Portland Head Light Attractions & Things to do

Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine.

Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows!

As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor.

This is The Real Portland Tour!

Check my website for a complete listing of tour days, times, and availability.

Duration: 1 hour 45 minutes.

The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland peninsula. Towards the end of the tour, we make a 20-30 minute stop out at Portland Head Light in Cape Elizabeth.
Duration: 1 hour 45 minutes.

Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that guide mariners into Portland Harbor.
Duration: 1 hour 45 minutes.

Leave the crowds and join us aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter capped by a stunning Maine sunset.  

We will wind our way through the islands of Casco Bay passing by Portland's best coastal sights, including historic 19th century forts, lighthouses, and the scenic Maine Coast.

This activities is perfect for families and small groups. Every charter is 100% private for you and your group!
Duration: 2 hours.

Embark on a journey that blends the thrill of exploration with the ease of modern technology on our City and Lighthouse E-Bike Tour in Portland, Maine! Experience the best of both worlds as you effortlessly pedal through the city's vibrant streets and along the breathtaking coastal landscapes on our cutting-edge electric bikes. This tour, led by a local guide, will show you all the highlights of Portland as well as some hidden gems known only to locals. Seeing the city on a bicycle lets you experience this sights, sounds and smells of Portland.
Duration: 5 hours.

Our 3-Hour tour leaves at 11:00 am and follows the scenic South Portland Greenbelt Pathway to three 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. Next, the tour will pass by Willard Beach before arriving at the final stop, the famous Portland Head Light located at Fort Williams Park in Cape Elizabeth. It is recommended that patrons bring a lunch or we can assist in purchasing lunch from a local food truck that serves Lobster Rolls.
Duration: 3 hours.

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!


Duration: 1 hour 30 minutes.

Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine coast, lighthouses, and Portland’s history. We have made some modifications to the 5 Lighthouse tour in response to COVID-19. We have modified the tour to allow us not to have guests in our vehicles. As a result of this change, guests will begin biking from the Ocean Gateway and return to the Ocean Gateway by bicycle.  Groups will generally see only 4 lighthouses (Bug Light, Spring Point, Portland Head Light, and Ram Island Ledge). Lunch will be provided by the award-winning "Bite into Maine" Food Truck
Duration: 5 hours.

A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many as four lighthouses can be seen including a close up view of Portland Head Light, Maine’s oldest and most photographed lighthouse.
Duration: 1 hour.

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter.  Leave the crowds behind as we tour the islands of Casco Bay and pass by 4 lighthouses, historic 19th century forts, and the scenic Maine Coast.  

Charters depart from Portland's Old Port. This authentic Maine experience is perfect for families and small groups. Each charter is private for groups of up to 6 and all ages are welcome!
Duration: 2 hours.

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, this tour lets you maximize your time. From breathtaking views at Portland Head Light and the charming atmosphere of Bug Light Park to the fascinating exhibits at the Maine Maritime Museum, each stop provides a unique glimpse into Maine’s rich maritime history. You’ll encounter local wildlife at the Maine Wildlife Center and explore the world-renowned L.L. Bean Headquarters, complete with the iconic giant Bean Boot photo op.
This exclusive tour is tailored to your interests, ensuring a memorable adventure filled with stunning scenery and engaging stories. With convenient scheduling and a knowledgeable guide, it’s a fantastic choice for exploring the best of Portland before returning to your cruise or evening activities.
*This is a new route.
Duration: 6 to 8 hours.

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 private tours ensure an intimate and personalized experience. Marvel at the iconic Portland Head Lighthouse located in Fort Williams State Park and indulge in some retail therapy at the renowned L.L. Bean Factory Store. Cross the unique Androscoggin Swinging Bridge and explore the breathtaking Coastal Maine Botanical Gardens. Discover the charm of Boothbay Harbor. Immerse yourself in Maine's fascinating past at the historic Fort Edgecombe State Historical Site. Uncover stunning lighthouses, picturesque gardens, and charming coastal villages on this unforgettable day trip along Maine's central coast.
Duration: 6 to 8 hours.

Experience COLORFUL Maine on this 2 hour sightseeing tour featuring Maine's fall color and the best coastal sights in the Portland area. It doesn't get any more "New England" than this!

Price is a FLAT RATE for a group up to 6. All charters are 100% private and all ages are welcome!

MONHEGAN, our sturdy lobster boat, is fitted with rollable side canvas to assure your comfort even if the autumn weather is a bit chilly. We'll have blankets waiting for you aboard for this cozy authentic New England experience!
Duration: 2 hours.

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.
Duration: 6 hours.

Embark on an unforgettable boat tour of Casco Bay in Portland, Maine, where nature, history, and natural beauty intertwine. Our journey begins as we glide past the majestic Fort Gorges and historic Fort Scammel. When the tide permits, we are able to disembark onto Fort Gorges for a quick side-adventure. Next, we’ll cruise by the spark plug-style Spring Point Ledge Light perched on the granite breakwater of South Portland.

The iconic Portland Head Light awaits us on the rugged cliffs of Cape Elizabeth, offering breathtaking ocean views followed by the eery and majestic abandoned Ram Island Ledge Light. We’ll then marvel at the stunning White Head Cliffs on Cushing Island and navigate through the scenic Diamond Pass, glimpsing all of Peaks Island's charm. Our adventure culminates at Half Way Rock, where we will hope to spot seals basking on their favorite sun-drenched rocks. Join us for this captivating tour, unveiling Maine’s rich heritage and natural splendor!
Duration: 2 hours.

Acadia was the main resort for 19th-century American billionaires, including the Rockefeller, Carnegie, and JPMorgan families. Enjoy the beautiful landscapes and vistas throughout the park. Visit the Portland Lighthouse and experience the beauty of the Portland coast. In-depth visit the Acadia National Park In-depth and hiking on the Cadillac Mountain. Visit Maine's top-rated tourist attractions - Bar Harbor. Take the Acadia Nature Cruise to explore the local ecology and watch the habitat of wild seals. Taste the local specialties of Bar Harbor - Lobster meal, Lobster ice cream, Blueberry Soda, Blueberry pie.
Duration: 2 days.

Visit the Portland Lighthouse and experience the beauty of the Portland coast.
Take a stroll through the quaint neighborhoods of the Old Port Area and the Lobsterman Park, enjoy the charming scenery, and learn about the history of Maine.

Boston → Fort Williams Park & Portland Lighthouse (60 mins) → Old Port+Lobsterman Park (120 mins) → Boston


Duration: 7 to 9 hours.

Venture with us on our private custom tour for 2.5 hours. The price is for a group of up to 11 passengers. Experience downtown Portland, Maine with our family owned and operated PRIVATE group tour. Visit 3 lighthouses for epic photo stops and tour through downtown Portland.

Since it is a private tour, the time allotted at each lighthouse can be changed and we can also modify the timing with more or less time through the City of Portland.


Duration: 2 hours 30 minutes.

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 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.
Duration: 2 hours.

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 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. This two-hour morning private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten.
Duration: 2 hours.