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    Browse Annapolis Boat Rentals

    5.0
    (628 Reviews)

    Page 2 of 3 • 52 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
    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
    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
    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
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
    Powerboats in Selby-on-the-Bay · 10 guests

    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    5.0
    Snoozed - Active 02 Sep 2025

    Top Destinations Nearby

    Annapolis Reviews

    1. BM

      Bernadette

      31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

      Capt Michael is amazing. His boat is beautiful and well maintained. He is friendly, professional and knows how to Captain. He was very flexible and understanding when we had a change of plans and dropped off some of our crew at another location. We highly recommend him for your fun day out on the bay and we will be booking him again!

    2. DL

      Debbie

      31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

      Everything went perfectly, from the time I initially reached out to the return back to the marina. Michael is an excellent captain, his boat is pristine in every way, and the trip was the best way imaginable to spend my daughters birthday with her 3 BFFs and their moms. I will be sure to consider Michael and his boat for another way to celebrate or spend a day on the water. He was flexible, communicative, knowledgeable, friendly, and willing to assure us all the best day ever. Can't be more grateful!

    3. bb

      brent

      31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

      From the very start of our day, Michael was very accommodating to all our desires and tailored the day to make it absolutely fabulous. Would 100% recommend him to everyone and plan to use him again next year. Great Experience!!!!!

    4. NM

      Nickita

      31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

      Michael was so much fun and had the best day planned for our group, he was super kind and personable and was a great captain! The boat was clean and was an absolute blast, highly recommend!

    5. Nick

      Nick

      31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

      Michael boat was awesome. Good space and seating for our 12 person group. My group and I had a great time! We would recommend.

    6. MM

      Marianna

      31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

      We had such a great trip! Micheal was very helpful and easy to communicate with. Such a memorable weekend for our group of 12

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