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Annapolis Yacht Charters

Few waterways in the world can match the Chesapeake Bay for sheer sailing pleasure, and our base at Port Annapolis Marina is right at the heart of this sailing paradise.

What’s on this page

Highlights

  • Beautiful scenery
  • Diverse cruising grounds
  • Quaint towns

Yacht rental Maryland

Annapolis port yachts charters at sunset

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 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 also a must. 

Captain John Smith, the first European to map Chesapeake Bay in 1609, 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 one of our Annapolis yacht charters.

Journey north while sailing Maryland and take in bustling, historic Baltimore Harbor, contrasting with the quiet anchorages of Mill Creek or Whitehall Bay. Sail south and you can visit the historic landmark towns of Oxford and Cambridge. Of course, you could book a longer charter and experience the best of both areas.

With so many delightful creeks, coves, rivers, towns and villages to visit, Annapolis makes for a dream sailing vacation.

Annapolis restaurant vacation

Available charter types

Bareboat

For experienced sailors, a bareboat charter is the perfect getaway..
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Skippered

Relax and leave all the sailing to a professional skipper.
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Easy crewed

The simplest, hassle-free way to charter a crewed private yacht.
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Fully crewed

Your own private yacht for an all-inclusive luxury sailing vacation.
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Cabin cruise

Reserve a private ensuite stateroom on a modern catamaran.
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Aqualodge

Get closer to nature on the perfect self-catering Caribbean holiday.
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Power Catamaran

Cruise faster and see more on the perfect charter boat.
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Things to do in Annapolis

Annapolis catamaran in port at sunset

Explore historic Annapolis

Downtown Annapolis is a lively area to walk around with a wide selection of interesting shops and restaurants. Just stroll down to “Ego Alley” at Annapolis Harbor and then grab a sandwich at Chick & Ruth’s Delly on Main Street. There are also tours of historic Annapolis and you can explore the nearby Naval Academy.

Sail to Baltimore

The harbor has an endless array of activities to enjoy, all within walking distance. With our Chesapeake Bay sailing charters you may even choose to spend more than one night in the harbor to allow plenty of time to take in the sights, including a stop at the Rusty Scupper Restaurant with its delicious seafood.

Visit Rock Hall

This quaint fishing town is a top cruising destination. It offers a bevy of marinas, shops and 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..

See the beauty of St. Leonard Creek

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 gathered from international voyages, Vera’s is a wonderful marina that welcomes all cruisers.

Discover the Chesapeake Bay Maritime Museum

While at the popular yachting center of St. Michael’s, pay a visit to the Chesapeake Bay Maritime Museum, which houses the largest collection of Chesapeake Bay artifacts, visual arts and indigenous watercraft.

Weather insights

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. With warmer temperatures up to mid-90°F, July and August are very popular, with 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.

Annapolis buildings with coloured doors and windows

Sailing the Chesapeake with Dream Yacht Charter

Maryland yacht charters

Sail Chesapeake Bay and make your way around the famous marinas and crab houses. Our Maryland yacht charter base has a vessel for every preference. Find out more about our Annapolis bareboat fleet.

Skippered Maryland yacht charters

Hire a skipper for your Chesapeake Bay sailing charters while you relax with your guests. This option means no sailing experience is needed.

Annapolis yacht charter in port for sailing

Annapolis sailing itinerary

Take a look at our suggestions for an Annapolis sailing vacation

7-day itinerary Annapolis south

Day 1: Herrington Harbour

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: Oxford

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 3: Cambridge

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

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

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: St. Michael

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.

7-day itinerary Annapolis north

Day 1: Rock Hall

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

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: Chester River

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: Mill Creek – Whitehall Bay

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: St. Michael

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: Wye Island

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.

14-day itinerary Annapolis south

Day 1: Solomon's Island

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: Deltaville – Dozier's Regatta Point Center

Cruise to Deltaville and visit Dozier’s Regatta Point Yachting Center with floating docks, a southern-style clubhouse, and a courtesy car. Dinghy to the Railway Restaurant across the creek from the marina, or drive into town (about 3 miles) to sample other local joints.

Day 3: Ocean Marine Yatch Center

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: Exploring

Spend the day in the local area exploring.

Day 5: Bay Creek

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

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: Onancock Wharf

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 – Excursions

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: Solomon's Island

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: Oxford

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

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

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: St. Michael

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: Sailing

It’ll take about 5-7 hours to sail back to base – the Chesapeake will always welcome you back!

21-day itinerary Annapolis

Day 1: Rock Hall

Rock Hall is a quaint fishing town and top cruising destination. It offers a bevy of marinas, shops, restaurants and a 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

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: Chester River

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: Mill Creek – Whitehall Bay

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

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: St. Michael

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: Wye Island

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

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: Deltaville

Cruise to Deltaville and visit Dozier’s Regatta Point Yachting Center with floating docks, a southern-style clubhouse and courtesy car. Dinghy to the Railway Restaurant across the creek from the marina, or drive into town (about 3 miles) to sample other local joints.

Day 10: Ocean Marine Yatch Center

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

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

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: Onancock Wharf

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: Crisfield – Janes Island – Smith Island

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

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: Solomon's Island

It’s back to Solomon’s Island, a fishing village with numerous dining options, shopping and special events.

Day 17: Oxford

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

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 Harbor

Herrington Harbor South and Herrington Harbor 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: Galesville

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: Sailing

Make your way back to base with a sail lasting 5-7 hours. And we hope to see you again soon.

Useful information for yacht charters in Annapolis

Annapolis port with yacht charters

How do I get to Annapolis from the US?

To reach our Annapolis base in Maryland, fly into Baltimore Washington International Airport (BWI) or Washington Dulles International Airport (IAD).

How do I get from the airport?

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. We can arrange airport transfers on request.

Baltimore Washington International Airport is a 40-minute taxi ride away, while Dulles airport is one hour and 20 minutes drive away.

What language is spoken in Annapolis?

The language spoken in Annapolis is English.

What is the currency for Annapolis?

The currency in Annapolis is the United States Dollar (USD).

What documents do I need to sail Annapolis?

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.

What is Wi-Fi like in Annapolis?

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.

What regulations are there in Annapolis?

Night sailing is not permitted. A fishing or crabbing license is required.

Where can I find weather forecasts in Annapolis?

You can find Annapolis weather forecasts from the WindFinder website.

What provisioning is there in Annapolis?

There are plenty of choices for provisioning ahead of your Annapolis yacht charter, so please refer to the base guide.

What baggage can I take on my Annapolis sailing vacation?

Please only take soft bags and not suitcases as they are too cumbersome on board.

What is the electrical current in Annapolis?

The land electrical current in Annapolis is 110V.

What is the dialing code for Annapolis?

The dialing code for Annapolis is +1 410.

Why should I book with Dream Yacht Charter?

Dream Yacht Charter is now the world’s leading yacht charter company and offers you:

  • A diverse fleet of yachts with a wide variety of models and manufacturers to suit every type of sailor.
  • We have +60 exciting destinations and we’re a pioneer in finding new sailing grounds.
  • You can be assured of our commitment to customer service excellence.
  • You’ll receive a warm and friendly welcome from our base teams who will share regional tips, recommendations and advice.
  • We’re a trusted seller of new and used boats and an innovator in charter management options – sailing is our business.

What licenses do I need to hire a yacht and sail myself?

The skipper of a yacht has primary responsibility for the safety of the crew and yacht at all times. Many destinations require just relevant experience demonstrated by a sailing resume.

To charter in the Mediterranean, it is mandatory that you hold a sailing license recognized by the local port authorities for bareboat charters in Italy, Greece, Croatia, Spain, Malta, Montenegro and Turkey. Other destinations that require a license include Madagascar, Seychelles, Thailand, Brazil and Sweden. For Belize, the port authority will issue a certificate of competency and an application is made on arrival.

You must take your proof of competency and original certificate with you on your charter. We advise you to contact our team about your qualifications and the destination requirements before booking.

By accepting the yacht contract you are confirming that you and/or members of your crew are capable and competent to sail the yacht in the conditions and cruising area of charter. We reserve the right not to hand over the yacht if, after inspection, it is the opinion that the charterer is not, or may not be competent to be in charge of the vessel.

What is a skippered yacht charter?

A skippered yacht charter is when you rent one of our boats for you and your guests and a professional skipper sails it for you. No sailing experience is needed.

You will need to choose a yacht with a cabin for your skipper to sleep in as they are responsible for your yacht for the duration of your charter. We will find the skipper for you once you have found your perfect destination and yacht.

You will need to pay for your skipper’s food. You can invite the skipper to dine with you on board or out at a local restaurant.

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