Along the Maine Coast by Land & Sea

  • Maine
  • Self Drive Ideas
  • 9 Days
from  £955pp
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Enjoy a maritime New England holiday, taking you along the stunning coastal roads of Maine and then by historic Windjammer on a 3 night cruise to explore the coast from the sea!

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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Day 1 Boston – Kennebunkport (84mi/135km)

Arrive Boston and travel north along the coast to Kennebunkport, Maine for your overnight stay.

Day 2 Kennebunkport– Camden (115mi/185km)

This morning explore Kennebunkport. This quaint fishing hamlet is one of the most picturesque and enjoyed seaside resort villages in New England. Walk the mile long Marginal Way over rocky ocean cliffs to Perkins Cove.
Enjoy a mouth-watering lobster luncheon before departing for Camden, taking time to enjoy the Maine Coastal Route through charming towns and villages. Upon arrival in Camden, head directly for the Harbor to board your Maine Windjammer Cruise. *Boarding is at 5:30pm and first night aboard is in berth.

Days 3 – 5 Sailing Maine’s Islands

After a hearty breakfast, get underway for a three-day adventure exploring the Islands of Maine. Long days to sail and explore, a shore-side lobster bake, and lots of time to relax and unwind. Shipboard routines quickly become a comfortable pattern. Rise early, maybe in time for an exhilarating sunrise. As you relax and enjoy the dawn of a new day, take in the sea air with a hot cup of coffee and fresh baked goods prepared on the wood stove. Awhile later, the sound of the ship’s bell will announce it’s time for a hearty downeast breakfast. As the crew prepares the schooner for the day’s adventure, there is time for a row or a swim or a walk ashore and the day’s adventure has just begun. This cruise can be a grand change of pace and certainly a highlight of any Maine vacation. Return to Camden Harbor by 10 a.m.

Day 5 Camden – Bar Harbor (76mi/122km)

Upon returning to land, enjoy the quaint village of Camden before departing for Bar Harbor, gateway to Acadia National Park. Spend the next 2 nights in Bar Harbor.

Day 6 Bar Harbor

A full day to explore one of the most beautiful national parks in the United States. Acadia on Mount Desert Island is a 35,000-acre park graced with natural scenic beauty. Within its boundaries you will find 120 miles of hiking trails and 27 miles of carriage trails. Acadia National Park is best known for its pine-covered forests and rugged coastline, not to mention Cadillac Mountain, the highest point on the United States Eastern Seaboard. Enjoy some of Bar Harbor’s restaurants and taverns this evening.

Day 7 Bar Harbor – Portland NH (174mi/278km)

Follow Maine’s scenic coastline south to Portland. This old harbor town has become a funky city filled with galleries, unique boutiques and shops, and incredible restaurants.

Day 8 Portland NH

Tour downtown’s Old Port historic district and some of the city’s historic homes. Portland is also a funky city filled with galleries, one-of-kind boutiques and shops, and incredible restaurants serving everything from New England clam chowder, lobster rolls and Maine seafood to nouveau cuisine. Head to Cape Elizabeth and visit the Portland Head Light & Museum, located along the spectacular shores of Fort Williams Park. The museum is located in the Keeper’s quarters Or you may choose to shop Freeport, home to outlet stores and the one-of-a-kind outdoor outfitter, LL Bean.

Day 9 Portland NH – Portsmouth – Boston (112mi/180km)

This morning depart Portland for Portsmouth, NH, a working port since colonial days and a treasure trove of historical offerings. Visit Strawberry Banke, a collection of 42 buildings reflecting four centuries of architectural and social change in one of America’s oldest neighbourhoods, or take advantage of the many shops and restaurants in this historic seaport community. Head back to Boston’s Logan International Airport for your departure flight.