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Sip and Sail Through Casco Bay With Us This Season

Sail-Casco-Bay

Last year was the first time we took our beer education and experience out on a sailboat. Our weekly Sails and Ales tour offerings featured a different local brewery each week, and the series was very successful. This year, as people are looking for safe ways to explore Portland, Maine, we have expanded our wind-powered options to include three different outings. Sip and Sail through Casco Bay with us on these new charter options in partnership with Calendar Islands Sailing Company!

Step aboard a beautiful 60-foot sailing yacht for 2 hours or more of sailing the tranquil waters on Casco Bay while you sample a selection of craft alcohol from our incredible local producers.

Casco Bay plays host to some of the most beautiful and diverse scenery on the Maine coast. From the rugged rocky cliffs of the many islands to the gently wooded shorelines of the mainland, the views will charm and captivate you.

​For the duration of this season, we will be offering these sailing trips on a private charter-only basis. We have made this change to maximize guest safety and comfort.

You can select your date and time when booking, which is based on the availability of the sailboat and the crew. The standard sail period is two hours, longer durations available upon request.

An expert from The Maine Brew Bus will be aboard to talk about in detail and answer your questions about the products being featured! Also included with your sail will be a charcuterie board featuring a selection of meats and cheeses and fresh fruit.

a tray of food on a wooden cutting board

Three different options of sailing adventures can be selected when booking with Calendar Islands Sailing Company: Sails and Ales, Waves and Wines, and Sails and Spirits.


Sails and Ales

a screenshot of a social media postA unique way to drink great local beer on the waters of Casco Bay!

Three 16-ounce cans of different types and styles of craft beer will be available for each person and are included in the charter price. A beer expert from Maine Brew Bus will talk about the brewery and answer your questions about the beer being featured.

Learn how to properly evaluate beer through your senses, and try pairing each beer with the different meats, cheeses, and fresh fruit on the charcuterie board.

Over the course of the cruise, your beer guide will discuss the key role that Portland had in kicking off Prohibition and how we have grown to now have over 150 breweries scattered throughout the state. – Learn more about our Sails and Ales outings

Waves and Wines

a screenshot of a social media postWith glasses of Maine wine in hand, let’s sail around Casco Bay on our Waves and Wines tour!

This sail will also feature three different wines from a Maine-based winery. We’ll talk about why some grapes actually work very well in Maine, and also how wines can be made from other native agricultural products.

A craft alcohol expert from Maine Brew Bus will pour each style and answer your questions about the wines that are featured.

Typical offerings may include Cellardoor Winery, eighteen twenty wines, or Blue Lobster Urban Winery. – Learn more about our Waves and Wines sails

Sails and Spirits

a screenshot of a social media postLearn about the craft distillers that are making great spirits here in Maine.

Enjoy the sights and sounds of sailing Casco Bay while you sip on a selection of spirits made by an excellent local distillery.

A craft alcohol expert from Maine Brew Bus will pour and answer your questions about the spirits that are featured!

Try the spirits straight, and then enjoy them as they are featured in specialty cocktails.

Distilleries featured may include Stroudwater Distillery, New England Distilling, or Maine Craft Distilling. – Learn more about Sails and Spirits

See the current Health and Safety policies for Maine Brew Bus tours here.


Don Littlefield is the General Manager of Brew Bus Tours. He enjoyed a lot of Sebago Lake water (to get ready to guide two biking brewery tours) while preparing this post. Twitter: @BeerinME