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
    (603 Reviews)

    Page 2 of 3 • 51 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
    $150+/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
    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
    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
    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
    Parker Southwestern | Seats 6 | 23'
    Powerboats in Annapolis · 6 guests

    Parker Southwestern | Seats 6 | 23'

    New
    $125+/hour
    Enjoy the best views of Annapolis, MD aboard the Island Princess
    Events in Annapolis · 128 guests

    Enjoy the best views of Annapolis, MD aboard the Island Princess

    New
    $480+/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
    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
    Sailing in Annapolis · 10 guests

    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

    New
    $232+/hour
    Come take a cruise on the Annapolis Jet Boat
    Powerboats in Kent Narrows · 11 guests

    Come take a cruise on the Annapolis Jet Boat

    New
    $360/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
    50′ VIKING - Your Chartered Experience Awaits!
    Events in Annapolis · 12 guests

    50′ VIKING - Your Chartered Experience Awaits!

    New
    $841+/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
    26’ CREST TRITOON | Excellent Pontoon | Seats 12
    Powerboats in Annapolis · 12 guests

    26’ CREST TRITOON | Excellent Pontoon | Seats 12

    New
    $194+/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
    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
    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
    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
    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
    Sailing in Saint Michaels · 6 guests

    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

    New
    $400/hour
    VIKO S 35 Sailboat in Deale
    Sailing in Deale · 6 guests

    VIKO S 35 Sailboat in Deale

    New
    $298/hour
    VIKO 30 Premium Sailing Yacht In Deale, MD
    Sailing in Deale · 5 guests

    VIKO 30 Premium Sailing Yacht In Deale, MD

    New
    $925/day
    34ft Sailing Yacht in Annapolis, Maryland
    Sailing in Annapolis · 4 guests

    34ft Sailing Yacht in Annapolis, Maryland

    New
    $250/hour
    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
    Events in Annapolis · 8 guests

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    5.0
    Snoozed - Active 02 Aug 2025

    Top Destinations Nearby

    Annapolis Reviews

    1. ET

      Eris

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      This is everything you could want. Great boat and captain. McCoy has everything you need for a great trip. Plenty of space onboard for all your food and drink and all the toys you could want for a fun day on the water. We count thank him enough fro a such great experience and a great price! We will be booking again for sure!

    2. WW

      Walter

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Overall, we had a good experience. We ran into some mechanical issues with the boat and had to cut our trip short. Captain McCoy offered to give me a partial refund and was very apologetic. Things happen sometimes, and we were not upset. We will come back.

    3. martine

      martine

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Our Trip with McCoy was great! He was very accommodating and knew the good swimming spots. Boat came with floaties and was very nice and clean.

    4. PM

      Pam

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Great communication, very helpful with questions. On time and the boat was very clean . Had a great time !

    5. MT

      Marija

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      We had a wonderful time at Captain McCoy’s boat. The boat is gorgeous, impeccably clean, and very spacious. The Captain played great music (we didn’t bring our own playlist). He found a great spot for our group to take a swim. It was a perfect balance of cruising and swimming and a perfect 2 hr cruise

    6. TS

      Tiffany

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Took my husband on a surprise boat ride for his birthday and he loved it!! McCoy was great at communication when I had questions. He took us on a 2 hour boat ride and made the trip so enjoyable and relaxing!! He played music for us and took us to see some beautiful sights. I will definitely be booking all my boat rides with McCoy in the future!

    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