Enjoy the best of Casco Bay with day charters leaving Portland. You pick your adventure. A relaxing sunset sail with a tastefully-prepared dinner of local cuisine. Or an invigorating paddle to an island destination, with Flying Circus nearby for your safety and convenience. We handle the logistics and food, so you can enjoy and unwind. Most charters listed below last four to six hours. This includes sail, island tour and meal. We charter only one tour a day, so we are flexible on the timing of yours. Realize that the wind for sailing typically “comes up” in the afternoon, so plan accordingly. The meals are prepared “homestyle” by Mike and crew on Flying Circus. We prepare our food with local organic products, much of which is from our garden at home. We try to showcase local seafood. We can accommodate individual food needs or allergies.
Relax while you sail the stunning coast of Casco Bay. This is a private charter for up to six of your guest. You provide the food and drink and we provide memories to last a lifetime. We suggest a afternoon sail that will take advantage of the wind that typically develops as the day progresses. Cost is $325.00 for up to six guest.
Learn-how-to-sail programs teach you the basics of cruising, with the goal of cruising independently and sailing bareboat charters. Learn coastal navigational skills, weather forecasting, and emergency preparation.
The Eagle Island Maine Historic Site, located 11 miles from Portland Maine, is devoted to the memory of Admiral Robert Edwin Peary, the famous Arctic explorer. Every summer, Eagle Island welcomes approximately 6,000 new visitors. The island overlooks Casco Bay and hosts a grand view of surrounding islands. The sail to Eagle Island weaves past islands, lighthouses, forts, and other historic markers woven into the lore of coastal Maine.
Sail out to historical Fort Gorges and witness the stonework and experience the history of this Civil War fort. You may choose to paddle a kayak or paddle-board and enjoy the water up close, or allow us to shuttle you to the fort in our rigid hull inflatable. Fort Gorges rests in the middle of Portland harbor and is a quick sail to Portland Headlight and other historical sites.
The Maine Island Trail Association (MITA) is the steward of these wild island gems. Each island deserves days to absorb and breathe its coastal rhythms. Unique in it own way, Little Chebeaque (100 acres) is known for its sandy beaches and mighty oaks that speak to the past. Jewell Island is a sentry that guards us from the rugged North Atlantic ocean. She is a wilderness of 221 acres that represents the character of coastal maine. On the island are World War II military tunnels and towers for exploration. Either one of these single-day island tours can include sailing and paddling.
This includes food and a four to six hour tour. This may include a paddling component and/or island tour.
There is a four-guest minimun, with six guests being the perfect size for a day charter. Call to discuss specific options for your group.
A non-refundable 50% deposit is required to reserve your charter date. We do not cancel charters due to rain, but may need to postpone charters based on high winds. We want you to have a magnificent experience. So if it is an inclement day out, we will do everything that we can do to insure your safety and enjoyment. If rescheduling is needed we will do our best to accommodate.
Tipping is appreciated. If you feel you have received exceptional service then we would gladly accept a token of your gratitude.
“I don't honestly know how to thank you for the beautiful day on the water Tuesday!! It was literally magical!!! The beautiful boat and the island-hopping through Casco Bay would have been enough...but you made it all so very personal by explaining the history of everything we saw. And our lunch was over the top! Lobster rolls and everything fresh from your garden...really? What an amazing time!! Your hospitality made me feel so blessed to spend time with you....“