Sightseeing★ 4.81 (962) · 50mUS$ 45View ›
Portland Harbor Cruise: 4 Lighthouses & Civil War Fort★ 4.80 (806) · 1h 45mUS$ 61View ›
Portland Maine: Hidden Histories Walking Tour with Local Guide★ 4.98 (626) · 2hUS$ 54View ›
Portland Old Port Walking Tour & Local History Stories★ 4.86 (518) · 2hUS$ 49View ›
Portland: Old Port Food Walking Tour with Local Tastings★ 4.80 (482) · 3hUS$ 160View ›
Portland Maine: Casco Bay Lighthouse Cruise & Fort Views★ 4.78 (318) · 1hUS$ 43View ›
Afternoon Windjammer Cruise: Casco Bay Sailing in Portland★ 4.66 (275) · 2hUS$ 69View ›Top rated (10)
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.
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: 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: 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 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.
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 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 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 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.
Lowest price (10)
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 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.
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.
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.
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.
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.
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.
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.
