Experience historic architecture, harbor views, and rich seaside culture with this driving tour of Portland, Maine! Cross the cobbled streets of Old Port, chock full of shops, restaurants, and bars, all complemented by the sparkli... More

Hop on the “Guardians of the Harbor” trolley tour, a narrated journey with three lighthouse stops. Explore Portland’s maritime history and scenic beauty, disembarking at each location. First, visit Bug Light Park and the Li... More

Explore the charm, history, and vibrant culture of Portland, Maine with this self-guided walking tour! Immerse yourself in the sights and sounds of this picturesque coastal city as you traverse the cobblestone streets of Old Port ... More

Discover the serene beauty of water-carved bends and meandering streams, where local wildlife thrives against a backdrop of rustic charm. As we embark on our journey, we'll navigate the gentle twists and turns of a meandering stre... More

Discover the best of Portland’s vibrant wine scene with the Portland Walking Wine Tour. Perfect for wine lovers and curious explorers alike, this leisurely walking tour takes you through the city’s charming streets to three ha... More

Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone streets and admire old brick architecture by the waterfront. Visit bustlin... More

Embarking on a private exclusive tour from Portland, Maine, offers a thrilling experience that highlights the region’s iconic attractions in just 6 to 8 hours. Perfect for cruise ship passengers or anyone with evening plans, thi... More

Embark on an exclusive private tour of Maine's enchanting central coast and starting in the vibrant city of Portland. In just one day, immerse yourself in the region's finest highlights. Led by knowledgeable local guides, our priv... More

Discover the charm of New England’s coast with a private tour from Portland, Maine, to Cape Ann and the North Shore of Massachusetts. This journey takes you to the stunning Castle on Crane Hill in Ipswich, offering views across ... More

Discover the rich history and stunning architecture of the Portland peninsula. Only 3.5 miles long and 3/4 miles wide the Portland peninsula is packed full of food, history and culture. This 2.5-hour tour will show you the best of... More

Immerse in and interpret the natural beauty of Maine by capturing the moment in a painting. We will hike and paint on location. No experience necessary. This is an all level class that can be enjoyed by beginner painters as well a... More

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 5... More

Sail 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 ... More

Book your private Arrival transfer from Portland International Jetport (PWM) to Portland hotels. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. Our transfers will pro... More

Operation City Quest of Portland is a great way to see the city! Use an app to submit photos of items you find around the city and challenges you complete for points. The items and challenges can be completed in any order you pref... More

The hour just before sunset is the best time for stand-up paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enough al... More

Explore Portland with Wacky Walks royal scavenger hunt. In our app-based scavenger hunt, your group will participate in competitions to become the King or Queen of your group throughout the game. The active King or Queen will lead... More

Step into the world of Let’s Roam, the undisputed champion of app-led scavenger hunts! Imagine strolling through city streets, hunting down top landmarks and uncovering secret gems, all while tackling brain-teasing trivia and th... More

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 a... More

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 d... More