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Browse Annapolis Boat Rentals

5.0

(511 Reviews)

Page 1 of 2 • 45 listings

Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0

$300/hour

Powerboats in Annapolis · 8 guests

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

4.9

Best of 2025

$225/hour

Sailing in Annapolis · 12 guests

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

5.0

$250+/hour

Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0

Superowner

$138+/hour

Instant Book

Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0

$250/hour

Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0

$400+/hour

Events in Deale · 10 guests

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

5.0

$500/hour

Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0

$150/hour

Sailing in Mayo · 6 guests

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

5.0

$175+/hour

Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0

$250+/hour

Instant Book

Powerboats in Edgewater · 6 guests

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

5.0

$225/hour

Instant Book

Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0

$400/hour

Powerboats in Deale · 6 guests

COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!

5.0

$200/hour

Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New

$250+/hour

Events in Annapolis · 12 guests

50′ VIKING - Your Chartered Experience Awaits!

New

$841+/hour

Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0

$425/hour

Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0

$400+/hour

Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0

$325/hour

Sailing in Rock Hall · 6 guests

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

5.0

$140+/hour

Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0

$150/hour

Events in Annapolis · 6 guests

Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

New

$300/hour

Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

New

$350/hour

Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New

$125+/hour

Powerboats in Stevensville · 6 guests

32' Center Console - up to 6 Guests from Stevensville, MD

5.0

$375/hour

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Annapolis Reviews

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
LC
Laura

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Amazing! I went with my family, ages 5 and up, and everyone had a fantastic time. Captain Dushaune is a gem - personable, patient, funny, prepared. His boat is beautiful and well maintained. He was laid back while also keeping us safe and happy. He knew the waterways well, took us to a perfect cove for swimming and relaxing. The marina where his boat is located is ideal - clean, easy parking, great views, great water access. I cannot wait to book with him again. Highest possible recommendation!
Marie

38-ft Hunter 376 Sailing Adventure in Annapolis
We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!
Sam

38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.
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!
stephan

Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
Tyler was an awesome host! His boat was great and he was very flexible and accommodating! We will definitely be using his services again!