We recommend altering any itinerary to match the conditions you find. Have a hot day, with wind forecast for the afternoon? Delay your departure and hang at one of the many clubs around Long Island Sound with a pool. With sailboat cruising it shouldn't be about the destination: it's how you get there that matters. Well... it's a little bit about the destination, too!
Day 1: Depart Chelsea Yacht Club and head to Shattemuc YC. One of our neighbors on the Hudson, they're very accommodating. If you pick up a buoy, our reciprocal privileges should get you a complimentary night. If you want to stay in the marina, give them a call to pre-arrange or book online through dockwa.com. Eat at the boathouse, which is right next door, or one of the many restaurants in Ossining if you don't mind hiking up the hill or down to the train station.
Day 2: Watch your tide charts! The point of starting at Shattemuc is that it's in Haverstraw bay. Nyack works just as well. You want to catch an ebb tide just as it is starting in Haverstraw. This will (with the average speed of a sailboat of around 6kts) put you at the Battery just about the time the tide is shifting up the East River. Yes, you have to go to the Battery; the bridges through the Harlem River are too low for sailboats. Leave with the tide, and you can make it to City Island about 8 hours later. If you still have it in you to go about an hour longer, Port Washington is a lovely harbor with sailing clubs friendly to transients.
Day 3: City Island to Northport Harbor, Long Island. A great harbor and a reasonable sail from City Island of about 4 hours. Give yourself a little break on day 2. I like Seymour's Marina, which has plenty of transient buoys and a dock that's right downtown. Great restaurants and a beautiful harbor here! Alternatively, anchor in Eaton's Neck. This is a small beautiful gunkhole and has great clamming, but some genuine hazards on the way in/out AND on anchorage - talk to one of us for tips.
Day 4: Northport Harbor to Westbrook, CT. A longer sail today to make some legs toward our destination. 50 NM out of Northport puts us in to Harry's Marine Repair (marina). Make your reservation through dockwa and watch the charts carefully going in. There is a very easy fuel and pumpout dock as you enter the harbor at SafeHarbor marina. Fuel up and fill the ice chest; fuel is cheaper and easier to get here than Block Island. Harry's is an awesome family-owned marina that feels a lot like CYC. You'll find friendly helpful people, and Bill's Seafood is a quick walk across the street. If you like a good burger, Haywire Burger Bar is 1/2 mile down the main street past Bill's and has excellent food and much better prices.
Day 5: Westbrook to Block Island. About 42 NM and 7 hours away. With nice summer conditions of Southwest wind, you might get lucky and have a spinnaker run the whole way. Time your departure time so you hit the Race with a favorable current (else get stopped dead). Plan to anchor your first night at Block; the public buoys are first-come, first-served and fill up by noon. People who want a buoy get up early and start hunting the mooring field to catch buoys as the departing boats get out. Anchor out in the field, or call the harbormaster to ask for a private mooring (one night arrangements only). Go ashore and enjoy dinner at the Oar. It's a short hike (or taxi ride) into town if you want to explore there. If you're anchored, keep your weather eye out. When conditions change and the wind kicks up, dragging is notorious in the pond. Best to set a heavy plow anchor.
Days 6-8: Explore Block Island. If you get up early in the morning (EARLY means EARLY! 5:30am get your anchor up and start looking for a public buoy) you are likely to find an open buoy, especially if you've arrived on a day more boats will be departing (example: many boats leave Sunday and Monday mornings, because their owners have to get back to work). The green buoys close to the docks are the public ones. Two boats are allowed to raft up on these buoys together (fun!) but both have to pay. In 2017 it was $45/night, and you can pay for multiple nights while you stay. Rent bikes and bike around the island. See the two lighthouses; stand on the far Northern tip of the island where waves crash in from two directions at once. Eat happy-hour buck-a-shuck oysters and fresh clams at the BeachComber restaurant. Visit the Alpaca farm, and shop in town. Enjoy the many great restaurants. The mooring field is a great place to watch for shooting stars. Be sure to try Payne's famous donuts and Aldo's bakery (Available in the mooring field to the call of "Aaaaandiamo"). Take your dinghy across the pond to the beach area and walk a few steps across the road to one of the best beaches on the island. Or go by dinghy to the harbor entrance to watch the sunset! There is free pumpout in the Salt Pond (holding tanks are mandatory or face a huge fine). You really do want a dinghy here; although there is a launch running 24 hours, it gets expensive and sometimes you have up to an hour wait.
Day 9: Block Island to Mystic Seaport. About 20 NM from the Salt Pond Entrance is the entrance to Mystic Seaport. While there are many marinas here, I love to make the trip in to stay at the Mystic Seaport Museum. Book through Dockwa and reserve your stay. They have great new docks and amenities (including free washers/dryers and excellent showers) for cruisers. Stay 2 nights if you have the time. If you arrive early enough in the day, you have a free ticket to all museum exhibits for everyone on board. After hours, you have your walk of the museum village (although exhibits are closed). A short walk/uber to Mystic town and great restaurants. Plan about an extra 45-60 minutes to get from harbor entrance in to the Seaport Museum, which includes passing under two timed bridges - check the timing or face a delay!
Day 10: Mystic to Milford. The anchorage outside Milford Harbor, in the shelter of Duck Island, is a favorite one (and free!). Clamming is possible on the sandy shores. About 8 hours sail from Mystic Harbor inlet.Â
Day 11: Milford to Port Washington Yacht Club. 42 NM and about 7 hours away, Port Washington Yacht Club accepts transient club members and has a beautiful clubhouse and pool. It's a short walk away from good seafood restaurants in town. Take your ballcaps off in the clubhouse and stand quietly for colors or prepare to be corrected!
Day 12: Port Washington to Chelsea. This is do-able in a single albeit long return trip. Check and double-check your times through the race. If you hit adverse current up the river (likely), pick up a buoy at 79th Street Boat Basin and sleep/rest for a couple of hours before continuing upriver. Pick up a buoy to the North end, away from the marina, and we've never been bothered/charged for a short stay. I've heard that if you wish to stay or go into the marina with your dinghy, there is a charge. Because the river floods from the city on up, you can ride the flood tide from here all the way to Chelsea, once it changes.
Some great add-on days:
We love Mt. Sinai harbor. Friendly place with a beautiful pebble beach. Call ahead as there's not may transient moorings and they fill up.
Anchor at Eaton's Neck. Many experienced cruisers talk about excellent clamming in this location. Although we're told that now the beach is private, there's an anchorage there. It's a tight anchorage - consider a second anchor so you don't swing, or make sure that when you do swing, you won't be aground. The tidal range in here is 8 feet! Don't even think about going there in fog, as the USCG foghorn will blow your sails off (reportedly).
Norwalk, CT has yacht clubs and access to great restaurants.
Hugenot YC in New Rochelle is friendly to fellow sailors!
Talk around for other destinations! There are many sailors around the club who have experience exploring the LIS and will share their favorite places.