Portland Head Light Attractions & Things to do

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.

Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailors for centuries, each offering a chance to delve into their rich history. While most lighthouses aren’t open for tours, you’ll still get up-close views and plenty of opportunities to admire their stunning architecture and scenic surroundings. As you navigate through Portland’s picturesque coastline, you’ll be surrounded by breathtaking views that are as storied as they are beautiful. This focused, relaxed tour is the perfect way to connect with maritime past while soaking in the charm of Maine’s coastal landscape.
Duration: 2 hours.

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.

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you'll board a comfortable vessel equipped for a thrilling marine adventure. As we cruise along the rugged coastline, keep your eyes peeled for the majestic giants of the sea – humpback whales, fin whales, and minke whales are frequently spotted in these waters.

Our experienced naturalist guides will be with you every step of the way, providing fascinating insights into the behavior and biology of these incredible creatures.

The tour also offers the opportunity to observe a variety of other marine life, including seals, porpoises, and a wide range of seabirds. Don't forget to bring your camera, as you'll want to capture these unforgettable moments.

Duration: 3 hours.

This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the bay at dusk. Enjoy evening breezes and city lights on this fully narrated tour of Casco Bay. A great way to end a hectic day or begin a romantic evening!
Duration: 1 hour 45 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.

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.

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 cruise through the islands of Casco Bay, passing four iconic lighthouses, historic 19th-century forts, and the stunning Maine coastline.

Charters depart from Portland’s Old Port and are perfect for families and small groups. Each charter is completely private for up to 6 guests, and all ages are welcome!

First round of drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the breathtaking views!
Duration: 2 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.

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.

Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay. Keep your eyes open for potential seal sightings, as well as the multiple lighthouses, islands, and forts you will see while cruising around.

We will turn the bow toward Portland so you can take in a Maine sunset from the water and then cruise through Portland Harbor as the city’s nighttime skyline illuminates. You won’t find a more spectacular experience in Maine!

GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!
Duration: 1 hour 30 minutes.

Have you seen these iconic beacons from the water? Now is your chance!
Board the Elizabeth Grace to cruise around Portland Harbor on this one of a kind sightseeing cruise. It is the perfect way to see the lighthouses, historic stone forts, and rocky islands that make Casco Bay a world-renowned destination. Relax with a drink as you take in the scenery!

GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!
Duration: 1 hour 30 minutes.

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.

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.

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experience!
Duration: 1 hour 30 minutes.

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.

Experience COLORFUL Maine on this 2-hour sightseeing tour, where you’ll take in the vibrant fall foliage and the best coastal sights in the Portland area. It doesn’t get any more “New England” than this!

This private charter is a flat rate for up to 6 guests—all ages welcome!

Step aboard MONHEGAN, our sturdy lobster boat, equipped with rollable side canvas for comfort even if the autumn air is crisp. Cozy up with the blankets we provide and enjoy an authentic New England experience.

To make your tour even more special, we’re including a round of drinks—choose from locally brewed Portland, Maine beer or a glass of wine as you soak in the breathtaking scenery.
Duration: 2 hours.

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts.
Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the tranquil waters of Casco Bay.
All ages are welcome! Whether you are nine years old or 99, cruising aboard Ruth is a unique adventure, a 39’ long classic, picnic style tour boat built in 1935 at Handy Boat in Falmouth, Maine.
Duration: 1 hour 30 minutes.

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking Maine sunset.

We’ll navigate through the islands of Casco Bay, passing by Portland’s most iconic coastal sights, including historic 19th-century forts, lighthouses, and the stunning Maine coastline.

This experience is perfect for families and small groups, offering a completely private and personalized tour just for you.

First round of alcoholic drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the view!
Duration: 2 hours.

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.
Duration: 2 hours.

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the tranquil waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, cruising aboard Ruth is a unique adventure, a 39’ long classic, picnic style tour boat built in 1935 at Handy Boat in Falmouth, Maine.
Duration: 1 hour 30 minutes.

Start your adventure with a visit to the charming Historic Bug Light Park (also referred to as the Portland Breakwater Light), where you can capture stunning photos and immerse yourself in the area’s rich maritime history. Then, head to the iconic Portland Head Light, one of the most photographed lighthouses in the world, offering sweeping ocean views and unforgettable moments. After soaking in the beauty of these landmarks, enjoy a refreshing beverage at a local brewery or pub, where you can savor the essence of Maine’s craft brewing scene.
Duration: 2 hours 30 minutes.

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.

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 Liberty Ship Memorial, reflecting wartime shipbuilding. Next, discover Fort Preble and Spring Point Ledge Light, learning its unique construction and the remaining WWII gun batteries. Finally, witness the iconic Portland Head Light at Fort Williams Park, Maine’s most vital and the nation’s third oldest lighthouse, also revealing remnants of coastal defenses.

The nation’s third oldest lighthouse and one of Maine’s most important beacons. This area also features great examples of remnants of coastal defenses.
Duration: 2 hours 30 minutes.

Set off on a refined culinary adventure through the serene waters of Casco Bay. Your journey begins at Portland Beer Hub, where you’ll gather before being escorted to the waterfront to board your boat. As you glide past the stunning coastline, savor freshly shucked oysters perfectly paired with crisp prosecco. Whether you’re toasting to a special occasion or simply indulging in a moment of pure relaxation, this experience blends Portland’s finest flavors with breathtaking coastal views—an unforgettable way to enjoy the best of land and sea.
Duration: 1 hour 30 minutes.

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: .

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: .

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: .

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.

Escape the crowds and embrace adventure with a cruise aboard our classic motor yacht, the Calista Ann! Whether you're a seasoned sailor or a first-timer, our Coast Guard certified professional captains will ensure an unforgettable experience on the water.
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: 3 days.

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.
Duration: 6 hours.