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    You are at:Home»Attractions»Sail Annapolis With These Boat Rental Services
    Attractions

    Sail Annapolis With These Boat Rental Services

    MD RecommendationsBy MD RecommendationsAugust 10, 2026Updated:September 17, 2026No Comments8 Mins Read
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    Boat Rental Annapolis

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    Quick answer

    Use this guide to plan sail annapolis with these boat rental services with safety, conditions, operator credentials, and seasonal access in mind. Confirm weather, water conditions, age or skill requirements, equipment, waivers, launch rules, and current operating details before departure.

    Plan with confidence

    Best for: Planning a Maryland water-based outing
    Verify first: Weather, water conditions, required experience, safety gear, waivers, and operator policies
    Editorial note: Listings and recommendations are selected for reader usefulness. Sponsorship does not guarantee inclusion, placement, or a favorable opinion.

    Annapolis, the capital of Maryland, is known as a historic district thanks to its old-timey brick walls, stained glass windows, and 18th-century houses and churches. Besides the architecture, the city has plenty of museums that pay homage to the past.

    Many don’t know this, but Annapolis is also known as the “Sailing Capital of the U.S.” It is home to the U.S. Naval Academy. Naturally, the city’s maritime heritage has made it a destination unlike any other. While visitors can tour the place on foot, sailing the sea can be a unique experience and even fish from the boats. Here’s why.

    Why Rent a Boat In Annapolis?

    Annapolis is the sailing capital of Maryland. Unsurprisingly, there are many things to do by boat. The sunset and the city’s skyline are the perfect backdrop for romantic dates aboard a cruise or yacht.

    Annapolis boat rentals also give you the freedom and convenience to visit places like the Chesapeake Bay while you enjoy the beautiful views. Travelers can also ride a rental boat to historic Kent Island where you can explore the wineries, enjoy seafood, and sunbathe at the beaches.

    The city is also home to the U.S. Naval Academy. As a result, you’ll find many sailing schools. So, novice and seasoned sailors alike will enjoy visiting this place to hone their skills.

    If all of this sounds good and you’re looking forward to visiting Annapolis, here are some boat rental services you may want to consider.

    Boat Rental

    Boat Rental Companies In Annapolis

    Take a look at some of these highly-rated boat rental companies in Annapolis. These companies have been in business for quite some time and offer other amenities.

    Annapolis Sailing School

    Along with teaching sailing to adults and youths, Annapolis Sailing School also has boat and yacht rentals in Annapolis. The company has Rainbow 24s in its fleet for anyone looking to relax with a day on the water. They even allow you to bring your own food so you can host a party or a small get-together.

    However, when renting from them, ensure that at least one person in your party has been ASA 101-certified or earned its equivalent. New customers without accreditation must accomplish an evaluation for sailing competency with the company before their first rental. This ensures maximum safety for customers.

    The charges are competitive, starting at $158 (+ taxes) on weekdays for an entire day or any fraction of it between 9 am and 4 pm. During holidays and weekends, prices go up to $225 (+ taxes) for half-day sessions that last from either 9 am to 12 pm or 1 pm to 4 pm. Late and cancellation fees may apply. Additionally, no children below the age of 5 are allowed. Alcohol, pets, and swimming off the boats are prohibited as well.

    • Operating Hours: Monday to Friday – 9 am to 4 pm, Saturday & Sunday – Closed
    • Address: 7001 Bembe Beach Road, Annapolis MD 21403
    • Phone: 410 267 7205
    • Email: Undisclosed but you can send them a message
    • Website: annapolissailing.com
    Boat Rental

    Annapolis Electric Boat Rentals

    Annapolis Electric Boat Rentals offers a unique and exciting way to tour Annapolis. Their eco-friendly vessels are battery-operated, silent, and luxurious. Plus, you can drive them yourself.

    With a top speed of 5 miles an hour, the boats are an excellent way to explore and observe the beauty of the water safely. The charges are as follows:

    • 1-Hour Rental (For up to 10 people) – $200
    • 2-Hour Rental (For up to 10 people) – $375
    • 3-Hour Rental (For up to 10 people) – $500

    This Annapolis boat rental company is a great way to have a good time while being environmentally conscious. The stunning waterfront homes, diverse array of boats, beautiful sunset, and impressive skyline make it even better.

    • Operating Hours: Monday to Sunday – 9 am to 5 pm
    • Address: 300 Second St, Annapolis, MD 21403, United States
    • Phone: +1 443-433-2129
    • Email: info@aebrentals.com
    • Website: aebrentals.com

    Chronic Sailing

    Chronic Sailing is all about quality. Whether you’re chartering a boat, are learning to sail, or are buying a boat from them, you’ll experience the finest of services. Captain Shawn Owen, Annapolis’ renowned captain, teaches sailing. Soon, with the help of other captains, it will also provide the public with boutique charters.

    Unlike other boat rental places, this Annapolis boat rental company provides boat rental with a captain. However, you will have to negotiate and pay the captain’s fee plus tip separately at the end of your trip. When boat or yacht renting in Annapolis with Chronic Sailing, amenities like restrooms, showers, parking, and access to the marina pool are all included in the rental price. Fuel is also part of the single-day fee. For multi-day charters, the customer will need to shoulder the cost of refueling.

    Chronic Sailing has multiple packages, from renting for a few hours to multiple-day packages. The prices vary based on the package you choose.

    • Operating Hours: Undisclosed
    • Address: 7082 Bembe Beach Rd #204, Annapolis, MD 21403, United States
    • Phone: 443 333 9113
    • Email: Undisclosed, however, you can send them a message
    • Website: chronicsailing.com

    Annapolis Bay Charters

    Annapolis Bay Charters is so much more than an everyday boat rental company. They have an impressive fleet of sailboats and powerboats, a service-oriented staff, and a yacht charter location, which makes visiting Chesapeake Bay’s hidden gems easy.

    Did we mention that Annapolis Bay Charters’ staff has over thirty years of experience? This helps them match guests with the right boat for their cruising vacations. You can also use their additional services like itinerary planning, sailing lessons with the NauticEd Sailing School, and provisioning.

    Although boat rentals with captains aren’t an option here, Annapolis Bay Charter can recommend a few people. However, you will have to negotiate your transactions with the captain on your own. Prices vary based on the charter and duration so contact them for the best deal.

    • Operating Hours: Monday to Friday – 8:30 am to 5 pm, Saturday & Sunday – Closed
    • Address: 7080 Bembe Beach Rd #211A, Annapolis, MD 21403
    • Phone: 443 333 9113
    • Email: info@annapolisbaycharters.net
    • Website: annapolisbaycharters.net

    Experience Annapolis From the Water With These Boat Rental Companies

    Annapolis is a place of wonder, relaxation, and beautiful historical monuments. Make the most of your trip by choosing the best Annapolis boat rental companies. Stunning sunsets and Maryland’s coastal area are a different experience compared to exploring the place on foot.

    If you want to learn sailing or operate a boat, consider the Annapolis Sailing School. On the other hand, Annapolis Electric Boat Rentals is an excellent option for an environmentally conscious alternative. Other companies like Chronic Sailing and Annapolis Bay Charters also offer great services for those who want to navigate Annapolis by water.

    For more helpful guides like this, explore our blog section!

    Before you launch

    Check the forecast and advisories, use properly fitted safety gear, follow operator and agency rules, and never exceed your experience level.

    Official sources and verification

    Use these authoritative resources to confirm time-sensitive details:
    Maryland boating information
    U.S. Coast Guard boating safety

    Related Maryland guides

    Baltimore Water Taxi: Connecting Baltimore Efficiently and Affordably
    Have Fun With These Great Things to Do in Annapolis
    Naval Academy: Attractions, Admissions & More

    Frequently asked questions

    How current is this guide to Sail Annapolis With These Boat Rental Services?

    This page has been editorially refreshed for 2026. Hours, prices, availability, policies, and conditions can still change, so use the linked official sources and confirm time-sensitive details directly.

    What should I verify before making plans?

    Confirm current hours, pricing or fees, reservations, accessibility, parking or transportation, cancellation rules, and any weather or seasonal restrictions that apply.

    How should I choose among the options in this guide?

    Start with your location, budget, timing, accessibility needs, and the experience you want. Then compare verified details and recent policies rather than relying on one factor alone.

    What safety checks matter most?

    Review the official alert and weather pages, choose an activity suited to your ability, carry appropriate gear and water, and follow all posted land or water safety rules.

    Are paid placements allowed on Maryland Recommendations?

    Advertising and clearly labeled sponsored or guest content may be available, but payment does not buy an editorial ranking, a favorable review, or guaranteed search visibility.

    Reach Maryland readers

    Maryland businesses and expert contributors can inquire about clearly labeled advertising, sponsored content, and guest-post opportunities. Payment does not buy an editorial ranking, a favorable review, or guaranteed search visibility.
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