Portland, Maine, US

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• Aug 23, 2020

• Arrives 07:00 AM

• Departs 04:00 PM

 

In Partnership With AFAR

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Squint your eyes and admit it: Doesn’t that skinny, bearded hipster walking down the cobbled street look a lot like a 19th-century sea captain heading to the wharf to check his ship? Modern Portland, first settled in 1633, carries the marks of both subsets of Mainers. The restored brick buildings and warehouses of the Old Port and the fine upright houses of prosperous captains, merchants and shipbuilders make the city’s past a living part of its present. And the waterfront is a going concern, not a museum: Fishing boats chug into and out of their berths, buoys clang, harbor seals bark. Those shop windows aren’t displaying hardtack, rope or hand salve, though. Juice joints, art galleries, bookstores (and comic-book stores!), worshipful temples to coffee, locavore bistros with national press, bespoke menswear designers and gelato shops all jostle for attention. Don’t limit your visit to the Old Port, though. Wander through the terrific art museum or take a tour of one of the city’s historic homes. Jump on a ferry or whale-watching boat and get out into the busy harbor. Head to the coast—craggy, windswept, dramatic—a glorious and undeniably New England panorama. Get out and take it all in. Welcome to Vacationland.

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Sample Port Activities

 

Portland Highlights, Fort Williams & Lighthouse

• Starting At $49

Portland is at once historic, quixotic and beautiful, tinged by worldly Boston, but still inherently Downeast.

Enjoy a scenic drive through the quaint streets of the Old Port, once the home of the warehouse district. The old red brick buildings have been transformed into charming restaurants, pubs, boutiques and galleries. You will pass a number of historic Victorian homes and neighborhoods, enjoying terrific views of Casco Bay and the islands from the East End Promenade. In the urban center Portland’s new Arts District is appealing and the thriving commercial and business districts are quite lively. Learn about the history, architecture, and the life of the people who call Portland home. The city was founded in 1632 and boasts architectural masterpieces ranging from Queen Anne, Colonial and Federal to Beaux-Arts, Classical and Romanesque. Visit Fort Williams Park located on the rocky coast in beautiful Cape Elizabeth. Fort Williams was a military outpost for coastal defense serving the United States from the Spanish-American War to the Korean War. Fort Williams is also the home of Portland Head Light, commissioned by President George Washington in 1797. Since its illumination in 1791, the lighthouse has marked the gateway to Portland Harbor for mariners over the centuries.

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Kennebunkport

• Starting At $59

Kennebunkport, a charming coastal village, is located 45 minutes south of Portland and gained worldwide exposure as the summer home of President George H. W. Bush.

The drive to Kennebunkport offers beautiful views of Maine’s rocky coast. Approaching the town, you will view the elaborate Federal- and Victorian-style mansions built by wealthy sea captains and merchants in the 1700s and 1800s.

Your guide will show you Walker’s Point -- the Bush estate and former Summer White House.

Stretch your legs at Dock Square in the center of Kennebunkport, complete with art galleries, antique shops, restaurants and upscale stores.

You will pass a number of picturesque villages on your journey back to Portland and the ship.

 

 

Kennebunkport & Scenic Cruise

• Starting At $89

Kennebunkport, a charming coastal village, is located 45 minutes south of Portland and gained worldwide exposure as the summer home of President George H. W. Bush. The drive to Kennebunkport offers beautiful views of Maine’s rocky coast. Approaching the town, you will view the elaborate Federal- and Victorian-style mansions built by wealthy sea captains and merchants in the 1700s and 1800s. Your guide will show you Walker’s Point -- the Bush estate and former Summer White House. Stretch your legs at Dock Square in the center of Kennebunkport, complete with art galleries, antique shops, restaurants and upscale stores.\Enjoy a scenic boat ride, plying the calm, protected waters of Maine for a panoramic view of the rugged, rocky coastline as well as a waterside glimpse of Walker’s Point. You will pass a number of picturesque villages on your journey back to Portland and the ship.

 

 

Peaks Island Lobster Bake

• Starting At $119

Take the ferry (not exclusive to Holland America Line guests) and transfer from Portland to Peaks Island, three miles away. The 20-minute voyage is a scenic introduction to Casco Bay.

Step ashore, where a short walk brings you to the Inn on Peaks Island. Here, a delicious lobster bake buffet lunch is served in typically ‘Downeast’ island surroundings.

You’ll have 30 minutes of free time to explore the waterfront area and indulge in some shopping, photography or people-watching.

Notes: \Free time may vary slightly based on the ferry schedule.

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Horse-Drawn Trolley

• Starting At $49

This tour offers an opportunity to see Portland as very few people see it. Enjoy the rustic beauty of a 19th-century horse-drawn wagon sightseeing tour through the narrow streets of Portland as your guide points out many historic sights.\A matched team of magnificent horses will pull you comfortably through the narrow streets of the city Henry Wadsworth Longfellow named a 'Jewel by the Sea'. Watch for Portland's working waterfront, the Eastern Promenade with its spectacular views of Casco Bay and the Calendar Islands, the Portland Observatory, used to notify the city of a ship's arrival, Monument Square with its tribute to those who gave their lives for freedom, and Henry Wadsworth Longfellow's home. You will also pass the Portland Museum of Art designed by I.M. Pei, and a unique combination of architectural styles that make up this vibrant city.

Along the way, your guide recounts the history of Portland from its beginnings as a part of Massachusetts, to its independence, and how the city was destroyed and rebuilt four separate times.

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Notes: Participants must be able to climb two steps to board the wagon.

 

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Portland Highlights & Schooner Adventure

• Starting At $109

Enjoy a scenic tour of Portland en route to the Portland Head Light lighthouse. First, you'll see the historic and contemporary sights of Portland as your air-conditioned transportation winds its way through Portland and drive along the Eastern Promenade with stunning views of Casco Bay and the Calendar Islands. Then, travel along the beautiful craggy coast to Cape Elizabeth, a charming little village situated on the southern shore of Casco Bay.

You'll visit Fort Williams, once a military outpost and today, a popular park and site of the Portland Head Light -- Maine's oldest lighthouse. Commissioned by President Washington in 1797 and dedicated by the Marquis de Lafayette, it stands 80 feet above the rocky cliff and 101 feet above the icy blue waters of Casco Bay. Its white conical tower, and rambling red roofs makes Portland Head Light not only Portland's most recognizable landmark but the most photographed lighthouse in the US. Return to Portland and embark on one of two authentic wooden schooners for a leisurely sail around Casco Bay. These legendary tall ships are 66 and 88 feet long, and boasts an experienced crew who will share with you their knowledge of the sea and sailing. Sit back, relax and take in the sights of Casco's waters, listen to the barking of the harbor seals and watch for an occasional eagle. If you prefer, you can join the crew and help hoist the sails and take a turn at the ship's wheel.

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Notes: Please bring a jacket or windbreaker as it can get cool out on deck.

 

 

A Culinary Walk through Portland: In Partnership with Food & Wine Magazine

• Starting At $79

Portland's reputation as the foodiest, friendliest small town in America is undeniable, and its restaurant scene is unrivaled in Maine.

This leisurely-paced walking tour carves a path through the streets of the charming Old Port, introducing you to some of the best bites in town along the way. A hundred years ago this area was home to fish houses, canneries, factories and textile mills. Today, the air is fragrant with the fresh ocean breeze and the aromas from coffee houses, bakeries and award-winning restaurants, all tempting you as you wind your way through the narrow streets. Your friendly and engaging guide will take you to several Old Port venues to sample Maine-inspired foods and meet the people who craft Portland's culinary delights.

 

Of course, you can't come to Maine without eating a lobster roll, and one of the best is found at the Highroller Lobster Company. This casual spot offers awesome sandwiches, a nostalgic red-and-white diner look and feel, indoor and outdoor seating, and plenty of great food. Their version of the lobster roll includes delicious fresh lobster meat served on a lightly-toasted fresh brioche bun with lettuce and your choice of sauce.

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Mainers love hot soup on a Fall day. At Lois Naturals, the ingredients are locally sourced and always fresh, the atmosphere is welcoming, and the steaming cups of creative soups (your choice of three) are a crowd-pleaser.

Your culinary journey also takes you to the Shipyard Brewing Company. Perched on the historic waterfront, this family-owned spot has been making beer in Maine since 1994 and is one of the largest craft breweries in the country. From seasonal blends to English-style ales, all the beer here is brewed by hand in small batches. You will enjoy three beer samples, with house-made soda alternatives also available.

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Next stop? Two Fat Cats -- one of Portland's finest bakeries. The Fat Cats' specialty is classic American baking. Don't miss the marshmallow buttercream-filled whoopie pie, whose name scarcely does this masterpiece justice.

Save room for the last stop -- Mount Desert Island Ice Cream. This icon was named one of the top 25 ice cream stores in the U.S. by Food & Wine magazine. Everything here is artisanal and handmade, and owner Linda Parker shows her local pride when she adds items like Maine sea salt to caramel ice cream. When President Barack Obama visited the original location in Bar Harbor, he went for coconut. Which flavor will you choose? Sample a scoop, then return to the ship. Guests who wish to stay in town to shop or explore independently are welcome to do so, but must make their own way back to the ship.

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Notes:  Wear comfortable walking shoes.

 

 

Portland Highlights, Fort Williams & Lighthouse (Wheelchair Accessible)

• Starting At $49

Portland is at once historic, quixotic and beautiful, tinged by worldly Boston, but still inherently Downeast.

Enjoy a scenic drive through the quaint streets of the Old Port, once the home of the warehouse district. The old red brick buildings have been transformed into charming restaurants, pubs, boutiques and galleries. You will pass a number of historic Victorian homes and neighborhoods, enjoying terrific views of Casco Bay and the islands from the East End Promenade. In the urban center Portland’s new Arts District is appealing and the thriving commercial and business districts are quite lively. Learn about the history, architecture, and the life of the people who call Portland home. The city was founded in 1632 and boasts architectural masterpieces ranging from Queen Anne, Colonial and Federal to Beaux-Arts, Classical and Romanesque.

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Visit Fort Williams Park located on the rocky coast in beautiful Cape Elizabeth. Fort Williams was a military outpost for coastal defense serving the United States from the Spanish-American War to the Korean War. Fort Williams is also the home of Portland Head Light, commissioned by President George Washington in 1797. Since its illumination in 1791, the lighthouse has marked the gateway to Portland Harbor for mariners over the centuries.

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Notes :  Only guests using a wheelchair can book this tour, as it ensures accessible transportation. Due to the specialized nature of some lift-equipped vehicles, priority is given to guests using a wheelchair and one companion only; additional companions may be required to travel on the transportation provided for tour 44201.