A Thank You to Our Fellow Portland Businesses

At Sail Portland Maine, we want to say thanks — and offer a little something just for our fellow local businesses.

30% Off Charters for Local Businesses

We’re offering 30% off our private sails to Portland-based restaurants, retailers, salons, service providers, and small businesses of all kinds. Use code B2B when booking online, and just confirm with a business email or reach out directly to the captain. That’s it.


Make It More Than Just a Day on the Water


🪴 Give your staff a chance to relax and recharge
🧭 Bring your team together outside the usual routine
🎁 Offer clients a memorable, local thank-you they won’t forget


We’ve got you covered. Our private charters cruise the beautiful waters of Casco Bay with views of lighthouses, islands, working lobster boats, and the Portland skyline — the good stuff, the real Maine.


What’s Included


  • Private boat charter aboard our motoryacht, Calista Ann (morning, afternoon, or sunset options)
  • Room for your whole crew (up to 12 guests)
  • Friendly, laid-back captain who knows the bay like the back of his hand
  • BYOB, snacks, whatever will make your trip enjoyable!


How It Works


  1. Book your private cruise below and enter code B2B
  2. Use a business email or connect directly with Captain Ian to confirm
  3. Hop aboard the Calista Ann and enjoy the best views of Casco Bay

We know what it takes to keep a business running in this city. Let us help you press pause, reconnect with your team, and soak up the Maine coast from a whole new perspective.

You take care of Portland — let us take care of you.

Cancellation Policy

We will give a complete refund in the event of unsafe conditions determined by the captain at the time of the sail. The trips are rain or shine. Also, we will refund you if you cancel with two weeks' notice before your scheduled reservation time. You may receive a voucher for the price of your charter within the 2 to 1 weeks before the scheduled trip. There are no refunds for cancellations received less than one week before date of your scheduled reservation and there are no refunds if you miss your reservation.

If you need to cancel your trip for any reason, please contact us as soon as possible.

CONTACT US