South Shore, Massachusetts
Sail Into the Golden Hour
Sunset cruises and private charters on Boston Harbor and the South Shore
What We Offer
Choose Your Sail
3 hoursSunset Cruise
The classic South Shore experience. Board at golden hour, watch the sun melt into the harbor, and sail home under the first stars of evening.
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Half or Full DayPrivate Charter
The entire boat is yours. Bring your crew, set your own pace, and explore the coastline on your terms.
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CustomSpecial Occasions
Proposals, anniversaries, birthdays, corporate outings — we'll help you create a moment that lasts a lifetime.
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The Experience
Where the City Fades and the Sea Begins
There's a moment, just after you leave the dock, when the world on land begins to fade. The noise quiets. The horizon opens. And all that remains is the wind, the water, and the people beside you.
We sail the South Shore of Massachusetts — a coastline of hidden coves, lighthouse silhouettes, and skies that seem painted just for evenings like this.
From Our Guests
Recent five-star experiences from Google.
Thales Paulino
Such an amazing experience with Captain Eric! We spent a beautiful Saturday afternoon sailing around the South Shore and watching the sunset, and it was honestly the perfect way to relax. Captain Eric was incredibly friendly and made the trip even more interesting by sharing stories about Boston’s history and the surrounding South Shore area along the way. The boat is incredible, very comfortable, spotless, and clearly very well cared for. There’s something about being out on the calm water that makes you completely disconnect and relax. By the end of the sail, I was wishing we could stay onboard for a few more days and just keep sailing! Highly recommend South Shore Sunset Sail Cruises if you’re looking for a peaceful, beautiful, and memorable experience on the water.
R Corsetti
South Shore Sunset Cruises is a fantastic way to spend a full day on the water or to capture a sunset with Boston in the background. Captain Eric is an absolute professional and knows his trade. Handling his boat with much skill, he is equally a wonderful host. He made us feel safe and welcomed. My party had a relaxing day on a well-appointed and modern 38’ sailboat enjoying both great sailing in good wind and some slower cruising to enjoy lunch. Captain Eric is also knowledgeable about the history and geography of the Boston Harbor Islands. Oh, did I mention Captain Eric is also a former naval officer? Nice to know we were in such great hands while gaining some interesting knowledge and having so much fun! We will definitely be back a few times each season!
Meghanne M.
Had a wonderful time on the Aloha! Afternoon sail was complete with sun, wind, and interesting tidbits of local history from Captain Eric. Will definitely book a sunset cruise someday.
carol campbell
Great experience. Eric and Kathleen are fabulous hosts. Beautiful and very clean sailboat Highly recommended
M.Q. McCarthy
We had an amazing experience sailing with Eric. The boat was gorgeous and comfortable. We sailed through the Boston Harbor and Eric had a lot of information to share. It was a really beautiful, memorable and one of a kind experience
John McCarthy
Eric was fabulous. He took my wife and I all around the harbor and narrated the history of various places. The sailboat is also amazing. Very comfortable and roomy. Eric is clearly a very experienced sailor and we felt safe at all times. Would definitely do it again when we are next in Boston!
Malakhi Wheaton
Captain Eric was great! The boat was clean and new. There was plenty of space on the boat, and guests could sit on the back or lounge on the front of the boat. There was plenty of shade from the hot summer sun and a refreshing breeze on the front of the boat. The boat was stocked with ice-cold water and soda as well! Captain Eric was a great guide as well who has a wealth of knowledge about the Hingham/Hull area and sailing, both from a lifetime of experience. As we went out onto the harbor, Captain Eric did a great job pointing out things along the shoreline and explaining sailing to us (we don’t know anything). The tour is totally customizable to your preferences as well, whether you want to spend the whole time sailing or want a chance to swim off of the back of the boat. We wanted to take the chance to swim, and Captain Eric stopped the boat so we could hop into the water and swim around for a bit. The boat had a convenient platform on the back that made getting in and out of the water a breeze. The boat was also stocked with fresh towels! Captain Eric was a fun, engaging, and accommodating captain. Tons of fun! Highly recommend!
Kathleen F
So fun!! We had friends visiting from out of town and wanted to do something special. The sunset views over Boston from the water were amazing. I grew up in the area and have never seen a sunset over the city like this before. Captain Eric made the trip fun and interesting. The boat was exceptionally clean and beautiful. My friends and I had such a memorable day, and we are already planning next year's charter! Highly recommend!!
Your Voyage Awaits
Seats fill quickly in summer. Reserve your sail today and step into the golden hour.