Admit it. You have always wanted to do this. A charter destination that is easy to get to, where you fly into a major airport and can be on your yacht within minutes. A charter where you can sample great local cuisine, experience an area rich in American history, a place where there are sandy beaches, tiny islands and towering lighthouses. Admit it. You wanted it and now you have it. A charter from New York City to Newport, via Long Island Sound. Time to get started.

Chelsea Piers. The perfect place to meet up with your charter yacht. The largest gymnastics facility in the state, the largest rock-climbing wall in the northeast, the longest indoor running track in the world, a huge fitness center, a golf driving range, an ice skating rink, plenty of restaurants and pubs and a 1.2 mile esplanade…now, this is the perfect place to have a marina! Re-opened in their present glory in 1995, Chelsea Piers were originally opened in 1910, after 30 years of talk and 8 years of construction. Designed by the same architectural firm that designed Grand Central Station, Chelsea Piers replaced a hodgepodge of run-down waterfront structures with a row of magnificent buildings embellished with a pink granite façade.

For the next 50 years, Chelsea Piers served the needs of the New York port, ending in the 1960’s as a cargo terminal. After that, Chelsea Piers became a neglected maritime relic, slated for demolition to make way for a new highway. When the highway was not constructed, they were sold at auction in 1992. By 1995, the present day structures had been built, a testament to the foresight of the new owners to create a facility that serves such recreational diversity so there is literally, something for everyone to enjoy.

The hazard to meeting your yacht at the Chelsea Piers Marina is that it will take several hours to round everyone back up from their various activities and get them back on the boat. And don’t leave behind the golfer…they will be up on one of the top floors, happily whacking balls into space and (admit it) aiming for the guy in the little machine that is vacuuming up the balls on the driving range. Once you have everyone back onto the yacht, your crew will throw off the lines and ease out into the Hudson River, giving you a tour of New York Harbor before heading up the East River toward Long Island Sound.

First stop will be in beautiful Greenwich, CT. Whether you stop for a couple of hours, or overnight, there is plenty to see and do in Greenwich. The Avenue is where is all happens, and is only steps from the marina. “The Avenue” is what the locals call trendy Greenwich Avenue, the main street of this small upscale community. This relentlessly upscale boulevard, with its pricey boutiques, old-style department stores, and fine restaurants caters to sophisticated pleasures. There is also the Bush-Holley Historic House for the history buff, Audubon Greenwich for the naturalist, and of course, polo matches in the Back Country for the polo enthusiast!

Leaving Greenwich behind, the next stop will be Norwalk. Like many waterfront areas, South Norwalk (locally known as “SoNo”) has undergone a radical transition from run-down to rehabilitated. The enhancement of the area centeres around the new Maritime Aquarium at Norwalk, which focuses on and promotes the marine and maritime life of Long Island Sound. Started in the mid-80’s, the Aquarium features not only sealife, but also a touch-tank, boat-building demonstrations and restored sailing vessels.

The Lockwood-Mathews Mansion Museum is nearby and is a 50-room, 1864 era estate filled with Victorian artifacts. If the Aquarium and the Mansion aren’t to your tastes, a quick trip to the world-famous Stu Leonard’s will be. Billing itself as the “World’s Largest Dairy Store”, this is a grocery store that is more fun than a carnival. Extraordinary, not ordinary is what it is and must be seen and experienced to appreciate it. Hint: make sure you get an ice cream cone when you leave. Fresh, homemade…yum!

Once you have torn yourself away from the delights of Stu Leonard’s and make it back to your charter yacht, head across Long Island Sound to Oyster Bay. In the mid-1700’s, both the English and the Dutch inhabited picturesque Oyster Bay, which accounts for the fact that the place has two main streets just a block apart. Which is a pretty rational explanation, since if the town was started today and it had two main streets, one would just attribute it to city council members who couldn’t come to a consensus! Oyster Bay boasts several attractions: Raynham Hall, once the home of a prosperous Revolutionary War-era merchant, Planting Field Arboretum, and of course, Sagamore Hill, the rambling hilltop estate that was once the summer home of Theodore Roosevelt. If you only have time for one excursion, go to Sagamore Hill and take one of the tours given there. Perhaps one of the most striking things about the house is its enormous number of preserved animal parts. The rhinoceros-foot inkwell, the chair made of moose antlers, the elephant-foot wastepaper basket…well, you get the idea. A bit morbid, but the kids will love it and maybe learn a bit of history about a former president.

Close to Oyster Bay is the small tourist village of Cold Spring Harbor. Tiny today, featuring only a few shops and galleries, several historic buildings, and two museums, it was a bustling whaling port in the mid-1800’s. The main street was called Bedlam Street during that time, for the cacophony of foreign languages heard there. On the village’s outskirts was Bungtown, a small settlement where barrels for whale oil were made.

A short trip up the coast brings you to the lovely restored 18th-century village of Stony Brook. Built on a hill sloping down to the water, much of Stony Brook’s charm is due to Ward Melville, owner of the Thom McAn Shoe Company. Back in the 1940’s, Melville became concerned about encroaching suburbia and had the village rebuilt along historical lines while at the same time successfully fighting for strict zoning codes. Thanks to his foresight, Stony Brook is the delightful community it is today.

Ready for a fright? Believe in ghosts? Then make sure that you go to the Country House Restaurant while visiting Stony Brook. Word has it, that the place is haunted. Built originally as a farmhouse in 1710, it was used as a stagecoach station in the late 1800’s. The restaurant was started in 1960. The ghost that haunts the building is that of Annette Wilson, a young woman who had been hanged by the British as a spy during the Revolutionary War, and buried in a small graveyard on the property. Her activity focuses around the kitchen, where towels have been seen floating by several startled witnesses!

Time to head back across the Sound to the Connecticut side. Now is your chance to see a little bit of Maine, because that is what the Thimble Islands resemble. A little bit of Maine washed down to Connecticut shore years ago, whether it was a monumental hurricane or just some heavy currents, it really doesn’t matter, because there they are. No dockage here, just nice, secluded anchorages. Perfect for a quiet lunch, a quick swim, exploring the islands in the tender. Maybe relaxing so much you won’t want to leave for your next adventure: a visit to Old Saybrook and Old Lyme, then on up the Connecticut River to Essex.

Old Saybrook and Old Lyme each offer its own list of attractions. Old Saybrook boasts most of the marinas and most of the restaurants, but its biggest draw is due to its 400 antique dealers clustered in four centers. They take credit cards and they ship. Happy shopping.

Old Lyme still has tree-lined streets where gracious captain’s homes sit back and watch the world go by, just as they have done since the 1800’s. If art galleries are your passion, especially Impressionist Art, then the Florence Griswold Museum is a must-see. This circa-1817 mansion was once the site of one of America’s most famous art colonies.

Welcome to the Number 1 Small Town in America. Or, at least that is what quite a few magazines and newspapers say every year. Although it’s on a river, many consider Essex to be the quintessential seaside New England village. With its many marinas and narrow, one-way streets lined with antique houses, the town has maintained much of its maritime heritage. In the last 300 years, more than 500 vessels have been built in Essex. Take your time, stroll the streets, poke into the shops, or just sit on the dock and watch the activity. Steamboat Dock is popular with crabbers and rod-and-reelers as well as a well-mannered pack of Labradors who pursue tennis balls…and ducks.

The have-to-go place in Essex is the Griswold Inn. It has been in continuous operation since 1776 and a taproom sign reads: “Because we cater to yachtsmen, a coat and tie are not required”. Hint: don’t even think about going without a reservation.

Time to head back to your charter yacht and head further on up the Connecticut coast to Mystic. After the English captured this area, they kept the Pequot name Mystic (originally mistick), meaning tidal river. Since the seventeenth century, Mystic has been building boats. It was at one time Connecticut’s most important and prosperous seaport with 20 whalers in its fleet until 1860 when petroleum replaced whaleoil. Today the Mystic Seaport Museum, the state’s number one attraction, pays homage to the region’s maritime history. The 17-acre living history museum that recreates a typical nineteenth century New England seaport, was begun in 1929. It now contains more than 60 historic waterfront buildings, 300 ships and boats, plus artifacts of early maritime America. Interpreters in period dress staff the shops, cook at the hearths and lead sea chanteys. Interesting for the adults and loads of fun for the children. The kids will even think that history is fun!

The next (and last) stop in Connecticut will be lovely little Stonington. This tiny village is filled with interesting architecture, ranging from colonial fishermmen’s houses to federal mansions to Victorian gingerbread homes. The community has a long and impressive list of resident artists and writers, with their works displayed in the local galleries.

Reminding visitors of Stonington’s past as a whaling and sealing port, the Old Lighthouse Museum, on Stonington Point, has a small museum containing seafaring artifacts. The lighthouse tower affords a view of three states: Fisher’s Island, New York; Rhode Island to the east; and Connecticut, as well as vistas across Long Island Sound. Look long and hard to the east, across the Sound, for that is where you will be heading next. Back over to Long Island, to visit Greenport on the North Fork and Sag Harbor on the South Fork.

There is an unmistakable look about Greenport: laid out in neat squares that slope down to the harbor, it is filled with old captains’ houses half hidden by the trees, fishermen’s cottage, funky antique shops, lobster pots hanging on fences, the harbor always full of fishing boats and pleasure craft. The Enterprise, the successful America’s Cup defender of 1930 called Greenport home, but the maritime industry has been active here since the early 1700s when cargo ships from the West Indies called here.

There are three things that you really must do while visiting Greenport. The first is to ride the Carousel in Harbor Front Park. Dating back to the 1920’s, this is the best $1 you will ever spend. If the music, the feel of your steed as it charges around and around, the breeze in you face don’t make you smile, try grabbing for the brass ring to win a second ride for free. In short, be a kid again.

Second, visit S.T. Preston’s, established in 1883. An unforgettable rambling barn of a store filled with everything from rope and paint to paintings and Top-Siders. Now that you have worked up an appetite, stop by across the street to Claudio’s restaurant for something to eat. Feel better? Now, last, but not least, go visit the East End Seaport Maritime Museum. Loaded with artifacts of the sea, one of the most popular exhibits are the Fresnel lenses, previously used in the lighthouses. Most impressive is the Fourth Order lens originally in the Plum Island lighthouse. Installed in 1897, it produced an amazing 350,000 candle strength and was visible for 14 miles. Don’t worry, Plum Island Lighthouse still has a light, just not one so strong.

Time to leave Greenport and head on over to Sag Harbor. You will pass by Shelter Island on the way. Lying in the middle of the bay between the North and South Forks, it is a quiet retreat of wooded hills, solitary beaches and expensive vacation homes it is reachable only by ferry.

Originally named Wegwagonock by the Algonquin Indians, when the first white settlers arrived around 1730 they renamed it Sag Harbor. Most likely because they couldn’t pronounce Wegwagonock! It quickly became a booming whaling port with a 31-boat whaling fleet at the height of its heyday. Sag Harbor slipped into sleepy hibernation after the whaling era ended, only to revive when tourism began to boom in the 1980s. There are now about 2,500 permanent residents, swelling to about 8,000 in the summer season.

There are plenty of shops and boutiques to explore along Main Street, including an old-fashioned five-and-dime store with two cigar-store Indians out front. There is one last Museum to poke about in…the Sag Harbor Whaling and Historical Museum, housed in a mansion built in 1845. An endless jumble of exhibits, it more resembles your Grandmother’s attic than a museum. Some exhibits are fascinating, others looking suspiciously like junk. Since admission is only $3, it is well worth a couple hours.

Time to get back to the boat. Time to head on North to Newport, where you are ending your journey. You still have a few hours cruising ahead, time to reflect on how glad you are that you finally admitted to yourself that this just might have been the best charter that you have ever been on. You are relaxed, everyone had a great time, the kids actually learned some history, you finally have eaten all the lobster that you can hold…the list goes on and on. Yes, this was a wonderful vacation. Now you just wonder why it took you so long to do it.