




Available languages
6 hours
Mobile ticket
All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests.
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
Travel time is included on the total tour duration
Eastern Promenade
The Eastern Promenade stretches along the eastern edge of the Portland peninsula, overlooking Casco Bay. It is easily accessible from downtown Portland and is a popular destination for locals and visitors alike. The park features a picturesque waterfront promenade that runs parallel to the shoreline, offering unobstructed views of the bay and its islands. Visitors can enjoy panoramic vistas of sailboats, fishing boats, and ferries navigating the waters, as well as views of nearby lighthouses and coastal landmarks.
Portland Observatory
The Portland Observatory is situated on Munjoy Hill, providing panoramic views of Portland Harbor, Casco Bay, and the surrounding coastline. The hillside location offers a strategic vantage point for observing maritime activities and signaling incoming ships. Built in 1807 by Captain Lemuel Moody, the Portland Observatory is the only known remaining maritime signal tower in the United States. It was constructed as a private enterprise to provide a communication system for merchants and shipowners to track approaching vessels and facilitate trade in Portland's busy harbor.
Pickup included
Private transportation
Air-conditioned vehicle
Local Driver Guide
Parking Fees
Lunch
Gratuities
Select a pickup point
All sales are final. No refund is available for cancellations.
20 reviews
Total reviews and rating from Viator & Tripadvisor
Jolene S,Oct 23, 2025
- Review from Viator
Our driver didn’t show up. I had no notice though he said he sent a text. He was sick and since we didn’t want to get sick I’m glad we didn’t go.
Cathy S,Oct 12, 2025
- Review from Tripadvisor
We love private tours and find them to be well worth the extra expense as having it personalized and flexible is great. Our tour guide Steve did not disappoint. He was highly knowledgeable,informative and punctual. He even went out of his way to help us find a last-minute restaurant for our anniversary dinner that evening. Highly recommend.

Cathy S,Oct 12, 2025
- Review from Viator
We discovered private tours a few years ago and would not have it any other way. Steve was incredible knowledgeable and informative. Highly recommend.
ginnys237,Sep 26, 2025
- Review from Tripadvisor
We had a great day with Don our private tour guide. We were hoping for a nice day taking in the beauty of coastal Maine and Don exceeded all or expectations! As a life long resident of Maine, he was able to share the history, geography, and his personal experiences! He was extremely knowledgeable on local stories such as York and its lighthouse, specifically the little baby being carried to the lighthouse and the Bush Compound and Churchill. Don took us to Barnacle Billy’s for lunch and the lobster rolls, service, cold draft beers, and atmosphere were all excellent! Our table had a beautiful water view and was centrally located 5 minutes out of downtown Ogunquit. We had time to shop in Kennebunkport and to take in the beautiful architecture including the wedding cake house! We also visited York Maine and Kennebunk! We really enjoyed spending the day with Don! Simply a fabulous day!!!
Paul J,Sep 18, 2025
- Review from Tripadvisor
The tour of Portland and Kennebunkport was excellent, relaxed, comprehensive, and absolutely beautiful. We were lucky to have Steve as our guide, and he was extremely knowledgeable, considerate, accommodating, organized, and pointed out so many places that were off the beaten path. We were picked up on time, even though we were almost an hour early getting off the ship. Steve was very easy to get a hold of and always answered his phone. We had a fantastic meal at the boathouse restaurant in Kennebunkport. We always had plenty of time to use the restroom, have free time to walk around and see the stores, as well as making sure that we hit all of the important sites. If you are considering a private tour of Portland and or Kennebunkport, this tour is absolutely for you and hopefully you will get Steve as your guide. Fantastic day, fantastic guide, fantastic tour!
T6777ZUamyg,Sep 14, 2025
- Review from Tripadvisor
Had a fantastic day in Portland & Kennebunkport! Took the 6 hour private tour & thoroughly enjoyed it. Our guide, Steve, was prompt, very knowledgeable, so courteous & very helpful with recommendations for dinners, etc. Highly recommend this trip!!




Crappie49,Jul 24, 2025
- Review from Tripadvisor
Steve our tour guide took us on a trip back in time. We had the most amazing time. Steve’s knowledge and attention to detail was impeccable. He made it perfectly clear that this tour was all about us and making sure we enjoyed the tour. At the end of the tour I realized two things. 1. That this tour had ingrained Maine as a destination that my family and myself would return to on a regular basis. 2. That I had made a true friend in Steve. Thank you sir…..







Pam T,Jul 3, 2025
- Review from Tripadvisor
Great Van tour, you get to cover a lot of ground comfortably with a great guide. Don was very accommodating and knowledgeable. We have a lovely day!
H8180UVgregoryr,Jun 11, 2025
- Review from Tripadvisor
Great tour around all of Portland Maine, and then up to Kennebunkport. Guide Steve McCarthy was knowledgeable, interesting, friendly, and a joy to be with. Recommend highly,
H8180UVgregoryr,Jun 10, 2025
- Review from Tripadvisor
Guide Steve Grasso guided four couples on a fabulous tour of Portland Maine up to Kennebunkport. Steve was knowledgeable, interesting and fun. Every part of the tour was enjoyable. HIGHLY recommended!






Operated by Maine Day Trips & Tours