Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Getmyboat Logo

    Browse Annapolis Boat Rentals

    5.0
    (565 Reviews)

    Page 2 of 3 • 61 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    5.0
    $140+/hour
    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
    Sailing in Saint Michaels · 6 guests

    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

    5.0
    $325/hour
    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
    Sailing in Annapolis · 12 guests

    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

    New
    $400+/hour
    Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography
    Events in Annapolis · 6 guests

    Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography

    New
    $255/hour
    STARZ -Lagoon 42 Catamaran in Chesapeake Bay
    Sailing in Annapolis · 13 guests

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    New
    $400+/hour
    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
    Sailing in Rock Hall · 4 guests

    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

    5.0
    $150/hour
    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
    Events in Annapolis · 6 guests

    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

    New
    $300/hour
    Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
    Sailing in Saint Michaels · 6 guests

    Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

    New
    $350/hour
    Cruise the South River on 46ft Meridian Sedan Bridge Yacht
    Events in Annapolis · 6 guests

    Cruise the South River on 46ft Meridian Sedan Bridge Yacht

    New
    $255+/hour
    21′ KENCRAFT | Center Console | Located On The South River
    Powerboats in Annapolis · 6 guests

    21′ KENCRAFT | Center Console | Located On The South River

    New
    $125+/hour
    Parker Southwestern | Seats 6 | 23'
    Powerboats in Annapolis · 6 guests

    Parker Southwestern | Seats 6 | 23'

    New
    $125+/hour
    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
    Powerboats in Annapolis · 6 guests

    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

    New
    $125+/hour
    30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity
    Powerboats in Annapolis · 6 guests

    30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity

    New
    $260/hour
    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
    Events in North Beach · 8 guests

    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

    5.0
    $400/hour
    32' Center Console - up to 6 Guests from Stevensville, MD
    Powerboats in Stevensville · 6 guests

    32' Center Console - up to 6 Guests from Stevensville, MD

    5.0
    $375/hour
    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
    Powerboats in Annapolis · 6 guests

    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

    New
    $125+/hour
    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
    Powerboats in Annapolis · 6 guests

    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

    New
    $125+/hour
    Come take a cruise on the Annapolis Jet Boat
    Powerboats in Annapolis · 11 guests

    Come take a cruise on the Annapolis Jet Boat

    New
    $360/hour
    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
    Sailing in Annapolis · 13 guests

    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

    New
    $350+/hour
    Cruise on the Shannon Brendan
    Fishing in Annapolis · 6 guests

    Cruise on the Shannon Brendan

    New
    $350/hour
    Sail the Sea on the Pintita
    Sailing in Annapolis · 20 guests

    Sail the Sea on the Pintita

    New
    $500+/hour
    26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12
    Powerboats in Annapolis · 12 guests

    26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12

    New
    $194+/hour
    46′ CARMEN | Take Everybody With You! | Captain Included
    Events in Annapolis · 30 guests

    46′ CARMEN | Take Everybody With You! | Captain Included

    New
    $670+/hour
    Maxum 30ft Yacht! Escape for a day on the Chesapeake
    Events in Selby-on-the-Bay · 6 guests

    Maxum 30ft Yacht! Escape for a day on the Chesapeake

    New
    $350/hour

    Top Destinations Nearby

    Annapolis Reviews

    1. Pamela

      Pamela

      Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

      We booked this experience for my husbands birthday and it was PERFECT! The Selina II IS STUNNING, and Captain Iris and her crew were absolutely wonderful. Captain Matt was fantastic! He took such good care of us while we sailed across the Chesapeake Bay and celebrated with a couple of glasses of delicious champagne! Look no further and book the Selina II, you won’t regret it, it’s absolutely worth it !!

    2. LT

      Lloyd

      43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

      Davis was our captain, he was great . Very informative and knowledgeable . We went on a 31/2 hour sail in the Chesapeake bay. Would definitely do it again

    3. MP

      Mohan

      Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

      Captain Rob made the trip memorable with the beautiful views of the Chesapeake sunset and anecdotes of the area and his marine career.

    4. ac

      akhil

      Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

      Great trip, knowledgeable crew - was very accommodating with my family.

    5. Teresa

      Teresa

      Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

      We loved it, had a great time. Will definitely go again!

    About

    1. About Getmyboat
    2. Careers
    3. Media Inquiries
    4. Terms of Use
    5. Privacy Policy
    6. Cookies Policy
    7. Accessibility Statement
    8. Member Interface Agreement
    9. Contact Us

    Learn More

    1. How It Works
    2. For Owners
    3. Mobile Apps
    4. Safety

    Experiences

    1. Boat Rentals
    2. Jet Ski Rental
    3. Fishing Charters
    4. Houseboat Rental
    5. Pontoon Rental
    6. Yacht Rental
    7. Sailboat Rental
    8. Bachelorette Party Boat Rental
    9. Party Boat Rentals

    Journal

    1. Company News
    2. Lifestyle
    3. Experiences Guide
    4. Destinations
    5. Tips for Renters and Owners

    Popular Destinations

    1. Miami
    2. Lake Lanier
    3. Lake Tahoe
    4. San Diego
    5. Lake Travis
    6. Newport Beach
    7. Chicago
    8. Lake Norman
    9. Key Largo
    10. Destin
    11. Marathon

    24/7 Live Support

    1. Help & FAQs
    2. +1 818 927 2148
    3. support@getmyboat.com

    Real reviews from happy Getmyboaters.

    4.9 out of 5! 500,000+ reviews

    • Download on the App Store
    • Get it on Google Play
    © Getmyboat 2025
    TermsPrivacy