Day 1 | Boston – Salem – Rockport, MA

Distance: 46.00 miles / 74.0 km

Arrive Boston, pick-up your rental car and drive north toward Salem. The infamous town of Salem was home to the witch trials of 1692. A group of girls and women in Salem Village, who had been dabbling with the occult, began acting in a strange manner, a local doctor claimed they were afflicted by the “evil hand” setting the stage for the accusation of approximately 190 people for witchcraft. The trials ended after 15 months. Well aware of its infamy, Salem has a number of attractions centered on this uneasy time, including haunted tours and re-enactments. Continue the drive to Rockport where your first overnight has been arranged. Rockport is a beautiful coastal Maine village with over 170 upscale outlets, designer shops, eclectic boutiques, B&B’s, hotels, fantastic restaurants & casual cafes. This lovely town at the tip of Cape Ann was settled in 1690. Over the years it has been an active fishing port, a center of granite excavation and a thriving artistic community with multiple galleries. The most artistically reproduced item in Rockport is a wooden fish warehouse on the town wharf. The red shack is known as Motif No. 1. Visit Thatcher Island to see the Twin Lighthouses. Among the oldest American lighthouses, these twin lights are the only surviving multiple lights on the U.S Coastline. The original 45-foot towers were constructed and lit in 1789. Visit the Bearskin Neck area where you will find multiple shops and galleries. Movies like “The Perfect Storm” and “The Love Letter” were filmed in this area.

Accommodations: (STD) Emerson Inn by the Sea or similar (1 Night) (SUP) Emerson Inn by the Sea or similar (1 Night)

Day 2 | Rockport – Boothbay Harbor/ Belfast, ME

Distance: 166.00 miles / 267.1 km

Leave Rockport and drive north through beautiful Coastal Maine toward Boothbay or Belfast. Along the way you will encounter different harbors where you can explore numerous lighthouses and charming harbor towns this region this region is famous for. You have the option to stay on land and visit the small towns or enjoy a one or two day sea excursion for a different perspective of this beautiful area. There are numerous options for those sea excursions such as cruises, sailing trips, whale watching cruises, etc.

Accommodations: (STD) Comfort Inn Ocean’s Edge or similar (2 Nights) (SUP) Tugboat Inn or similar (2 Nights)

Day 3 | Boothbay Harbor/ Belfast, ME

Distance: 0.00 miles / 0.0 km

Depending on the choices made yesterday, today you may be enjoying the second day of a two-day sea excursion. If you decided to stay on land, today you may continue to explore the towns and lighthouses or follow one of the many nature trails the area has to offer. Another option is to embark on a short sea excursion for a different point of view of the region you already explored by land.

Day 4 | Boothbay Harbor/ Belfast – Bar Harbor, ME

Distance: 122.00 miles / 196.3 km

Depart Boothbay Harbor or Belfast this morning and drive toward Bar Harbor. On your way to Bar Harbor you will pass Camden where you’ll be able to enjoy numerous water-related sports and activities. Swim in warm lake waters, cast a lure for mackerel or stripers, sea kayaking and hiking guided outdoor adventures are just but a few of the choices available. Explore beautiful bays, islands, lakes, and natural landscapes in mid-coast Maine. Continue on your journey. Located in Downeast, Bar Harbor was once considered a small fishing and ship-building community. Today, it is a favorite destination for people throughout the world. A visit to Bar Harbor affords the comforts and luxury of a classic retreat, but also offers spectacular beauty and natural wonder for those who would prefer to spend their time outdoors.

Accommodations: (STD) Best Western Inn or similar (2 Nights) (SUP) Bar Harbor Regency Hotel & Marina or similar (2 Nights)

Day 5 | Bar Harbor, ME

Distance: 0.00 miles / 0.0 km

Today you can explore Bar Harbor and its surroundings at your leisure. Visit Mount Desert Oceanarium which includes a lobster museum, a marsh tour, and a lobster hatchery. For a touch of nature, visit Acadia National Park, New England''s only national park; it offers 6000 acres of mountains, rugged coastline, islands, forests and lakes where you can hike, bike, canoe, fish, and explore this Park’s trails. For an alternative, rent a bicycle and explore the area as the locals do. Peddle alongside crystal-water lakes and rose-colored mountains. For a different view, take a bus or trolley tour and hear about the local history from well-versed local guides. Or, take an insightful and entertaining walking tour of downtown. If you rather explore Maine from the water side, paddle a canoe or kayak either on your own or in the company of a well-experienced guide.

Day 6 | Bar Harbor – Kennebunkport/ Ogunquit, ME

Distance: 205.00 miles / 329.8 km

Leave the small fishing community of Bar Harbor and drive toward Kennebunkport. Kennebunkport is one of Maine''s most popular summer vacation destinations. Experience the tranquility and enjoy the beauty of this quiet seaside village with its charming shops and galleries, country grocery store, lobster pounds, fish markets and restaurants known for their fabulous fresh seafood. Goose Rocks Beach is a beautiful and pristine three-mile-long beach and with sand dunes and wonderful views a favorite of walkers of all generations. Ogunquit was named by the Micmac Indians for its natural beauty and charm. Throughout the years the town has maintained its New England village spirit and appeal. The Ogunquit area is one of Maine''s oldest vacation destinations. It offers a wealth of arts and entertainment choices, as well as shop-lined streets, trolley rides, ocean side dining and inviting beaches such as Ogunquit Beach.

Accommodations: (STD) Ogunquit River Plantation or similar (1 Night) (SUP) Nonantum Resort or similar (1 Night)

Day 7 | Kennebunkport/Ogunquit – Portsmouth – Boston, MA

Distance: 87.00 miles / 140.0 km

Drive via Portsmouth back to Boston and drop-off the rental car The geographic location, historic past and cultural strength of Portsmouth makes it one of the most culturally rich destinations in the country. The region as a whole is noted for its many restaurants, attractions and shopping opportunities.