Going East as Far as Boston

An overnight single-shot approach from CYC to the Sound could find you as far east as Milford, CT the afternoon of the first day, but if you slam into an easterly as you emerge from the East River, pick up a mooring at one of the yacht clubs in Port Washington. Assuming you stick to the Connecticut shore, we frequent:

Milford: The Milford Landing Marina is at the extreme end of the harbor. It's built on the site of the former waste treatment plant and provides the easiest walk to town. The Harbormaster at the Landing Marina can recommend where to eat and has discount coupons to some of the better spots, such as the Stone Bridge. The Yacht Club at the entrance to the harbor is fine and has a pool, but it's a hike to town.

Clinton: Cedar Island Marina. The marina restaurant is usually staffed with CIA graduates. Big pool, but expensive. Not much in town.

Connecticut River: As you approach from the west, be mindful of Long Sand Shoal, which runs parallel to the shore from off Duck Island to the river's mouth. It gets down to four feet at low water even though it's a good two miles offshore. The easiest approach is to stay between the shoal and the mainland. The Connecticut River is a tidal estuary like the Hudson, so it's another place you'll want to time your passage based on the current. Most of the facilities are on the west bank. Just south of the Rt. 95 bridge is the Between the Bridges Marina, a BOAT/US discount marina. The Saybrook Fish House is a pleasant walk. One of the many clubs at which CYC is welcome is the North Cove YC, which is in the cove itself. Further up the river is Essex. The Essex YC has moorings, and the little Chandlery Marina, which is adjacent to the Club, is reasonable. Essex Island Marina is expensive, as is Brewer's, but both have pools. The Griswold Inn is the primary restaurant, but book early on the weekends. If you're into geology, check out the little museum at the foot of the main street.

Mystic: Before going into Fisher's Island Sound, spend a lot of time visualizing the chart because it's one of the 10 most hazardous cruising grounds in the country--full of clumps, grounds, hummocks, reefs, and rocks. They're named and marked, but they're still things that can go bump, even in the middle of the day if you're not paying attention to what red and green are red and green relative to. Mystic is up the harbor from Noank. Getting from the Sound into the harbor at Noank is a bit zig-zaggy; follow the buoys carefully and then proceed up the well-marked channel that meanders through the mooring area. A warm, fuzzy hangout in Mystic is Ft. Rachel Marina. It's real friendly, inexpensive, and it's mostly sailboats. "Dutcha" (so named because of her national origin) runs the office. Ft. Rachel is the first left you can make after clearing the railroad bridge, and it's only the one row of fingers built off the rip-rap that forms the rail bed. They use Ch. 10. (Yes, trains go by, but we're used to that.) Mystic is worth a couple of days so you can go to the Seaport Museum. Good tourist shopping downtown, along with two or three good eateries. Unfortunately, the A&P moved out east on Rt. 1 between Mystic and Stonington.

Stonington: An alternative to Mystic. Dodson's Boatyard has moorings and some dock space and a Laundromat. Go to Noah's for dinner.

If you don't want to continue east, from the Connecticut River, Mystic, or Stonington, you can go to Block Island and/or over to the protected but breezy waters of Gardiners Bay, which, along with Shelter Island Sound, Noyac Bay, and the Peconic Bays, separates the north and south forks of Long Island. This area is an excellent choice if you want a change of scene from the Sound but don't want to press on to the Vineyard, the Cape, or Boston.

Block Island

New Harbor (Great Salt Pond) is an easy sail and landfall from the jumping off points in Connecticut or from Greenport, Sag Harbor, or Montauk on the Long Island side.

Crowded and expensive during the summer, but just the opposite after Labor Day. Avoid Block Island Race Week, when you can walk across the Pond on the boats.

Most of the restaurants are in Old Town. The walk is just the right distance to build up an appetite on the way over and to walk off dessert on the way back. During the day, rent a bike and circumnavigate the island. If it's hot, bring a water bottle and wear your bathing suit. Cool off in Sachem Pond on the northern end or on the beaches adjacent to Old Town, one of which is a nude beach (you'll have to determine which one this is by inspection).

Rhode Island East to Martha's Vineyard and North to Salem

Watch Hill, RI: This is in Little Narragansett Bay and is accessible by leaving the bifurcation marker at Stonington to port and following the channel around Sandy Point to starboard. The channel is narrow and shallow. There's a yacht club with first-come, first-served moorings just outside the cove at the far south end of the bay and municipal docks (no facilities) inside. A large restaurant with porch seating overlooks the harbor from the east; dine there on a Wednesday evening when the club races their classic one designs.

Pt. Judith: A great place to duck into when the weather closes in or if you run into fog. There are a number of marinas and moorings in Galilee and Point Judith Pond. The Pond is a good hurricane hole.

Wickford (North Kingston), RI: On the west shore of the real Narragansett Bay, far from the madding crowds of Newport. Sail up the west side of Conanicut Island. There's a hospitable club there, and up the channel to port after clearing the breakwaters are the Wickford Shipyard and Brewer's. The Shipyard has a nice pool, but don't let them put you in a shallow slip. Call the Carriage House and Mike, the owner (or somebody), will come and get you and then bring you back after a great meal. The village features 17th and 18th century homes.

Newport: If you must have madding crowds, the Newport Yachting Center is a BOAT/US discount marina, but even then it's not cheap. However, it is at the epicenter of this sailboat Mecca, and such notables as Shamrock dock there. Some of the better restaurants are the little ones on America's Cup Avenue south of the main part of town.

New Bedford YC: NBYC is in South Dartmouth, MA on the west shore of Buzzards Bay, not New Bedford itself. (South Dartmouth is Padanaram to the locals.) The club is on the north shore of the harbor, right next door to the Concordia boat works. Good food at the club, especially the steamship roast on Friday evenings. There's a good breakfast place in town.

The South Shore: From Padanaram, you can go up Buzzards to the Cape Cod Canal or through Woods Hole or Quicks Hole to the Vineyard. If you're looking to go through Woods Hole but are early for the current, pull over and anchor in Hadley Harbor. Transiting the Canal and "The Holes" requires the same kind of planning as the East River and Plum Gut because the currents run up to six knots. If you wind up at the east end of the canal in the late afternoon, stay at the little harbor of refuge there and go to the restaurant across the road. The Sandwich shopping center is just up the road. From the canal, you can go to Situiate, Plymouth, press on to the Constitution Marina in Boston, or head over to Provincetown. A walking tip for the Constitution Marina: there's a shortcut that goes across the Charles River lock gates and puts you right in the Italian restaurant section of the north end. Don't plan on leaving Boston early in the morning--even if there's no fog in the harbor, there will be in the Roads.

The North Shore: East of Boston, Salem is the place to go. Nice marina, and the restaurant at the Peabody museum serves a great lunch (but check out the extensive maritime collection anyway).

Martha's Vineyard: The Vineyard is actually a county of the Commonwealth. It's "dry," but you can bring your own bottle to restaurants. There's an expensive marina in Vineyard Haven. Oak Bluffs and Edgertown are other destinations.

Gardiners Bay, Including Greenport, Shelter Island and Montauk

Plum Gut: If you want to go into Gardiners Bay from the west, you have to transit Plum Gut, the narrow opening between Orient Point and Plum Island. Wicked current, so this is another passage that has to be timed to suit the currents. The idea is to go through at the end of the eastbound ebb so you can pick up the ensuing westbound flood toward Greenport or Sag Harbor. Coming from the east (Block Island) or north (Fisher's Island Sound), you can go in behind Little Gull Island, but if the current is westbound, you'll have to bear off considerably to the south because the current is actually setting to the northwest and will be pushing you back toward the Gulls and Plum Island.

Orient by the Sea: This is a little marina around the corner from Orient Point and just west of the New London and Department of Agriculture ferry docks. Only a few slips, but it has a good restaurant for a place that's in the middle of nowhere and good swimming off the adjacent beaches to the west. Go in/out at half tide or better if you draw over four feet.

Orient Harbor: A great spot to anchor, but can be bumpy if the prevailing southwest wind blows all night. Small yacht club at the east end.

Greenport: Unlike the upscale towns on the South Fork, Greenport is a working fishing and boat building town. Best place to stay is at the marina associated with Townsend Manor. Has pool and Laundromat, but it's gotten pricey since the mid-90s. Hang a right after clearing the breakwater and run parallel to it into Sterling Harbor. The Manor is at the start of the left fork of the harbor across the creek from the hospital. Brewer's is on the opposite shore. The advantage of Townsend's is that you can walk into town. Brewer's has a courtsey van that goes to town, but check to see when the last run back is--taxi service in Greenport is spotty. Instead of going into Sterling Harbor, you could dock at Claudio's on the waterfront itself, but it's busy and bouncy, and you'll be a tourist attraction. Preston's is the major chandler. Greenport is one of the few harbor towns that has a movie theater right in town instead at some distant mall. (Northport and Sag Harbor are others). Best place to eat is the Rumb Line--guess what the various big boat parts that hang from the ceiling are. An alternative is the Chowder Pot Pub, which is on the west side of town across the street from the LIRR station. The liquor stores in town carry wines from the local North Fork vineyards. The chardonnays and merlots are the best outside California.

Dering Harbor: This harbor is opposite Greenport on Shelter Island. There's a marina and the Shelter Island YC, which runs hot and cold with respect to CYC members.

Sag Harbor: OK because it's not a real South Fork town like Easthampton. A nice day's sail from Greenport is to catch the current going west into Little Peconic Bay, hang out there until the current goes east, and then go around the south side of Shelter Island into Sag Harbor. On both sides, leave plenty of room for the little ferries to maneuver in the current. In Sag Harbor, call up the harbormaster on VHF channel 9 to check on availability at the municipal marina or go to the Yacht Club just beyond it. The YC is the more expensive, and the private marina adjacent to the municipal marina to the north is very expensive. Both there and at the Yacht Club the megayachts will block your view and the breeze. The local theater features Broadway casts because so many actors and actresses summer in the Hamptons. The whaling museum is worth a visit. If you think you've had rough passages, read some of the personal logs.

West Harbor: If you want to anchor out instead of going into Sag Harbor, there's a beautiful little harbor on the southeast corner of Shelter Island, just west of the ferry crossing. If it's low tide, hug the red just inside the entrance. There's a designated anchorage in the southeast corner marked by buoys. The Shelter Island side of the route into Sag Harbor offers a number of other quiet anchorages that are protected from the west.

Coecle's Harbor: Another protected and picturesque harbor, this one is on the north side of Shelter Island. Also a bit shallow. The marina will provide transportation to town for dinner.

Three Mile Harbor: East of Sag Harbor on the South Fork. One of the restaurants that caters to the marinas just inside the entrance has a fully rigged 5.5 Meter that sailed in the 1954 Olympics behind the bar. The owner claims he can have it sailing in a week. Look for the restaurant with the tall cupola. There are restaurants and a movie theater in East Hampton, which is a short cab ride from any of the marinas.

Montauk Pond: Mostly for shark fishermen. Good place to anchor out and buy fresh fish, though.

West Along the North Shore of Long Island

Mattituck: The first harbor west of Orient Point is Mattituck. Watch the current here if the wind is onshore. The channel between the breakwaters isn't very wide, and if the wind is out of the north with an ebb pouring out of the creek, very steep standing waves can build up. There's a restaurant and boatyard along the west bank of the creek, but if you want access to the village, you'll have to go to Matt-a-Mar or the municipal facility at the very end of the creek (an excellent hurricane hole). Matt-a-Mar has an Olympic pool and Laundromat. Famous for mosquitoes.

Mt. Sinai: A weekend alternative to Port Jefferson. Three marinas and a yacht club.

Port Jefferson: Or Port Jeff, as it's generally known. A lot of people like to anchor out behind Old Field Beach or Mt. Misery Point; great if you have a dink and kids who what to frolic on the dunes, but creatures of comfort head for Bayles Dock, the marina at Danfords Inn. Bayles is expensive during the high season. Alternatively, you can take one of the municipal moorings (call the harbor master on the VHF channel that's posted on the sides of the yellow launches) and use the launch service or your dinghy to get to shore. Make enough trips on the launch, however, and it can get as expensive as a slip. Port Jeff used to be a regular town, complete with a couple of major food stores. Now it's a major tourist destination for people coming out from the City or from Connecticut via the ferry, and the IGA we used to stock up at during 70s has yielded to candle and T-shirt boutiques. With the exception of Danfords, avoid the tourist trap restaurants on the main drag. There are some good small places toward the east end of town. There are some beautiful old houses up the hill on the east side, too. The presence of elegant old houses on the high ground in such harbor towns as Port Jeff and Mystic are common because this is where the local captains and merchants lived. The captain's wives could keep lookout for their returning husbands and the merchants for their cargoes.

Huntington Bay: The mouth of the bay features the little anchoring hole at Eaton's Neck, a favorite CYC overnight anchorage. In Northport, we used to go to the marina at the very end of the harbor. It was a funky, laid-back place with a half-century of mildew on the shower stall walls, but it's since been replaced by an upscale marina and tennis club. No more mildew, but it's one of the most expensive places to stay--right up there with the private marina at Sag Harbor. So, now your best bet is to take a mooring at the Northport YC, which has always been hospitable, has a nice pool, and is a reasonable walk to town. The downside of the club is that it's an hour from the Sound.

Hempstead Harbor: Ignoring the marinas way down in Glenwood Landing, there are two basic choices here, either a mooring at the very hospitable Sea Cliff YC or one of the marinas along the south side of Glen Cove Creek. There are some good restaurants up in the village of Sea Cliff, but it's quite a climb up the steps across from the club. The park at the top of the steps has a great view of the harbor.

Manhasset Bay: The big Brewer's marina is a good fuel stop, but take a mooring at one of the yacht clubs along the east shore. The Kinckerbocker is closest to Louie's restaurant, which features great seafood. Since Consolidated Marine on City Island took out its fuel pumps some years ago, Brewer's is the most easily accessed fuel stop in the area.

Now it's back through Throgs Neck. This time, you must be at Throgs Neck about halfway through the ebb cycle so that you ride out the tail end of the ebb going down the East River. The object here is to minimize the time you'll have to buck the ebb that will still be coming down the Hudson when you round The Battery. Or, depending on the time of day and how long you'd have to buck the flood, this might be a good time to head for one of the Jersey marinas for the night and pick up the next day's flood up the Hudson.