The Beauty of Maryland’s Eastern Shore: Sailing in Rock Hall, MD

Sailing in Rock Hall, MD the “Pearl of the Chesapeake”

Rock Hall, MD is often referred to as the “Pearl of the Chesapeake.” For boaters, it’s a playground and for tourists-in-the-know, it’s a quiet escape from the more popular beach towns of Delaware and Ocean City, MD.

Rock Hall MD

A financially-friendly way to enjoy sailing

Living in the Chesapeake Bay area I’ve experienced my fair share of boat envy here and there.

However, I stand firm in my convictions with my husband that we do. not. need. a. boat. A kayak, no problem. A boat, no!

It doesn’t matter how enticing they look in the summer months (and boy, are they tempting)!

Shardana Two Wheels

A smarter way to get our taste of the boating life is to hire a charter boat like the one offered by Shardana Saling Charters. I think it’s a fair compromise — there’s minimal financial commitment, maximum relaxation, and zero responsibility.

Shardana stern dingy

When the excursion is over, we can pack up and go home. We don’t have to worry about slip fees or storage costs, maintenance, upkeep, taxes, fuel and most importantly, a second mortgage!


I chatted about these very details with Davis Jones, part owner along with Andrew Seligman of Shardana Sailing Charters. Davis took me out on the water for a couple of hours in Rock Hall, answering my dozens of questions and feeding my boat life craving.

New kids on the block

Shardana Sailboat

The Shardana Sailing crew is new to the Rock Hall area. Its’ team of captains sail from Osprey Point Marina in a new 42.5' Sloop, a Catalina 425 that has all the bells and whistles for up to six passengers not including two crew members.

Before sailing away, Captain Davis and his first mate, Yvonne showed me around the boat. I quickly got acquainted with all the beautiful features of the vessel.

Shardana Crew

It was a beautiful day. We had perfect conditions for sailing.

Osprey Nest Eastern Shore

Let me tell you, time really does fly when you’re having fun. And although Shardana offers half-day (3.5 hours) excursions, you really should go out for a full day (7 hours).

Relaxing on Shardana Sailboat

A sunset cruise is 2.5 hours but I guarantee you, after relaxing on the Shardana, you’ll wish you booked more time. Luckily, they have options for longer sails ranging from an overnight sail (24 hours) to weekend sails, 5-day sails (Monday-Friday) or custom multi-day cruise packages.

Getting to know the Shardana crew

Depending on availability of the Shardana’s crew members, all of whom work full-time jobs, you will either have a 1 or 2-person crew to see to your needs.

Shardana Top Deck

I liked having both Davis and Yvonne on the boat with me. Not only were they friendly, patient, and passionate about sailing, I loved hearing their individual stories of how they got started sailing.

Shardana Crew Working

Davis got started, thanks to his church and Yvonne grew up on the water. Interestingly enough, she lived on a boat and sailed for months with her husband and young kids. Talk about a traveling mom!

To sail the Shardana yourself or not to sail

And while Davis was eager to teach me how to sail, knowing that I wouldn’t need to if we got in a pinch made me feel more relaxed.

Me Sailing the Shardana

I had a chance to get behind the wheel but man is there a lot to remember!

Shardana Compass

There are red and green buoys to stay on the left or right of, channel markers, passing boats, changing winds, jibs, sheets, compasses, monitors, Coast Guard chatter and sailing protocol to follow.

Shardana emergency bell

And although it didn’t take me long to learn the important safety tips, etc., I’m at my best just relaxing on the boat.

Shardana sheet

The great thing about the Shardana Sailing operation is that they cater to all types of clients, whether you want to learn, do nothing or take over the helm because you’re a seasoned sailor.

They will cater the sailing to whatever you want to experience.

Let the pros create your sailing itinerary

There are some customers who know exactly where they want to go, and others who don’t. The Shardana team offers a number of route options on the Eastern Shore depending on the length of your sail.

They take into consideration what you want to see and do, then go from there.

Shardana charting course

Passengers who are familiar with the quaint towns and inlets of the Chesapeake area are welcome to work with the crew to chart their own excursion.

Guests who are less familiar with the area and open to suggestion can enjoy waterways from Baltimore and Annapolis all the way to Hampton and Norfolk, Virginia. And there is plenty of things to see and do in Hampton, Virginia if you do decide to take that trip.

There are well over a dozen cute towns to see along the way.

Features on the Shardana Sailboat

Shardana Bow

The Catalina 425 has several places for you to take in the scenery whether you sit on one of the cushioned couches near the captain or on the bow or below deck.

Shardana Seating

If you’re sailing overnight and want to spend the night on anchor or just need a place for younger kids to take a nap, there are three rooms to choose from for an even more chill experience.

Shardana Main Bedroom

Below deck, you will also find 2 bathrooms, one with a separate shower and one that converts into a shower room thanks to a pretty smart hook and hosing.

Shardana 2nd Bathroom

You can cook a meal for your guests in a well-equipped kitchen complete with a sink, gas stove, burners, and microwave.

Shardana Kitchen

You will also find a small fridge and freezer in the kitchen area aka galley.

Shardana fridge

And, there’s a separate wine cooler! -> This is my kind of boat!! If I were to ever buy a boat, THIS would be necessary. :)

Shardana wine cooler

Enjoy your meal above deck or in the dining/living room area.

Shardana dining area

Conceal the table and add a large cushion, this area becomes an additional sleeping space. It easily converts into a queen size bed, spacious enough for two adults.

Shardana Converted Bed

Directly across is another seating area that turns into a twin bed.

Shardana from Room

There is more than enough storage space on the Shardana to keep your items undamaged and safe from the unpredictable seas.

Shardana Lower Deck

I truly enjoyed sailing with Shardana Sailing Charters.

Whether you’re looking to buy a boat or you just want to be a passenger for a day or two, you’ll leave wanting more.

Originally published at Mom’s Guide To Travel .