Travel Guide for
Portland

Two Hour Lighthouse Bicycle Tour from South Portland-Mellow

Our 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble, before returning to the bike shop.

Guided RIB Boat Adventure of Portland

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses and our unique 14-passenger RIB boat is suited to tour the region while everyone gets a front-row seat so you can see and experience more of it. Learn about Portland’s nautical history, view wildlife like seals, harbor porpoises, and sea birds, and stop for photos at quintessential sights like all four lighthouses, Fort Gorges, seals, and the working waterfront while also escaping to lesser-known areas of the bay where wildlife viewing is the best. This is a unique tour that is unmatched in the breadth of its experience with a local captain to guide you and answer your questions about the region. Please join us for the Best Of Casco Bay!

Sunset & Scenic Private Boat Tour of Portland & Casco Bay

Private Casco Bay Cruise – Up to 5 Guests Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves, spot local wildlife, and soak in the iconic charm of the Maine coastline. Departures daily at 10 AM, 4 PM, and our most popular sunset cruise at 6:30 PM.

Sea Kayak to an Island Tour in Casco Bay

Learn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay!  Often we paddle south to the end of Mere Point for a photo op and then on to visiting an island for a stretch break, snacks, and shoreline exploring. Then we paddle back on a different route close to an island to our launching point. Your Master Maine Guide will share history of the area while adapting the tour to paddling conditions and participants abilities. Sea kayaking is an easy, fun way to sightsee from the water.  We often see different kinds of sea gulls, cormorants, ducks, great blue herons, snowy egrets, osprey and sometimes bald eagles. If we are lucky, we will see a seal. Paddlers of all ages will love exploring Casco Bay in this protected, scenic, historic area! No experience is needed. This a family-oriented experience. Single and double kayaks are used on this guided tour by a Master Maine Guide.

Sunset Tour by Kayak on Sebago Lake Maine

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 stream, revealing the untouched beauty. Let the tranquil waters carry you along as you immerse yourself in the sights and sounds of the natural world. Throughout the tour, our knowledgeable Registered Maine Guide will regal you with captivating stories, bringing the scene to life with native lore and insights. Surrounded by panoramic views we pause and marvel as the sun sets behind the Towering pines. Whether you're a seasoned paddler or a complete beginner, rest assured this outing requires no previous experience - just a sense of adventure and a desire to unwind.

Portland Explorer: Working Waterfront Walking Tour with Seafood

Dive straight into Portland’s working waterfront—where the smell of the sea, and the bustle of the wharves, set the tone for an unforgettable walk through the city’s past. This immersive experience blends local history with maritime culture, offering a deeper look at how Portland grew from a rugged seaport into one of New England’s most vibrant coastal cities. As you stroll the cobblestone streets and working wharfs, your guide will share tales of shipbuilders, merchants, fires, and fishermen who shaped Portland’s story.

Private White Mountains Tour with Mount Washington Cog Railway

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.

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group, your pace, and a relaxed day along Maine’s scenic shoreline. Visit historic York’s colonial landmarks, walk through the Old Burying Ground, and enjoy views from John Hancock Wharf before stopping at Cape Neddick Light, one of New England’s most photographed lighthouses. Continue to Ogunquit for time at Perkins Cove, with the option for a short scenic stroll along the Marginal Way overlooking the Atlantic. In Kennebunkport, enjoy unhurried time in Dock Square to browse shops, walk the harbor, and dine at a local restaurant of your choice. A scenic stop at The Colony Hotel adds classic New England charm and sweeping coastal views. Because this tour is private, the experience remains flexible and comfortable, allowing you to explore at your own pace and focus on the scenery and stories that interest you most.

Private Portland to Cape Ann, MA Castles & Coast

Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blends grand seaside estates, medieval-style architecture, colonial history, and authentic harbor towns into one unforgettable journey. Admission is included to the breathtaking Crane Estate at Castle Hill in Ipswich, where sweeping lawns lead to panoramic Atlantic views. A favorite filming location for major Hollywood productions, its dramatic setting feels timeless and cinematic. You’ll also enjoy a guided tour inside Hammond Castle, a stunning 1920s seaside castle overlooking the ocean. Explore historic Ipswich, one of America’s oldest towns, and visit Gloucester’s iconic Fisherman’s Memorial while strolling its working harbor. With private transportation and relaxed pacing, this tour offers an elegant and memorable way to experience the beauty, history, and charm of coastal Massachusetts in a single day.

Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

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.