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Top 10 places to anchor, raft-up, or just cruise by this weekend

Bermuda Lagoon

Bermuda Lagoon is a great place to anchor and enjoy the surroundings - at high tide! Photo by Allen Clark /

Vol. 1, No. 35

This holiday weekend, Long Island Sound will be packed with recreational boaters.  If you’re a boat owner and you’re like me, you prefer to have a destination when you’re out on the water.  Here are some of my favorite places to drop the hook for an hour or two or just cruise by.

1. Cockenoe Island – Cockenoe is the most popular boating destination in Westport.  This weekend, Cockenoe harbor will look like a parking lot full of fun.  If you can plan your visit around the tide, going into the lagoon is extra neat.

2. Bermuda Lagoon – Bermuda Lagoon is a high-tide destination as well, so be sure to check your tide table

3. Saugatuck River – Most boaters don’t think to go up the Saugatuck unless they dock their boat there, but at high tide, going all the way to Downtown Westport can be a fun outing. 

4. Southport Harbor – The Pequot area has an interesting juxtaposition of manicured mansions and a small, quaint old-timey harbor and waterfront.

5. Sheffield Island – Sheffield Island in Norwalk is a great place to stop for the day and check out the island and the lighthouse.  It’s also a popular overnight anchorage.

6. Scott’s Cove – Some pretty amazing properties overlook Scott’s Cove in Darien, including the Convent of St. Birgitta, a very unique property on Long Island Sound. 

7. Ziegler’s Cove – It doesn’t get any better than this; Ziegler’s is my favorite place to drop anchor and spend the afternoon with friends. has a nice review and navigation advice.

8. Five Mile River – The Five Mile River is just a great place to cruise.  You can even pick up some sandwiches at the Rowayton Market while you’re there.

9. Captain Islands – If you’re looking for a longer trip from the Westport/Fairfield area, Greenwich Harbor can be a great destination.  After cruising past the very high-end Indian Harbor Yacht Club, Belle Haven Club, and Riverside Yacht Club, a stop at Great Captain to take a swim will bring you back down to Earth. has a good write-up on the Captain Islands. 

10. Milton Point – The Rye/Mamaroneck waterfront offers a protected harbor and a notable attraction for boaters: Playland’s Wednesday and Friday night fireworks.  While you may be able to fulfill your desire to see fireworks closer to home this weekend, the weekly fireworks show can be a good attraction to keep in mind for the rest of the summer.