Dining
Frank Pepe Pizzeria Napoletana
Begin your journey at the legendary birthplace of New Haven-style 'apizza'. Order the iconic White Clam Pizza from their original 1925 coal-fired oven for a true taste of American culinary history.
4
Days
15
Stops
active
Region
New Haven, CTPortland, ME
Embark on a classic New England coastal journey, savoring everything from legendary New Haven pizza to fresh lobster in Maine. This scenic trip blends historic Gilded Age mansions, charming seaside towns, and stunning Atlantic beaches for a perfect four-day escape.
Trip highlights
The route
- 1New Haven, CTStart · 41.3083, -72.9279
- 2Frank Pepe Pizzeria NapoletanaStop · 41.3117, -72.9155
- 3Hammonasset Beach State ParkStop · 41.2738, -72.5594
- 4The BreakersStop · 41.4697, -71.2982
- 5Gurney's Newport Resort & MarinaStop · 41.4914, -71.3274
- 6Cliff WalkStop · 41.4670, -71.3021
- 7The House of the Seven GablesStop · 42.5819, -70.7694
- 8Beauport Hotel GloucesterStop · 42.6105, -70.6558
- 9The Franklin RestaurantStop · 42.6126, -70.6636
- 10Motif No. 1Stop · 42.5929, -70.6171
- 11Good Harbor BeachStop · 42.6206, -70.6329
- 12The Nubble LighthouseStop · 43.1584, -70.5927
- 13The Press Hotel, Autograph CollectionStop · 43.6593, -70.2581
- 14Eventide Oyster Co.Stop · 43.6575, -70.2548
- 15Portland Head LightStop · 43.6234, -70.2079
- 16Old PortStop · 43.6576, -70.2520
- 17Portland, MEEnd · 43.6591, -70.2568
Day 2
Outdoor Adventure
Hammonasset Beach State Park
Stretch your legs at Connecticut's largest shoreline park. Walk along two miles of sandy beach, search for seashells, or simply enjoy the beautiful views of Long Island Sound.
Historical Site
The Breakers
Step into the Gilded Age at the Vanderbilt's opulent summer 'cottage,' the grandest of Newport's famous mansions. The sheer scale, lavish interiors, and stunning oceanfront setting make this a quintessential American landmark.
Lodging
Gurney's Newport Resort & Marina
Settle in for the night at a resort on a private island offering panoramic water views, a classic New England lighthouse, and easy access to downtown Newport's historic wharves.
Day 3
Scenic Viewpoint
Cliff Walk
Experience one of New England's most famous walks. This 3.5-mile public path offers a stunning juxtaposition of natural ocean beauty on one side and the architectural grandeur of the Gilded Age mansions on the other.
Historical Site
The House of the Seven Gables
Visit the seaside mansion that inspired Nathaniel Hawthorne's classic 1851 novel. This National Historic Landmark offers a unique look into 300 years of New England history, complete with a secret staircase.
Lodging
Beauport Hotel Gloucester
Stay at a luxury oceanfront hotel on Pavilion Beach. Enjoy stunning harbor views, a rooftop pool, and the perfect location for exploring America's oldest seaport.
Dining
The Franklin Restaurant
Dine at a beloved local institution known for its upscale yet comfortable atmosphere and delicious, creative American cuisine. A perfect spot for a memorable dinner in Gloucester's historic downtown.
Day 4
Scenic Viewpoint
Motif No. 1
Photograph the most-painted building in America. This iconic red fishing shack on the harbor is the quintessential symbol of New England's maritime heritage and artistic soul.
Outdoor Adventure
Good Harbor Beach
Relax on a beautiful, expansive white sand beach with picturesque views. At low tide, you can walk out to Salt Island, making it a perfect spot for a classic New England beach day.
Scenic Viewpoint
The Nubble Lighthouse
Behold one of the most iconic and photographed lighthouses in the world. Located on a rocky 'nubble' just offshore, it's a breathtaking sight against the dramatic Maine coastline, especially at sunset.
Lodging
The Press Hotel, Autograph Collection
Check into your hotel in the heart of the Old Port, cleverly housed in the former headquarters of the Portland Press Herald. The sophisticated, newsroom-themed decor offers a unique and stylish base for exploring the city.
Day 5
Dining
Eventide Oyster Co.
Indulge in a modern take on the classic American oyster bar. Famous for its pristine raw bar and the Brown Butter Lobster Roll served on a steamed bun, this James Beard Award-winning spot is a must-try Portland experience.
Historical Site
Portland Head Light
Visit Maine's oldest lighthouse, commissioned by George Washington in 1791. Set in the beautiful 90-acre Fort Williams Park, the lighthouse and its museum offer stunning coastal views and a deep dive into maritime history.
Local Experience
Old Port
Wander the charming cobblestone streets of Portland's historic district. Explore the unique boutiques, art galleries, and lively pubs set against the backdrop of a working waterfront, perfectly capturing the city's vibrant character.
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