New York's Summer Playground

1 day

Sag Harbor

Sag Harbor offers pristine beaches, breathtaking ocean views, historic homes, antique shops, hideaway inns and gourmet eateries in a truly unique setting of century old streets. Lunch or dinner at Sunset Beach Hotel and Restaurant feels more like St. Tropez than Eastern Long Island, making Sag Harbor an excellent place to start your New England cruising.

1 day

The Hamptons

The villages and hamlets which make up The Hamptons to east of New York’s Long Island provide the perfect style and finesse for a luxury yacht charter getaway. Quaint boutiques, antique shops, art galleries and gourmet restaurants abound. Choose from chic, celebrity-filled Southampton, beach perfect East Hampton, and laid-back Westhampton.

1 day

Block Island

Known for excellent cycling, hiking, sailing, fishing, surfing, and beaches, Block Island was named by The Nature Conservancy as one of the twelve sites in the list of “Last Great Places” in the Western Hemisphere. Approximately 20 percent of the island is set aside for conservation. Visit the Mohegan Bluffs, just walking distance from the Southeast Lighthouse. A long staircase of over one hundred steps leads to the bottom of these clay cliffs and looks out over the Atlantic. A visit to Block Island is not complete without a stop for a bowl of New England Clam Chowder at the National Hotel.

1 day

Newport

A contemporary city with a rich yachting heritage, Newport has something for almost everyone - from interesting shops and restaurants, museums, art and jazz festivals, to beautiful beaches, ideal sailing conditions, historic mansions, and the world famous “Cliff Walk.” Visit the Breakers, the grandest of Newport’s summer “cottages” and a symbol of the Vanderbilt family’s social and financial preeminence in the turn-of-the-century America.

1 day

Falmouth

This relaxed, picturesque seaside town on Cape Cod’s southern shore mostly draws visitors passing through en route to and from Martha’s Vineyard, but if you stay long enough to explore its beautiful waterfront and historic streets, you’ll understand why many visitors often come back to stay year-round. Wander around the traditional, historic Main Street area, with its cute boutiques, trendy restaurants, and classically New England village green, and slow down to the Falmouth pace of life. Visit the colonial churches, hike out to the old lighthouse, and sail along the shore to get a glimpse of the rugged coastline and typical New England coastal architecture. Spend an afternoon lounging on its endless soft beaches, making sure to catch the sunset before heading in to the marina for dinner at a classic clam shack.

1 day

Hyannis

Predominantly visited for its port and ferry, this small town in Barnstable, on the southern coast of Cape Cod, boasts a charming waterfront district of historic buildings, shady parks, and cute boutiques. The Kennedys are known longtime Cape-goers, and President John F. Kennedy gave his acceptance speech here, so you can now visit a memorial to him on the Lewis Bay waterfront as well as a museum in the Old Town Hall that focuses on his time spent in Hyannis. Wander down to Craigsville Beach, the main shoreline in town, enjoy freshly-shucked oysters at the Naked Oyster downtown, and take in the gorgeous views of the cape as you sail nearby.

1 day

Martha's Vineyard

The beautiful island of Martha’s Vineyard is a world apart, offering a vacation ambiance unlike any other. The seaside villages attract year round visitors to their stunning beaches, gingerbread houses, bountiful recreational activities and unique New England Charm. Martha’s Vineyard boasts the oldest working carousel in the country, complete with 22 wooden horses with real horsehair manes. If traveling with kids, you might also consider taking a tour of the Farm Institute, where you’ll see Milk Goats, explore lush vegetable and flower gardens, and see lambs, piglets, and calves. And no trip to the Vineyard is complete without stopping for some Murdick’s fudge.

1 day

Nantucket

An island of class, culture, and undeniable style, Nantucket is located 30 miles out at sea off the coast of southern Cape Cod, MA. Known for its pristine beaches and cobblestone streets lined with historic homes, Nantucket offers a glimpse into yesteryear. Famous for its film and wine festivals and 4th of July fireworks celebrations, Nantucket is one of the most unique, and visually stunning places in the world. Originally a booming whaling port, Nantucket has been named a National Historic District and little has changed architecturally since the 17th century, with seaside cottages and old fashioned lamps still lining the streets.

1 day

Provincetown

Perched way out on the edge of Cape Cod, this friendly and relaxed seaside town also happens to be home to the country’s oldest art colony. As part of the Cape Cod National Seashore, it has miles of gorgeous beaches for you to explore on foot or by boat. Get out into Province Lands for miles of scenic hiking and bicycling routes through majestic dunes and rugged wilderness, as well as for the stunning views both out over the Atlantic and in towards Boston and the rest of the Cape. Set up shop in one of the appropriately charming inns and then join locals and tourists alike in walking around the cute streets, stopping in designer boutiques, locals shops, friendly cafés, and acclaimed restaurants. Check the calendar before you come, as there are always festivals going on in Provincetown, from a film festival in June to a Tennessee Williams festival in September.

1 day

The Kennebunks

Like many of Maine’s picturesque coastal towns, the Kennebunks – Kennebunkport and it’s ‘Lower Town’ neighbor, Kennebunk – first built ships and then welcomed the well-heeled of Boston and New York for bucolic seaside summers. Nowadays, you’ll find them two of southern Maine’s most charming towns; the former an elegant destination of historic summer mansions and designer boutiques, the latter an unpretentious artsy enclave, both with excellent restaurants and artisanal groceries. Stroll around Dock Square, stopping in at cute shops as HB Provisions for local blueberry jam and local art galleries. Dine at a classic Maine clam shack or one of New England’s best restaurants, including the White Barn Inn, also home to the best lodging around. Take a sailboat out on the harbour, surf the consistently big breakers of the beach, bicycle around the rolling countryside, and go out on a lobster boat for a look into one of Maine’s longest-standing traditions.

1 day

Portland

As you sail along the coast toward Maine’s largest city and creative hub, we hope you’re noting the lighthouses. They dot the shore all the way along the state, each majestic and iconic in its own way. Nothing will prepare you for the historic charm and beauty of Portland, though, which has managed to become one of those cities that moves forward by maintaining its heritage; in this case, that’s lobster and local arts and crafts. Add that to one famously booming restaurant soon and you’ve got one of New England’s best destinations. Wander amongst the cute boutiques and design shops of the Old Port, meander up to the parks and cafés of Munjoy Hill, explore the galleries and studios of Congress Street, stock up on Maine-made goods at the Public Market House, and delve into the renowned dining scene at Duck Fat and Farmer’s Table. Bike along the rocky, picturesque coastline, or get the best views from above in a hot air balloon. Sail around the bucolic islands of Casco Bay, and don’t forget to have a lobster roll.

1 day

Boothbay

Whether you prefer to explore the stunning botanical gardens, hike one of the nature preserves, spend a day on the water, take in a concert or theater performance, play a round of golf, or simply explore the shops, restaurants, and art gallaries, the Boothbay Harbor region has something for everyone. A unique vacation awaits you as you explore the great outdoors. There are miles of hiking trails just waiting to be discovered that offer everything from relaxed strolls to challenging hikes. A trip to Boothbay wouldn’t be complete without soaking up a little of the local culture. With over 200 artists in the region, you will discover studios and galleries from Broadway musicals to classical concerts to performances by Grammy-Award winning artists. Take a tour of a local lighthouse in the area, or visit a local museum to experience the Maine of bygone days.

1 day

Camden

Nestled in the heart of Maine’s mid-coast region, where the mountains tumble all the way down to the water, these two towns offer some of the best hiking opportunities in the state – with the best views, too, of course. Head up into Camden Hills State Park and up Mount Battie as much for the panoramic view back over the harbour as for the scenery on the hike. Explore the bay on one of the area’s signature windjammers, or kayak inland past Islesboro. Back in the charming towns, explore the waterfront lobster shacks and dine waterfront with a glass of local wine; Maine’s first vineyard, Cellardoor Winery, is just ten minutes away. Head inland a bit to the surprisingly large Farnsworth Museum, with a good collection of Maine art, and to take a cooking class at the highly-acclaimed Salt Water Farm.

1 day

Ft. Knox

Fort Knox, Maine’s largest historic fort, features stunning military architecture and master granite craftsmanship. Constructed between 1844 and 1864 by master craftsmen and never fully completed, this is an unaltered example of mid 19th century granite coasted fortification. It is also New England’s finest unmodified specimen of military architecture of the period. The fort was strategically located on the narrows of Penobscot River to protect the river valley from naval attack. Although it never saw combat, Fort Knox garrisoned during the Civil and Spanish American Wars.

1 day

Penobscot

The head of Penobscot Bay is frequently called the “Gateway to Down East Maine”, It’s also the “Gateway to Acadia”. Enjoy the view from the top of Penobscot Narrows Bridge and Observatory at historic Fort Knox. Check out the panorama of Deer Isle and Camden Hills from Caterpiller Hill along route 15 in Sedgwick. Visit the picturesque coastal towns around the bay or explore Penobscot and join its ecclectic crowd. Neighboring areas are worth visiting for arts, crafts, dining, outdoor recreation, boat building, organic fruits and vegetables, unique history, and just plain relaxation. If you like the sound of wind in the woods, waves on the shore, and birds in the brush; the smell of fresh cut hay and beach roses; the taste of wild blueberries, fresh seasfood and local produce, you’re going to love it here.

1 day

Mt. Desert Island

Mount Desert Island is the largest island off the coast of Maine and the second largest on the eastern seaboard of the United States. Widely known as the home of Acadia National Park and the town of Bar Harbor, it draws millions of visitors each year yet only has an approximate year round population of 10,000. If you viewed the island from the air, you would notice north and south aligned gouges scooped out of the land as if by a very large hand. In this case the hand was that of a huge, slow moving, continental glacier over a mile high, almost 2 miles thick in some places. When the glacier finally melted and retreated, it left rounded and bare mountain tops, elongated ponds and lakes, many boulders, and the seven mile long Somes Sound.

1 day

Acadia

Acadia National Park is one stop that is a must see for nature lovers and those who simply appreciate wildlife. One of the most unique historical apects of how Acadia National Park formed is that it is due to the vision and donations of private citizens who anticipated the dangers that overdevelopment would bring to this coastal wonderland and acted quickly to prevent it. John D. Rockefeller, Jr., played a critical role by buildng the now famous carraige roads and donated over 11,000 acres of land. There have since been countless others who have donated their time and resources towards the continued realization of this dream so that we may all experience its raw natural beauty. Take a trip out to the beautiful park for a long hike and breathtaking views. You will not be disappointed!

1 day

Bar Harbor

One of Maine’s iconic destinations, along with its Acadia National Park, Bar Harbor was for decades New England’s premier summer resort, where estates belonged to families such as the Rockefellers, Astors, and Carnegies. Now, it attracts visitors as much for the national park and outdoorsy activities as it does for the cute town. Hike up Acadia’s Mount Cadillac and amongst its scenic lakes, cliffs, and valleys. Sail and kayak between the tiny islands that dot the bays, all ruggedly beautiful and green in the summer. Watch for a variety of whales, including humpback, finback and Minke, as well as porpoises, seals, and puffins. After you’ve worked up an appetite, eat and drink with the locals at the off-the-beatentrack Lompoc Café, the local and organic Red Sky, and the waterfront lobster roll mecca Seafood Ketch.