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    Annapolis, Maryland Boat Rentals

    5.0
    (545 Reviews)

    Page 2 of 2 • 38 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Sail Up to 13 Guests | 44ft Leopard Catamaran
    Sailing in Saint Michaels · 13 guests

    Private Sail Up to 13 Guests | 44ft Leopard Catamaran

    New
    $580/hour
    Luxury Lagoon 42 Catamaran for 12 in Annapolis
    Sailing in Annapolis · 12 guests

    Luxury Lagoon 42 Catamaran for 12 in Annapolis

    New
    $335+/hour
    Durfour 430 Sailing Yacht to Discover the Chesapeake Bay
    Sailing in Annapolis · 12 guests

    Durfour 430 Sailing Yacht to Discover the Chesapeake Bay

    New
    $210+/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
    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
    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
    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
    Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included
    Sailing in Saint Michaels · 6 guests

    Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

    New
    $585/hour
    Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included
    Sailing in Saint Michaels · 13 guests

    Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included

    New
    $645/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
    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
    Snoozed - Active 25 Aug 2026
    45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity
    Powerboats in Annapolis · 32 guests

    45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

    New
    Snoozed - Active 25 Aug 2026

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