Sunsets in Portland, Mainecasco bay sunset | sunset sail portland maine can be pretty incredible, which makes our sunset sail at Sail Portland Maine a no-brainer! Whether you’re a hopeless romantic wanting to share a special evening with your significant other (or even having thoughts of proposing!) or a group simply looking to enjoy the show, a Casco Bay sunset will give you an experience that is second-to-none.

We offer two-hour public or private chartered sails with several trip options for you to choose from throughout the day or evening. The Eleanor Hawkes has space for a group of up to 6 people, making it one of the smallest chartered cruises in Portland – and thus, one of the most crowd-free and intimate experiences on the harbor! Our newest cocktail cruiser, the Calista Ann, has space for a minimum of 8 guests and a maximum of 12 guests, so you can still have that same private experience for a slightly larger group!

Frequently Asked Questions

Below are some of the most common frequently asked questions we get about our sunset sails:

How long are the sails?

Sails generally last two hours for public and specialty sails. Longer trips are available upon request.

What should we bring?

Any food or beverage you like. The boat will have complimentary bottles of water onboard. BYOB!


What do I wear?

Dress as you would for walking around town, but be sure to bring an extra sweater/sweatshirt and a windbreaker with you. If you’re “on the fence” about shorts versus long pants…go with the long pants. Also useful is a baseball type cap with visor, sunglasses (polarized are best) and sunscreen. And, of course, don’t forget your camera!

Here is a helpful packing guide to help you prepare.

Is there a bathroom aboard?

Yes, but it is very small. There are public restrooms very near the piers at the marina from which our boats leave.

Sail Portland Maine

Enjoy the most best sunset sail in Portland, Maine, taking in fiery views of the city skyline and watching it reflect off the Casco Bay. Whether you’re visiting for the first time, on a family vacation or even a romantic date, our goal at Sail Portland Maine is to provide you with the best experience possible on the harbor. For a memory you’re sure to talk about for years to come, reserve your sail with us today!