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    Browse Annapolis Boat Rentals

    5.0
    (631 Reviews)

    Page 2 of 3 • 51 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    SLOWDOWN - DUFOUR 430
    Sailing in Annapolis · 12 guests

    SLOWDOWN - DUFOUR 430

    New
    $250+/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
    50′ VIKING - Your Chartered Experience Awaits!
    Events in Annapolis · 12 guests

    50′ VIKING - Your Chartered Experience Awaits!

    New
    $841+/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
    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
    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
    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
    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
    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
    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
    Parker Southwestern | Seats 6 | 23'
    Powerboats in Annapolis · 6 guests

    Parker Southwestern | Seats 6 | 23'

    New
    $125+/hour
    26’ CREST TRITOON | Excellent Pontoon | Seats 12
    Powerboats in Annapolis · 12 guests

    26’ CREST TRITOON | Excellent Pontoon | Seats 12

    New
    $194+/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
    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
    $280/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
    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
    46′ CARMEN | Take Everybody With You! | Captain Included
    Events in Annapolis · 30 guests

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

    New
    $670+/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
    Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain
    Powerboats in Annapolis · 6 guests

    Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

    5.0
    Snoozed - Active 22 Sep 2025

    Top Destinations Nearby

    Annapolis Reviews

    1. Danylle

      Danylle

      Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

      Mike and Holly were great hosts! Very nice, knowledgeable of the water and the areas, showed us some great spots, allowed us to be completely relaxed and comfortable. Not to mention, took tons of fun pics of our group! Thank you so much, Mike and Holly. Don’t think, just book! …but not on a date that I want.. lol We will be booking again!! Thank you!

    2. ML

      Melissa

      Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

      Holly and Mike were outstanding captains! Loved getting to see different areas of PCB and had an amazing time in the sandbar off shell island!!! Thanks again for a wonderful time! Definitely will be back!

    3. Ts

      Teresa

      Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

      Cannot say enough good things! Holly and Mike were great, treated us like family and were very accommodating! Super friendly and quick with communication. Thanks again so much! We had a blast 😊

    4. Jimmie

      Jimmie

      Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

      I had a really great time. The couple was very nice and helpful to answer any questions we had. I would recommend them for all your Panama City boating rental needs.

    5. DB

      David

      Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

      Had a wonderful experience with Mike and Holly. The boat was very comfortable and they went above and beyond to make sure we had a good time.

    6. Jae

      Jae

      Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

      Absolutely great time! Mike and Holly treated my friends and me like family. Super grateful for their amazing service

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