Let’s Go Sailing in Maine – Book Your Charter Today!

Sail Maine with Seakindly Charters.
Enjoy sunset cruises and day sailing in Maine aboard Juliet with Captain Brock and Seakindly Charters.

Seakindly Charters offers private, captained charter sailing trips out of Portland, Maine, aboard a lovely 35-foot cruising sailboat named Juliet. We specialize in day trips and sunset cruises on Portland Harbor, Casco Bay, and offshore along the stunning Maine Coast.

Join us for a custom two, four, or six-hour sailing tour. The sightseeing is fantastic. You’ll see the Old Port’s working waterfront, beautiful Casco Bay islands, lighthouses, lobster boats, seals, porpoise, and other marine wildlife (possibly whales!). And the sailing in Maine is absolutely world class!

We can accommodate groups up to six people, and we welcome aboard individuals, couples, friends, families, and kids–anyone looking to have a great time out on the water.

If you or your group members have sailing experience, feel free to hoist the sails and take the helm. If you don’t have sailing experience, we can show you the ropes and give you a few sailing lessons. Either way, feel free to simply sit back, enjoy the ride, and let Captain Brock take care of everything during your sailing adventure!

Learn more about Seakindly Charters, our sailing trips, the boat, and Captain Brock >>

We Love Sailing in Maine Even in Light Wind

Maine is a sailor’s paradise during the spring, summer, and fall months with warm weather and ideal wind. But we love sailing in Maine when it’s calm, too. Enjoy this video of sailing vessel Juliet cruising Portland Harbor and Casco Bay in light-wind conditions.