Portland and Kennebunkport

Portland and Kennebunkport are steeped in Maine's maritime history and serve up some of the best cuisine in the USA.

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On a peninsula on Casco Bay, Portland is one of the USA’s oldest, most historic cities and the original capital of Maine. It retains small town charm with Victorian buildings, a thriving arts scene, busy waterfront and top-class cuisine.

Known as “the restaurant city”, Portland frequently tops polls for best food in the USA with a host of celebrity chefs, and hundreds of restaurants and breweries. Seafood is of course a speciality with lobster rolls and oysters galore, but the city also has a huge range of international and fusion food as well as craft breweries and cocktail bars.

Half an hour south of Portland is Kennebunkport, a lovely harbour town with art galleries, historic homes, boutique stores and restaurants. The town is well-known as a summer retreat of the Bush family.

The best views over Portland's harbour are from Portland Observatory, America’s last standing maritime signal tower, while Victoria Mansion is the most impressive example of pre-civil war architecture with original interior décor. Portland Museum of Art, the largest gallery in Maine, has over 22,000 works from local, national and international artists.

On the edge of Portland in Fort Williams Park on Cape Elizabeth, Portland Head Light is one of New England’s most beautiful lighthouses, dating from 1791 and still functioning today. One of the best ways to appreciate Portland is on a cruise around the bay and across to islands such as Peaks and Long Island, which offer great hiking, cycling and kayaking.

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Creating tailor-made Holidays for 40 years

Places to Stay in Portland and Kennebunkport

Browse our unrivalled portfolio of accommodation in Portland and Kennebunkport. Every option has been carefully chosen by our team of travel experts.

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About Us

Brought to you by Journey Latin America, the team behind the UK's No.1 Specialist in travel to Central and South America, Journeyscape is a collection of inspiring, authentic and extraordinary journeys delivered with exceptional customer service across the USA and Canada.

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Holiday Styles

Centred around Canada and the USA's most unforgettable experiences and unique activities, our holiday styles cater to every interest.

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How we travel

Whether it's a tailor-made holiday created from scratch, or a pre-designed holiday crafted by our experts, we can provide an incredible holiday experience based on your specific preferences.

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Your edit for North America inspiration

Inspired by the landscapes, culture, wildlife and cuisine of Canada and the USA, explore our entertaining range of articles, travel tips, destination guides, recipes and much more.

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Meet Our Team

Real North America Travel Experts

Rob Holmes, Travel Expert
Rob Holmes - Travel Expert

Rob has been travelling to both the USA & Canada for nearly 20 years and in that time, has been lucky enough to visit 35 (and counting) of the 50 States, plus extensive travels through Canada.

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Dominique Kotsias - Product Manager

Dominique caught the North America travel bug when she was in her late teens and has travelled extensively throughout the USA and Canada, particularly drawn to the countries' outstanding natural beauty and wildlife. With over 10 years of product and marketing experience in North America, Dominique’s passion for the destination is infectious.

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Ben Line - Head of Sales

Ben Line is the Head of Sales at Journeyscape and our sister brand Journey Latin America, having lived abroad and travelled extensively over the years.

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Joshua Salter - Travel Expert

Joshua has been travelling to the USA since childhood, visiting his father and four siblings on the west coast. He is fortunate to have travelled to 42 of the 50 US states, and hopes to complete the set by his next big birthday.

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Stuart Whittington - Head of Product

Stuart is the Head of Product at Journeyscape and our sister brand, Journey Latin America. He is passionate about new adventures, venturing off the beaten path, and firmly believes that travel, when planned well, can be a force for good for all people and places involved.

Why Journeyscape?

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Journeyscape brought to you from the award-winning experts at Journey Latin America