OVERVIEW

Get a wonderful overview of Portland during a panoramic driving tour, and then enjoy free time shopping in Kennebunkport, an equally picturesque coastal village. Your tour commences with a scenic drive through the Old Port, a former warehouse district that is now home to quaint restaurants, unique stores, and art galleries. Continuing, you will pass through the New Arts District, the heart of Portland’s cultural resurgence, and pause for photos at Portland Head Light, Maine’s oldest lighthouse. You will make another photo stop at the extraordinary Wedding Cake House in Kennebunkport. With its carved buttresses, spires, and lacy spandrels, this 1826 home is one of the most photographed buildings in the state. Just as famous is the George H.W. Bush family summer estate, which you will pass on the way to Dock Square, where you will enjoy free time to shop and dine on your own.

HIGHLIGHTS

• See Portland’s best, most characteristic architecture.
• Pause for photos at Maine’s oldest lighthouse.
• Spend about 1½ hours of free time exploring Kennebunkport.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Enjoy beautiful views of Maine's famous rocky coastline as well as a visit to the charming coastal village of Kennebunkport, which gained worldwide exposure as the summer home of the Bush family. Located just 45 minutes from Portland, you’ll enjoy a scenic drive through Kennebunkport passing the stunning mansions that were built by wealthy sea captains and merchants in the 1700’s and 1800’s. A stop will be made in the center of town at Dock Square to enjoy some free time to stroll the picturesque streets lined with shops, galleries, unique boutiques, antique stores, restaurants, and pubs. Your return route will take you past Walker's Point, and the Bush estate where world leaders often gathered when George H. Bush was president.

HIGHLIGHTS

• Explore famous rocky coastline of Maine.
• Enjoy scenic 45minutes ride to charming costal village of Kennebunkport.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Explore three historical lighthouses on Portland’s rocky coastline, including the oldest one in Maine. The views will be spectacular before leaving town, as you will pass architectural landmarks such as the Portland Observatory and New Arts District. Lighthouse aficionados will find even more to enjoy at Bug Light, a cast-iron lighthouse with Corinthian columns that was modeled after an ancient Greek monument. Only 26 feet high, it was built in 1875 and became known as The Bug because of its small size. Close by lies Spring Point Ledge Lighthouse, a sparkplug-style lighthouse made of brick on a cylindrical cast-iron caisson. It was built in 1897 in response to the many vessels that ran aground on the dangerous ledge there. A bit further south, you will find Maine’s oldest lighthouse. First illuminated in 1791, Portland Head Light now contains a museum that you may browse.

HIGHLIGHTS

• Visit three iconic Maine lighthouses.
• Notice their vastly different architecture.
• Browse a museum in Maine’s oldest lighthouse.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

Picturesque, historic, and entertaining, the lively city of Portland incorporates the character and charm of its past with a developing urban community. Your tour begins with a scenic drive through the quaint streets of the Old Port where street lanterns highlight a gracious mix of architectural styles. Once a warehouse district, the buildings have been transformed into charming restaurants, pubs, boutiques, and galleries. You’ll continue to Munjoy Hill for terrific views of Casco Bay and the islands from Fort Allen Park. You’ll pass the Portland Observatory and through the commercial center where you’ll see the new arts district, as well as the facade of city hall before entering the Western Promenade, one of America’s best preserved Victorian neighborhoods. Entered into the National Register of Historical Places in 1982, it remains one of the wealthiest areas of the city. Situated along the beautiful coast of Cape Elizabeth is Fort Williams, home of the oldest lighthouse in Maine. First illuminated on January 10, 1791, Port Head Light has since stood at the gateway to the harbor for mariners traveling Maine’s perilous coast. A short photo stop will be made here before returning to your ship.

HIGHLIGHTS

• Drive through Portland’s New Art District.
• See Western Promenade, one of America’s best preserved Victorian neighborhoods.
• Catch sight of oldest lighthouse in Maine.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

See affluent Kennebunkport from several revealing perspectives: driving past its landmark attractions, strolling its shop-lined streets, and cruising the Kennebunk River. During the drive to Kennebunkport, you will be treated to spectacular views of Maine’s rocky shoreline. As you will soon see, the village features numerous restored homes from the 18th and 19th centuries, including the ornate Wedding Cake House. Be sure to notice its elegant carved buttresses, spires, and lacy spandrels. The cruise will afford a different perspective of affluent Kennebunkport, including a view of the summer residence of the George H.W. Bush family on Walker’s Point. Following your enlightening sight-seeing cruise, you will have some free time in Dock Square, Kennebunkport’s town center and home to a collection of upscale shops, restaurants, and art galleries. It’s an excellent place to wander about, browse at your leisure and simply enjoy the seaside atmosphere.

HIGHLIGHTS

• Take in the sights while driving Maine’s scenic coast.
• Enjoy a relaxing cruise on the Kennebunk River.
• Spend free time browsing affluent Kennebunkport.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Travel through the scenic White Mountains in a meticulously restored 1950s-era railway car that evokes a period when life was more leisurely. You will get a hint of the natural beauty that lies ahead on the 1.5-hour scenic bus drive to North Conway, a delightful town in New Hampshire near the White Mountain National Park. After a bit of free time to explore, you will board the Conway Scenic Railroad in the 19th-century train station and settle in for a breathtaking ride through the majestic White Mountains, which cover nearly a quarter of the state. Along the way, you will pass over towering trestles, through Mount Washington Valley and up into an alpine setting that is spectacularly photogenic. Enlightening commentary will enhance the experience by describing the points of interest in fascinating detail. You will eventually disembark at the late 19th-century Crawford Notch train station for the two-hour return drive to Portland.

HIGHLIGHTS

• Ride the vintage Conway Scenic Railroad into the majestic White Mountains.
• Enjoy panoramic views of the White Mountains and its namesake national park.
• Pass over train trestles, through Mount Washington Valley and into an alpine setting.
• Enjoy the train’s historical ambiance and a boxed lunch along the way.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Settle in for a spectacularly scenic drive around Portland and take in the historical landmarks that define the city. While driving between the Eastern Promenade that fronts Casco Bay and the elevated park along the Western Promenade, you will see a collection of outstanding 19th-century architecture that includes Victoria Mansion. This National Historic Landmark exemplifies the Italian villa style that was fashionable at the time. In the New Arts District, you will pass highlights such as the Portland Museum of Art, the State Theatre and the home where poet Henry Wadsworth Longfellow grew up. Now home to the Maine Historical Society, it is the first house museum in Maine. On the other side of the Fore River, you will find Bug Light Lighthouse, a 19th-century cast-iron lighthouse that was modeled after a monument that stands near the Acropolis in Athens. Only 26 feet high, it became known as The Bug because of its small size.

HIGHLIGHTS

• View the most meaningful landmarks in Portland on a panoramic drive through the city.
• See poet Henry Wadsworth Longfellow’s house, the first home museum in Maine.
• Drive through the historical districts between the Eastern and Western promenades.
• Pause for photos at the diminutive Bug Light Lighthouse, a cast-iron treasure.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Enjoy a relaxing two-hour schooner sail, and a scenic drive of Portland with a visit to the historic Portland Head Light, the oldest commissioned lighthouse in the United States. Begin with a scenic drive through the quaint streets of the old port where street lanterns highlight a gracious mix of architectural styles. Once home of the warehouse district, the red brick buildings have been transformed into charming restaurants, pubs, unique boutiques, and galleries. Passing through the urban center, see Portland’s new arts district, as well as the thriving commercial and business districts. Situated just outside the city center and along the beautiful rocky coast of Cape Elizabeth is Fort Williams, the site of the America’s oldest lighthouse. First illuminated on January 10, 1791, Portland Head Light has since stood at the gateway to the harbor for mariners traveling Maine’s perilous coast. A short photo stop is made here. You'll return to Portland to board an authentic Maine built, wooden schooner for a leisurely sail on Casco Bay. The schooners are the ideal way to experience the beauty of Maine’s rugged coastline. Join the crew as they hoist the sails, take command at the ship’s wheel, or simply relax and enjoy the scenery as you ply the calm waters. Under full sail you’ll glide past the bustling waterfront, secluded islands, historic forts and lighthouses, your guide will point out the sites along the way.

HIGHLIGHTS

• Drive through Old Port and Western Promenade with Victorian residential neighborhood.
• Enjoy photo stop at Portland Head Light and Fort Williams Park.
• Drive through Portland’s New Art District.
• Board schooner for an amazing scenic cruise of coastline in Casco Bay.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Cruise to Peaks Island for a traditional Maine lobster bake with all sorts of delectable side dishes. A ferry will take you across Casco Bay to the island, which lies just three miles offshore. On the way over, you will pass the 19th-century Bug Light Lighthouse, an elegant cast-iron beacon with Corinthian columns. First settled by the Abnaki Indians, Peaks Island didn’t start to flourish until the late 1890s, when Portland’s population grew, and an amusement park went up. It is hard to imagine, but Peaks Island was once called the “Coney Island of Maine.” Today, the population is about 1,000, and the lifestyle is low-key and quintessentially New England. Upon arriving, you will walk to the nearby Inn on Peaks Island, a seasonal lodging that features outstanding views of the sea and classic Maine cuisine. There, you will enjoy a traditional lobster bake with New England clam chowder, steamed mussels and sides such as corn on the cob.

HIGHLIGHTS

• Take the ferry across Casco Bay to Peaks Island and enjoy the scenery on the way over.
• See a 19th-century cast-iron lighthouse modeled after a monument in Athens, Greece.
• Enjoy a classic Maine lobster bake with clam chowder and steamed mussels, as well.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Bicycle along a popular coastal promenade to the state park on forested Mackworth Island, where you will hike along a picturesque loop trail before bicycling back to Portland. Meeting at the pier, you’ll receive a safety briefing and helmet and then begin your biking adventure. Riding a bicycle allows you a wonderful up-close view of the area. As you pedal along the tree-lined Eastern Promenade, you can expect to see other bikers, joggers and walkers enjoying this waterfront trail. The promenade was built along a former rail corridor and offers spectacular views of Casco Bay. Every so often, you will pause for the guide to elaborate on the significance of landmarks like Fort Gorges, which perches on uninhabited Hog Island. The fort wasn’t finished until the end of the Civil War, by which time weaponry had changed making it obsolete. Later, you will learn fascinating facts about Bug Lighthouse, which was once just a wooden tower, and the Casco Bay Islands, also known as the Calendar Islands, because there are supposedly 365 of them. Upon reaching Mackworth Island, you will hop off your bike for a one-mile hike along a trail that encircles the island. In 1946 Maine’s governor set aside the island “as a sanctuary for wild beasts and birds,” and in fact, buried his own dogs here. During your hike you may also spot seagulls and ospreys. After leaving Mackworth Island, you will pedal back to the pier.

HIGHLIGHTS

• Bicycle along a popular coastal promenade to the state park on forested Mackworth Island
• Visit many landmarks as you pedal along the tree-lined Eastern Promenade.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Stroll through the Old Port, sampling your way through several venues that offer delectable snacks that reflect Portland’s distinct cuisine. You will follow a route through the historical streets around the waterfront, an area that was once home to canneries, factories, and textile mills. Today, the revitalized warehouse district features dozens of quaint restaurants, coffee houses, bakeries and shops selling gourmet merchandise. The guide will bring you to some of the finest venues to sample their wares. The exact stores and restaurants always vary, but you can be sure that the offerings will be heavily influenced by what’s freshest and most indicative of the local cuisine. Some of these Maine-inspired foods may include lobster, chowder, organically grown vegetables, fresh-baked pastries, and seasonal berry jams. As you sample the various culinary treats, the proprietors will describe how they were prepared and where the ingredients were obtained.

HIGHLIGHTS

• Walk through the waterfront area sampling snacks prepared with local ingredients.
• Become familiar with Maine’s characteristic cuisine, especially local favorites.
• Learn how the delicacies were prepared and what makes them so special.
• Remain in downtown Portland afterwards, if you please.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.

OVERVIEW

Settle in for a panoramic drive around historical Portland that focuses on the lighthouses along the rocky coastline. As an introduction to Portland, you drive past the lobster boats on the working waterfront and down cobblestone streets lined with Victorian mansions once owned by wealthy sea merchants. The city’s rich maritime heritage will be most evident at beacons such as the Portland Head Light, which George Washington commissioned in 1791. Classic Maine sweets such as Whoopie Pies and Needhams – a chocolate, coconut and potato treat – will be served there. You will also see the Spring Point Ledge Lighthouse, which resembles a spark plug sitting at the end of a granite breakwater, and Bug Light, a 19th-century cast-iron lighthouse. A short walk will bring you to the Liberty Ship Memorial that honors a former World War II shipyard.

HIGHLIGHTS

• Admire the Victorian architecture throughout Portland’s historic district.
• Gain an understanding of Portland’s maritime heritage through its lighthouses.
• Stop at Maine’s oldest lighthouse and see two unusually shaped 19th-century beacons.
• Savor a blueberry drink, maple syrup and Whoopie Pies, the state’s official dessert.

HELPFUL HINTS

• Dress in weather-appropriate clothing.
• Wear flat comfortable walking shoes.