Five ways to spend Father’s Day on Casco Bay

Father’s Day is coming up this weekend and the weather forecast is looking promising. If you haven’t already made plans with your dad, you should consider spending a day on the bay! What dad wouldn’t want to enjoy the holiday soaking up the sunshine among the Calendar Islands? Whether you are looking for adventure, relaxation, or a new activity to share with your father, Casco Bay has something for everyone.

Here are five things to do on Casco Bay this weekend:

1.) Go Sailing

I always recommend sailing to people visiting Portland for the first time as well as to those locals who have yet to discover it. There are a few ways to get aboard for Father’s Day. Two-hour sails on traditional windjammers and schooners are available downtown. Contact Maine Sailing Adventures and Portland Schooner Company for updated schedules and special events. Beer and wine are available aboard and these magnificent vessels provide a great setting for a picnic on the bay.  Think your dad might be interested in learning how to sail? Check out my previous post for a variety of ways to help him get started!

Sailing Casco Bay with Maine Sailing Adventures

Sailing Casco Bay with Maine Sailing Adventures

2.) Visit an Island

Casco Bay is full of beautiful islands within reach of Portland. Hop on a ferry from the Casco Bay Lines terminal, or catch a private ride on one of the water taxis. Peaks Island is the most popular destination with restaurants, inns, small shops, and historic sites. Bike and kayak rentals are available as well. Another popular destination is Long Island which is excellent for walking and biking, with a beautiful beach looking out to the Gulf of Maine. For a lovely dinner on the bay, Diamond’s Edge Restaurant on Great Diamond Island is a short ferry ride from Portland but feels worlds away.

3.) Tour the Bay

A variety of companies provide harbor tours from Portland offering opportunities for fishing, historic sightseeing, and whale watching. If sailing isn’t your thing, consider Portland Discovery Land and Sea Tours for a look at some wildlife and a glimpse into Casco Bay’s maritime history. Casco Bay Lines also conducts scenic tours of varying lengths. For an all-inclusive look at life on the bay, check out the Mailboat Run which delivers passengers and mail to numerous islands. Riding along for the entire voyage takes approximately three hours round trip and takes you across the majority of Casco Bay.

4.) Go Fishing

Is your dad an outdoorsman? Take him out for a day of fishing. There are places to fish from shore as well as a fleet of charter boats ready to take you out. I won’t list all of the available boats here, but a quick google search will provide lots of options. If you decide to fish without a guide be sure to familiarize yourself with the local regulations. Stripers have been sighted in the bay, so why not find one of your own?  The Tackle Shop on India Street in downtown Portland has everything you need for an afternoon of fun.


A nice halibut on a boat out of Portland

5.) Go Kayaking

If you want to get up close and personal with Casco Bay, get in a kayak and explore. It’s alright if you don’t own one, rentals are available at Portland Paddle and Maine Island Kayak Co. Explore the shorelines surrounded by wildlife at your own pace. Kayaking is the best way to visit Fort Gorges, a historic structure in the middle of the bay. Land your kayak on the small beach and explore the impressive fort. If you have never kayaked, consider a lesson and be sure to keep clear of larger vessels crossing the bay.


Find your own adventure on the bay!

Happy Father’s day to all the great dads out there. I wish I was able to spend mine with my dad, but I’ll be out of town this weekend. When we get back I think we’ll have to go for a sail!

Matt Garand

About Matt Garand

Lifelong Mainer, and professional mariner, Matt Garand is the creator of A Life Aboard, a look at year-round living on a sailboat in Maine. Matt and his wife, Skye, live aboard in South Portland and use every available chance to throw off the lines and explore the coast.