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    Saint Michaels, Maryland Boat Rentals

    Page 1 of 1 • 24 listings

    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
    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
    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
    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
    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
    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 Jul 2025
    43ft Cruiser Express Yacht for Daily Charter
    Events in Selby-on-the-Bay · 8 guests

    43ft Cruiser Express Yacht for Daily Charter

    5.0
    $400/hour
    Luxury cruise on the Chesapeake - Leave your stress in the wake!
    Events in Selby-on-the-Bay · 12 guests

    Luxury cruise on the Chesapeake - Leave your stress in the wake!

    5.0
    Snoozed - Active 23 Jun 2025
    Private Yacht Charter: On 40ft Regal Commodore
    Events in Selby-on-the-Bay · 10 guests

    Private Yacht Charter: On 40ft Regal Commodore

    5.0
    $300/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
    Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
    Sailing in Mayo · 6 guests

    Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

    5.0
    $175+/hour
    VIKO S 35 Sailboat in Deale
    Sailing in Deale · 6 guests

    VIKO S 35 Sailboat in Deale

    New
    $298/hour
    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    Sailing in Deale · 10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    5.0
    $250+/hour
    Instant Book
    COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!
    Powerboats in Deale · 6 guests

    COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!

    5.0
    $200/hour
    Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine
    Events in Deale · 10 guests

    Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

    5.0
    $500/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
    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
    Sailing in Annapolis · 12 guests

    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

    5.0
    $400+/hour
    SLOWDOWN - DUFOUR 430
    Sailing in Annapolis · 12 guests

    SLOWDOWN - DUFOUR 430

    New
    $250+/hour
    JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
    Sailing in Annapolis · 12 guests

    JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

    5.0
    $250+/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
    STARZ -Lagoon 42 Catamaran in Chesapeake Bay
    Sailing in Annapolis · 13 guests

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    5.0
    $400+/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
    50ft Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    5.0
    Snoozed - Active 23 Jun 2025

    Top Destinations Nearby

    Saint Michaels Reviews

    1. CB

      Caroline

      Private Yacht Charter: On 40ft Regal Commodore

      Captain Dennis is absolutely fantastic. Great communication, fabulous boat and amenities, and a wonderful captain. Would highly recommend!

    2. MR

      Matt

      STARZ -Lagoon 42 Catamaran in Chesapeake Bay

      Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!

    3. hg

      hunter

      Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

      we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!

    4. CE

      Clifford

      SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

      Sarah was helpful in lining me up for a sail boat for Mothers Day and in recommending a captain and in adjusting time to meet our needs.

    5. RM

      Rachel

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

      Michael is a great host. He’s so nice and hangs out with us. We really enjoyed his boat!

    6. SM

      Scott

      Luxury cruise on the Chesapeake - Leave your stress in the wake!

      Captain Scott helped make Mother's Day for my Fiance the best she's ever experienced!

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