At Sail Portland Maine, we believe Portland’s small businesses deserve a break — the kind with sea breeze, harbor views, and room to reconnect. That’s why we’re now offering an exclusive small business discount to our fellow local companies. Whether you’re running a restaurant, shop, or creative studio, you can enjoy 30% off private charters designed specifically for Portland’s hardworking business community.
A Local Charter for a Local Crew
Our private charters aren’t your typical outing. They’re designed to give you and your team a front-row seat to Casco Bay — lighthouses, rocky islands, working lobster boats, and the best views of the Portland skyline you’ll find anywhere.
You’ll be cruising on the Calista Ann, our beautiful, spacious Motor Yacht, designed to provide comfort and style as you enjoy the stunning views of Casco Bay. With room for up to 12 people, it’s perfect for small teams or intimate gatherings, ensuring a personalized and memorable experience on the water.
Plus, your charter is totally customizable. Morning coffee cruise? Late afternoon reset? Sunset on the water after a long week? We’ll make it happen.
Who It’s For
These charters are ideal for:
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Staff appreciation days — Show your team they’re more than just essential.
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Team-building outings — Skip the awkward icebreakers and let the conversation flow naturally on the bay.
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Client thank-yous — Impress your customers with a real taste of Portland’s charm.
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Retail, food service, trades, creatives — if you’ve got a tight-knit crew, this is for you.
From One Local to Another
Sail Portland Maine is a small business too, and we get what it means to wear all the hats. That’s why these charters were built with Portland’s business community in mind — not as a tourist offering, but as a real resource for connection, celebration, and a bit of well-earned rest.
Captain Ian has been cruising these waters for years, and he’s happy to work with you to create a trip that fits your schedule and style. Whether you’re looking for something low-key or a bit more curated (think drinks, snacks, or even a narrated harbor tour), you’ll get something personal, professional, and distinctly Maine.
Let’s Get You on the Water
We’re not blasting this offer out to tourists or listing it on the front page. This is just between locals. If you’re a Portland-based business interested in planning a cruise for your team or clients, reach out directly to Captain Ian to learn more about our small business discount for local companies. You keep Portland running — let us help you catch your breath. We’ll see you on Casco Bay!