Portland, Maine – Sailing with the Portland Schooner Company & our Visit to Kennebunkport.

Scarborough, Maine is a great launching point for so much to do “Downeast” as the local Mainers like to call it. We were minutes from Old Orchard Beach, Pine Point Beach, Portland, and a drive an hour north or south to Freeport (home to LLBean) or Kennebunkport (home to the Bush family compound).


Our view at the Arundel Wharf Restaurant in Kennebunkport, ME

We drove down to Kennebunkport and had a delicious dinner at Arundel Wharf Restaurant. While the parking was a bit tight, the views made up for it. The restaurant had plenty of seating, both indoor and outdoor. We were able to watch the boats come in and out of the harbor. After dinner, we walked into the quaint town of Kennebunkport.

After walking around town, we drove out to the coast to see the Bush Family Compound. While we couldn’t get an up close look, we were able to see much of it from afar.

Sailing Casco Bay with the Portland Schooner Company

Our friends, Charles & Laura, invited us to join them on a cruise around Casco Bay with the Portland Schooner Company. It was a wonderful way to see Portland and the surrounding harbor area.

Sailing with the Portland Schooner Company

Important Details

Parking: We paid $15 for 24 hours. We also did this cruise during the week, and parking was filling up by mid-morning.

To get to the Cruise boarding area, you have to walk around the Casco Bay Lines building. This is where you would catch the ferry if you were so inclined.

I would caution that the walkway down to the ship can get a bit wobbly with the water moving about, especially if the ferry is coming or going.

Pricing: We chose the 1st Afternoon Sail. Check the website for times because they change by the month. Also, there are a variety of special events listed on the website.

Two-hour Public Sails:
Morning Sail: $49 adult / $33 infant/child, 0-12
1st Afternoon Sail: $54 adult / $38 infant/child, 0-12
2nd Afternoon Sail: $54 adult / $38 infant/child, 0-12
Sunset Sail: $59 adult / $59 infant/child, 0-12

Our thoughts

Everyone wants to experience the northern part of Maine, but you should add a visit “Downeast” to the Portland/Scarborough area to your #travelbucketlist.

Join us next week as we take a trip on the Amtrak from Portland to Boston for the day!

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