Portland Head

Rated 4.7 Stars, based on 527 Reviews.

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.

Rated 4.9 Stars, based on 814 Reviews.

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.

Explore Portland, Oregon! This signature bike tour is an ideal introduction to the City of Roses. Visit historic Old Town, pedal the Waterfront Park Esplanade, cruise the Green Park Block corridors, Portland State University and explore the Pearl District with our experienced guides and comfortable rides. E-bikes available! Important –  • Minimum age is 10 years • Minimum height of 4'11" to participate

Explore the essential food and drinks at the heart of downtown Portland, Oregon on this all-inclusive walking tour led by an experienced, professional, Portland-native guide and standup comedian. Meet local vendors and hear their stories while getting inside knowledge about the city, its history, its food, and its identity. This is your insider access to some of the best-known and best-hidden bites that define downtown. This tour is operated by a small local business, and due to our lean business model and relationship to other local small businesses, we are capable of offering unrivaled value and flexibility.

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.

It's all about the bike ride! We like to spend more time riding in the neighborhoods Portlanders love, but always stopping to smell the roses. Start in the inner Eastside at 833 SE Main #121, where we will safely fit you for a bike and helmet, ready for a sweet 8-11 mile ride through a pretty residential neighborhood, to our favorite rose garden, into an art-heavy industrial district, across the sexy Tilikum Bridge, and onto Portland's waterfront. From there, it's a trip along the edge of downtown and more stories, before we head over another bridge back to our shop! You'll visit most of the city's quadrants, ride over two bridges, and along the Willamette River. We'll visit almost-secret beaches, read poetry written in sidewalks and rocks, see public art of every shape, color and texture. And have you tried some of the city's best doughnuts or ice cream? We’ll tell you our favorites! All along the way, we'll tell the stories of the city we love. Bikes, helmets and water provided.

Join Secret Food Tours through Downtown Portland, Oregon. Delight in the fusion of international flavors with locally sourced and crafted ingredients, showcasing the vibrant diversity of the city. Immerse yourself in our city’s rich history, while capturing the essence of Portland’s food scene. You will discover local culinary gems by savoring an array of extraordinary and authentic dishes.

Learn the story of the Portland, Oregon while enjoying its highest and most intimate viewpoints, smelling roses, wandering through gardens, peaking into a forested park and sampling donuts. After we pick you up at Director Park downtown, we’ll drive up the city's north/south dividing line, head to the summit of King’s Heights, and walk the grounds of the mansion built by a newspaper baron to the view that was once available only to the city’s elite. We'll visit Washington Park, and walk through our favorite secret garden, and into the Rose Test Garden. In season, we'll smell the roses — literally and figuratively! Next: the city center and cultural district. It wouldn't be Portland without a stop for doughnuts, so we'll discuss the history of the city's foundation and the design of these blocks after we duck into one of our favorite shops and grab a treat. We'll visit the South Waterfront, an inner Eastside neighborhood, and give you lots of foodie ideas before we drop you off!

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!

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.

Spend a day along Oregon’s gorgeous coastline, filled with dramatic headlands, beaches and historical lighthouses on this tour from Portland. Walk on the beach in the quaint town of Manzanita, explore Short Sands Beach, enjoy spectacular views from Neahkahnie Point,  and explore Cannon Beach, where you’ll explore tide pools at Haystack Rock and enjoy free time to peruse shops and art galleries.

Portland’s famous food carts are scattered all over the city's five (now six) quadrants, over 600 in total, in over 60 pods — collections of food carts! Starting at our shop, 833 SE Main Street #124, we'll put you on one of our lightweight bicycles and guide you on a 8-12 mile (11-17 km) culinary experience through some of our best-loved chefs and makers, sampling everything from Oregon farm-to-table delights to snacks appropriate to late-night cravings. Our focus is on locally-owned businesses with a great story; we’ll take you to a few of our favorites, many of which were important in creating the food cart scene as it exists today. Without these unique and passionate people, we may not have even half of what Portland offers to residents and guests alike. Expect flavors and fusions that tell not only a culinary, but also a cultural, tale. Bikes, helmets and plentiful food samples provided. We keep groups small, so you'll have an intimate experience with your passionate guides!

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Portland, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll experience free-fall conditions with the help of an instructor. No experience is necessary, and afterward, you can take home a personalized flight certificate.

This is our favorite tour! One of the most unique experiences in the world, riding down the historic highway built for Model Ts with the spectacular Columbia Gorge unfolding beneath us. We transport our guests and bikes in comfortable vans, and our guides ride with our small groups for much of the ride. You'll get personal attention and the safest experience we can provide. Beyond the 180 years of pioneers and loggers, before the century-old highway, this was the land of people with a rich mythology. We tell the stories that have been told to us by the indigenous people as best we can. You'll visit waterfalls, with engaged hiking and a leisurely approach to the tour itinerary. We want you to enjoy yourself — whether you are traveling alone or with a big group. Ages 13 and up. (We can accommodate much bigger groups traveling together, please reach out!) Please note there are cars that share the scenic highway.

The Portland Pubs Walking Tour is a leisurely 3-stop, 1 mile stroll through Portland’s Old Port neighborhood. This journey through history, narrated by the beverages inspired by Maine’s tenacious spirit, takes you past prominent landmarks and to our working waterfront. Along the way, you’ll visit producers like Liquid Riot, a brewery and distillery that pays homage to the infamous Portland Rum Riots of 1855, and Shipyard Brewing Company, a cornerstone of Maine’s craft beer culture for over a quarter-century. This bus tour’s final tasting will be held at Portland Beer Hub, the home of Maine Brews Cruise. Portland Beer Hub is a combo beer bar and retail space in the heart of the Old Port. The selection here includes beers from over 30 breweries across the state of Maine. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases! Please note that tour stops may change without notice due to events and the availability of staff at each venue.

Our small group eastside makers and artisans walking tour takes you to the side of the river where the hotbed of innovation has always been, across from downtown Portland in a neighborhood packed with breweries young and old. We'll head toward the river from our inner Eastside shop into an industrial neighborhood rich with food and art, exploring the past and the present of Portland's craft culture. Portland was a leader in the DIY culture and is home to every kind of food and beverage, from tea and kombucha to coffee and handmade soda; candies to hot sauces; imports and things made of recycled goods right in the warehouse district. All of these thrive in this neighborhood, where Around Portland Tours makes its home. The tour in total is 2-3 miles of walking, with tastes of tea and a snack as well. We always keep groups very small, so you'll have an intimate experience with your passionate guides!

Meet downtown and head to the Columbia Gorge to enjoy 3 amazing waterfalls. All of the waterfalls are located in the Columbia Gorge which is about 30 mins outside Portland. Each of the hikes will be about a mile or less. We will visit the most famous and some also lesser known waterfalls.

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 bustling neighborhoods like Old Port and the Art District, stop at shops and restaurants whenever you please, and breathe in the coastal air. Then take a drive out to the east and west promenades, before swinging down to the famous Portland Head Light lighthouse. It’s the most comprehensive way to experience this unique, quirky city! After booking, check your email to download the separate Audio Tour Guide App by Action, enter your unique password, and access your tour. These steps require good internet/Wi-Fi access. From there, follow the audio instructions and the route. Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months. This isn't an entrance ticket. Check opening hours before your visit.

Portland is justly famous for both its craft roasted coffee and its doughy sweets — ride and explore in a 6-8 mile bike tour. 10 a.m. daily. Bike, helmet, one doughnut and one coffee included! At our shop at 833 SE Main Street #121, we are also in the literal center of Portland’s craft coffee roasting icons (three of the city’s best roasters surround our block). We'll begin with coffee, tea or hot cocoa at a shop that roasts its own beans, and sample some single-origin coffee so we'll be ready for lots of sweets to come. The itinerary will vary based on doughnut shop hours, we'll typically introduce you first to a hidden gem of a shop — the one locals prefer — then head to the another favorite shop (famous for their apple fritters!) Portland’s doughnut scene isn’t just about eating pastries; it’s also about the culture that makes it possible. Did you know the doughnut-loving Homer Simpson was based off a Portlander? Which came first, the Homer doughnut or the city’s doughnut boom?

Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate channel on Portland's own "Jungle Cruise" to the spectacular city riverfront where we'll sail close to shore and then ease the sheets for a fun run up the west side of Ross Island and then back to the dock.