Portland – Kennebunkport Private Escorted Tours

Portland & Kennebunkport Tours

Something for Everyone

~ See and hear about Portland's historic landmarks. ~ Photograph the rocky coast of Maine at Portland Head Light. ~ Enjoy the best New England clam chowder along with the best Maine lobster available ~ Shop in Maine's best quintessential areas - Old Port, Portland and Dock Square, Kennebunkport. ~ Private cruise ship Portland shore excursions available for individuals, couples and large groups. ~ Tour is typically 9:00AM to 3:00PM (6 Hours Total and we can extend a bit for an additional fee)

Start your private daytrip with a narrated tour of Portland’s historic landmarks.  Portland was founded in 1632 and has a long and colorful history. See magnificent views of Casco Bay as you proceed around the Portland peninsula. After a short drive to Cape Elizabeth, stop and explore Portland Head Light that was first lit in 1791. Commissioned by President George Washington, it is Maine’s oldest lighthouse.  A short stroll along its cliffs brings Ram Island Ledge Light into view across the ship channel. 

Driving the back roads, you will be able to experience the views of the magnificent rocky coast, with winding ways through farmland and saltwater marshes, on the way to the quintessential New England town of Kennebunkport.

Explore Kennebunkport, which is alive with history, grand ocean views, wonderful restaurants, and interesting shops.  You will see many historic ship-captain homes from the 19th century with interesting stories.  A view of the summer home of Presidents Bush is interesting and very scenic as it juts out into the Atlantic Ocean.

Stopping in Kennebunkport, for the freshest lobster rolls and seafood, provides an opportunity to have a memorable lunch and explore the local shops.

Historic Landmarks

Learn about early Portland and its historic and unique landmarks on our driving tour: Fort Allen Park, Portland Observatory, Eastern Cemetery, First Parish Church, Wadsworth-Longfellow House, Victoria Mansion and more.

Portland Observatory
Professional Guide

Enjoy spending time with our experienced local guides who will make sure you have a comfortable, fun and memorable experience.

Rocky Coast

Photograph the glaciated rocky coast of Maine and its iconic lighthouses.

Portland Head Light
Pickup & Drop-off

We pick you up at your location, ship pier or train station to start your day trip in the most comfortable way. Private and customized Portland cruise ship shore excursions available for individuals, couples and large groups.

Portland Old Port
"I cannot give enough praise for the tour we received from Leigh. Before going with Leigh, we told her what we were most interested in seeing and doing, and she designed the perfect tour! (For those who are unsure what they want to see, she’ll also design a tour on the fly.) We asked to see lighthouses and buildings and areas of historical significance. Since we’d never been to Maine before, we wanted to get a taste of everything possible. Her knowledge of the area and its history was exceptional. We immensely enjoyed everything about the tour, including her. By the end of the day we felt like we’d made a new friend. I highly recommend Leigh and these tours. They are well worth the money."
Babb's Covered Bridge
Janis L.
"We loved this fantastic service that Maine Day Trip Tours provides. The tour was fabulous as well as educational. Norm knew a great deal about the history of Maine. I can honestly say I had so much fun."
Babb's Covered Bridge
Doris W.

Create Your Own Itinerary

Do you have something special in mind? We can’t wait to show you around!