Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Browse Annapolis Boat Rentals

All Annapolis Listings

Page 1 of 354 listings

Pro line Center Console Magothy River - Perfect for fishing exploring cruising
Powerboats in Severna Park · 12 guests

Pro line Center Console Magothy River - Perfect for fishing exploring cruising

5.0
$65+/hour
Instant Book
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Powerboats in Annapolis · 8 guests

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

4.9
Best of 2025
$225/hour
2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
Powerboats in Severna Park · 4 guests

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

5.0
$120/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$138+/hour
Instant Book
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
Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$350/hour
Instant Book
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
$275/hour
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0
$250/hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
$325/hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
$150/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
Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
Powerboats in Edgewater · 6 guests

Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!

5.0
$225/hour
Instant Book
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
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95+/hour
Instant Book
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
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
26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12
Powerboats in Annapolis · 12 guests

26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12

5.0
$194+/hour
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
FIREWORKS ON THE BAY!  COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!
Powerboats in Deale · 6 guests

FIREWORKS ON THE BAY! COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!

5.0
$200/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
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
SLOWDOWN - DUFOUR 430
Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New
$250+/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour

Annapolis Reviews

  1. AI

    Amy

    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

    Dushaune was amazing! The best boat ride we have ever had. He is extremely nice and drove us to a swimming area that was amazing. We enjoyed just hanging in the water, talking with him. We lost track of time because we were having so much fun. Would definitely love to go on a ride with him again.

  2. DC

    Donte

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

  3. HT

    Hien

    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

    Dushaune is a great captain and great host, he is down to earth, knowledgeable, funny. We are a group of 6 with very different characters and age (from 7-50) but all of us had fun. We felt great after the ride. Thanks Dushaune. Highly recommended

  4. GA

    Giselle

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

  5. Ashraf

    Ashraf

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    The whole experience was above and beyond the expectations the boat is tidy and clean and Sunmi is very helpful and knowledgeable. Elevate your experience and book this boat with Sunmi.

  6. DP

    Dina

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    Sunmi was the ultimate professional, from communication to arrival time. I will def book again with him!!! The boat was easy to navigate and had the perfect day on the water.