Named “Best Island in the World” by National Geographic, Nantucket couples luxury with historic charm for a tourism experience that draws in nearly 50,000 people every summer. Once the world’s leading port for whaling, this 50 square mile island is now a designated National Historic District dedicated to sustainability and the conservation of its moors, sand dunes, forests, and grasslands.
This island is famous for historical sites, including grand steeple churches and the Brant Point Light, and natural beauty. In addition, Nantucket boasts a variety of activities exclusive to the island. Biking is the most popular means of getting around the island. Roam the cobblestone streets to find specialty shops, art galleries, brand name boutiques, cottages, and mansion of whaling captains.
Enjoy the sun and calm waves at Surfside, Jetties, and Children’s beaches. Visit Madaket beach for striking sunsets and Great Point for shore fishing. Nantucket bluefish are some of the largest found anywhere, ranging from 8 to 15 pounds.
Dock at Nantucket Boat Basin, a pet friendly marina admired for its customer and concierge services. At the end of the day, wind down with fresh juice or homemade ice cream at the Juice Bar, or relish in seafood and waterside views at CRU Oyster Bar or Brant Point Grill.
Carved by glaciers millions of years ago, the epic Aquinnah Cliffs line the half-mile stretch of pristine coastline that makes up Moshup Beach â a prime destination for sunning and swimming.
Protected by the Nantucket Sound, scenic Jetties Beach is just a mile from downtown Nantucket. For a mellow locale and rolling waves, Siasconset Beach offers a peaceful retreat.
As evidenced by local fishermen frequently lining the jetties, the village of Menemsha is ideal for fishing including fluke, sea bass and scup.
Surf cast for the notorious Nantucket Blues a.k.a. bluefish especially from Great Point at sunset. Frequently referred to as the best in the world, Nantucket bluefish are some of the largest anywhere â ranging from 8 to 15 pounds.
The first lighthouse constructed on Martha's Vineyard, Gay Head Lighthouse was built in 1799 and has since been restored from the original wooden structure to today's brick exterior.
Brant Point Light is America's second-oldest lighthouse, standing just 26 feet tall. On the island's northernmost point, Great Point Lighthouse aids mariners.
On the southeastern side of the island, the stately Edgartown village was the center for whaling activities between 1820 and 1865 with over 100 whaling captains living here.
Classified as the Whaling Capital of the World, Nantucket was once the headquarters for whalers for over a century starting in 1750. Today, visit the Nantucket Whaling Museum to observe the collection of whaling equipment, scrimshaw and artifacts.
Accommodating vessels up to 200 feet, Vineyard Haven Marina offers concierge services for shoreside excursions including island tours and local restaurants.
With a full range of guest services, Nantucket Boat Basin is complete with pet-friendly accommodations and concierge services to assist in reservations, transportation and activities on the island.
The Great Loop, the Downeast Loop, the Triangle Loop, Florida's Little Loop boaters seem to be quite loop happy. So here's one to add to your loopy list: the Nantucket Sound Loop, circling from Cape Cod in the north to Martha's Vineyard and Nantucket in the south. There are many well-protected harbors, the fishing is very good, beaches run for miles, and there are quintessential small towns everywhere.
Great place to start is in Woods Hole, just down the road from Falmouth on the Cape. It's less than 12 miles from the Cape Cod Canal and less than 25 from Newport, Rhode Island. From there, the loop runs east-southeast to Martha's Vineyard, east to Nantucket, north up to Hyannis, and west over to Cotuit Bay before heading southwest to return to Woods Hole. This route stays inside the Nantucket Sound, safe from large ocean swells. There are many shoals scattered around the sound, but they are well charted and marked, and there's plenty of room to avoid them. The longest run is about 25 miles, which means easy day trips for even the slowest of vessels. By going north from Nantucket to Hyannis, the trip takes advantage of the prevailing southwesterly winds that dominate here during the summer.
In Woods Hole, tie up in Hadley's Harbor, a very unique place. The Forbes family installed mooring buoys here in the inner harbor they are marked private but that seems to be a technicality, as cruising boats use the moorings regularly. Oh, and by the way, they're free. The only problem with that is that they're also often full. Your other options are to anchor in outer Hadley's Harbor or proceed to a mooring or slip in Woods Hole harbor. While you're in town, don't miss the tour at the Woods Hole Oceanographic Institute, it is excellent. And when you're motoring out of Woods Hole, pay attention to the current as you're maneuvering toward open water there are rocks all around!
Next up, Martha's Vineyard. This is a very big island with many ports to choose from. I like staying in Vineyard Haven Harbor. It's in the center of the island, is sheltered from the winds, has options for anchoring, mooring or dockage, and the excellent local bus system makes it easy to get around. Plus, the collection of classic yachts moored here is great fun to check out. To the east, Oak Bluff has moorings and dock space options and seems to be party central. Edgartown, farthest east, is an outstanding little village with anchoring, mooring, and some dock space as well. A walking tour of the many old sea captains' houses is a great way to stretch your legs. Take the ferry across to Chappaquiddick to explore the marshes and beaches.
After the Vineyard, it's on to Nantucket. This has to be the most New England of New England destinations. Many of the streets are cobblestone, and the buildings are postcard perfect. There is room to anchor, a large mooring field, and in the harbor is the excellent Nantucket Boat Basin (508-325-1350, nantucketboatbasin.com), which has earned the Marinalife Transient Marina Of The Year Award for three years running. George Bassett, the dockmaster for 28 years, has built up an 86 percent customer return rate, in large part because it's all about customer service at Nantucket Boat Basin. George and his 40-person staff keep everyone happy, and it's important to book your reservations early to make sure you get a spot. The wharf-like setting is charming and one-of-a-kind, with shops and restaurants just steps away. It has the appearance more of a fishing village than a marina, and it works very well. Arrange for a bike rental to venture along the island's paved bike trails past beautiful homes and pristine beaches. You can also run your dinghy five miles from Nantucket Boat Basin up to the Head Of The Harbor and the stunningly gorgeous Coskata-Coatue Wildlife Refuge.
There's nothing quite like Nantucket.Next, head 25 mile north to Hyannis. Don't lie, the first thing you think of when hearing Hyannis is Kennedy, and rightly so. That family made the town famous, and still has a compound there. You can anchor in the outer harbor not far from several of their moored boats. Visit the John F. Kennedy Hyannis Museum to learn even more about one of our best-known presidents. But there is also so much more to Hyannis. Well-protected Lewis Bay is accessed via a deep channel, and has a mooring field run by the Hyannis Yacht Club and a large area available for anchoring. Further into Hyannis' inner harbor you'll find the Hyannis Marina (508-790-4000, hyannismarina.com), a resort-like facility with all the usual extras plus 200 slips for yachts up to 200 feet, a pool, Trader Ed's Cabana Bar, Tugboat's Restaurant, three courtesy cars, and one of the best-stocked marina ships stores I've ever seen. Carla Sullivan, dockmaster for 18 years, runs a tight ship if you need it, she can get it. She regularly attends to the needs of the megayachts that frequently tie up, but gives the royal treatment to every boat that lands at her docks, no matter how large or small. If you can pull yourself away from the marina, there are all kinds of excellent restaurants and attractions to check out. The Black Cat Tavern has some of the best chowda around. Downtown there's a unique collection of waterfront artists' studios, a maritime museum, and plenty of shops to fulfill the need for retail therapy.
There are nice beaches on the inside and outside of Egg Island, just a quick dinghy ride from anywhere in the harbor.
The last stop on this loop is Cotuit Bay. The channel at the entrance to Cotuit Bay is quite shallow, so the preferred entry route is the channel into West Bay, followed by an immediate turn into the Seapuit River behind Dead Neck. This route gets dredged frequently and big sailboats use it regularly. There are marinas further up West Bay and a mooring field in Cotuit Bay, but I like to anchor behind Dead Neck in the no-wake zone. There is a sandy bottom with good holding behind the barrier-island bird sanctuary. You can walk around the beach to the sound to swim in the ocean, or just relax in the peaceful, quiet setting. From the West Bay channel, it's an easy day trip back to Woods Hole.
Falmouth Harbor, less than 10 miles west of Woods Hole, has plenty of marinas if anchoring out for a night is not your cup of tea. You can do this loop in a week, though it's better if you give it two weeks, and you could easily spend a month or two doing it, exploring all that the many islands and harbors have to offer. However long you go for, enjoy Nantucket Sound!
Sited on the banks of Carter Creek where it flows into the Rappahannock River, Irvington boasts deep, protected waters and a quaint Colonial ambiance. The village once thrived as a stop for steamboats carrying goods and travelers across southern Chesapeake Bay, which is why The Steamboat Era Museum here is so popular today. For more history, head to Christ Church (finished in 1735), where you can tour one of the nation's finest examples of Georgian architecture. Hit the farmers' market for fresh seafood, meat and vegetables or visit one of the vineyards in the area. Dock at The Tides Inn Marina.
Chesapeake Bay possesses a seemingly endless array of temptations for boaters, yet St. Michaels remains a perennial favorite for its sheer beauty and well-roundedness. Yes, it has picturesque streets lined with vintage homes leading to a gorgeous harbor. Yes, is has charming storefronts, trendy retailers and fine art galleries. Yes, it has spas and retreats for pampering and relaxation. Yes, it has fine dining from waterfront crab houses to gourmet brasseries. And yes, it even has the Chesapeake Bay Maritime Museum and the St. Michaels Museum on St. Mary's Square. What's not to love? Dock at St. Michaels Marina or at the Chesapeake Bay Maritime Museum, a members-only marina.
The entire city of Cape May is designated a National Historic Landmark due to its unprecedented concentration of Victorian buildings. It's also called the nation's oldest seashore resort and has all the trappings to back it up, including a two-mile boardwalk paralleling the beach with arcades, seafood joints and shopping galore. Cape May makes a great base for outdoor fun bird-watching, boat tours, dolphin cruises, kayaking and canoeing and the Naval Air Station Wildwood Aviation Museum is just a short cab ride away. Dock at South Jersey Marina or Canyon Club Resort Marina.
This village at the eastern end of Long Island's North Fork is modest and casual with the look and feel of an authentic whaling town. Vessels of all sizes are moored in the deep-water harbor, seagulls soar overhead, and, occasionally, there's a whiff of fried clams on the air. From the waterfront, you can walk to restaurants, shops and even a vintage carousel. Visit the East End Seaport Museum & Marine Foundation and the famous S.T. Preston and Son Chandlery for some nautical seasoning. Dock at Mitchell Park Marina or Brewer Yacht Yard at Greenport.
Well known as an old shipbuilding town, Mystic is also home to some of the finest modern marine facilities on Long Island Sound. There's plenty to do, particularly for those cruising with kids. The waterside streets are lined with shops, galleries and restaurants, and there's also a planetarium and children's museum. No trip here is complete without a tour of Mystic Seaport, the nation's leading maritime museum or the Mystic Aquarium & Institute for Exploration. Dock at Mystic Shipyard, Brewer Yacht Yard at Mystic or Seaport Marine.
The Vineyard, as locals call it, is the bigger, more outgoing sister of Nantucket. The island is closer to Cape Cod, making it a more convenient, and is adorned with picturebook beaches, elegant inns, and upscale dining and shopping, which draw celebrities and serious vacationers alike. Brightly painted gingerbread cottages line the streets of Oak Bluffs (also the home of the Flying Horses, the oldest working carousel in the U.S.). Visit Aquinnah Beach to see the famous color-streaked cliffs there. Dock at Oak Bluffs Marina, Vineyard Haven Marina or Edgartown Town Docks.
The world's former top whaling port is now a remote summer vacation spot with a serene seaside look and feel. Restaurants and boutique stores line the streets of Nantucket Town, where you will also find the majority of dining and nightlife options, and the Museum of Nantucket History includes exhibits on the history of the island. Beachcombing, swimming, surfing and fishing are all glorious ways to spend a day, or a week, here. Bring your bike, too, as that is the best way to get around the 50-square-mile island. Dock at Nantucket Boat Basin.
Boston is one of the oldest cities in the U.S. and has an amazingly rich history and culture. You can still visit where many of the crucial events of the American Revolution occurred along the Freedom Trail, which is marked by a red line of bricks embedded in the ground. The Inner Harbor is home to the USS Constitution at the Charlestown Navy Yard as well as the Boston Tea Party Ships & Museum at Fort Point Channel. It also offers the Boston Harbor Islands National Recreation Area and numerous waterfront restaurants. Dock at The Boston Yacht Haven, Constitution Marina or Marina Bay.
It's the Maine coast as it was meant to be. Lobster boats and schooners ply the harbor in front of a charming downtown studded with locally owned shops, galleries, seafood eateries and cafes there's even a beautiful public library right on the waterfront. Take a day-trip to the outlying islands and their 18 lighthouses, or head inland and experience Camden Hills State Park, a mecca for outdoor enthusiasts featuring 30 miles of scenic hiking and mountain biking trails, breathtaking views of the surrounding hills and lakes and well maintained campgrounds. Dock at Wayfarer Marine.
Dotted with historic homes and featuring the nation's third-tallest monument, the 352-foot Doric column Perry's Victory and International Peace Memorial, this village on South Bass Island is Americana at its best. It ranks in the top five confectionary destinations in the state, and its largest souvenir shop reportedly has 1,000 items with the town's name on it. Enjoy winery tours, park tours, cave tours and home tours via rented golf cart, or spend your days kayaking, parasailing, fishing, biking, hiking or golfing. It's the quintessential choose-your-own-adventure family vacation spot. Dock at Miller Marina or The Crew's Nest.
The world's largest freshwater island, Manitoulin in northern Lake Huron has been called a place of convergence. Indeed, history, culture and natural beauty merge in the two-dozen settlements spread across its 1,000 square miles of boreal forest, bluffs and meadows. The Holy Cross Mission and Ruins in Wikemikong commemorates early Jesuit visits to the island, which began around 1648. Sheguiandah holds a prehistoric quarry that has yielded stone pools and arrowheads dating back 9,000 years. Gore Bay, one of the larger communities, offers modern amenities such as shopping, restaurants and facilities for tennis and golf. Dock at Spider Bay Marina in Little Current.
With its megawatt downtown and world-famous attractions, it's not surprising to see the Windy City listed here. Navy Pier, once a shipping and military training facility, is now a major tourist draw with 50 acres of promenades, shops, eateries and amusements. Shoreline Sightseeing operates nine touring boats and 11 water taxis that offer guided skyline tours, fireworks cruises, and special events such as Brew Cruises and Wine Tasting Cruises. Then, of course, there's Michigan Avenue, Shedd Aquarium, Millennial Park, the Field Museum of Natural History and much more. Dock at DuSable Harbor, Burnham Harbor or 31st Street Harbor.
The hundreds of islands breaching the sparkling blue waters here are everything you've heard rugged, wild and richly fertile in scenery. May through September is the ideal time to visit, when the weather is mild and the whales (orcas, mainly) are on the move. You can take advantage of the many lovely resorts and lodges, the attractions of the charming seaside towns, or simply find your way to remote anchorages and deserted bays. Dock at Port of Friday Harbor on San Juan Island or Deer Harbor Marina on Orcas Island.
Surrounded by Acadia National Park's pine-covered mountains and granite cliffs, this New England seaside gem has attracted visitors since the mid-1800s. Artists chose this beautiful port for painting dramatic seascapes, and America's wealthiest tycoons (Rockefeller, Ford, Vanderbilt and more) built grand summer homes along West Street. Historic lighthouses along the shore keep watch over local maritime treasures from whales to lobstermen. The town is known for elegant architecture amidst quaint shops, pubs and galleries.
Eating: Fine dining options include La Bella Vira at the Harborside Hotel, The Reading Room, Havana, Asticou Inn Restaurant and The Burning Tree Restaurant. Casual fare is available at The Travelin' Lobster, Stewman's Lobster Pond and Paddy's Irish Pub.
Docking: Bar Harbor Regency Hotel & Marina accommodates vessels up to 150 feet, complete with T-shaped floating docks, heated outdoor jacuzzi and pool, tennis courts, and courtesy transportation.
As Maine's largest city, Portland presents the charm of a classic seacoast town with a cosmopolitan edge built around museums, a new science center, first-rate symphony orchestra and theater. Its rich maritime history is on display in the restored Old Port District where buildings have been revitalized into chic boutiques, art galleries, luxury spas, brewpubs and innovative restaurants. Portland has been nationally recognized for its vibrant culinary scene and was voted America's Foodiest Small Town by Bon AppÃ©tit Magazine.
Eating: To feast upon exceptional New England seafood and spirits, try Eventide Oyster Co., Piccolo and Scales Restaurant. Find more relaxed dining at The Grill Room & Bar, DiMillo's on the Water (a floating restaurant in the harbor), Central Provisions, The Highroller Lobster Co., and Boone's Fish House & Oyster Room.
Docking: Accepting vessels up to 250 feet, Dimillo's Old Port Marina is equipped with floating docks and ValvTect fuel. Courtesy GPCVB
Tucked away between Portland and Portsmouth, this delightful town is home to a pair of U.S. presidents and miles of stunning beaches. Some seaside stretches are covered with white sand; others display dramatic rock formations, yet all of them merge together to forge a spectacular shoreline. Kennebunkport's historic downtown and Dock Square bustle with unique stores, galleries and antique shops. The Intown Trolley chugs past historic sites, including ship captains' homes, St. Ann's Episcopal Church, the Colony Hotel, the Customs House, St. Anthony's Franciscan Monastery, Gooch's Beach and the Bush estate. Nature lovers can hike trails or bird watch at nearby Rachel Carson Wildlife Refuge, a salt marsh estuary and favorite landing zone for a menagerie of migratory birds.
Eating: Exquisite organic dishes are served at Earth in the luxurious Hidden Pond Resort. Meals made of local lobster, oysters and other aquatic treats are on tap at The Clam Shack, The Burleigh, The Dory, 95 Ocean and Federal Jack's Brewpub.
Docking: Next to Dock Square, Chicks Marina can accommodate vessels to 165 feet in length.
Founded in 1630, Boston is an urban explorer's playground where skyscrapers meet cobblestone streets and visitors can enjoy endless activities and timeless adventures. As soon as you pull into the harbor, its rich history and culture are at your fingertips with attractions such as the New England Aquarium, Boston Tea Party Museum, Institute of Contemporary Art and Boston Children's Museum.
Eating: Each neighborhood has its own unique character and serves an abundance of ethnic dishes, sophisticated nouvelle cuisine and traditional New England fare. For an exceptional regional culinary experience, check out L'Espalier, Ostra, Menton Restaurant and Meritage Restaurant & Wine Bar.
Docking: Vessels up to 300 feet can find a home at Boston Yacht Haven with a full range of services from multi-phase, mega-yacht power to wave-attenuating floating docks. In Charlestown, right on the Freedom Trail, Constitution Marina offers detailing services, floating docks and a swimming pool, while Charlestown Marina has the capability to host vessels up to 400 feet with upgraded Ipe Decking.
The best vantage point in Provincetown is at the top of the Pilgrim's Monument, a 252-foot granite structure that commemorates the Mayflower pilgrims' landing here in 1620. The museum tells the tale of their five-week stay in the area before sailing off to Plymouth. For more local lore, Whydah Pirate Museum uses artifacts, treasure and interactive displays to share the story of a slave ship that was overtaken by buccaneers and sank offshore during a storm in 1717. History is a highlight, but the town's gorgeous beaches, walkable dunes and woodland trails are also a big draw. To top it off, the thriving arts community attracts visitors with galleries, theater, music, literary events and hand-crafted goods.
Eating: Locals recommend The Red Inn and Spindler's Restaurant for fine dining and spectacular seafood. The hot spots for comfort cooking and easy atmosphere are The Lobster Pot and Local 186.
Docking: Provincetown Marina in eclectic P-Town accommodates vessels up to 300 feet and offers ample amenities such as a fuel dock, captain's lounge, and upgraded restroom and laundry facilities.
This 50-square-mile island is fun to explore on a bicycle. Pedal around at an easy pace to see endless beaches, seaside cottages, captain's mansions, steepled churches, 18th-century lighthouses, designer boutiques, specialty shops, chowder shacks and cobblestone streets that line the historic wharves. Nantucket was once the world's leading port for the whaling industry, which is detailed in a local museum. For an exciting day trip, rent a 4x4 SUV for an off-road adventure along 16 miles of sand roads and beaches to Great Point Light to catch an idyllic sunset.
Eating: When all this sightseeing brings on a thirst, you can plan cocktail hour at Cisco Brewers, Triple Eight Distillery or Nantucket Vineyards. Visiting yachts have many restaurant options that feature local seafood and oysters, such as Brant Point Grill at the White Elephant Hotel, Toppers Restaurant at the Wauwinet Resort, Nantucket Prime, CRU Oyster Bar, The Boarding House and Slip 14 Restaurant.
Docking: In historic Nantucket Harbor, welcoming vessels up to 250 feet, Nantucket Boat Basin offers a full range of luxury amenities including fuel, slip-side cable television and complimentary pet amenities. On-site concierge services are also available to arrange restaurant reservations, excursions and transportation to the island's nearby beaches, charming boutiques and galleries.
From presidents to pop stars, Martha's Vineyard is a vacation haven for affluent travelers who want to relish windswept beaches, red clay cliffs and natural beauty. The islands interior pristine woodlands are ideal for hiking or horseback riding. Horticulturalists flock to Polly Hill Arboretum and Mytoi Gardens. Edgartown bustles as the island's largest town and center of upscale nightlife. Its well-preserved 19th-century buildings serve as a time capsule to when ship captains led whaling fleets into the Atlantic. Trails near Menemsha reveal panoramic views of the rocky ocean edge and delightful fishing villages.
Eating: High-end restaurants include Garde East, Beach Road Restaurant, Red Cat Kitchen at Ken N' Beck and The Sweet Life Café. Casual food is served at Waterside Market, Offshore Ale Co., Copper Wok Pan Asian House & Sushi Bar, Nancy's Restaurant, The Black Dog Tavern and Little House Café.
Docking: Hosting vessels up to 200 feet, Vineyard Haven Marina has ample beach front access, a private waterfront boaters' lounge and on-site massage services.
Newport is home to world-class festivals, music, seafood, tennis, polo and more. The Cliff Walk, a 3.5-mile oceanfront path, traces the edge of the sea and passes by elegant Gilded Age mansions built by America's wealthiest families. Colonial Era fans can tour 17th-century churches, forts, windmills and historic buildings from farmhouses to stately residences. Visitors looking to unwind can enjoy stylish pampering at various spas or engage in retail therapy at local boutiques. Liquor connoisseurs can take tours and sample the wares at hot spots such as Newport Storm Brewery, Distilling Company (aged rum) and Vineyards.
Eating: When hunger hits, you can find upscale dining at 22 Bowen's Wine Bar & Grille, The Mooring Seafood Kitchen & Bar, Clarke Cooke House and Midtown Oyster Bar. More relaxed atmosphere is at Perro Salado and the Smoke House restaurant.
Docking: In the midst of downtown, Newport Yachting Center hosts vessels up to 140 feet and provides boaters with ValvTect fuel, and access to the pool and health club.
Bar Harbor & Acadia National Park Scenic Air Tours, Bar Harbor, Maine
Soar into the skies for a heavenly view of Maine's spectacular coastline, rugged mountains and seaside towns for an experience of flight you won't forget.
Bar Harbor Inn Spa, Bar Harbor, Maine
Let certified spa staff perform their therapeutic magic with a variety of soothing massages, body treatments, facials, manicures and pedicures.
Kennebunkport Festival, Kennebunkport, Maine
Experience the largest multi-day art, food and wine festival featuring more than 30 events and some of the country's top chefs (June 4-9, 2018).
Lucky Catch Lobster Cruises, Portland, Maine
Live the life of a New England waterman pulling up traps filled with lobsters. Cook your catch at home or let chefs in a nearby eatery prepare them for you.
Boston Freedom Trail Boston, Mass.
Walk in the footsteps of our founding fathers along a 2.5 mile urban hike to Revolutionary War sites, churches, museums, burying grounds, celebrated ships and historic markers.
White Elephant Spa, Nantucket, Mass.
The White Elephant Spa offers a revitalizing, refreshing and invigorating experience by using nature's organic ingredients.
Nantucket Film Festival, Nantucket, Mass.
As one of the world's premier cinematic events, movie buffs come from around the globe to preview screenings, signature programs, and interviews with top directors and producers (June 20-25, 2018).
Wequassett Resort & Golf Club, Harwich, Mass.
Designed by Brian Silva, Golf Magazine 1999 architect of the year, the course at Wequassett Golf Club blends perfectly with the Cape's unique topography and natural beauty.
Newport National Golf Club, Middletown, R.I.
Newport National Golf Club offers a dramatic setting overlooking the Atlantic Ocean and Sakonnet Passage. The 200-acre landscape nursery is both a championship course and open space tribute to environmental sensitivity.