New England Charter Itineraries

New England Charter Itineraries includes sample itineraries for Maine, Massachusetts, Rhode Island, Connecticut, and the state of New York.
All itineraries are customized based on the charterer’s preference and, most notably, the weather.

The charter season in New England starts late spring and ends in early October. The weather is cooler except for July and August, when there could be hot days and cool evenings. Traveling with a selection of clothing for local weather is essential.

Many yachts relocate from Florida, the Bahamas, and the Caribbean to New England for the charter season. Sailboats, motor-yachts, and a few catamarans are the usual charter options.

New England Charter States

Maine Sailing Itinerary

Maine Sailing Itinerary
Maine Sailing Itinerary from Mid-Coast and Downeast Maine (a 7-Day sail) New England yacht charter "Fiona Rois" Explore the rugged and beautiful coast of Maine, where there are literally hundreds of picturesque islands, coves, and harbors. The following New England sailing vacation offers visits to out-of-the-way fishing villages accessible only by boat, as well as seacoast towns with restaurants and shops. Allow Luxury Yacht Charters to plan every detail of your Maine Sailing Itinerary. All you have to do is relax and enjoy the ride. Day One Meet your yacht charter in Southwest Harbor and enjoy lunch on board while watching the harbor activity. Sail through the famous Hinckley Yacht moorings and view some of the prettiest sailboats ever. Then set sail for Frenchboro, Long Island, passing Placentia, Black, and Gott’s island. If the tide is low, you can see seals on rocky ledges along the way. Frenchboro is a...

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New York Charter Itineraries

New York Charter Itineraries
Your captain will assist you in creating the perfect New York Charter itinerary. There's so much to see and do in this area of New England that you could easily spend a week or longer exploring. New York: Places to See There is much to see just in the New York City harbor. Cruise around the inner harbor, checking out all the sights of New York, such as the Seaport, Statue of Liberty, aircraft carrier Intrepid, and the Brooklyn Bridge. Statue of Liberty. Photo by Priyanka Puvvada on Unsplash. Long Island and Greenwich, Connecticut, are also excellent options for your New York Charter itinerary. Depart Brooklyn and sail up the East River into Long Island Sound. Enjoy lunch as you travel 45 miles (about 4 hours) to Huntington Harbor, Long Island. While in Huntington, visit the town and its nightlife. The next day anchor just outside the bay and take...

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Newport Charter Itinerary

Newport Charter Itinerary
Lighthouse in New England NEWPORT TO NEWPORT - 7 DAY ITINERARY Start your Newport Charter Itinerary from one of the many marinas in the town. Explore the town before you board your yacht, or on your return. There are many sights to see, shops to explore, and food to sample. Day 1: Newport Arrive at your yacht in Newport, one of the world’s yachting capitals. The historic waterfront and Bannister’s Wharf are worth exploring, as are the fabulous mansions such as the Vanderbilts’ ornate Breakers. Have a drink at The Candy Store, a watering hole for America's Cup crews, or savor a bowl of award-winning chowder at The Black Pearl.  Day 2: Block Island This is a quiet island with just a single village surrounded by miles of fine beaches and hiking trails. Rent a bicycle and enjoy the flat terrain, but be sure to stop at Aldo’s Bakery for to-die-for goodies.  Day 3: Nantucket Called the “Grey Lady” for...

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Newport Leisure Charter Itinerary

Newport Leisure Charter Itinerary
This 8-night Newport Leisure Charter Itinerary lets you cruise at a relaxing pace. You'll have plenty of time to enjoy sightseeing, watersports, and exploring in the tender. Day 1: Newport to Cutty Hunk, MA Begin your journey with a scenic two-hour cruise from Newport Harbor to historic Cuttyhunk Island in the Elizabeth Islands group. The Island is the outermost of the Elizabeth Islands. Moreover, yacht charter guests enjoy the ambiance of the area. Day 2: Cuttyhunk, MA Cuttyhunk has a lovely harbor with good fishing and scenic hiking trails. Spend the day enjoying this quiet destination's solitude and peaceful ocean atmosphere. Or, if you'd like, try something more active such as jet skiing or kayaking. Nature lovers will enjoy looking at seals at Gull Island. Day 3: Vineyard Haven, Martha's Vineyard After a leisurely breakfast, cruise one and a half hours from Cuttyhunk to Vineyard Haven. Take your time exploring...

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Newport to Portland Maine Itinerary

Newport to Portland Maine Itinerary
The New England Coast is known for its rugged coastline and historic ports. When you sail the Newport-Portland, Maine itinerary, you will experience this beautiful area's history, wildlife, and cuisine. Day 1: Newport, Rhode Island Meet your yacht in Newport. This town is home to the famed New York Yacht Club, which kept America's Cup trophy safe for 132 years. Visit historic buildings, peruse the boutiques, and enjoy dinner at a waterfront restaurant. Day 2: Block Island Block Island is a great first stop on your sailing vacation. Whether you enjoy outdoor activities, art, music, shopping, dining, or simply enjoying the scenic beauty, this island has it. Best of all, you won't find any traffic lights or chain stores here. Day 3: Nantucket Charming Nantucket awaits you with sandy beaches and cobblestone-paved streets. Visit Cisco Beach and the Jethro Coffin House (the oldest house on Nantucket). See the Sankaty Head...

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Newport with Woods Hole Itinerary

Newport with Woods Hole Itinerary
This sample Newport with Woods Hole Itinerary prepared by Captain Meagher, combines history, seafood, island life, and shopping. Enjoy jet skiing, seals, and fresh seafood while relaxing on your private yacht. Day 1: Newport / Cuttyhunk Welcome aboard your Yacht on your Newport itinerary. As soon as you are settled in we will depart Newport for Cuttyhunk Island. Leaving Newport Harbor is always exciting. Newport has the distinction of being the Sailing capitol of the East coast. However, it was also home to America’s Cup for 126 years, the longest winning streak in sports history. Today the harbor is filled with both modern and classic sailing vessels. Departing Newport, we will pass some of the famous Newport mansions including the Vanderbilt estate “The Breakers”. Leaving the Providence river, we will be cruising through Block Island Sound into Buzzards Bay. Then anchoring in the harbor on the only town on the island of...

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Maine, the Pine Tree State, offers relatively unspoiled beauty. The state’s 230 miles of coastline have lighthouses, small beaches, fishing villages, many bays, and islands. Lobsters and seafood lead the cuisine offerings in Maine. And Portland has become known for its fine dining. Acadia National Park, on Mount Desert Island, is a national treasure. For the active guest, there is hiking.


Massachusetts offers Nantucket Island, Martha’s Vineyard, Cape Cod, and many other select ports.

Rhode Island, the smallest state, is the yacht charter hub for New England. Along with Newport being the Queen of American Resorts. Its Gilded Age of 19th-century mansions, charming shops, restaurants, and cafés are all within walking distance. Before departing on your yacht enjoy the Cliff Walk, a national historic trail along the bluffs. The Museum of Yachting, the Touro Synagogue National Historic Site, the oldest Jewish house of worship in the USA. In addition, Newport hosts many summer music festivals, which are a treat.

Connecticut offers charming towns along the coast with marinas. Old Saybrook and Mystic are two destinations along the coast. Moreover, Mystic’s seaport looks like a whaling village from the 1800s.


New York combines the excitement of New York City with the tranquility of the Hamptons on Long Island. Furthermore, explore the Hudson River or sail from the Hamptons to Block Island, Mystic, Nantucket, or Martha’s Vineyard.

New England Charter Itineraries has many options. For the sailor, or those who wish to relax in luxury while enjoying the surrounding beauty.

Please contact us at 1 (321) 777-1707 or complete our contact form to start planning your yacht charter vacation! It's never too early, or too late to inquire about your bespoke private yacht charter.

You make the memories. We make the arrangements.