Portland, Maine Port Guide

Join a guide born and raised in Portland for an authentic 1-hour and 45-minute historical tour covering my hometown's current happenings, rich history, and three lighthouses. This insider’s experience visits standard sites plus hidden places other tours don't go.

Walk brick sidewalks with a locally-raised guide who shares extraordinary, exciting, and surprising stories omitted from history books about the wit and grit of Portland's people of all backgrounds. Broaden your sense of what Maine’s largest city and the state have been and could be.

Trace the steps of Black Portlanders whose labor, skill, and insight were essential to Maine’s earliest settlements and moved the region toward freedom, democracy, opportunity, and equality. Meet the Black Yankees who founded communities, overturned statewide slavery, drove maritime industries, and gained political influence.

Skip the city for a dedicated tour of three iconic Maine lighthouses to admire their stunning architecture, scenic surroundings, and rich history. While most are not open for tours, you will get up-close views of these beacons that have guided sailors for centuries.

Explore Portland’s history since 1632 on this 2-hour "Walk Through Time" starting on Commercial Street and visiting the Old Port, downtown, and waterfront. Learn about railroads, fires, wars, poets, and Hollywood producers at locations that may include the lobster statue.

This 3-hour tour departs at 11:00 am and follows the scenic South Portland Greenbelt Pathway to visit the Portland Breakwater "Bug Light" and Spring Point Ledge Light near historic Fort Preble. The journey continues past Willard Beach to the final stop at the famous Portland lighthouse.

Experience coastal Maine’s beauty and history on a 10–12 hour full-day adventure from Portland to the Acadia and Bar Harbor area, featuring rugged shorelines and crashing waves. The journey includes three hours of travel each way with scenic photo stops breaking up the drive.

Immerse in Maine's natural beauty by hiking and painting on location to capture the moment. This all-levels class requires no experience and is designed for both beginners and experienced painters.

Led by a Master Maine Guide, this 3-hour morning tour begins with land-based sea kayaking basics before launching at Mere Point in Brunswick for a leisurely paddle in Northwest Casco Bay. The route often includes a photo op at Mere Point, an island stretch break with snacks and shoreline exploration, and a return trip via a different route close to an island.

Discover Portland’s colorful history and multimedia images on a fun, family-friendly 50-minute Vintage Fire Engine tour led by a knowledgeable local guide. Relive stories while seeing lighthouses, Civil War forts, city parks, and notable buildings.

Explore the busy inner harbor, Diamond Pass, and the main shipping channel to see Civil War era forts. Get close-up views of as many as four lighthouses that guide mariners into Portland Harbor.

Friendly local guides narrate this tour of Portland’s award-winning food scene, combining social history with the stories of talented artisan entrepreneurs like bakers, brewers, chefs, and confectioners. Experience a unique blend of culinary education and creativity where taste meets history.

Enjoy a fully narrated 60-minute cruise through Casco Bay to see lighthouses, forts, lobster boats, seals, and seabirds. View as many as four lighthouses, including a close-up of Portland Head Light, Maine’s oldest and most photographed beacon.

This fully narrated 105-minute dusk cruise of Casco Bay’s inner islands and lighthouses offers a relaxing way to enjoy evening breezes and city lights. It is a great way to end a hectic day or start a romantic evening.

Sample treats from Portland's best donut shops, including skipping the line at the famous Holy Donut and visiting local favorites, while learning about the city's history. Your guide will also share Maine's connection to the invention of the donut.

Explore the Maine coast, lighthouses, and Portland’s history on a bicycle tour of Casco Bay that includes lunch from the award-winning "Bite into Maine" food truck. While it is a 5-lighthouse tour, groups generally visit four: Bug Light, Spring Point, Portland Head Light, and Ram Island Ledge.