Sunsets in Portland, Mainecasco bay sunset | sunset cruise portland maine can be pretty incredible, which makes our sunset cruise 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 trips 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 charter boat, the Calista Ann, has space for up to 6 guests to keep the crowd free intimate experience.

Frequently Asked Questions

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

How long are the trips?

Trips generally last two hours for public and specialty cruises. 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 cruise 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 trip with us today!