Portland Head Lighthouse, Maine
Portland

Portland holidays - Historical, laidback and fresh

For a true taste of nautical culture, Portland, Maine is a city full of maritime heritage and delicious seafood. Offering bustling waterfronts, plenty of fishing excursions and fresh, decadent lobsters dishes, a trip here will be plain sailing.

A cultural city filled with museums, seafood restaurants and ferry rides

The hub of Maine life, Portland offers a wealth of delights, from historic buildings and cutting-edge art to scenic coastline, fantastic shopping and an incredible food and drink scene. In short, it offers all the perks of urban life but in a compact area and all without the crowds, congestion, expense of much bigger cities.

Portland has a long-standing connection with the sea and vestiges of its once booming maritime trade are still clear today, especially around the atmospheric working wharfs of Commercial Street. In more recent decades, Portland has been busily reinventing itself and is now widely reputed as one of America’s most exciting up-and-coming small cities. This is most evident in the thriving Old Port district, an historic area featuring attractive redbrick buildings, restored warehouses and a lively street culture. Here you’ll find a wealth of hip coffee shops, boutiques and bars lining the bustling waterfront and picturesque cobblestone streets.

Head to Congress Street for an exciting dose of the city’s flourishing art scene. The Portland Museum of Art is not to be missed, but there are countless more galleries, studios and art-inspired tours and events to dive into. Other stand-out cultural venues in Portland’s Art district include the Children’s Museum of Maine, Institute of Contemporary Art, SPACE gallery and copious theatre houses.

Portland is particularly renowned for its exceptionally high concentration of restaurants and watering holes. In fact, it’s become something of a foodie mecca, offering everything from fine dining to tantalising ethnic eats, farm-to-table fare and of course the freshest of seafood. Tuck into great value Vietnamese or Thai, seek out an eco-conscious vegan eatery, feast on lobster and other classic local staples, then wash it down at any number of quality craft breweries.

As a small city nestled on a peninsula in Casco Bay, Portland offers easy access to the great outdoors and all the quintessential aspects of a Maine holiday. Within the city you’ll find acres of trails, cycleways and parkland to explore. Head out to the coast for beautiful beaches, seaside villages, historic forts, lighthouses and spectacular views, all within easy reach of the city. Fast ferries also plough routes between dozens of offshore islands, perfect for those in search of a peaceful retreat.

Top reasons to visit Portland, Maine

  • Big city attractions and sophistication: Beautiful architecture, charming streets and a smattering of excellent galleries, museums and performance spaces
  • Urban thrills and spills: Head to The Old Port district for hundreds of boutiques, coffee shops, microbreweries and vibrant nightlife
  • Food and drink: Portland is home to one of the densest concentrations of restaurants on the East coast. With something to suit every taste and budget, it doesn’t get much more delicious, innovative or diverse
  • Escape is never far away: Take a scenic ride around on the mail boat. This commuter ferry will take you around Casco Bay and past some of the most stunning shoreline scenery
Why American Sky?
Award Winning
We're award winning Our awards reflect our dedication to delivering incredible tailor-made holidays
Why American Sky?
Protected
Your money is safe We safeguard your money with CAR protection and have membership to codes of best conduct.
Why American Sky?
Award Winning
We answer quickly On average, calls are answered within three rings. We also respond within hours to emails.
Why American Sky?
Award Winning
We offer expert advice and great service Our luxury tailor-made holidays are created with impeccable service from start to finish.

Recommended holidays

Jackie Sheehan
Call our travel experts now
01 6649999 Call us Mon-Sun 9am-9pm