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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.
Acadia: Private Park Loop, Cadillac Summit & Lobster LunchYou’ll ride Acadia’s famous Park Loop Road with a local guide, take in sweeping views from Cadillac Mountain’s summit, feel sea spray at Thunder Hole, and finish with lunch at an authentic lobster pound overlooking Great Harbor. Expect honest stories, salty air, and plenty of time to pause wherever curiosity pulls you.
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.
Bar Harbor Culinary Walking Tour: Taste & Local HistoryA 3-hour culinary walking tour of Bar Harbor starts at the Village Green and moves through town with a live English-speaking guide, stopping to taste dishes at local establishments while learning the history of the food and the place. Lunch is included across the tastings. Minimum age is 21.Is it for me?Book this for a first morning or a free afternoon when you want to eat your way into a place and understand it at the same time—the guide and the proprietors do the talking, so you just walk, taste and listen.
Schooner Surprise Day Sails Camden Maine Historic WindjammerDay sails and sunset tours on Schooner Surprise depart from Camden, Maine, carrying a maximum of 18 passengers on a historic windjammer. You sail past Curtis Island Lighthouse, across Penobscot Bay, and along the rocky coast while the crew points out wildlife, local landmarks and the history of the area. Options include daytime sails, live music sails, sunset sails, full moon sails and eco-tours with an ornithologist, running daily from mid-May through mid-October. The crew invites you to help haul sails and steer, or to sit back with binoculars and blankets provided.Is it for me?Spend your afternoon or evening aboard Camden's only historic working schooner, where you can haul sails with the crew or simply settle in with wine and views of the Camden Hills.
Boothbay Harbor: 2-Hour Schooner Sail & Maine CoastYou board at Boothbay Harbor's historic waterfront and sail for two hours past lighthouses, fishing boats, and remote islands only accessible by water. The schooner's small size and unobstructed deck give you 360-degree views from any seat, and the engine gets you to open water fast so the sails can go up. Bring your own drinks and snacks, use the onboard restroom, and step off the dock back into the village shops and restaurants within walking distance.Is it for me?Book this if you want to see the Maine coast from the water without arranging a private charter or spending half a day on a larger tour boat — two hours is enough to feel like you've sailed, short enough to fit into a day that includes exploring the village.
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.
Acadia: Small Group Hiking Tour & Picnic Lunch with WildlifeYou’ll walk Acadia’s coastal trails with a small group, hear stories from your guide, watch for eagles and seals, and share a picnic lunch by Jordan Pond (don’t skip the popover). Expect salt air, laughter, and quiet moments that stay with you long after you’ve left Maine’s wild coast behind.
Kennebunkport Walking History Tour: 200+ YearsA two-hour walking history tour of Kennebunkport's Historical District, led by a live guide in English, takes you through the neighborhoods of the town's earliest residents. The route stays in the quieter areas away from the Lower Village, and all surfaces are wheelchair accessible. Gratuity to the guide is your choice at the end.Is it for me?If you're staying in Kennebunkport and want to understand the town's roots without arranging transportation or research yourself, a guided walk through the actual neighborhoods where the first residents lived gives you the story and the place at once.
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.
Bar Harbor: Fat Tire E-Bike Rental Acadia Carriage RoadsYou pick up a fat tire e-bike with a full battery, helmet, and a map marked with local recommendations, then spend four hours riding Acadia's gravel Carriage Roads without a car in sight. The e-assist handles the climbs; the detailed route keeps you from getting lost; the water and ponchos are already packed. You cover the main attractions—Jordan Pond, Eagle Lake, the Rockefeller bridges—in a single morning or afternoon, and return the bike with the battery still half full.Is it for me?Pick this if you want to see Acadia's main attractions—Jordan Pond, Eagle Lake, the Rockefeller bridges—in one morning or afternoon without arranging a guide or hiking on foot; the e-assist and the four-hour window are what make 20 to 30 miles possible in a single rental.
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 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.
Acadia: Private Day Tour & Hike with Gourmet PicnicYou’ll walk Acadia’s iconic trails with a local guide, hear waves crash at Thunder Hole, try fresh popovers by Jordan Pond, and share a gourmet picnic lunch outdoors. Expect quiet moments above glassy lakes and views from Cadillac Mountain—plus plenty of small surprises along the way.
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.
