The Chesapeake Bay is an enormous inland waterway in the Mid-Atlantic States of Virginia and Maryland. It is a sailor’s paradise with over 5,000 miles of shoreline to explore. You will enjoy delicious seafood (especially the famous Bay crabs!), gorgeous sandy beaches, inland rivers, and historic towns like Annapolis and the vibrant port city of Baltimore. In the Southern part of the Bay, you can see the famous wild horses on the islands of Chincoteague and Assateague. Sailing northward into Maryland, you can stop in Soloman’s Island, visit St. Mary’s City and sail up the Patuxent and St. Mary’s Rivers. You won’t want to miss Smith and Tangiers islands, written up in National Geographic for continuing maintaining traditional lifestyles. In the northern part of the Bay, you can stop in Baltimore, Annapolis, Georgetown and Chestertown. The sailing is all “line of sight” with the breeziest times of year in the spring and the fall. In the middle of the summer, the weather can be very hot and humid and less breezy (or even still) with afternoon thunderstorms that break the heat. The waters of the Bay are brackish (a mixture of salt and fresh) varying from very salty near the mouth of the Bay to almost fresh at the northern end.

Our Charter Yachts in Annapolis

Below is a list of our available Charter Yachts in Annapolis. Select the ones you are most interested in or simply contact us and we'll take care of all your yacht charter needs.

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Mahe 36 - (2 Cabins) - A/C - Annapolis The 36 follows on the heels of the successful 40 foot Fountaine Pajot. She has all of the most popular and requested features including: Walk out cockpit, one level floor from cockpit to interior, aft galley serving the cockpit and Fountaine Pajots famous Belize 43 - (4 Cabins) - A/C - Annapolis She was the Annapolis Boat Show Boat for Fontaine Pajot in 2006 showcasing the culmination of design improvements and features of the Belize model line. Featuring new color schemes below with the beautiful charcoal gray accents this boat shows she can loo Jeanneau 54DS (3 Cabins) - A/C - Annapolis An amazing boat, this blue hull beauty looks fast and elegant, even while still at the dock. Her bow thruster makes this boat one of the easier boats in the fleet to get underway. The powerful sails can take you well over 10 knots assisted by the fully el Jeanneau 40.3 - (3 Cabins) - A/C - Annapolis The first thing you will notice when you approach her,is the beautiful, wide teak decks. Titled “Boat of the Year” in 2005 by Cruising World, this 40 footer is the perfect size for a couple or a family not to mention an extremely capable sailing vessel. Jeanneau 49DS (3 Cabins) - A/C - Annapolis This deep blue 49DS is the sexiest boat in Annapolis. Featuring the unmistakable “cat’s eye” windows,she is a testament to Jeanneau’s design prowess. Featuring one of a kind Ultra Leather below decks, this three cabin 3 head boat will pamper you like the Jeanneau 43 DS - (4 Cabins) - A/C - Annapolis This Jeanneau has it all; the most unique trait is her Pullmans bunk aft of the large V-berth. Great for storage or kids, the boat can sleep 10 with her convertible salon table. Below Deck she is very roomy and bright with plenty of natural light provided Jeanneau 49DS - (3 Cabins) - A/C - Annapolis Equipped with a 3 blade folding propeller and full electric winches servicing the roller furling Genoa and Mainsail, she is a force to be reckoned with on the water. Featuring a forward master V-berth and two spacious aft cabins, La Sonata has plenty of r Jeanneau 49DS - (3 Cabins) - A/C - Annapolis she ready for her maiden voyage on the bay. Featuring a deep Flag Blue hull she will surely catch an envious eye of fellow boaters on the bay as they try to catch you. The sea goddess’ beauty is only matched by her performance common to the Jeanneau 49DS. Jeanneau 42i - 3 Cabins - A/C - Annapolis The next great charter boat around the world. She features everything you could ask for, and more including twin helm stations, traditional coach roof design featuring the feather light injection molded decks. This technological achievement transfers th Jeanneau 39DS - (2 Cabins) - A/C - Annapolis This yacht is a 2007 Jeanneau 39DS, one of the first in the country! What a joy to sail! She is a 2 cabin, 1 head boat that has an enormous amount of room below deck. She has a convertible salon table berth making her an easy boat to sleep six.She has a u Jeanneau 43 DS - (3 Cabins) - Annapolis Her 3 cabin layout with 2 full size heads is ideal for chartering. Our most functional boat in the fleet, the galley is first rate with full size 12V refrigeration and spillover ice box. The headroom is ideal for tall guests over 6 foot or people that can Lavezzi 40 - (3 Cabins) - A/C - Annapolis This 3 cabin layout offers generous room for all occupants featuring a very functional galley area in the salon. The cockpit area is extremely roomy with a large table surrounded by comfortable seating. The helm station offers excellent visibility for a c Jeanneau 42 DS- (2 Cabins) - A/C - Annapolis The first 5 star 42DS on the Bay featuring a generator. As with her sister ship 42DS vessels, she is complete with an electric coach roof winch and furling sails, it is however the additional primary electric winches that set Wicked Good apart. The two Jeanneau 39i - 2 Cabins - A/C - Annapolis Featuring the classic coach roof design, her sightlines in the cockpit are excellent. Her rigging is extremely easy to use and operate from to cockpit requiring very little effort to reign in her powerful sails. The boats sailing demeanor underway is th Jeanneau 49DS - (3 Cabins) - A/C - Annapolis Once out on the water, she shows the speed and maneuverability common only to Jeanneau sloops. Fast and nimble, she can tack on a dime and still reach 9 knots in as little as 15 knots of wind. Below decks her 3 cabin layout, featuring 2 large heads, makes Jeanneau 42DS - (2 Cabins) - A/C - Annapolis This 42 DS is Loaded!She has an enormous flat screen TV in the Salon with DVD player and Raymarine Chartplotter adaptation that is just plain cool. New last year, this extremely luxurious boat was a favorite of couples and families. Her ease of sail is ex Jeanneau 42DS - (2 Cabins) - A/C - Annapolis This Jeanneau is new to our fleet in 2007. Commissioned in the second full year of production, this Jeanneau 42DS has all the right equipment to ensure her occupants have a great time. On deck, her powerful sails make this boat a light air wonder. On t Orana 44 - (4 Cabins) - A/C - Annapolis Experience the feeling of sailing from the incredibly stable platform of the new Orana, Samaquan. Zoom past the mono-hulls as your lunch is uninterrupted on the cockpit table and your crew is comfortably lounging in the expansive cockpit. Samaquan sleeps Jeanneau 36i - 2 Cabins - Annapolis She will take you anywhere you want to go on the bay. The combination of her size and sailing ease make this a great boat to get started on your adventures out on the bay. Her two cabin layout is very spacious offering plenty of room to move around belo MARTHA ANN - 140ft Westship - New England - Caribbean This voluminous, exquisitely finished yacht showcases the Old World craftsmanship of the artisans at Westships state-of-the-art construction facilities. The most dramatic of the areas aboard Martha Ann is the sweeping expanse of the main salon. Features Jeanneau 43DS (3cabins) - Annapolis This exciting new model features the modern styling that has made Jeanneau the number one name in deck salons throughout the world. The Jeanneau 43DS features an ultra modern hull, providing exceptional speed while under sail or power. A very spacious ow Delphia 40 - 3 Cabins - Annapolis Come charter this fabulous charter boat. She is a spacious 40ft Delphia and offers plenty of room with her great 3 cabin layout. Beneteau 393 - 2 Cabins - Annapolis The 393 continues to get excellent reviews from our charterers for its sailing performance Jeanneau SO 35 - 2 Cabins - Annapolis, USA The Jeanneau Sun Odyssey 35 is a yacht to please all sailors. With the same hull as the Sun Fast 35 racer, she is a brisk performer with perfect balance and very impressive acceleration, yet a very stable cruiser that is comfortable and secure in fresher Catalina 360 MkII - 2 Cabins - Annapolis, USA The Catalina 360 is a true classic that has been in production for many years. Ad Astra is fun, safe, and responsive to sail. The cockpit is very roomy, and with the walk-through transom and wide, uncluttered decks. Bavaria 37 - (2 Cabin) - Annapolis, USA The Bavaria 37, one of Sail Magazine`s top 10 yachts for 2000, combines the space of the family cruiser with `superior performance` as rated by Sail Magazine. Jeanneau 37 - 2 Cabins - Annapolis, USA The Jeanneau Sun Odyssey 37 is a yacht to please all sailors. She is a brisk performer with perfect balance and very impressive acceleration, yet a very stable cruiser that is comfortable and secure in fresher winds. The wide, non-skid side decks provide Delphia 37 - 2 Cabins - Annapolis, USA The Delphia 37 boasts the same legendary build quality Delphia is renowned for. This excellent yacht offers boat loads of light below plus extra headroom for a very spacious feel. She is comfortable, sea kindly and designed to keep you and your crew safe Beneteau Oceanis 393 - 3 Cabins - Annapolis USA The 393 continues to get excellent reviews from our charterers for its sailing performance. What makes it a very popular choice, is the forward cabin which boasts a large Pullman bunk, seating area, and an en-suite head. Orana 44 - (3 Cabins) - A/C - Annapolis This catamaran is hull number 19 of an entire new line of Fountaine Pajot yachts. This Orana is a 44 foot 3 cabin yacht that offers exceptional quality and amenities that few cats can offer. This “Owner’s version commits an entire hull to one cabin and Jeanneau 49DS - (3 Cabins) - A/C - Annapolis One of the few 2008 49’s to be made before their end in production, this award winning yacht is the sum of Jeanneau manufacturing expertise. Once underway, she shows the speed and maneuverability common to Jeanneau sloops. Fast and nimble, she can tack Jeanneau Prestige 36 - 2 Cabins - A/C - Annapolis This Prestige is an enormously capable boat featuring two helm stations one on the fly bridge and one below in the main salon. Visibility from both stations is superb. She is appointed in the finest of Jeanneau traditions featuring beautiful teak woodwork Sun Odyssey 40.3 - 3 Cabins - Annapolis Titled “Boat of the Year” in 2005 by Cruising World, this 40 footer is the perfect size for a couple or a family not to mention an extremely capable sailing vessel. Lagoon 38 - 3 Cabins - Annapolis The Lagoon 380 is a yacht that will impress all sailors and their crew. It`s a fast, smooth sailing catamaran that points quite high to windward, and tacks smoothly, with ease. The sailing performance of this boat has `converted` many a monohull sailor to