Long Island Sound gives you many choices for a cruise. You could stay in a marina every night with a meal at a good restaurant, but what if you just wanted to enjoy the natural wonders of the Sound and mostly anchor out but still with options to enjoy several towns along the way? I've put together an itinerary that's easy on your budget, as much as possible; you own a boat after all. Take a look. 

Day 1: Through Hell Gate to Port Washington.

The approach to Long Island Sound is from the west through Hell Gate. It's an area famous for swirling currents up to 5 kts in a narrow, winding passage that demands attention from the Captain. You'll pass boats of all sizes and types, including ocean-going barges and tugs, which take up much of the channel. Having an AIS receiver is a great help since it "sees" around corners to give you an advanced warning of an approaching ship before it suddenly appears around a turn – taking up your entire field of view! You want that warning!

There is no such thing as a "slow pass" near Hell Gate. People are in a hurry, and you had better be prepared for rough water. I prefer to transit when the current will push you along your way since I have a sailboat where 5 kts is a big deal. Be aware that the current you're using to go faster increases the bow wave of vessels coming towards you. An innocent-looking pass can result in a larger-than-expected wave onto your boat; grab and hold on! As if this was not enough, the bow waves reflect off the concrete walls on either side of the East River, giving each wave a "second chance" of disrupting your passage. 

If you choose slack current for your transit, you may encounter a barge convoy since slack time makes the sharp turns at Hell Gate easier to maneuver. One time, I didn't follow my own advice and arrived at Hell Gate at slack and met a convoy of barges just south of Hell Gate. All was fine until one tug pushing a barge decided to pass another barge in the East River. I veered to starboard and got an "up-close and personal look" at morning joggers along the walkway by FDR Drive. There's more room in the channel than it looks, but it didn't look like much at the time. 

After Hell Gate, it's a trip through the Brothers and to a wider passage to Long Island Sound. The first stop is for a free mooring (blue icon) at the town of North Hempstead in Port Washington, which maintains yellow moorings at no charge for the first night and a free dinghy dock for going ashore. 

Day 2: Anchor at Northport by Sand City Island.

Enjoy the solitude of an anchorage by Sand City Island in Northport Bay. A trip to the sandy beach is in order, especially if you have kids aboard and want to spend a day in the sun. There are several places to anchor, but I enjoy anchoring by the 8.5 depth mark farther east of the anchor icon for more solicitude and then dinghying over to the beach. 

Day 3: Anchor at Old Field Beach at Port Jefferson

Once through the entrance, you take a sharp turn to starboard and follow the ATONs to the Old Field Beach Waterway Guide marker. There's a sandy beach to explore or relax in the sun and breezes. Alternatively, you can pick up a mooring at the Port Jefferson Yacht Club for $50 and explore the town. 

Day 4: Slip at Safe Harbor, Branford, Connecticut

It's time to spend some of the money we've saved for a slip at Safe Harbor Bruce & Johnsons, mainly to enjoy a unique dining experience at Lenny's Restaurant, which we've walked to many times. If you're a fan of whole belly fried clams, this is the place for you – there's no better on the East Coast that I've found. Alternatively, you can anchor near the R6/G7 markers if you want to avoid the cost of a slip and take your dinghy up the Branford River with choices of several restaurants with dinghy docks – but then you would miss whole clams at Lenny's. 

Days 5: Milford Landing Marina at Milford, Connecticut

Take a dock at the Milford Lisman Landing Marina and explore Milford, Connecticut. It's a delightful town with lots to see and places to dine. Be sure not to miss Scoopy Doo's for ice cream after dinner, it's next door to the marina and it's excellent! Another option for a calm night is to anchor in the Gulf outside of the entrance and dinghy to Landing Marina. 

Day 6: Anchor at Mt Misery Cove at Port Jefferson

The Sand Pit (aka Pirate's Cove) is fun to explore in a dinghy. You can climb the sandy sides for stunning views of the surrounding area or just enjoy a day in the sun on the beach. Alternatively, you can see if a dinghy dock is available at Danfords Marina or Port Jefferson Yacht Club and enjoy the town's attractions.

Day 7: Anchor outside the mooring field at Northport

Anchor outside the mooring field and explore Northport by taking your dinghy (or your boat) to the Northport Village Dock. It's free before 5:00 pm, but there is a flat rate charge of $20 if you stay past 5:00 pm (you must leave by 10:00 pm). The Harbor House Restaurant is not to be missed for lunch or dinner. 

Day 8: Return to the free moorings at Port Washington

Port Washington is a good staging area for catching the current you want through Hell Gate, and you can catch up on what you missed on your first day. I prefer having the current behind me on the way west, so a good study of current charts is in order. If the United Nations is in session, check to be sure the East River is open! We've sat at Port Washington for days when the Coast Guard closed the entire East River, complete with gunboats ensuring no one passed. They sometimes leave the eastern passage open, but not always. Call ahead to the Coast Guard to be sure. If you take the east passage, you must call ahead for the Roosevelt Island Bridge to lift if you cannot clear 40 ft in height. 

The 2024 Long Island Sound Chartbook by Bob423 is available from Amazon as a planning aid. It reproduces 28 NOAA paper chart collections from New York City to Block Island, including adjacent rivers and around Shelter Island in 204 8.5 x 11 color charts. See the link for a detailed list of NOAA charts included. 

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For even more insight into cruising Long Island Sound, explore these Waterway Guide articles:

📖 Cruising Long Island Sound

📖 Cross-Sound Distances on Long Island Sound