Coastal Maine Day Trips
There are a lot of ways to get out on the water in Maine, but this one’s a little different. We’re a small, family-run sailing charter, and Sasa isn’t just a boat—it’s our home. Every sailing day trip in Maine we offer is private, unique, and fully customizable, built around your group’s vision of a perfect day on the water. Whether we’re exploring the islands of Casco or Penobscot Bay, sailing to Sequin Island Lighthouse, or anchoring at a secluded island for a swim, the goal is simple: give you a day that feels easy, personal, and genuinely fun.
Half-Day Charter
A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This private Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, and maybe sneak in a swim on a warm day.
Example Itinerary:
We’ll depart from downtown Portland and sail into Casco Bay, passing Portland Head Light for an up-close view from the water before weaving through quintessential Maine islands. When the moment’s right, we’ll drop anchor for a swim or a relaxed break before a serene sail back to the harbor.
What’s included:
Private sailboat, captain + crew
Light refreshments (fresh pastries or charcuterie, based on time of day), a post-swim digestif (usually a crisp, refreshing glass of wine), and non-alcoholic options such as sparkling waters and sodas
Option to take the helm or brush up on your sailing skills
Time to swim or relax at anchor
A flexible route based on conditions and your vibe
Not included:
Onshore stops for lunch, shopping, or exploring (like Peaks Island).
If you’re looking to get off the boat and explore, check out our full-day sailing charter options.
Full-Day Charter
If you want the full experience, this is it. A full day sailing charter in Maine gives you the best of Maine from the water, time sail, relax and swim, and then stop at some of Maine’s hidden gem islands and coastal towns to explore, grab a bite, and get the full coastal Maine experience.
Example Itinerary:
Departing from Rockland Harbor, we’ll sail north along the coast toward Camden, passing classic Maine shoreline and quiet coves along the way. Once in Camden, we’ll pick up a mooring and head ashore for lunch and exploring in an iconic Maine waterfront harbor. Then back on the boat for a perfect afternoon sail, an optional swim stop, and plenty of time left for relaxing and taking it all in.
What’s included:
Private sailboat, captain + crew
Light refreshments (ie fresh pastries or charcuterie), a post-swim digestif (usually a crisp, refreshing glass of wine), and non-alcoholic options such as sparkling waters and sodas
Option to take the helm or brush up on your sailing skills
Time to head ashore and explore coastal Maine towns or private islands, a stop to swim or relax, and take it all in
A flexible route based on the itinerary and sailing waters of your choosing
SUNSET SAIL
Simple, stunning, and hard to beat. A sunset sail is shorter, but the timing does most of the work. The light, the breeze, the end-of-day calm make this the perfect way to experience one of Maine’s spectacular sunsets.
Example Itinerary:
We’ll head out from the harbor of your choice in the late afternoon, find a good stretch of water, and sail through golden hour as the sun drops. No big agenda, just a great time on the water, and really great views.
What’s Included:
Private sailboat, captain + crew
Sunset snack essentials (wine + charcuterie), and non-alcoholic options such as sparkling waters and sodas
Option to take the helm or brush up on your sailing skills
Sunset timing on the water
A flexible route based on the itinerary and sailing waters of your choosing
