Romance Road

  • Maine + 1 more
  • Self Drive Ideas
  • 11 Days
from  £1,589pp
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Discover the beautiful scenery of New England staying in iconic Inns and hotels

A Free Personalised Road Book is included as standard with our Self Drive itineraries. 


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.


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Days 1 – 3 Boston – Rockport (42 mi/68 km)

Arrive Boston and travel north to Rockport, a 45 minute drive from Boston’s airport. Rockport is the epitome of quaint, New England charm. Stroll along the streets of downtown, sunbathe on the rocks and beaches, take walks through the woods or along the shore, or watch the whales from boats out of Rockport or Gloucester. Spend two nights at Cape Ann’s only historic grand hotel, Emerson Inn by the Sea. This lovely Rockport inn is an historic gem.

Days 3 – 6 Rockport – Sebago Lake Region (131 mi/211km)

For over one hundred years the Sebago Lake Region in southern Maine has been the premier destination for water recreation, lake and mountain vistas, and calm. Migis Lodge is made up of a luxurious main lodge building and 35 cottages nestled amid 125 acres of pine forest, stretching along 3,500 feet of Sebago Lake shoreline. Spend the next three nights at Migis Lodge enjoying golf, tennis or the spa, lunching on the private island, or gazing at dramatic sunsets.

Days 6 – 9 Sebago Lakes Region – Camden (110 mi/177 km)

Travel north to mid-coast Maine and check-in to the Inn at Ocean’s Edge for three nights. Take a bicycle on the ferry to Isleboro for scenic exploration or sample local tastes at a Lincolnville winery. Walk along the rocky shore in front of the Inn or on sandier Lincolnville Beach just a mile away. Schooners depart from Camden hourly and shopping along Main Street is a must. Or, just relax at the Inn enjoying such amenities as the infinity edge pool, spa, treatment rooms and outdoor fireplace.

Days 9 – 11 Camden – Prouts Neck (97 mi/156 km)

Journey south along Maine’s coastal roads to Prouts Neck, just outside of Portland. Stay two nights at the historic Black Point Inn. Built in 1878, the Inn is surrounded by the Atlantic Ocean on three sides, with 18 holes of links golf, hiking and running trails, miles of sandy beaches, tennis, a swimming pool and beach club. Enjoy unpretentious downeast hospitality while sipping cocktails on the porch or dining in its highly acclaimed fine dining restaurant overlooking the ocean. On day 11, return to Boston, less than 2 hours from Prouts Neck for the flight home.