TOP 10 Luxury sailing vacations in Maryland

Sail Alyosha is a premier travel agency located at 12817 Harbor Road in Ocean City, Maryland. Specializing in providing unforgettable sailing experiences, Sail Alyosha offers a wide range of services including sunset cruises, private charters, and sailing lessons. Whether you are looking to explore the beautiful waters of the Atlantic Ocean or simply relax and enjoy the stunning views, Sail Alyosha has something for everyone. With experienced captains and top-of-the-line sailboats, you can trust that your sailing adventure will be both safe and enjoyable. Book your next sailing excursion with Sail Alyosha and create memories that will last a lifetime.

Sundance Sailing Charters is a premier travel agency located at 78 George Street in Georgetown, Maryland, United States. Specializing in unforgettable sailing adventures, they offer a variety of charter options for exploring the beautiful waters of the Chesapeake Bay and beyond. Whether you're looking for a relaxing day on the water or a week-long sailing excursion, Sundance Sailing Charters has you covered. Their experienced crew and top-of-the-line vessels ensure a safe and enjoyable experience for all passengers. Book your next sailing adventure with Sundance Sailing Charters and create memories that will last a lifetime.

Located at 951 Fell Street in Baltimore, Maryland, Bay Dream Sailing is a premier tourist attraction and travel agency that offers unforgettable boat tours along the stunning waters of the Chesapeake Bay. Whether you're celebrating a special occasion like a birthday or anniversary, or simply looking for a unique way to explore the city, a boat tour with Bay Dream Sailing is a must-do activity in Baltimore. With private cruises available, you can enjoy a personalized and intimate experience on the water with your loved ones. Our experienced Captain, who is also the Commodore of the Sassafras River Yacht Club, has spent 25 years navigating the Chesapeake and is excited to share his passion for the waterways with you.

Boat Baltimore offers exclusive private boat charters in the heart of Baltimore, Maryland. Located at 321 East Cromwell Street, our travel agency provides intimate sailing yacht cruises, large group charters, and fishing adventures. As Baltimore's only locally owned private boat charter, you'll never have to share the boat with strangers. Our 45ft sailing yacht, SAEDA, offers private two-hour cruises for up to six passengers departing from the Baltimore Peninsula four times a day. Kids sail for free!

Reflections DC - Private Sailing Cruises offers unforgettable experiences on the water, allowing guests to explore the stunning waters of the Chesapeake Bay. Located at 4817 Woods Wharf Road in Shady Side, Maryland, this travel agency specializes in private sailing cruises, providing a luxurious and intimate setting for guests to relax and enjoy the beauty of the surrounding landscape. Whether you're looking for a romantic sunset cruise or a fun-filled day on the water with friends and family, Reflections DC - Private Sailing Cruises has something for everyone. Book your sailing adventure today and create lasting memories on the open seas.

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.

St. Michaels Sailing Charters is a premier tourist attraction located at 23672 Mount Pleasant Landing Circle in the picturesque town of Saint Michaels, Maryland, United States. Offering unforgettable sailing experiences on the beautiful waters of the Chesapeake Bay, visitors can enjoy a variety of charter options including private cruises, sunset sails, and sailing lessons. With experienced captains, top-notch vessels, and stunning views, St. Michaels Sailing Charters is the perfect destination for those looking to explore the bay in style. Whether you're a seasoned sailor or a first-time visitor, this institution promises a memorable and relaxing maritime adventure.

Carnival Cruise Line is a renowned travel agency located in Baltimore, Maryland, United States. Offering a wide range of exciting cruise experiences, Carnival Cruise Line is known for its fun-filled vacations at sea. With top-notch amenities, delicious dining options, and thrilling onboard activities, Carnival Cruise Line is the perfect choice for travelers looking to explore the world in style. Whether you're looking to relax on a tropical beach or embark on an adventure-filled journey, Carnival Cruise Line has something for everyone. Book your dream cruise today and set sail with Carnival Cruise Line for an unforgettable vacation experience.

Sea Time North is a cozy lodging institution nestled in the heart of Ocean City, Maryland, United States. With its prime location just a stone's throw away from the beach, guests can enjoy breathtaking ocean views and easy access to the sandy shores. The institution offers comfortable accommodations, friendly staff, and a relaxing atmosphere perfect for a beach getaway. Whether you're looking for a weekend escape or a longer vacation, Sea Time North provides the perfect home away from home.

Ocean Princess is a charming lodging institution located at 11 134th Street in the beautiful coastal town of Ocean City, Maryland, United States. Situated just steps away from the sandy beaches and crashing waves of the Atlantic Ocean, Ocean Princess offers guests a serene and relaxing retreat by the sea. The cozy accommodations and friendly staff make for a truly unforgettable stay, with ocean views and easy access to all the attractions and amenities of Ocean City. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, Ocean Princess is the perfect choice for your next coastal escape.

River City Cruise Co. is a premier travel agency located at 10282 River Landing Road in Denton, Maryland, United States. Specializing in river cruises, our experienced team is dedicated to providing unforgettable travel experiences for our customers. Whether you're looking to explore local waterways or embark on a luxurious cruise vacation, River City Cruise Co. has you covered. Book your next adventure with us and set sail on a journey of a lifetime.

M/V Bay Breeze is a charming bar and travel agency located at 208 Bank Street in the picturesque town of Chesapeake City, Maryland, United States. This unique establishment offers a relaxing and inviting atmosphere where patrons can enjoy a drink while planning their next adventure. With a focus on providing exceptional service and personalized travel experiences, M/V Bay Breeze is the perfect destination for those looking to unwind and explore new destinations. Whether you're stopping in for a cocktail or booking your next vacation, M/V Bay Breeze is sure to leave a lasting impression.

Salisbury Cruise Club is a premier travel agency located at 3911 5 Friars Road in Salisbury, Maryland, United States. We specialize in creating unforgettable cruise experiences for our clients, offering a wide range of cruise packages to destinations all around the world. Our team of experienced travel experts is dedicated to providing personalized service and helping you plan the perfect cruise vacation tailored to your preferences and budget. Whether you're looking for a relaxing Caribbean getaway or an adventurous Alaskan expedition, Salisbury Cruise Club has you covered. Book your dream cruise with us today and set sail on the vacation of a lifetime.

Miss Ocean City Fishing is the premier bay fishing boat in Ocean City, Maryland. Our 52-foot boat is certified by the United States Coast Guard and offers a clean and comfortable experience for all passengers. With plenty of seating and a clean restroom onboard, our 3-hour bay fishing trips are perfect for both experienced anglers and those new to fishing. We prioritize the comfort of our guests by limiting our trips to a maximum of 33 passengers, ensuring a more personalized experience. Book your trip online using special codes and secure your spot on the best bay fishing boat in Ocean City!

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.

Cruises Plus is a premier travel agency located at 100 West Road in Towson, Maryland, United States. Specializing in luxury cruises and vacation packages, Cruises Plus offers a wide range of options for travelers seeking unforgettable experiences on the high seas. With a dedicated team of travel experts, exceptional customer service, and competitive pricing, Cruises Plus is your go-to destination for all your cruise vacation needs. Book your dream getaway today and set sail with Cruises Plus!

Sea Seminars is a premier travel agency located at 1301 York Road in Timonium, Maryland, United States. Specializing in oceanic adventures and cruises, Sea Seminars offers a wide range of travel packages to exotic destinations around the world. With a team of experienced travel experts, Sea Seminars is dedicated to providing top-notch customer service and creating unforgettable travel experiences for all clients. Whether you're looking to explore tropical islands, embark on a luxury cruise, or discover underwater wonders, Sea Seminars has the perfect travel package for you. Book your next oceanic adventure with Sea Seminars and let the journey of a lifetime begin.

Travel Dream Weaver is a travel agency located at 6081 Otterbein Lane, Ellicott City, Maryland, United States. Whether you are planning a simple trip or a milestone celebration, Travel Dream Weaver can make your travel experience a breeze. They offer free VIP treatment with preferred partners, exclusive perks, and upgrades. With industry resources at their fingertips, Travel Dream Weaver can plan trips anywhere in the world and find the best available rates on accommodations. Their booking services are completely free, with the only fee charged for full day-to-day itinerary planning if requested.

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!

Z Flight Parasail and Watersports is a premier travel agency located at 300 Second Street in Annapolis, Maryland, United States. Offering the lowest price parasail flights in Marathon with no coupon code needed, Z Flight provides an unforgettable experience for guests. In Marathon, guests can enjoy scenic views of the island, wildlife, Sombreo Key Light, and more. In Annapolis, visitors can take in views of downtown Annapolis and the Naval Academy, with the option to venture out to the Thomas Point Lighthouse. With over 30 years of experience in the boating industry and a 100% safety record, Z Flight Watersports is the top choice for families and locals looking for a thrilling adventure on the water. Gift cards are available for purchase and can be used towards any Z Flight Watersports experience. Refunds are offered in case of trip cancellations due to weather or mechanical issues, with a 24-hour cancellation policy for individual bookings and a 7-day policy for group and private charters. Don't miss out on the opportunity to create cherished memories with Z Flight Parasail and Watersports.

Marauder Charters is a premier school and travel agency located at 255 Alexander Lane in Solomons, Maryland, United States. Our institution specializes in providing top-notch education and hands-on training in the field of maritime travel and adventure. Whether you are looking to learn how to navigate the open seas or book an unforgettable sailing experience, Marauder Charters has you covered. Join us for an exciting journey into the world of boating and exploration.

Ambassador Cruises is a premier travel agency located at 3169 Eutaw Forest Drive in Waldorf, Maryland. Specializing in luxury cruises, Ambassador Cruises offers a wide range of travel packages to exotic destinations around the world. With a team of experienced travel experts, Ambassador Cruises provides personalized service and attention to detail to ensure an unforgettable vacation experience for every client. Whether you're looking for a romantic getaway, a family vacation, or a group trip, Ambassador Cruises has the perfect package for you. Book your dream cruise today and set sail on the adventure of a lifetime with Ambassador Cruises.

Smith Island Cruises is a premier travel agency located on the picturesque Smith Island in Maryland, United States. We offer unforgettable cruises and tours around the island, allowing visitors to explore the beauty and charm of this unique destination. Our experienced guides provide insightful commentary and ensure a memorable experience for all guests. Join us for a relaxing and scenic cruise along the shores of Smith Island and discover the hidden gems of this enchanting location. Visit us at 4065 Smith Island Road and embark on an adventure of a lifetime with Smith Island Cruises.

SeaAffinity, Inc. is a premier travel agency located in the vibrant city of Baltimore, Maryland. Situated at 2809 Boston Street, this institution specializes in creating unforgettable oceanic experiences for travelers looking to explore the world's most beautiful and exotic destinations. With a team of experienced professionals and a passion for all things nautical, SeaAffinity, Inc. is dedicated to providing top-notch service and personalized itineraries that cater to every client's unique preferences and desires. Whether you're dreaming of a luxurious cruise, a thrilling scuba diving adventure, or a relaxing beach getaway, SeaAffinity, Inc. has the expertise and resources to make your travel dreams a reality. Come visit us and let us help you embark on the journey of a lifetime!

Liberte, The Schooner is a renowned travel agency located at 222 Severn Avenue in Annapolis, Maryland, United States. Specializing in luxury sailing experiences, Liberte offers guests the opportunity to explore the stunning Chesapeake Bay aboard their beautiful schooner. With experienced crew members and top-notch amenities, guests can relax and enjoy the breathtaking views while sailing the waters of the East Coast. Whether you're looking for a romantic sunset cruise or a unique corporate event venue, Liberte, The Schooner is the perfect choice for a memorable and unforgettable sailing experience.

Chester River Yacht & Country Club is a prestigious institution located at 7738 Quaker Neck Road in Chestertown, Maryland, United States. This exclusive club offers a luxurious and picturesque setting for members to enjoy a wide range of amenities and activities. From sailing on the beautiful Chester River to playing a round of golf on the pristine course, members can indulge in a variety of leisure pursuits. The club also features exquisite dining options, a state-of-the-art fitness center, and social events throughout the year. With its stunning waterfront location and top-notch facilities, Chester River Yacht & Country Club provides a sophisticated and welcoming atmosphere for those seeking a premier country club experience.

West Marine is a premier clothing store located at 2700 Lighthouse Point East in Baltimore, Maryland. Specializing in high-quality marine apparel and gear, West Marine offers a wide selection of clothing, accessories, and equipment for boating enthusiasts. Whether you're looking for stylish nautical fashion or durable gear for your next sailing adventure, West Marine has everything you need to stay comfortable and protected out on the water. With a commitment to quality and customer satisfaction, West Marine is the go-to destination for all your boating apparel needs.