Matinee Bay Cruise - Photo Credit: Kristina O'Brien Photography
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Private, Luxury Boat Cruise

Discover the beauty of Casco Bay aboard Wayfinder, a private luxury charter for up to six guests. Cruise past historic lighthouses, secluded islands, and abundant coastal wildlife while enjoying personalized service and breathtaking views. Whether relaxing with cocktails, sightseeing, or celebrating a special occasion, Wayfinder offers an unforgettable Maine experience on the water.

Packages & Deals > Find Your Way Charters > Happy Hour + Drinks > Private, Luxury Boat Cruise
Valid Jun 1, 2026 to Nov 1, 2026
About the Deal & How to Redeem

Our tours depart from either the Portland Old Port or Yarmouth Boat Yard. We offer a variety of tour options to help you create your ideal experience on the water. In addition to fully custom tour options, we offer the following packages:

Matinee Bay Tour: ($600.00 total for 6 guests) Set sail for a leisurely cruise and experience the beauty of Casco Bay. This private boat charter lasts approximately two hours, allowing you to visit some of Casco Bay’s most iconic sights. Designed for up to six guests, our tour includes a selection of beer, wine, and non-alcoholic beverages. We will ensure the boat is stocked with Maine-made snacks and treats tailored to your desires and dietary needs. NOTE: The starting time for these private boat charters is between 10 AM and 1 PM

Seal Colony Visit: ($700 total for six guests) Cruise out for a visit to one of our thriving Harbor Seal Colonies on one of the best Casco Bay tours. This two-hour private charter starts on the Royal River and heads out into Casco Bay, where you can see our local Harbor Seals up close. This tour includes up to six guests and includes a customized selection of beer, wine, and non-alcoholic beverages. Additionally, we will stock the boat with delicious Maine-made snacks and treats, catering to your desires and dietary needs.

Sunset Cruise: ($1,000 total for six guests) Set sail for a leisurely cruise in Casco Bay to watch the sun set. We will explore the iconic sights of the bay and enjoy a beverage of your choice while taking in the best view of the Portland Head Light. This private boat charter includes up to six guests. The tour includes a customized selection of beer, wine, spirits, and non-alcoholic beverages. Additionally, you will receive a Boat and Tote bag filled with Maine-made snacks and treats that cater to your desires and dietary needs.

Beer or Wine Tasting Cruise: ($1,400 total for six guests) Experience the best of Maine with our private boat charters. Savor some of the state’s best craft beer selections while taking in the stunning views of Casco Bay. Indulge in a wine-tasting experience featuring bottles curated to match your preferences. This exclusive tour is designed for up to six guests, and we’ll stock the boat with Maine-made snacks and treats tailored to your desires and dietary needs. Join us for approximately four hours of unforgettable Maine experiences.

Sea Glass Hunt: ($1,400 total for six guests) With its rough waters and rocky beaches, Casco Bay provides the perfect environment for the creation of sea glass. Unlike the mainland, where these treasures get picked over by the crowds, the islands offer plenty of opportunities for great finds. On this Casco Bay tour, embark on a private charter for a unique Maine experience. This private, four-hour tour accommodates up to six guests and includes an extended stop at the beach for hunting. Enjoy a picnic lunch while you hunt.

“Rum Runner” Spirits Experience: ($1,600 total for six guests) The “Rum Runner” Tour offers a unique opportunity to explore the stunning beauty of Casco Bay while indulging in rare and interesting spirits. This private boat charter accommodates up to six guests and features six tastings from four selections of spirits, including whiskey, bourbon, rum, and more. For an updated list of our available selections, feel free to reach out. This memorable experience lasts four hours, with destinations chosen by you, ensuring a personalized adventure.

For more information about any of these tour options, please feel free to visit our website at findyourwaymaine.com or to call (207)358-8245. In the event of unpleasant or unsafe weather, we will endeavor to reschedule the cruise for you, with a full refund offered if that is not possible.

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