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    Annapolis, Maryland Boat Rentals & Yacht Charters

    5.0
    (699 Reviews)

    Page 2 of 3 • 52 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests
    Powerboats in Edgewater · 25 guests

    Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests

    5.0
    $525/hour
    Hinckley| 13 PPL | St. Michaels & Annapolis | $3K 4hrs
    Powerboats in Saint Michaels · 13 guests

    Hinckley| 13 PPL | St. Michaels & Annapolis | $3K 4hrs

    New
    Superowner
    $750/hour
    Instant Book
    Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht
    Events in Annapolis · 128 guests

    Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

    5.0
    $480+/hour
    Big Thrills, Big Water, Big Fun — Introducing the 24′ Hurricane Sundeck
    Powerboats in Annapolis · 12 guests

    Big Thrills, Big Water, Big Fun — Introducing the 24′ Hurricane Sundeck

    5.0
    $175+/hour
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Annapolis · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $425/hour
    26′ Bennington Pontoon | Adventure Awaits | Seats 12
    Powerboats in Annapolis · 12 guests

    26′ Bennington Pontoon | Adventure Awaits | Seats 12

    5.0
    $194+/hour
    Annapolis | 50 Prestige Yacht for 13 People
    Events in Annapolis · 13 guests

    Annapolis | 50 Prestige Yacht for 13 People

    New
    Superowner
    $650/hour
    42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    5.0
    $150+/hour
    $375hr | 12 Guests | Annapolis Area
    Events in Edgewater · 12 guests

    $375hr | 12 Guests | Annapolis Area

    New
    Superowner
    $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
    27' Godfrey Tritoon Pontoon Boat - Perfect for Cruising and Entertaining
    Powerboats in Annapolis · 12 guests

    27' Godfrey Tritoon Pontoon Boat - Perfect for Cruising and Entertaining

    New
    $175+/hour
    Luxury 2022 Excess 11 Catamaran for 12 in Annapolis
    Sailing in Annapolis · 12 guests

    Luxury 2022 Excess 11 Catamaran for 12 in Annapolis

    New
    $335+/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
    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
    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay
    Sailing in Annapolis · 12 guests

    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

    New
    $334+/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
    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
    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
    Meridian 541 Sedan Motor Yacht Ideal For Chesapeake Bay Cruising
    Events in Annapolis · 12 guests

    Meridian 541 Sedan Motor Yacht Ideal For Chesapeake Bay Cruising

    New
    $1,280/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
    23ft Parker Center Console | Seats 6 | Edgewater, Maryland
    Powerboats in Annapolis · 6 guests

    23ft Parker Center Console | Seats 6 | Edgewater, Maryland

    New
    $125+/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

    Top Destinations Nearby

    Annapolis Reviews

    1. Lauren

      Lauren

      Charter 42' Lagoon Catamaran in Annapolis, MD

      We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!

    2. AH

      Abby

      Big Thrills, Big Water, Big Fun — Introducing the 24′ Hurricane Sundeck

      A wonderful boat day! I would recommend Griff and use him again!

    3. DW

      Denzel

      Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests

      Amazing host and experience. Will definitely do this again

    4. JA

      Joey

      Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

      Booked a private yacht charter along the Island Princess for 3 hours and had a great experience! Captain Steve was kind, accommodating, and knowledgeable during our journey! Would 100% recommend! Thank you!

    5. KC

      Kevin

      Charter 42' Lagoon Catamaran in Annapolis, MD

      Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!

    6. LT

      Lloyd

      42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

      Davis was our captain, he was great . Very informative and knowledgeable . We went on a 31/2 hour sail in the Chesapeake bay. Would definitely do it again

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