U.S. Flagged Charter Itineraries [Private Yacht Vacation]

In a time when traveling requires more precautions than ever, take advantage of the opportunity to explore some amazing domestic destinations. On a private yacht charter vacation, you can aboard a U.S. flagged yacht and bring along your personal party. Whether you travel to the northeast, or the southernmost point of the United States, the the adventures are endless. Get an idea of what your perfect charter vacation could look like with these 3 sample destination itineraries.

Destination #1 — Maryland

Day 1: Baltimore Harbor includes any water west of the National Aquarium in Baltimore and the Rusty Scupper Restaurant. You’ll find a variety of things to see and do at Inner Harbor, all within walking distance. Locals and visitors alike can’t get enough of the fine dining, cultural experiences, and exciting nightlife. During your week of cruising you will want to get close to the multiple lighthouse you can only appreciate by water.

Day 2: Sail to Chester River, the second-longest river on the Eastern shore. The Chester is bordered along much of its shoreline by rolling countryside and grand estates. Nearly 3 miles across at its widest point, the river gradually narrows to about a quarter mile at Chestertown, with good navigating depths in a well-buoyed channel. Beyond Eastern Neck Island – which features a wildlife refuge – the Chester River fans out in four generous branches, all of which are inviting.

Day 3: The quiet anchorages of Mill Creek and Whitehall Bay lie between the Chesapeake Bay Bridge and the Severn River. Be sure to pay attention to the winding, well-marked channel. Once inside, you’ll find good depths for peaceful anchoring and with the famous Cantler’s Restaurant, known for some of the best steamed crabs in the area.

Day 4: Another quaint waterfront village, St. Michael’s sits on a bucolic peninsula. It became an important shipbuilding center especially noted for its “Baltimore Clippers” – the fastest sailing vessels oftheir time. Today, the town is better known as a popular yachting center, and the site of the Chesapeake Bay Maritime Museum. The museum houses the largest collection of Chesapeake Bay artifacts, visual arts, and indigenous watercraft. Make sure to try one of the waterfront restaurants and enjoy the blue crabs as well as other local seafood like a local.

Day 5: Sail into the Wye River on the Eastern shore. The river’s branches embrace Wye Island along 21 miles of shoreline. You won’t find supplies or public facilities anywhere on the island. Secluded anchorages and a rich historical heritage are the main attraction. Stately old homes, many dating back to colonial times, stand on the banks at every turn.

Day 6: Make your way Annapolis, Maryland’s capital city, sailing capital of the USA, is on Chesapeake Bay. Its historic district includes 18th-century brick houses and the domed 1700s Maryland State House. On Church Circle, the Romanesque-style St. Anne’s Episcopal Church has Tiffany glass windows and a historic cemetery. The sprawling waterfront grounds of the United States Naval Academy feature beaux arts architecture, monuments and a naval history museum.

Day 7: Depart Annapolis after a leisurely brunch and memories of a lifetime to take home with you.

Destination #2 — New England

Day 1: Newport, Rhode Island: Meet your yacht in Newport, regarded as the sailing capital of the world – fittingly so as it’s home to the famed New York Yacht Club, which kept the America’s Cup trophy safe for more than a hundred years.Once in the harbor you will see megayachts and watch the sailboat races. You can be inspired at the legendary mansions, be energized by the vibrant nightlife, and savor local flavor at our many celebrated restaurants, wineries and breweries. Take time to visit some of the historic mansions that line the shore, peruse the boutiques and enjoy dinner at The Dining Room at Castle Hill Inn, for delectable seafood and wonderful sunset views.

Day 2: Block Island is located about twelve miles off the Rhode Island coast. To reach the island you must take a ferry or a small plane. Once you arrive, you will be overwhelmed by the island’s elegant beauty and small
town charm. Block Island activities include biking, parasailing, hiking on the many nature trails and beaches, sunbathing, kayaking, shopping, dining, horseback & moped riding. There are also plenty of beaches where you can while away the afternoon – the crew will pack you a picnic lunch. Dine on board this evening, enjoying island views.

Day 3: Nantucket Island, located just 30 miles off the coast of Cape Cod, feels like its own little world. An ideal one, where the beaches are always perfectly windswept, the lighthouses are straight out of a postcard,
and life goes at a slower pace. Could it be “the best island in the world”? National Geographic said it was. Did you know you don’t even need a car on Nantucket? It’s too charming for cars! You can just take the ferry over and ride a bike, with a little bell and a basket. Swimming, surfing, boutique shopping, fishing, and dining on fresh seafood are all glorious ways to spend a day, or a week, here.

Day 4: Martha’s Vineyard Once you’ve been “on island” on The Vineyard, as locals call it, you’ll never want to be “off island” again. After breakfast on board, the yacht will leave for Martha’s Vineyard, a longtime playground of the elite. The island is a summer haven, dotted with pretty beaches, harbor towns and cliffs topped by lighthouses. After a visit to the brightly colored cliffs at Aquinnah, sail around to Vineyard Haven and stop at the Black Dog Tavern for clam chowder at lunch. A bit further down the coast is Edgartown, famed as the location where the movie Jaws was filmed. Your captain will recommend an elegant restaurant for dinner ashore this evening.

Day 5: Martha’s Vineyard to Hyannis: Wake up to find the yacht en route to Hyannis on Cape Cod – famed as the Kennedy family’s getaway. Those interested in presidential history should visit the JFK Hyannis Museum on Main Street. Dine on fresh seafood tonight, overlooking the harbor bustling with yachts and local boats.

Day 6: The Elizabeth Islands: Head for the Elizabeth Islands, where you can stop off for a swim before anchoring in Hadley Harbor, secluded among forests and pastures. Cars are forbidden here, so the only way to arrive is by yacht, hiking in or on horseback. Take out the kayaks and water toys and enjoy frolicking in this quiet, picturesque spot.

Day 7: Hadley Harbor to Newport: One last breakfast in this idyllic setting, then it’s a few-hour cruise to Newport. Stroll through the town and have another clam chowder or lobster before the plane home. 

Destination #3 — South Florida

Day 1: Meet your captain and crew in Fort Lauderdale to begin your journey and cruise to Miami for your first night out. Enjoy the night life scene that only South Beach can bring and spend your night club hopping.

Day 2: Depart from Miami in the morning, when your captain will take you to Key Largo. Enjoy your day lounging in the sun en route, and spend the night in Ocean Reef, a private club community where you can enjoy fine dining and unparalleled service.

Day 3: Head to Marathon Key, and stop by the Hungry Tarpon restaurant for lunch. Don’t forget to try their signature dish, the tuna tacos. AFter lunch, pull into Marathon Key for the night.

Day 4: Enjoy a harbour cruise in Marathon and then shoot down to Stock Island, the perfect place to stop for one day. Here you can explore the beautiful, lush wildlife the Keys has to offer, or, hang at some of the friendliest local bars.

Day 5 + 6: Next, venture to everyone’s favorite spot: Key West. Enjoy this historical, vivacious city. Spend your days exploring Ernest Hemingway’s home (watch out for the 6-toed cats!), or shop ’til you drop on Duval Street. With a bustling night life, enjoy hopping from restaurants to bars. Don’t forget to have a slice of key lime pie before heading back to the ship.

Day 7: Depart from Key West and hit Little Palm Island for lunch, a gorgeous resort that is nestled in paradise. Spend the evening there before heading back home.

*Note: The Florida Keys may be closed during the date of a potential future charter due to the coronavirus pandemic. Please see the Florida Keys website to stay up-to-date on current travel regulations. The above is a sample itinerary, which may be adjusted based on regulations or personal preferences.

Ready to explore all of your charter options? Contact our Charter team to get started.