Top Portland Tours, Sightseeing & Cruises - page 3

As night falls on Portland’s historic waterfront, discover why this is the #1 ghost tour in Portland, ME. Operating nightly, year-round, this one-mile walking tour is led by expert local guides who know the city’s legends, history, and hidden corners firsthand. This outdoor-only experience weaves together documented history, local folklore, and chilling tales that bring Portland’s past to life. Along the route, you'll visit iconic locations including Bell Buoy Park, Andy’s Old Port Pub, the Portland Harbor Hotel, and even a section of the Berlin Wall. Each stop is connected to real events, maritime tragedies, mysterious deaths, or unexplained stories that have become part of Portland’s haunted legacy. Perfect for private groups, bachelorette parties, birthdays, and special events, this unforgettable ghost tour is proudly USMC Disabled Combat-Veteran-owned and women- and minority-led, offering an evening of haunting history, immersive storytelling, and unforgettable mystery.

Walk around Portland while completing the 3Quest Challenge scavenger hunt! Use our app to find a list of objects (provided in riddle form) around the city and participate in fun challenges for points. Collect points and take a look at your score compared to others on the app's leaderboard. All of the objects and challenges will be divided into 3 quests. Complete the 1st quest, 2nd quest, and 3rd quest, in order, to complete the game! Set a time limit of 2 hours for yourself if you'd like to make the challenge even more intense! During the game, you'll have a remote host who will follow along virtually with you and chat if you need any help! Come explore Portland with us by completing all 3 Quests!

Discover Maine's picturesque coastline on the South Coast Tour, featuring iconic locations like Nubble Lighthouse and the charming villages of York, Ogunquit, and Kennebunkport. Enjoy breathtaking ocean views along Marginal Way, savor the freshest New England clam chowder, and indulge in delicious Maine lobster. This private driving tour, lasting 6.5 hours, is perfect for couples, families, or groups, with flexible pick-up options along the coast. Whether you're an avid photographer or a history enthusiast, the knowledgeable guides will tailor the experience to your interests, ensuring a memorable adventure along Maine's stunning shores. Explore coastal gems including Nubble Lighthouse and Perkins Cove Enjoy lunch featuring Maine lobster along the water Private tour accommodating up to 5 passengers. We have larger vehicles at an additional cost. Guided experience with insights into local history and culture

Enjoy a relaxing morning paddleboarding along Portland's Casco Bay. After a brief instruction, set out for a stand-up tour of the area—searching out native wildlife such as great blue herons and osprey as you slowly explore the waters. Learn about the area's fascinating history, from ways Native Americans used the land to how lobsters play a big part in the local economy. This leisurely and informative 2-hour tour includes an on-shore snack break before making your way back to Mere Point.

Witness the stunning transformation of Portland Harbor and Casco Bay during a private sunset powerboat cruise. Aboard the classic Avelinda, enjoy a two-hour journey as the sun sets, painting the sky with vibrant hues. Marvel at iconic lighthouses like Portland Head Light and glide past charming islands, keeping an eye out for local wildlife such as seals and seabirds. This intimate experience is perfect for all ages, whether celebrating a special occasion or simply relishing the natural beauty of Maine's coastline. - Exclusive private cruise for up to 6 guests - Comfortable Maine-built powerboat with marine restroom - Experienced captains share local history and ecology - Flexible scheduling with multiple evening departures available - Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

On this walking tour, we’ll explore the city’s significant role in the Underground Railroad and the individuals who helped shape its fight for freedom. The tour is self guided on our walking tour app. It's hands free, plays as you walk and you can go at your own pace, anytime, it never expires. You’ll walk through historic streets where ordinary citizens took extraordinary risks to assist those escaping slavery. We’ll visit former homes, churches, and workplaces that served as safe havens and meeting places for abolitionists, reformers, and community leaders. Each stop demonstrates how Portland’s waterfront and neighborhoods became centers of courage, compassion, and quiet resistance. Let’s start our journey at the Mariner’s Church Banquet Center, a landmark that saw both Portland’s growth and its dedication to justice.

Unlike large group bus tours, this experience is designed to be personal, flexible, and immersive. You’ll walk the streets of Salem with a knowledgeable guide who doesn’t just point out landmarks but brings their stories vividly to life—from the haunting legacy of the Witch Trials to the maritime wealth that built the city, and the literary genius of Nathaniel Hawthorne. What makes this tour unique is the balance of history and atmosphere: you’ll explore centuries-old cemeteries and mansions, admire harbor views and gardens, and even encounter touches of pop culture like the Bewitched statue. With small groups and a customizable pace, you’ll have the freedom to linger where your interests lie most—whether it’s taking photos, diving deeper into Salem’s legends, or enjoying a quiet moment in a hidden garden. This isn’t just sightseeing—it’s a chance to experience Salem’s past and present through stories, scenery, and atmosphere in a way that big tours can’t match.

Join us for an exciting Private Coastal Tour from Portland to Camden, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is **Camden Hills State Park**, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mount Battie. We'll finish with a brief stop at the Maine State Capitol, designed by the same architect as the U.S. Capitol, offering a fascinating glimpse of Maine’s history. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. Guests are encouraged to help raise the sails with a deckhand and steer the ship for themselves. Your charter is your time to relax, celebrate, entertain, and sail, so you get to set the pace and atmosphere. Beer, wine, and other alcoholic beverages are permitted on board.

Explore the stunning scenery and rich maritime history of Casco Bay on a private 2hr, 4hr or 6hr powerboat cruise. Ideal for families, friends, or small groups, this exclusive charter offers a personal adventure, allowing you to encounter marine wildlife, view iconic lighthouses, and discover unique islands at your own pace. With flexible scheduling and customizable experiences, this cruise promises an unforgettable day on the water, complete with opportunities for swimming and exploring Maine’s rugged coastline. - Private cruise for up to 6 passengers, ensuring an exclusive experience - Encounter marine wildlife like seals, porpoises, and seabirds - View famous lighthouses including Portland Head Light and Bug Light - Flexible departure times and customizable itineraries available – Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

Join us for an exciting **Private Coastal Tour from Portland to Camden**, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is **Camden Hills State Park**, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mt Battie. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

Experience the enchanting history of Portland through a captivating exploration! Solve intricate riddles and uncover local gems while learning fascinating trivia about the city's roots. This adventure encourages playful engagement—snap pictures of landmarks, answer questions about your surroundings, and embrace the unexpected (like pretending to fly!). It's the ultimate way to enjoy Portland's unique charm, discover its ties to Japan and the sea, and test your wits.

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

Experience the beauty and history of Ipswich and Cape Ann on this private tour. Wander Castle Hill’s grand estate, explore Ipswich’s heritage, and enjoy Gloucester’s seaside character. When available, Hammond Castle offers an unforgettable glimpse into medieval architecture on the New England coast. End your journey at Russell Orchards for fresh, local charm

All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger van that can take up to 12 passengers. We’re happy to customize the experience to match your interests. This particular tour covers all the major sights in Portland, followed by a visit to the South Portland lighthouses, including admission to Fort Williams Park to see the Portland Headlight. After exploring Portland, you'll journey down the highway to Kennebunkport, a charming coastal village that served as the summer retreat for former President George W. Bush and his family. While we have a standard route, as a private tour, we can personalize the itinerary to suit your preferences.

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

Use an app to survive a zombie apocalypse in Portland . In Zombie Scavengers, explore the city however you'd like to search for items needed to survive a zombie apocalypse. You'll get points for finding these items. You can also do some zombie themed challenges for points on the app as well. Strategize in order to get the most points and survive the apocalypse. Your remote host will be there for you via chat if you need anything. Can you survive the apocalypse in Portland?

Some cities are best seen from a car window. Portland, Maine is not one of them. On this fully private e-bike tour, it's just your group, a local guide, and five hours of spectacular coastal scenery — with a Maine lobster roll along the way. Ride through the Old Port's cobblestone waterfront and fishing piers. Climb to Fort Allen Park for sweeping Casco Bay views. Cruise the Eastern Promenade before crossing to South Portland to walk the breakwater to Bug Light, designed by the architect of the U.S. Capitol dome. Continue to Spring Point Ledge — the only lighthouse of its kind you can reach on foot — then Portland Head Light, commissioned by George Washington in 1791. Finish on the Western Promenade, a hidden hilltop park with views to the White Mountains that most visitors never find. Lunch is a fresh Maine lobster roll at a waterfront spot worthy of the occasion. No strangers, no set pace — just your group and the best of coastal Maine.

All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests.

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses, historic forts, and natural features. A round of drinks is included to toast the sunset with, but more beverages are available to purchase onboard.

See some of Maine's most picturesque scenery with this private full-day tour from Portland. Your driver will pick you up at your hotel or vacation rental and take you out for a day of exploration, stopping by coastal towns, iconic lighthouses, viewpoints, and other areas of interest along the way.

It is the only regularly operating pedicab in Portland. Portland Pedicab creates the feeling of joy for all by allowing passengers to spend the time viewing Portlands scenery while heading to their destination. This is a great mode of transportation for those that like to be outside! Music which is provided, is always an option while enjoying the views of Portland.

While walking tours are helpful for getting oriented, they rely on guides and discourage independent exploration. With this interactive scavenger hunt, explore Portland at your own pace while completing game-like challenges and hunting for particular items along the way. Submit photos of items found around the city, communicate with a game host via chat during the hunt, and compare scores with other teams across the country when you’re done.

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.