harbor sail portland maine

When the weather is warm, there isn’t any better place to enjoy yourself than gliding through the glassy waters of the Casco Bay during a harbor sail in Portland, Maine. Sail Portland Maine is here to give you a personal sailing experience unlike any other! Our day sails take you through the harbor, where you’re likely to see some of the diverse wildlife, historic structures, lighthouses, coastal islands, and more.

We provide daily two-hour public or private harbor sails with multiple trip options for you to choose from. The professionally-captained Eleanor Hawkes has room for up to 6 people, making it one of the smallest chartered sails in Portland – and one of the most intimate, crowd-free experiences on the water! Our newest boat, the Calista Ann, has room for a minimum of 8 guests and a maximum of 12 guests, so you can still experience the same privacy 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 happens if it rains at the time of my sail?

We typically continue our sails in a shower or light drizzle, but will usually cancel the sail in a steady rain or downpour that would make the trip uncomfortable. *See cancellation/rescheduling policy


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.


May we bring along food and/or alcoholic beverages?

Yes, you may bring along any food, beer or wine.


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

Make the most out of the summer season with the best harbor sail in Portland, Maine. Whether you’re visiting from out of town, planning a unique, intimate event, or simply spending time with loved ones, let us provide you with the best possible chartered sailing experience. For a memory you’re sure to reminisce about for years to come, book your sail with us at Sail Portland Maine today!