Top Portland How to Get Around in 2026

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.

During Crazy Dash of Portland, you'll use an app and walk through the city to collect points by finding items around the city and performing challenges. You can find the items in any order you want. Check out the rankings in the app to see your score compared to other teams across the nation. Crazy Dash comes with a remote host to chat with you in case you need anything. Crazy Dash is our most relaxed scavenger hunt. Come explore with us in Portland!

Take in the famous autumn foliage of New England during a private 2.5-hour sightseeing cruise from Portland. With room for six people, it's an ideal intimate experience for couples, friends, or families. It’s also a great opportunity to photograph the leaves and wildlife from a unique perspective. Learn about the area from your private guide as you cruise at a gentle pace.

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.

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.

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!

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?

Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean views, and savor local flavors. With a personalized itinerary, this tour offers the flexibility to explore at your own pace, while an expert guide provides insights into each destination. Enjoy a relaxed atmosphere with included snacks, bottled water, and lunch to keep you energized throughout the day. - Private tour lasting approximately 7 to 8 hours - Customizable itinerary to suit your interests - Included lunch, snacks, and bottled water - Pickup from your location in an air-conditioned vehicle

Spend three hours kayaking through Casco Bay with this small-group tour led by a professional guide. You'll launch from Mere Point in Brunswick and paddle over to a couple of different islands, with the opportunity to see all sorts of marine birds, and maybe even a seal or two, along the way.

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 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.

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

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designer, John Alden. Heart's Desire measures 53' feet and features some of John Alden's trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine.

This isn’t just another sightseeing trip—it’s a curated journey through Maine’s most iconic landmarks and hidden gems, woven together into one unforgettable day. From the elegance of Portland Head Light, the nation’s most photographed lighthouse, to the playful charm of Eartha, the world’s largest rotating globe, every stop reveals a different facet of Maine’s character. Guests walk a historic suspension bridge built by the engineers of the Brooklyn Bridge, explore the state’s proud maritime heritage in Bath, and visit the legendary L.L. Bean flagship store in Freeport. What sets this tour apart is the balance of scenery, history, and culture: stunning coastal views, hands-on heritage at museums and memorials, and Maine icons you won’t find grouped together anywhere else. And because it’s a shorter itinerary, it’s the perfect choice for cruise ship passengers or travelers with limited time who still want a rich, memorable Maine experience.

Crowded public cruises make it harder for groups to enjoy Casco Bay together. From Portland's Old Port, charter a classic wooden boat for up to 16 guests, with the full boat to yourselves, passing Portland Head Light, historic forts, and other coastal landmarks while watching for harbor seals and seabirds. Bring your own food, use the onboard glassware and utensils, and purchase beer or wine onboard for a relaxed sightseeing cruise shaped around your group.

Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular mountain scenery, historic rail travel, charming villages, and iconic landmarks that showcase New Hampshire’s famous mountain region. The highlight of the tour is the Mount Washington Cog Railway, where guests board the historic train and travel to the summit of Mount Washington, the highest peak in the northeastern United States. At the summit, guests can enjoy panoramic views, explore the observation area, and visit the small museum. The tour also includes scenic drives along portions of the famous Kancamagus Highway, widely considered one of the most beautiful mountain drives in the country. Along the way we visit picturesque villages such as Jackson and North Conway, see the historic Mount Washington Hotel, and stop at scenic overlooks and waterfalls that make the White Mountains unforgettable.

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, and most recently Massachusetts.

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.

The streets of Portland, Maine, are the site of this exciting scavenger hunt. Scour these city streets in search of a variety of objects, landmarks, and works of art. You’ll be given clues about the town’s art, history, and culture to help you find your way from item to item. As you find and photograph each item, your team will earn points. Try to get the most points to rank highest on a leaderboard with other teams across the country completing other scavenger hunts.

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!

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.

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.

Skip the generic, slow-moving walking tours—instead, explore Portland with your crew via scavenger hunt. Solve riddles, take wild photos, and complete challenges as your smartphone leads you across the city’s best landmarks, clue by clue. As you race the clock, learn all about Portland’s nooks and crannies, testing your mettle and your will to win.