Only a handful of waterways in the world can match the Chesapeake Bay for sheer sailing pleasure and Annapolis is right in the heart of this sailing paradise. Get in touch to sail this fantastic USA destination!
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Yacht rental Maryland
Only a handful of waterways in the world can match the Chesapeake Bay for sheer sailing pleasure, and our base in Annapolis is right in the heart of this sailing paradise.
At about 200 miles long, Chesapeake Bay is the largest estuary in the United States with thousands of miles of shoreline to explore. It offers sailors protected waters, great anchorages, gorgeous natural scenery, and scenic towns and villages steeped in history.
Before embarking on your Chesapeake yacht charter, seeing the sights of Annapolis is a must. Stroll down to “Ego Alley” at Annapolis Harbor and then grab a sandwich at Chick & Ruth’s Delly on Main Street. Visit the Maryland State House, the oldest state capitol in continuous legislative use and topped by the largest wooden dome in the nation.
Get in touch to book your dream yacht charter.
Get to know the bay
Chesapeake Bay takes its name from the Powhatan word “Chesepioc” and translates as “Great Shellfish Bay”. The French founded Annapolis as a settlement called Port Royal in 1605 and Captain John Smith became the first European to explore and thoroughly map the Chesapeake Bay in 1609. He wrote in his journal that “heaven and earth have never agreed better to frame a place for man’s habitation” – something you’ll get to experience on our Annapolis yacht charters.
While sailing Maryland, a northward itinerary can include the bustling, historic Baltimore Harbor and contrast with the quiet anchorages of Mill Creek or Whitehall Bay. If you sail to the south, you can visit the historic landmark towns of Oxford or Cambridge. Of course, the best option may be a longer charter that allows you to see the best of both cruising areas!
With so many delightful creeks, coves, rivers, towns and villages to visit, Annapolis makes for a dream sailing vacation. Read our cruising guide to the Chesapeake.
Our Maryland yacht charters are located at our base in Port Annapolis Marina near beautiful downtown Annapolis.
What our customers say
“The boat was a blast and sailed great. I can only speak praises of the way we were treated and will proceed to recommend to all my sailing friends to charter from you when in the Chesapeake area.”
Fernando (Annapolis)
Sailing the Chesapeake with Dream Yacht Charter
Maryland yacht charters
Sail Chesapeake Bay and explore the famous marinas and crab houses. Our Maryland yacht charter base has a yacht for every preference. Find out more about our Chesapeake bareboat charters.
Skippered Maryland yacht charters
Hire a skipper for your Chesapeake Bay sailing charters while you relax with your guests. No sailing experience is needed to enjoy a sailing vacation in Maryland. Find out more about our Annapolis skippered yacht charters.
Downtown Annapolis is a lively area to walk around with a wide selection of interesting shops and restaurants. There are also tours of historic Annapolis and you can explore the nearby Naval Academy.
The harbor has an endless array of activities to enjoy, all within walking distance. You may even choose to spend more than one night in the harbor to allow plenty of time to take in the sights during your Chesapeake Bay sailing charters. Enjoy a stop at the Rusty Scupper Restaurant with its delicious seafood for dinner.
This quaint fishing town is a top cruising destination. It offers a bevy of marinas, shops, restaurants and has a burgeoning artist colony, making it one of the top things to do in Annapolis. Overlooking Rock Hall Harbor and the Chesapeake Bay, Waterman’s Crab House is well known for its award-winning steamed crabs, among other delights.
St. Leonard Creek is considered one of the most beautiful areas on the Patuxent River. This five-mile-long creek is on the river’s north shore and features a mix of marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek is Vera’s White Sands Beach Club. Decorated with South Sea treasures culled from international voyages, Vera’s is a wonderful marina that welcomes all cruisers.
While at the popular yachting center of St. Michael’s, pay a visit to the Chesapeake Bay Maritime Museum. The museum houses the largest collection of Chesapeake Bay artifacts, visual arts and indigenous watercraft.
When is the best time to go to Annapolis?
The best time to visit Annapolis is between May and June or between September and October. The weather is beautiful and there tends to be a steady breeze. July and August are popular with warmer temperatures, up to mid-90°F , and busier marinas.
Water temperatures reach the upper 60°F to about 80°F by the middle of the summer.
What are the sailing conditions in Annapolis?
Winds are typically from the south or west during the sailing season, with an average speed of 5-10 knots.
You have plenty of places to explore during your Annapolis yacht charter. There are many excellent itinerary suggestions for legs between four and six hours, which will allow you to hit the best spots on Chesapeake Bay!
Mooring balls are rare. Chesapeake Bay anchorages will usually require anchoring or getting a slip at a marina, depending on your wishes.
Get in touch to book your dream yacht charter.
Our Maryland base manager, (details in the Downloads section), will be pleased to welcome you on arrival to Port Annapolis Marina.
To reach our Annapolis base in Maryland, fly into Baltimore Washington International Airport (BWI) or Washington Dulles International Airport (IAD).
We can arrange airport transfers on request and Baltimore Washington International Airport is a 40-minute taxi ride away, while Dulles airport is one hour and 20 minutes away by car.
Get in touch to book your dream yacht charter.
The language spoken in Annapolis is English.
The currency in Annapolis is the United States Dollar (USD).
Visitors to the United States will need a passport valid for the duration of your stay. Talk to us to make sure you have the correct documents before you travel for your Annapolis sailing vacation.
Transfers from the airport are available via shuttle van, shared private car service or airport taxi. Depending on the number of people in the group a private car service/or airport taxi might be less expensive than the Super Shuttle. An airport taxi can be hailed directly from the airport and we recommend that you ask the fare before getting into the taxi.
Wi-Fi is available at Port Annapolis Marina on the docks and in the DYC office. The boats are not equipped with Wi-Fi. Internet access can also be found at various restaurants, cafes and marinas throughout the cruising ground, which you can use while sailing the Chesapeake.
Night sailing is not permitted. A fishing or crabbing license is required.
You can find Annapolis weather forecasts from the WindFinder website.
There are plenty of choices for provisioning ahead of your Annapolis yacht charter, please refer to the base guide.
Please only take soft bags and not suitcases as they are too cumbersome on board.
The land electrical current in Annapolis is 110V.
The dialing code for Annapolis is +1 410.
Day 1: Begin by sailing to Herrington Harbour. Herrington Harbour South and sister marina Herrington Harbour North are both located on the western shore of the Chesapeake Bay and offer overnight slips, several restaurants and lounges, and a wide range of amenities. Due to Herrington Harbour South’s popularity, it’s best to make reservations. We recommend Mango’s Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere.
Day 2: Sail to Oxford, located on the eastern shore and bordered on three sides by the Tred Avon River and Town Creek. The community make visitors feel like old friends and works hard to maintain a serene, boater-friendly atmosphere. It boasts a walkable downtown with plenty of shops, restaurants, and attractions.
Day 3: Cambridge lies about 13 miles from the mouth of the Choptank River. It was settled in 1684, and is one of the oldest towns in Maryland. Known for its elegant 19th-century homes and maritime museums. Highlights include Richardson Maritime Museum, Meredith House with its Heritage Museum and Gardens, the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample protected anchorage.
Day 4: St. Leonard Creek is considered one of the most beautiful areas on the Patuxent River. This five-mile-long creek on the river’s north shore features marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek is Vera’s White Sands Beach Club. Decorated with South Sea treasures culled from international voyages, Vera’s is a wonderful marina that welcomes all cruisers.
Day 5: Solomon’s Island is a charming island town between the Patuxent River and Chesapeake Bay. Solomon’s is a fishing village, alive with work-boats and fishing fleet, but offers numerous dining options, shopping, and special events. Be sure to visit The Tiki Bar and order a Mai-Tai, it’s the first completely open air bar in southern Maryland. The bar’s annual opening is a tradition, drawing crowds near 10,000.
Day 6: Another quaint waterfront village, St. Michael’s sits on a bucolic peninsula. It was an important shipbuilding center, known for its Baltimore Clippers – the fastest sailing vessels of their time. Today, the town is a popular yachting center and home to Chesapeake Bay Maritime Museum.
Day 7: It’ll take 5-7 hours to sail back to base – the Chesapeake will always welcome you back!
Get in touch to book your dream yacht charter.
Day 1: Rock Hall is a quaint fishing town and top cruising destination with marinas, shops, restaurants and a burgeoning artist colony. Overlooking Rock Hall Harbor and the Chesapeake Bay, Waterman’s Crab House is well-known for its award-winning steamed crabs. Swan Creek is a favorite destination for cruisers because of its rural beauty. Located directly north of Rock Hall Harbor, this well-protected creek offers a wonderful place to anchor.
Day 2: 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. Discover fine dining, cultural experiences and exciting nightlife.
Day 3: Sail to Chester River, the second-longest river on the eastern shore, with rolling countryside and grand estates. The river gradually narrows to about a quarter mile at Chestertown. Beyond Eastern Neck Island – which features a wildlife refuge – the Chester River fans out in four generous branches, all of which are inviting.
Day 4: 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. You’ll find good depths for peaceful anchoring and the famous Cantler’s Restaurant, known for some of the best steamed crabs in the area.
Day 5: Quaint waterfront village, St. Michael’s sits on a bucolic peninsula. It was an important shipbuilding center noted for its Baltimore Clippers – the fastest sailing vessels of their time. Today, it’s a popular yachting center and the site of the Chesapeake Bay Maritime Museum.
Day 6: Sail into the Wye River on the eastern shore and discover Wye Island along 21 miles of shoreline. Secluded anchorages are the main attraction and you won’t find supplies or public facilities on the island. Stately old homes, many dating back to colonial times, stand on the banks at every turn.
Day 7: Make your way back to base with a sail time of between 5-7 hours – we look forward to seeing you again soon.
Get in touch to book your dream yacht charter.
Day 1: Solomon’s Island is an island town between the Patuxent River and the Chesapeake Bay. Solomon’s is a fishing village, alive with work-boats and an active fishing fleet, but also offers numerous dining options, shopping and special events.
Day 2: Cruise to Deltaville and visit Dozier’s Regatta Point Yachting Center with floating docks, a southern-style clubhouse, and a courtesy car. Dinghy to Railway Restaurant across the creek from the marina, or drive into town (about 3 miles) to sample other local joints.
Day 3 – 4: Ocean Marine Yacht Center is just 0.5 miles south of mile marker zero on the Intracoastal Waterway in Portsmouth, VA. This complex features a modern marina. Getting hungry?There are plenty of great restaurants minutes away from the marina.
Day 4: Spend the day in the local area exploring.
Day 5: Bay Creek has the perfect blend of elegant homes, great dining, a word-class golf resort, plus a state-of-the-art beach club and fitness center – coastal living at its best. Bay Creek is a true escape, and it neighbors historic Cape Charles on the Chesapeake Bay, minutes away from Norfolk and Virginia Beach.
Day 6: Chesapeake Bay Marina at the Tides Inn Resort provides the beauty and tranquility of a secluded harbor and the facilities of a world-class destination resort. Located on Carters Creek, 11 miles from Windmill Point, the marina accommodates up to 24 vessels of various sizes.
Day 7: The channel to Onancock Wharf twists and turns, but never fear – it’s plenty deep and easy to follow. There’s no grocery in walking distance, but special arrangements can be made with the harbormaster for transportation. They can provide a list of restaurants in town, where you’ll also find plenty of shops and art galleries.
Day 8: Somers Cove Marina in Crisfield offers a swimming pool, picnic tables, barbecues and golf packages. If you’d like to pick up provisions, there’s a grocery store about a mile away. Excursions at Janes Island State Park and boat trips to Smith Island and Tangier Island are tried-and-true favorites.
Day 9: It’s back to Solomon’s Island, where Zahniser’s Yachting Center offers a full service resort marina and boatyard. Centrally located to town, it also features a swimming pool, restaurant, courtesy bicycles, a grocery shuttle and more.
Day 10: Sail to Oxford, located on the eastern shore and bordered on three sides by the Tred Avon River and Town Creek. The community makes visitors feel like old friends and works hard to maintain a serene, boater-friendly atmosphere. It boasts a walkable downtown with plenty of shops, restaurants, and attractions.
Day 11: Cambridge, with its elegant 19th-century homes, lies about 13 miles from the mouth of the Choptank River. It was settled in 1684, and is one of the oldest towns in Maryland. Highlights include the Richardson Maritime Museum, Meredith House, the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample anchorage.
Day 12: Herrington Harbour South and Herrington Harbour North on the western shore of the Chesapeake Bay offer overnight slips, several restaurants and lounges, and a wide range of amenities. It’s best to make reservations. We recommend Mango’s Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere.
Day 13: 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, it is a popular yachting center, and the site of the Chesapeake Bay Maritime Museum.
Day 14: It’ll take about 5-7 hours to sail back to base – the Chesapeake will always welcome you back!
Get in touch to book your dream yacht charter.
Day 1: Rock Hall is a quaint fishing town and top cruising destination. It offers a bevy of marinas, shops, restaurants and burgeoning artist colony. Overlooking the bay, Waterman’s Crab House is well-known for its award-winning steamed crabs, among other delights. Swan Creek has long been a favorite destination for cruisers because of its rural beauty. Located directly north of Rock Hall Harbor, this well-protected creek offers a wonderful place to anchor.
Day 2: 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. Enjoy fine dining, cultural experiences and exciting nightlife.
Day 3: Sail to Chester River, the second-longest river on the eastern shore. Chestertown has 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 4: The quiet anchorages of Mill Creek and Whitehall Bay lie between the Chesapeake Bay Bridge and the Severn River. Try the famous Cantler’s Restaurant, known for some of the best steamed crabs in the area.
Day 5: Annapolis is the capital of Maryland, and also considered to be America’s sailing capital. You may dock, anchor, or take a mooring ball in this harbor, then explore the city’s history, quaint streets, shops and restaurants. It’s also home of the US Naval Academy: a must-see.
Day 6: Quaint waterfront village, St. Michael’s sits on a bucolic peninsula. It is an important shipbuilding center especially noted for its Baltimore Clippers – the fastest sailing vessels of their time. Today, the town is a popular yachting center, the site of the Chesapeake Bay Maritime Museum.
Day 7: Sail into the Wye River on the eastern shore. The river’s branches embrace Wye Island with its secluded anchorages – you won’t find supplies or public facilities. Stately old homes, many dating back to colonial times, stand on the banks at every turn.
Day 8: Solomon’s Island is between the Patuxent River and the Chesapeake Bay. Zahniser’s Yachting Center offers a full-service resort marina and boatyard. Centrally located to town, it also features a swimming pool, restaurant, courtesy bicycles, a grocery shuttle and more.
Day 9: Cruise to Deltaville and visit Dozier’s Regatta Point Yachting Center with floating docks, a southern-style clubhouse and courtesy car. Dinghy to Railway Restaurant across the creek from the marina, or drive into town (about 3 miles) to sample other local joints.
Day 10: Ocean Marine Yacht Center is half a mile south of mile marker zero on the Intracoastal Waterway in Portsmouth, VA. This complex features a modern marina. Getting hungry?There are plenty of great restaurants minutes away from the marina.
Day 11: Bay Creek has the perfect blend of elegant homes, great dining, a word-class golf resort, plus a state-of-the-art beach club and fitness center – coastal living at its best. Bay Creek is a true escape and neighbors historic Cape Charles on the Chesapeake Bay, minutes away from Norfolk and Virginia Beach.
Day 12: Chesapeake Bay Marina at the Tides Inn Resort provides the beauty and tranquility of a secluded harbor and the facilities of a world-class destination resort. It’s on Carters Creek, 11 miles from Windmill Point.
Day 13: The channel to Onancock Wharf twists and turns, but it’s plenty deep and easy to follow. There’s no grocery in walking distance, but special arrangements can be made with the harbormaster for transportation. They can provide a list of restaurants in town, where you’ll also find plenty of shops and art galleries.
Day 14: Somers Cove Marina in Crisfield offers a swimming pool, picnic tables, barbecues and golf packages. If you’d like to pick up provisions, there’s a grocery store about a mile away. Excursions at Janes Island State Park and boat trips to Smith Island and Tangier Island are tried-and-true favorites.
Day 15: St. Leonard Creek is one of the most beautiful areas on the Patuxent River. This five-mile-long creek on the river’s north shore features marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek is Vera’s White Sands Beach Club. Decorated with South Sea treasures culled from international voyages, Vera’s is a wonderful marina that welcomes all cruisers.
Day 16: It’s back to Solomon’s Island, a fishing village with numerous dining options, shopping and special events.
Day 17: Sail to Oxford on the eastern shore and bordered on three sides by the Tred Avon River and Town Creek. The friendly community offers a serene, boater-friendly atmosphere and walkable downtown with plenty of shops, restaurants and attractions.
Day 18: Cambridge lies about 13 miles from the mouth of the Choptank River. It was settled in 1684, and is one of the oldest towns in Maryland. Highlights include Richardson Maritime Museum, Meredith House, the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample anchorage.
Day 19: Herrington Harbour South and Herrington Harbour North on the western shore of Chesapeake Bay and offers overnight slips, several restaurants and lounges and a wide range of amenities. Make reservations in advance and then dine at Mango’s Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere.
Day 20: The quiet anchorage at Galesville in the West River is the perfect penultimate destination for your charter. Spend some well-deserved time relaxing and taking in the natural beauty of the region.
Day 21: Make your way back to base with a sail lasting 5-7 hours – we hope to see you soon!
Get in touch to book your dream yacht charter.
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