The Rocky Coast of Maine

Featuring Kennebunkport, Boothbay Harbor and Rockport

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Maine’s seaside towns are known for their perfect waterfront locations and bustling summer scene. Feel the coastal charm as you enjoy the area’s lighthouses, crashing surf, rocky shores and, of course, lobstah!

Day 1 - Kennebunkport (D)
Cross the border into Maine and enter the “Vacation State.” Arrive at Dock Square, the hub of the hubbub in Kennebunkport, built on wharves over the river. A colorful jumble of onetime fishing shacks, Dock Square now boasts galleries, cafes, boutiques and restaurants galore. Enjoy plenty of time for shopping and lunch on your own before joining your local guide for a tour of the ’Port. Drive past sandy beaches, rocky coastline and the George Bush Estate on Walker’s Point. Learn about the legend of the Wedding Cake House and visit the seaside Franciscan Monastery.

Check into the Boothbay Harbor Inn, your home for three nights. The Inn boasts the best location in town, on the waterfront and adjacent to the town’s famous wooden footbridge leading to the heart of downtown. Finish the day with a three-course Lobster Bake Dinner served at the Inn’s Waterfront Restaurant.

Day 2 - Boothbay Harbor (B)
Begin the day with a guided tour of Boothbay Harbor focusing on the town’s history and folklore. Then, take to the water with a narrated cruise, with close-to-shore cruising displaying the neighboring islands, rocky coast, old fishing villages and summer homes. The boat will dock in the center of downtown Boothbay, where you’ll spend a seaside afternoon with lunch and shopping on your own. Relax this evening at your waterfront hotel, or ask your Tour Director for recommendations for dinner spots and fun things to do this evening.

Day 3 - Rockport and Camden (B)
Today, explore the picturesque villages of Rockport and Camden, known as the prettiest towns in Maine. These mid-coast towns boast charming town centers, New England architecture and ocean views. Begin
at Pemaquid Lighthouse, one of Maine’s most scenic beacons and one of the few you can go inside! Visit the fisherman’s museum, see the church-turned-gallery, winding up in Camden, where the mountains meet the sea! After time on your own for shopping and lunch, we’ll finish the day with a visit to Camden Hills State Park. Motor to the summit of Mt. Battie with stunning, panoramic views of Penobscot Bay. The rest of the day and evening is yours. Make it a night on the town, take a sunset swim or relax at the hotel.

Day 4 - City By The Sea (B, D)
Spend the day in Maine’s largest City-by-the-Sea! On a guided tour of Portland, explore this old port’s fishing wharves, seaside promenade, sea captain houses and historic neighborhoods overlooking the bay. Finish with a breathtaking stop at the world famous Portland Head Light, the most photographed lighthouse in America.

The afternoon is yours to discover this quintessential Maine town. On your own, choose from the many restaurants and cafes for lunch, while visiting all of the sites. Finish the day with a farewell lobster dinner at Demillo’s overlooking Portland Harbor and Casco Bay. After dinner, turn in for a good night’s rest at the Hilton Garden Inn in downtown Freeport. 

Day 5 - Freeport to Home (B)
Freeport is known as the outlet shopping capital of the country. What will you find at the famous brand stores and local shops? It wouldn’t be a trip to Maine without a visit to the flagship LL Bean Store – don’t miss it before we head home with souvenirs, good memories and new friends!

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  • $949 Triple
  • $999 Double
  • $1,425 Single


  • Boothbay Harbor Cruise, Lobster Bake Dinner
  • Guided Tour Kennebunkport, Boothbay Harbor,
  • Rockport and Camden, Boothbay Inn Waterfront Hotel
  • 4 Nights Hotel, 6 Meals
  • Upper Class Tour Director, Taxes & Gratuities


Sunday August 11th, 2019

  • Yonkers 6:00am
  • Mamaroneck 7:00am


Thursday August 15th, 2019

  • Mamaroneck 6:15pm
  • Yonkers 7:00pm