TOP 10 Best Yacht rentals in Annapolis, Maryland

The Waterfront Oasis of Annapolis is a luxurious lodging facility located at 233 Mountain Laurel Lane in the picturesque city of Annapolis, Maryland. Situated right on the waterfront, this oasis offers stunning views of the water and a peaceful atmosphere perfect for relaxation and rejuvenation. Guests can enjoy spacious and elegantly appointed rooms, top-notch amenities, and personalized service that will make their stay unforgettable. Whether you're looking for a romantic getaway, a family vacation, or a peaceful retreat, the Waterfront Oasis of Annapolis is the perfect destination for your next escape.

Annapolis Sailing Adventures is a premier travel agency located in Annapolis, Maryland, United States. We offer a variety of sailing experiences, including private charters, sunset cruises, and sailing lessons. Our experienced captains will take you on a memorable journey on the beautiful Chesapeake Bay. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Annapolis Sailing Adventures has something for everyone. Come aboard and experience the thrill of sailing in one of the most scenic locations in the United States.

Eastport Yacht Club is a premier sailing and social club located at 317 First Street in Annapolis, Maryland, United States. With a rich history dating back to 1982, the club offers a vibrant community of boating enthusiasts, sailors, and social members. Situated on the picturesque shores of the Chesapeake Bay, Eastport Yacht Club provides top-notch facilities and amenities for its members, including a marina, clubhouse, and a full calendar of events and activities. Whether you're a seasoned sailor or just looking to connect with fellow water lovers, Eastport Yacht Club is the perfect place to enjoy the beauty of the bay and foster a love for all things nautical.

The Annapolis Yacht Club is a prestigious and historic institution located at 2 Compromise Street in Annapolis, Maryland. With a rich maritime tradition dating back to its founding in 1886, the club offers members and guests a wide range of amenities and activities, including sailing races, social events, dining options, and access to a beautiful waterfront setting. Boasting a welcoming and inclusive atmosphere, the Annapolis Yacht Club is a cherished destination for boating enthusiasts and community members alike.

The Annapolis Yacht Club Activity Center is a premier waterfront facility located at 314 6th Street in Annapolis, Maryland. This state-of-the-art institution offers a wide range of activities and amenities for members and guests to enjoy. From sailing and boating excursions to fitness classes and social events, the Annapolis Yacht Club Activity Center is the perfect destination for those looking to experience the best that the Chesapeake Bay has to offer. With stunning views of the water and a welcoming atmosphere, this institution is a must-visit for anyone looking to embrace the maritime culture of Annapolis.

SailTime Annapolis is a premier sailing school and store located at 105 Eastern Avenue in Annapolis, Maryland, United States. Offering a range of sailing courses for all skill levels, SailTime Annapolis provides hands-on instruction and certification for aspiring sailors. Additionally, the store offers a wide selection of sailing gear, equipment, and accessories for enthusiasts looking to enhance their sailing experience. With a knowledgeable staff and top-notch facilities, SailTime Annapolis is the perfect destination for anyone looking to learn how to sail or improve their skills on the water.

Bosun Yacht Services, LLC. is a premier yacht services store located at 7310 Edgewood Road in Annapolis, Maryland, United States. We offer a wide range of products and services for yacht owners and enthusiasts, including marine supplies, maintenance, repairs, and more. Our knowledgeable staff is dedicated to providing exceptional customer service and helping you find everything you need for your boating adventures. Visit us today and experience the Bosun Yacht Services difference.

Annapolis Water Taxi by Watermark offers a convenient and scenic way to explore the charming city of Annapolis, Maryland. Located at 1 Dock Street, this institution provides water taxi services for locals and tourists alike. Whether you're looking to enjoy a leisurely cruise on the water or need a quick and reliable transportation option, Annapolis Water Taxi by Watermark has you covered. Sit back, relax, and take in the stunning views of the city's historic waterfront as you travel from one destination to another. With experienced captains and a fleet of well-maintained boats, you can trust that your journey will be both safe and enjoyable. Don't miss the opportunity to experience Annapolis from a unique perspective with Annapolis Water Taxi by Watermark.

The Captain's Cottage is a charming lodging located at 985 Awald Road in Annapolis, Maryland, United States. This cozy retreat offers a unique and inviting atmosphere for guests looking for a relaxing getaway. The cottage is tastefully decorated with a nautical theme, paying homage to the maritime history of the area. Guests can enjoy comfortable accommodations, modern amenities, and personalized service from the friendly staff. Whether you're in town for a weekend escape or a longer vacation, The Captain's Cottage is the perfect place to unwind and experience the beauty of Annapolis.

Watermark Tours, Charters, Cruises is a premier tourist attraction and travel agency located at 1 Dock Street in the charming city of Annapolis, Maryland, United States. Offering a variety of tours, private charters, and scenic cruises, visitors can explore the historic waterfront and iconic sites of Annapolis from the water. With knowledgeable guides, luxurious vessels, and unforgettable experiences, Watermark Tours, Charters, Cruises is the perfect destination for those seeking to discover the beauty and history of this picturesque city. Whether you're looking for a relaxing cruise, a private charter for a special occasion, or a guided tour of Annapolis, this institution has something for every traveler.

Darling Charters is a premier travel agency located at 1 Dock Street in Annapolis, Maryland. Specializing in luxury yacht charters and personalized travel experiences, our team of experienced professionals is dedicated to creating unforgettable vacations for our clients. Whether you're looking to explore the Chesapeake Bay or sail to exotic destinations around the world, Darling Charters is here to make your travel dreams a reality. Contact us today to start planning your next adventure!

Seas the Bay Private Sailing Charters is a premier travel agency located in Annapolis, Maryland, United States. Specializing in private sailing charters, they offer unforgettable experiences on the beautiful Chesapeake Bay. Whether you're looking for a romantic sunset cruise, a fun day out on the water with friends, or a corporate team-building event, Seas the Bay has you covered. Their experienced crew will ensure a safe and enjoyable journey as you take in the stunning views and relax on the open water. Book your private sailing charter today and make memories that will last a lifetime.

Ohana Charters is a travel agency located at 500 Piney Narrows Road in Chester, Maryland, United States. Specializing in Annapolis Charter, Catamaran Charter, Sailing Charter, and more, Ohana offers a luxurious and unique sailing experience on the Chesapeake Bay. Guests can enjoy stunning sunsets, delicious food, and the opportunity to enhance their sailing skills. Whether celebrating a special occasion like an anniversary, birthday, or graduation, or simply looking for a relaxing getaway, Ohana Charters provides a memorable and unforgettable experience on the water. With the option for overnight stays, intimate family reunions, or exclusive events, Ohana Charters offers a variety of packages to suit every need. Experience romance, relaxation, and adventure aboard Ohana Charters for an unparalleled sailing experience.

Schooner Woodwind Offsite Business Office is a travel agency located at 1930 Lincoln Drive in Annapolis, Maryland. Our office is dedicated to providing exceptional service and assistance to our clients in planning their travel adventures on the Schooner Woodwind sailboats. Whether you are looking to book a private charter, a team building event, or a unique corporate outing, our experienced team is here to help create a memorable and enjoyable experience for you and your group. Contact us today to start planning your next sailing adventure on the beautiful waters of Annapolis.

Granmar Sailing is a premier travel agency located at #8 Randall Street in Annapolis, Maryland, United States. Specializing in sailing adventures, Granmar Sailing offers a variety of packages for individuals and groups looking to explore the open waters. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Granmar Sailing has something for everyone. With experienced captains and top-of-the-line equipment, you can trust that your sailing experience with Granmar Sailing will be safe, enjoyable, and unforgettable. Book your next sailing adventure with Granmar Sailing and set sail for an experience of a lifetime.

Picture Perfect Sailing is a premier sailing institution located at 980 Awald Road in Annapolis, Maryland, United States. Escape the hustle and bustle of everyday life and enjoy quality time with family and friends on the beautiful Chesapeake Bay. Whether you are looking for a day sail or an overnight adventure, our experienced skippers will take you on a memorable journey. Choose from a variety of sailing charters, starting at $650 for 2 guests on weekdays. Your charter includes a skipper, snacks, and beverages. For a longer experience, opt for our all-day sailing or overnight options. Sail to destinations such as Baltimore or Saint Michaels and create memories that will last a lifetime.

Classic Sail Charters is a premier sailing school located in Annapolis, Maryland, offering private sailing adventures for up to six passengers. With world-class sailing yachts, experienced captains, and top-notch service, we ensure that your charter experience is truly unforgettable. Our charters are exclusively for private parties, allowing you to customize your adventure. Join us at 980 Awald Road for a unique and luxurious sailing experience on the beautiful Siena yacht. With Captain Nate, Payton, and Tony at the helm, you can relax, learn some sailing skills, and enjoy the stunning views of the West River. Whether you're looking for a romantic engagement shoot, a family outing, or a relaxing day on the water, Classic Sail Charters has something for everyone. Book your trip today and set sail for an unforgettable experience on the Chesapeake Bay.

Chesapeake Boating Club, located at 213 Eastern Avenue in Annapolis, Maryland, is a unique institution that offers sail and power boat charters and rentals. Founded in 1992 in the Historic Eastport section of Annapolis, the club prides itself on providing flexible, fun, and affordable boating experiences. With a variety of boats ranging from 17' to 36' in length, members can choose the right vessel for any adventure on the Chesapeake Bay. In addition to boat rentals, the Chesapeake Boating Club also offers instruction in sailing and powerboating. The club's experienced J World coaches provide online educational seminars during the off-season to help members enhance their boating skills.

Fawcett Boat Supplies is a premier store located at 919 Bay Ridge Road in Annapolis, Maryland, United States. Specializing in all things related to boating, they offer a wide range of high-quality products and accessories for boat owners and enthusiasts. From safety equipment and maintenance supplies to navigation tools and outdoor gear, Fawcett Boat Supplies has everything you need to make the most of your time on the water. Their knowledgeable staff are always ready to assist customers in finding the perfect products for their boating needs. Visit Fawcett Boat Supplies today and experience top-notch service and a vast selection of marine supplies.

Back Creek Café & Boat Supply is a unique institution located at 7310 Edgewood Road in Annapolis, Maryland. This cafe and food establishment is not only a place to grab a bite to eat, but also a hub for all things boating and marine-related. The institution is conveniently located at VHF Channel 16 | 38°57’42.0”N | 76°28’55.8”W, making it easily accessible for boaters in the middle region of the Chesapeake Bay. Back Creek Café & Boat Supply is one of the largest Certified Clean Marina Facilities in the area, offering a full range of services for boat owners.