See the Coast of Maine in Six Days –The best of Kennebunkport, Rockland & Bar Harbor

While this itinerary starts from Southern Maine in Kennebunkport and heads up the coast to Rockland then Bar Harbor, it can certainly be enjoyed in the opposite direction too.

If you’re seeking an itinerary that offers a taste of the region’s adventure, culinary scene and must-see’s and must-dos, choose this itinerary which highlights the best parts of each region.

Day 1:  Kennebunkport, Maine:  Stay at Captain Jefferds

Your day starts with a hot, full breakfast to fuel your day, served by your innkeeper with any food allergies or restrictions in mind (be sure to tell the inns of these food needs prior to arrival).

Spend some time going over your itinerary for the day with your innkeeper who will offer maps, directions, tips on great photo hotspots, and little known places to discover Maine’s coastal beauty.

ME - Nubble Light - York ME 04Nubble Light

First event of the day:  Enjoy a driving tour of Kennebunkport, stopping along the way to walk on the many beaches to smell the salt AIR and even take a dip in the cold Maine waters.  Along the way photo stops will surely include Walker’s Point, President Bush’s summer home, and St. Anne’s Church, set on a cliff overlooking the ocean. If lighthouses are a must-see for you, head to York Beach on your driving tour for a view of the quintessentially Maine Nubble Light and a walk along York Beach’s wide sandy shores. 

Return to Dock Square to visit the beautiful shops and visit Alissons Restaurant, famous for their seafood or The Clam Shack, famous for its lobster rolls, open May through October. 

Seashore Trolley Museum

Seashore Trolley Museum

Spend the afternoon exploring two museums capturing the lore of the Kennebunks.  First, The Brick Store Museum, open year round in Kennebunkport, and learn all about the history of the region.  Next, a trip to the Seashore Trolley Museum, also open year-round in Kennebunkport, will reveal a surprisingly interesting look at the history of transportation in Southern Maine.  

Return to the inn for complimentary afternoon refreshments and to rest and re-group.

Enjoy dinner at a Kennebunkport favorite, Federal Jack’s offering locally crafted beers and a wide variety of options.  If fine dining and elegant service are more your style, consider the White Barn Inn, one of the only five-star/5 diamond dining experiences in Maine.  

Day 2:  Kennebunkport Maine: A day of foodie & FUN adventure

Fuel up for the day with a homemade and hearty breakfast at your inn.  

Your innkeeper is happy to provide directions and maps to help plan the day.

Start your day by getting in on one of the Kennebunkport Foodie Tours.  Enjoy a walking tour of Kennebunkport’s locally made specialty foods. (Additional fee; open June through October).

Delicious Lobster Roll

For lunch, enjoy a trip to Mabel’s Lobster Shack, a favorite of President Bush’s, or Cape Pier Chowder where you can dine on the pier on fresh lobster off the boat from May – October.  

Visit one of the local wine purveyors for tastings.  HB Provisions offers tastings year round on Thursday and Down East Wine Imports offers free wine tastings on Saturdays until 5pm. 

Spend some time on the water enjoying a sail aboard Schooner Eleanor.

End your day at one of Kennebunkport’s many fine restaurants.  Your innkeeper can help make reservations and offer suggestions depending upon your inclination for the evening.

Day 3:  Kennebunkport to Rockland:  Stay at Granite Inn, LimeRock Inn or Berry Manor Inn

Start the day with breakfast at the inn and check out by 11:00am.

Suggested stops along the way: 

Coastal Maine Botanical Gardens

  • Stroll along Portland, Maine’s Commercial Street stopping into shops and visiting Portland’s restaurants.
  • Continue up the Coast to Boothbay region and stop by the Coastal Maine Botanical Gardens to stretch your legs and view beautiful gardens and floral exhibits. 

Check in to Berry Manor Inn, LimeRock Inn or Granite Inn any time after 3:00pm.

Stroll down to Main Street and Rockland’s vibrant harborfront to visit stores and acclimate to your next destination or stroll out on to the Rockland Breakwater, a .7 mile seawall suitable for walking (wear sturdy shoes or sneakers) to the lighthouse at the end for a fabulous view of the harbor.

Evening:  Enjoy dinner at one of Rockland’s original restaurants, Café Miranda, offering a wildly varied menu with an eclectic flair. Open year-round.  

Day 4:  Rockland, Maine:  A day on Penobscot Bay & Rockland

Start out the day with a gourmet multi-course breakfast served by your innkeepers.

Take some time to go over your itinerary with your innkeeper who will share ideas for best routes and things to see along the way.

Enjoy a Day on the Bay.  First, jump aboard Captain Jack’s Lobster Adventure and learn all about Rockland’s self-proclaimed title of Lobster Capital of the Universe along with other lobster lore.  You’ll pull traps with Captain Jack, a salty Rockland Lobsterman anytime May – mid-October. 

A Morning in Maine Coastal Ketch

Return to the dock and go for a sail on the Morning in Maine, a historic 55’ ketch where you’ll learn all about the history and natural resources of the region.

Return for lunch at The Brass Compass, just a short stroll from the pier, where you simply must try the Lobster Club Sandwich, which won a throwdown with Bobby Flay. You can also sample some fine home cooking at Home Kitchen Cafe.

Spend the afternoon exploring Rockland’s wonderful museums, starting with the Farnsworth Art Museum and Wyeth Center.  You’ll find a gem of a collection from the famous Wyeth painters here along with works from other Maine artists too.

Next, it’s on to the Maine Lighthouse Museum housing the largest collection of lighthouse artifacts in the country, and a fabulous shop for finding lighthouse souvenirs.

Finish up your museum visits with a stop in at the Project Puffin Center on Maine Street to learn all about the work the Audubon Society is doing to save these quintessentially Maine birds.

Return to the inn for a complimentary afternoon slice of pie, cookie or snack and get ready for a night on the town.

Enjoy dining in one of Rockland’s fabulous restaurants including In Good Company, Rustica Cucina Italiana or Primo, owned by James Beard Award winning chef, Melissa Kelly (reservations required well in advance here).  If a beautiful ride and a lobster dinner on the wharf or next to the ocean is more your idea of fun, enjoy the beautiful ride to McLoon’s Lobster Shack or Ship to Shore Lobster.  

Day 5:  Rockland to Bar Harbor: Stay at Saltair Inn

View from the Penobscot Narrows Bridge Observatory

Enjoy a hearty breakfast with other guests then bid your innkeepers goodbye by 11:00am.

Drive up Route 1 through scenic towns like Camden, Belfast and take time for photos at the Penobscot Narrows Bridge.

Arrive in Bar Harbor in time to check in, enjoy a complimentary afternoon refreshment, and explore the locally owned Main Street shops and eateries.

If you haven’t gotten enough lobster yet, visit Thurson’s Lobster Pound located right next to a working harbor in a quintessentially Maine setting.  If a departure from lobster is more in order, you might try Poor Boy’s Gourmet, a local favorite casual hangout where everything is delicious. 

Day 6:  Bar Harbor: A day in Acadia National Park

Early risers may want to get up with the milkman and drive to the top of Cadillac Mountain to be among the first in the country to see the sunrise.  This is a favorite activity among visitors to Bar Harbor.

Return to the inn for a hot and hearty multi-course breakfast, or if you’ve made arrangements ahead the night before, take a breakfast-to-go with you for the day.

Jordan Pond in Acadia National Park

Spend the day in Acadia National Park, driving the Park Loop, renting bikes and taking a ride on the famous Carriage Trails (45 miles of interconnected car-free gravel roads), and enjoying the delicious hot and steaming popovers at the Jordan Pond House.  You’ll want to reserve a full day for exploring Acadia. 

Return to the inn for a complimentary beverage and homemade snack before dinner.   

Enjoy dinner at one of the many excellent restaurants in town.  Your innkeepers are more then happy to suggest options and make reservations.

Day 7:  Return home

You’ll finish your itinerary with another hot and hearty breakfast.  Be sure to bid goodbye by the 11am check out time and then plan to return home.