A coastal city full of New England charm.
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Overview
Portland, Maine, a vibrant city perched on a peninsula in Casco Bay, perfectly blends historic charm with a thriving contemporary scene. Renowned for its picturesque working waterfront, cobblestone streets of the Old Port, and beautifully preserved 19th-century architecture, the city exudes a distinct New England character. Beyond its maritime heritage, Portland has earned a reputation as a culinary hotspot, boasting an impressive array of award-winning restaurants, craft breweries, and artisan food producers.
The city offers a refreshing mix of cultural experiences, from independent boutiques and art galleries to historic lighthouses and scenic boat tours. Its compact, walkable downtown makes it easy for cruise visitors to explore its unique neighborhoods, soak in the salty air, and discover why Portland consistently ranks among America's most livable and charming small cities. It's a place where history feels alive, and modern creativity flourishes against a backdrop of stunning coastal beauty.
Wander through Portland's charming Historic Old Port district, a vibrant area filled with cobblestone streets, Victorian-era brick buildings, and a bustling working waterfront. Discover unique boutiques, art galleries, souvenir shops, and countless restaurants and pubs.
Tip: Take your time to explore the side streets and alleys; you'll often find hidden gems and beautiful architectural details.
No visit to Portland is complete without seeing the Portland Head Light, Maine's oldest lighthouse and one of the most photographed in the world. Located in Fort Williams Park in Cape Elizabeth (a short drive from the port), it offers breathtaking coastal views and a museum in the former keeper's quarters.
Tip: Allow ample time for photos and a walk around Fort Williams Park, which boasts dramatic cliffs, walking trails, and remnants of old military batteries.
Portland is a celebrated culinary destination. Sample some of the freshest Maine lobster, whether in a classic lobster roll, steamed, or in a bisque. Explore the city's diverse dining scene, from casual seafood shacks to upscale farm-to-table restaurants, and don't miss its thriving craft beer and coffee culture.
Tip: Consider a food tour or a self-guided culinary walk to sample a variety of local specialties, including whoopie pies and blueberry treats.
Experience Portland's picturesque setting from the water on a Casco Bay Islands cruise. These scenic boat tours offer stunning views of the city skyline, historic forts, various lighthouses, and the charming islands dotting the bay, providing a different perspective of the coastline.
Tip: Choose a tour that matches your desired duration and focus, whether it's a quick harbor tour or a longer island-hopping excursion with narration.
Immerse yourself in art and culture at the Portland Museum of Art (PMA), Maine's oldest and largest public art institution. The PMA features a diverse collection spanning European, American, and contemporary art, with a strong focus on Maine artists and landscapes.
Tip: Check for any special exhibitions that might be running during your visit, as the PMA often hosts engaging temporary displays.
Enjoy a leisurely walk or bike ride along the Eastern Promenade, a scenic 68-acre public park offering stunning panoramic views of Casco Bay, the islands, and the city skyline. It's a popular spot for locals and visitors alike to enjoy the fresh ocean air and picturesque vistas.
Tip: Find a bench and simply take in the views, or head down to East End Beach for a closer look at the water.
Aboard
Silver Shadow
From
New York City, New York
1 Sailing
Sep 2, 2027
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Aboard
Norwegian Breakaway
From
Boston, Massachusetts
6 Sailings
Sep 5 - Oct 17, 2027
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Aboard
Zuiderdam
From
Quebec City, Quebec
1 Sailing
Oct 2, 2027
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Aboard
Volendam
From
Montreal, Quebec
1 Sailing
Jun 26, 2027
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Aboard
Caribbean Princess
From
Boston, Massachusetts
3 Sailings
Sep 7 - Oct 19, 2027
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Aboard
Sapphire Princess
From
Boston, Massachusetts
1 Sailing
Sep 23, 2026
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Aboard
Sapphire Princess
From
Boston, Massachusetts
1 Sailing
Sep 3, 2026
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Aboard
Caribbean Princess
From
Toronto, Ontario
1 Sailing
Oct 24, 2027
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per person*
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Aboard
Caribbean Princess
From
Boston, Massachusetts
1 Sailing
Oct 19, 2027
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per person*
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Aboard
Caribbean Princess
From
Boston, Massachusetts
2 Sailings
Sep 7 - Sep 28, 2027
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