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Enjoy A Luxury Yacht Charter Vacation In the Chesapeake Bay

By Rob Bowman | Posted On Jul 18, 2019
Updated On Jun 03, 2020

Cruising the Chesapeake Bay on a luxury yacht charter at the end of Summer or early Fall couldn't possibly be any more enjoyable. With the nighttime temperatures cooling and the water still warm, there are countless opportunities to play during the day and enjoy spectacular restaurants, sightseeing of the water-front villages, and taking in the historical heritage that Annapolis has to offer. Once the summer tourists are gone, the shoreline of the Chesapeake takes a step back in time as it reveals quaint villages and many rivers and creeks that can be explored on your tender. Spend your day immersing yourself in the culture and food of the Chesapeake Bay, only to return to your luxurious hotel on the water to be pampered by crew and enjoy the evening stars at sea. 

Below is a sample itinerary of what your day could look like on a yacht charter vacation to the Chesapeake Bay as well as several yachts open to book. If you would like to reserve your week in the Chesapeake on any yacht, please contact United Yacht Charter Director Nicole Haboush at (561) 558-3113 or by email at

Sample Itinerary:

Day #1: Cruising Baltimore Harbor includes any waters west of the National Aquarium in Baltimore and the Rusty Scupper Restaurant. You will never be bored heading to shore in the Inner Harbor as there are a variety of things to do all within walking distance of the dock. Local and visitors alike can't get enough of the fine dining, cultural experiences, and exciting nightlife. Cruising during the day will be taking in the multiple lighthouses that scatter the Chesapeake Bay and can only be appreciated by boat.

Day #2: Visit the Chester River, the second longest river on the Eastern Shore, and enjoy the breath-taking views from the flybridge of your private yacht. Whether you hire a captain or not, the Chester River is three miles across at its widest point and gradually narrowing to about a quarter of a mile; although with good navigating depths and a well-buoyed channel. Much of the shoreline here is bordered with rolling countryside with grand estates that are magnificent to see by water. Beyond Eastern Neck Island - which features a wildlife refuge - the Chester River fans out in four generous branches that are all waiting to be explored.

(Seen below: Take in Baltimore's Inner Harbor skyline from the bridge of your private yacht.)

yacht charter vacation baltimore harbor

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 along with the famous Cantler’s Restaurant which is known for some of the best steamed crabs in the world.

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 of their 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.

(Seen below: The quaint town of St. Michael's is a unique day trip by yacht that will introduce you to some of the best seafood anywhere and several local historic sites.)

luxury yacht charter st michaels

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 to Annapolis, Maryland’s capital city, sailing capital of the USA, and right on the Chesapeake Bay. Its historic district includes 18th-century brick houses and the domed 1700's 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.

(Seen Below: The city docks in the heart of downtown Annapolis. Enjoy the shopping, restaurants, and stop and have a painkiller at Pusser's Caribbean Bar & Grill.)

luxury yacht charter vacation annapolis

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

So you've decided that the Chesapeake Bay is where you want to take your luxury yacht charter vacation. Now it's time to select the right yacht for your perfect trip. Below are four yachts for charter, with or without a captain, that can be booked today. If this sounds like a vacation for you, please contact United Yacht Charter Director Nicole Haboush at (561) 558-3113 or by email at

Option #1: "Renaissance" - 116' Hargrave Motor Yacht - From $85,000

Enjoy the views of the Chesapeake Bay from Renaissance, a 2016 Hargrave 116' motor yacht that features five luxurious king-berth staterooms, including an on-deck master suite and two lower king suites that can be converted into twin staterooms. Whether coming with family and friends or entertaining clients, Renaissance is designed to pamper all of your desires on this luxury yacht vacation. Learn more about the captain, private chef, and crew, as well as what a menu could look like during your vacation, by following this link

Option #2: "MB3" - 100' Hargrave Motor Yacht - Price From $55,000

luxury yacht charter hargrave MB3

Go exploring along the Annapolis coastline in "MB#", a 2018 Hargrave 100' luxury motor yacht. Noted for its world-class amenities and seasoned crew, your time aboard MB3 will be nothing short of spectacular. MB3 features accommodations for 8 guests including a full-beam master stateroom with his-and-hers baths, as well as two additional private VIP staterooms. A fourth cabin has twin bunks that can convert to a king stateroom is desired. Enjoy a plethora of water toys, amazing cuisine from your private chef, and stellar views as you enjoy your luxury yacht vacation. Learn more about chartering MB3 by following this link.

Option #3: "Lexington" - 85' Horizon Motor Yacht - Price From $37,500

luxury yacht charter lexington horizon 85 

If fun in the sun is what you're after, Lexington is equipped to handle your luxury vacation. Enjoy a number of water toys on board including wakeboards, kayaks, water skis, towable banana boat, paddleboards, and more on board this 85' Horizon luxury yacht. Lexington can accommodate 8 guests in 4 comfortable staterooms including an absolutely exquisite master suite. To browse more photos of Lexington and envision how you'll spend your yachting vacation, please follow this link.

Option #4: "Down Time" - 65' Sea Ray L650 Flybridge - Price From $30,000

"Down Time" offers a luxurious New England yacht charter experience with a wonderful crew on board. Sunbathe in the comfortable bow lounge adjustable pads or enjoy a sunset from the flybridge as you cruise the Maryland coastline. Down Time can accommodate 8 guests in 4 staterooms including a master suite with large hull-side windows to enjoy the views while relaxing inside. Open up the sunroof in the hardtop for an exhilarating experience as you cruise in the upper 20 knots. Down Time is an incredible yacht charter option for the Chesapeake Bay at a reasonable price. To browse more photos of Down Time, please follow this link.

United Yacht Charter Director Nicole Haboush is committed to making your luxury yacht charter vacation perfect. With over 25 years of experience arranging private, luxury charters, Nicole is accustomed to working with VIP's in the entertainment industry, corporate and private sectors, and even royal guests. For more information on our unique concierge yacht charter service, please contact Nicole at (561) 558-3113 or by email at

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