28 boat rentals in Annapolis, MD
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Annapolis, MD
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Rent a Boat Charter in Annapolis, Maryland with Sailo!
Looking for a boat rental Annapolis, MD? Let's start choosing the right private yacht rental in Annapolis, MD - the charming capital of Maryland — is quintessentially maritime. Home of the US Naval Academy, this amazing town preserves the authentic Colonial atmosphere: cobblestone streets, original lamp posts and brick row houses. Sailing is ingrained in Annapolis — a boat rental comes naturally if you choose to spend a few days around here.
How to rent a boat in Annapolis, Maryland?
Check out our extensive inventory and pick the yacht rental in Annapolis, MD that suits your plans for having fun on the water. Whether you are into watersports, looking for a relaxed cruise, or to go for a fishing trip, this famous boating destination has something for every taste. If you’re around for the 4th of July, you’ll get the chance to enjoy the amazing fireworks right from your boat!
A boat rental to Chesapeake bay is the perfect choice for a romantic sunset cruise to enjoy the scenic skyline, or a visit to the historic Kent island. There are many things to do by boat in “America’s Sailing Capital”. Browse, pick your Annapolis, MD boat rental and get ready for a memorable nautical adventure! We also invite you to check our top boat selections in other locations in Maryland: Pasadena boat charters and Solomons Island boat rentals.
Sailo concierge team is here to help you rent the perfect private boat charter in Annapolis to go sailing in Maryland. To ask for more details or request special arrangements on your private yacht rental in Annapolis, MD, please send a direct message to the boat representative, or reach out to us on live chat.
Annapolis, MD could be the ideal yachting playground for you
Boating in Annapolis is a thrilling experience and one best savoured with your own private yacht charter. Choose your perfect boat rental in Annapolis and step aboard with your family or friends for a spectacular day on the water. Escape the crowds and enjoy some of the most beautiful scenery in Maryland from the deck of your own yacht charter.
Top private boat rentals in Annapolis, MD
Want to rent a boat in Annapolis, MD? You’ll find 9 boats waiting for you to take them on an adventure here on Sailo. Choose from our sailboat rentals in Annapolis, MD. Another great choice is a catamaran rental in Annapolis, MD. Fans of luxury motor yachts will be spoiled for choice with our multiple motor yacht charters in Annapolis. Maryland is an excellent place to enjoy a party, so discover our party boat rentals in Annapolis, MD for 13+ guests in Annapolis and see for yourself.
How to find a boat charter in Annapolis, Maryland?
Choosing the perfect Sailo boat for you in Annapolis, MD is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day boat rental in Annapolis, MD, the group size is very important, as well as the type of boat you want for your adventure in the waters of Maryland. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a Annapolis boat charter with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis yacht charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!
How much does it cost to rent a yacht charter in Annapolis, MD for a day?
Annapolis boat rentals prices vary significantly. You can find great budget friendly private yacht rentals in Annapolis, MD starting from $250 for a daily trip. Luxury or party yacht rentals for the day can cost up to $6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Annapolis with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.
Can I pay in installments for my Sailo Annapolis boat rental?
A lot of our boat owners allow payment in installments, particularly for the weekly yacht charters in Annapolis, MD. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.
Responsible boating guidelines
- Take your rubbish home
- Use eco-friendly sunblock
- Avoid single use plastic
Popular locations to rent a boat in Maryland
| Number of boats | 28 boats available |
|---|---|
| Types of boats | Motor, Party, Sailboat, Catamaran |
| Average price | $2,525 per day |
| Minimum price | $250 per day |
| Maximum price | $7,250 per day |
| Manufacturers | Beneteau, Jeanneau, Sea Ray, Lagoon, Bali, Bavaria, Catalina, Azimut |
The cost for a private charter in Annapolis varies significantly based on the vessel type, with sailing yachts typically ranging from $150 to $400 per hour and luxury motor yachts starting around $450 per hour. For a comprehensive full-day experience on a premium vessel with a professional captain, you can expect to spend approximately $1,200, though larger yachts designed for corporate events or weddings will be priced higher based on their specific amenities.
A quintessential Annapolis itinerary involves a scenic cruise past the United States Naval Academy to see the stunning chapel dome and Bancroft Hall from the water. Many boaters also enjoy navigating through the famous "Ego Alley" at the City Dock, cruising under the massive spans of the Chesapeake Bay Bridge, or heading south to view the historic Thomas Point Shoal Lighthouse, which is the most iconic and photographed lighthouse in Maryland.
The Annapolis Harbor is one of the busiest maritime hubs on the East Coast, requiring constant vigilance to navigate through heavy traffic, racing sailboats, and commercial vessels. A USCG-licensed captain manages these technical challenges and the currents of the Severn River, allowing you to relax while a professional handles the docking in tight spaces like Spa Creek or Back Creek and ensures compliance with all local "no-wake" zones.
Most private charters depart from central maritime locations such as the Annapolis City Dock, which serves as the historic heart of the city. Other popular boarding spots include the professional marinas in Eastport along Back Creek or private slips near Spa Creek, providing immediate access to the Chesapeake Bay and the city’s renowned waterfront dining district.
Annapolis is perfectly situated as the primary jumping-off point for a day trip across the Chesapeake Bay. A standard full-day charter provides ample time to reach the historic maritime town of St. Michaels, allowing you to experience the transition from the bustling state capital to the tranquil, scenic harbors of the Miles River on the Eastern Shore.
Most rentals on Sailo operate on a BYOB basis, which is ideal for a casual afternoon of snacks and refreshments while anchored in a quiet cove. However, the city is a premier "dock-and-dine" destination, and your captain can pull up to waterfront favorites like Pusser’s Caribbean Grille or Carroll’s Creek Cafe. Many luxury hosts also offer catering add-ons featuring local Maryland crab cakes and seasonal seafood if requested in advance.
If you book a captained rental, you do not need any license as the captain’s professional credentials cover the legal operation of the vessel. For bareboat (self-drive) rentals, Maryland law requires anyone born on or after July 1, 1972, to have a Boating Safety Education Certificate. Visitors can typically use a valid certificate from another state that is recognized by the NASBLA to ensure they remain compliant with local safety regulations.
For standard local sightseeing loops within the Severn River or Spa Creek, fuel is frequently included in the total price of a captained charter. For longer voyages that involve high-speed travel across the Chesapeake Bay Bridge or a trip to the Eastern Shore, fuel is typically charged based on actual consumption at the end of the journey. You should always review the "Price Includes" section of the specific listing to confirm the fuel policy.
Most private recreational yachts are limited to a maximum of 6 or 12 guests depending on their specific USCG certification and vessel size. For much larger celebrations such as a corporate retreat, a wedding, or a major alumni event, the area has access to Inspected Passenger Vessels available on Sailo that are certified to carry 30 to 50 or more guests with a full professional crew for comprehensive event hosting.
Safety is the primary concern for all maritime operations, and the captain has the final authority to determine if conditions are safe to leave the dock. If a trip is canceled by the captain due to dangerous weather like high winds or thunderstorms, your Sailo host will work with you to either reschedule the charter or provide a full refund. Most captains are still willing to sail in light rain or overcast conditions as long as the water remains calm and visibility is safe.