Top Portland Private and Luxury

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.

Get more out of your time in Portland with this two-for-one adventure: a city trolley tour and lighthouse visit. You'll start with a narrated trolley journey, witnessing the most beloved sights of the Portland peninsula. After catching the Portland Observatory, the Wadsworth-Longfellow House, and more, you’ll then visit the city’s most famous landmark: Portland Head Light, Maine’s oldest—and most photographed—lighthouse.

Embark on a boat to a private island historic fort that’s only accessible with this tour. Leave from Portland and for a boat ride on Casco Bay, landing at the privately owned Fort Scammel on House Island. There, explore the architecture and preserved ruins of the stone fort—the only fort in the Portland harbor to see battle. Discover underground passages and learn the history of this previously inaccessible site.

Board your boat, the Elizabeth Grace, near the Portland ferry terminal and cruise around Portland Harbor at sunset, when Casco Bay and the coast of southern Maine are the most romantic. See lighthouses, historic forts, and stray groups of swimming seals and enjoy local craft beer from the boat. As the sun sets, turn toward Portland to see the town light up before returning to harbor.

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation, or renting a car, on this guided tour of Portland's must-see sights. Stop in downtown Portland, and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Half maritime adventure, half sightseeing exploration, the best way to catch Portland’s history is from the water. Gliding along Diamond Pass, you’ll catch views of Civil War–era forts, historic lighthouses, and likely some lobster boats bobbing in the breeze. Perfect for all ages, you’ll get to know the city and its maritime heritage, all while taking in its most scenic side.

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.

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.

Experience Portland's rich history from its most impressive vantage point: the water. Adventuring along Diamond Pass, you'll glimpse a Civil War–era fort, old-school lobster boats, and all the lighthouses Portland is so famous for, including Portland Head Light, Maine’s oldest. Suitable for all ages, this excursion is both a dive into Portland's past and a sightseeing adventure, a two-fer that’s leisurely, scenic, and fun.

Relax and unwind at sunset on this guided cruise of Casco Bay, Maine. Set off from the city of Portland and listen as your guide narrates your journey, sharing interesting facts and history about the area as you pass lighthouses and former military forts. It’s an ideal way to end a busy sightseeing day or begin a romantic evening.

Witness the stunning sunset over Casco Bay on this two-hour public powerboat cruise aboard the classic Maine-built vessel, Avelinda. As the sun sets, enjoy picturesque views of iconic lighthouses like Portland Head Light and serene islands such as Peaks Island. With a maximum of six guests per boat, relish an intimate experience while keeping an eye out for local wildlife like seals and seabirds. Captains with extensive local knowledge share tales of the region's rich history, making this cruise a perfect way to unwind and soak in the beauty of Maine's coast. Open to all ages, it’s a memorable outing for families and couples alike. - 2-hour scenic sunset cruise through Casco Bay - Maximum of 6 guests for an intimate experience - Spot local wildlife and iconic Portland lighthouses - Knowledgeable captains share local history and ecology

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more.

Experience the beauty of Casco Bay and set sail from Portland, Maine for an unforgettable sunset cruise. Bring your own snacks and drinks, kick back, and relax as your captain sails towards incredible views. Feel free to ask your captain and crew questions about the scenery, and remember to keep your eyes peeled for seals and seabirds.

With this small-group walking tour, you'll go beyond lobsters and lighthouses and get a look at the true Portland, Maine—across 400 years of history. Meander downtown and the Old Port, visiting hidden landmarks and learning about Wabanaki leaders and other people and events left out of the history books. Discover centuries of destruction, revival, underrepresented perspectives, and other elements that mainstream tours gloss over.

Maine is known for its seafood, and with this tour, you'll get to learn all about the industry, with the chance to sample some local delicacies along the way. You'll take a walk along the waterfront where lobster boats dock to unload their catches before heading out to a lunch of lobster rolls served with clam or seafood chowder and craft beer or soda pop.

See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.

Maine's Black community is small, but its history here goes back more than 400 years. On this guided tour, you’ll dive deep into Portland’s Black history, discovering how this community—national leaders, laborers, skilled workers, activists, and more—fought for freedom and equality and defined the state's path. From Frederick Douglass to lesser-known Black Yankees, there’s far more here than meets the eye, and with this tour, you’ll learn all about it.

Unlike large group bus tours, this experience is designed to be personal, flexible, and immersive. You’ll walk the streets of Salem with a knowledgeable guide who doesn’t just point out landmarks but brings their stories vividly to life—from the haunting legacy of the Witch Trials to the maritime wealth that built the city, and the literary genius of Nathaniel Hawthorne. What makes this tour unique is the balance of history and atmosphere: you’ll explore centuries-old cemeteries and mansions, admire harbor views and gardens, and even encounter touches of pop culture like the Bewitched statue. With small groups and a customizable pace, you’ll have the freedom to linger where your interests lie most—whether it’s taking photos, diving deeper into Salem’s legends, or enjoying a quiet moment in a hidden garden. This isn’t just sightseeing—it’s a chance to experience Salem’s past and present through stories, scenery, and atmosphere in a way that big tours can’t match.

Brewery-hop at brunch time—and visit several of Portland's best-known breweries and beer bars—on this small-group tour. With round-trip coach transit included, you can leave the driving to someone else and focus on enjoyment. Head to breweries that locals love, and enjoy in-depth tours and tastings, plus a light snack to help soak up those suds. By the end of the trip, feel newly immersed in one of the country's top craft beer scenes.

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.

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Experience the stunning beauty of Casco Bay on a personalized intimate (up to 6 guests per trip), public 2-hour powerboat cruise. Whether you're looking for a scenic sightseeing tour, an up-close encounter with Maine’s wildlife or a journey through the region’s rich maritime history, this exclusive charter is designed to provide an unforgettable adventure. Departing from the working waterfront, you’ll glide past busy wharves lined with lobster boats, ferries, and historic brick buildings that reflect Portland’s seafaring heritage. From the start, the mix of city energy and natural beauty sets the tone for an unforgettable journey on Casco Bay. Seals often bask on rocky ledges, ospreys and bald eagles soar overhead, and in the summer months, porpoises sometimes surface alongside the boat. Whether it’s spotting seabirds, breathing in the salty ocean air, or simply enjoying the thrill of the ride, a powerboat cruise from Portland offers both adventure and relaxation in equal measure.