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    Annapolis, Maryland Boat Rentals & Yacht Charters

    5.0
    (633 Reviews)

    Page 2 of 3 • 49 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Annapolis | 50 Prestige Yacht for 13 People
    Events in Annapolis · 13 guests

    Annapolis | 50 Prestige Yacht for 13 People

    New
    Superowner
    $650/hour
    Discover the Spirit of the Chesapeake Bay and Cruise the South River
    Events in Annapolis · 6 guests

    Discover the Spirit of the Chesapeake Bay and Cruise the South River

    New
    $255+/hour
    Limited Availability
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Annapolis · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $425/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
    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
    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay
    Sailing in Annapolis · 12 guests

    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

    New
    $334+/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
    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

    New
    $175+/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
    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
    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
    Luxury Lagoon 42 Catamaran for 12 in Annapolis
    Sailing in Annapolis · 12 guests

    Luxury Lagoon 42 Catamaran for 12 in Annapolis

    New
    $335+/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
    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 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
    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
    Rent a 31ft Sailing Yacht In Rock Hall, MD
    Sailing in Rock Hall · 4 guests

    Rent a 31ft Sailing Yacht In Rock Hall, MD

    New
    $250/day
    Newest Electric Powered Luxury Deck Boat - Extra Large Deck- Full Day Bed
    Powerboats in Annapolis · 9 guests

    Newest Electric Powered Luxury Deck Boat - Extra Large Deck- Full Day Bed

    New
    $275+/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
    50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

    5.0
    Snoozed - Active 02 Jul 2026
    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
    Snoozed - Active 02 Jul 2026
    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

    Top Destinations Nearby

    Annapolis Reviews

    1. ML

      Martha

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

    2. Jordan

      Jordan

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!

    3. 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!

    4. James

      James

      Charter 42' Lagoon Catamaran in Annapolis, MD

      First class operation. Wonderful time and would recommend to anyone looking to spend a day on the Chesapeake. Thank you Captain Chris!

    5. KS

      Kevin

      Charter 42' Lagoon Catamaran in Annapolis, MD

      Best day on the water ever. 40 years of sailing experience here and most knowledgeable friendly captain ever. Highly recommended.

    6. DW

      Dominique

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      Amazing experience! Amazing, professional crew! It was very easy to book from the beginning. We had an amazing time! Group of 12.

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