South Shore, Massachusetts
Our Story
A love of sailing, a beautiful boat, and the most stunning sunsets in New England.
How It Started
Born on the Water
South Shore Sunset Sail Cruises started with a simple idea: share the magic of sailing on Boston Harbor with people who've never experienced it — and with those who can't get enough of it.
The Aloha is a stunning 38' sailboat that has called Hingham Harbor home for years. She's spacious, comfortable, and perfectly suited for the waters of the South Shore — from the quiet coves near Hingham to the open expanse of Boston Harbor.
Every sail is different. Some guests come for a romantic evening on the water. Others bring their families, their friends, or their colleagues. Some just want to watch the sun go down from somewhere beautiful. Whatever brings you aboard, we promise you'll leave with something you didn't expect — a sense of calm, a memory you'll keep, and maybe a new love for the sea.
What We Believe In
Safety First
Your safety is our top priority on every sail. Aloha is fully equipped and maintained to the highest standards.
Personal Experience
Every charter is private — just your group and your captain. No strangers, no crowds, just the open water.
Local Knowledge
We know these waters intimately. From the best sunset angles to the hidden anchorages, we'll show you the South Shore at its finest.
The Vessel
Meet Aloha and Captain Eric
Aloha is a 2018 Jeanneau Sun Odyssey 389 — a spacious, comfortable sailboat built for the New England coast. With a wide cockpit perfect for socializing, a fully equipped cabin, and sails that catch even the lightest summer breeze, she's the ideal vessel for an unforgettable evening on the water. At the helm is Captain Eric, a former Naval Officer who has been sailing since the age of five. With more than 25 years on Boston Harbor, he brings deep local knowledge and a genuine love of the sea to every sail. When he's not aboard Aloha, Captain Eric serves as a part-time captain of an 80' Schooner in Boston Harbor and teaches the Massachusetts Safe Boating Course — so you're in very good hands.
Come Sail With Us
We'd love to have you aboard. Reach out to check availability and plan your perfect sail. Call 781-635-7963