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Browse Annapolis Boat Rentals

Page 1 of 242 listings

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
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.9
$165/hour
2022 Sea Ray SDX Boat with Captain Included!
Powerboats in Edgewater · 6 guests

2022 Sea Ray SDX Boat with Captain Included!

New
$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
$450/hour
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 2023
$225/hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0
Superowner
Best of 2023
$138+/hour
Catamaran in Maryland
Sailing in Annapolis · 12 guests

Catamaran in Maryland

5.0
Superowner
Best of 2023
$390/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
$250/hour
Enjoy a Day on the Bay and Cruise the South River
Powerboats in Annapolis · 6 guests

Enjoy a Day on the Bay and Cruise the South River

5.0
$135+/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
$50/person
Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
Powerboats in Edgewater · 6 guests

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

5.0
$200/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
Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED
Powerboats in Annapolis · 5 guests

Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

5.0
$200/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
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600/day
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
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
Cruise the Chesapeake Bay on a beautiful 34ft Maxum Yacht
Powerboats in Deale · 6 guests

Cruise the Chesapeake Bay on a beautiful 34ft Maxum Yacht

5.0
$225/hour
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0
$150/hour
50ft Catamaran Charter with Water Toys in St. Michaels, MD
Sailing in Saint Michaels · 12 guests

50ft Catamaran Charter with Water Toys in St. Michaels, MD

New
$525/hour
Cruise the South River on 46ft Meridian Sedan Bridge Yacht
Events in Annapolis · 6 guests

Cruise the South River on 46ft Meridian Sedan Bridge Yacht

New
$255+/hour
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
$65/person
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
Relaxing Excitement of the Chesapeake Bay and tributaries on our Ocean Yacht
Travel in Annapolis · 6 guests

Relaxing Excitement of the Chesapeake Bay and tributaries on our Ocean Yacht

New
$300/hour

Annapolis Reviews

  1. George

    George

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

  2. TM

    Tom

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Captain Alberto and Grace were amazing, and helped with a very romantic sunset sail. The were ver gracious, accommodating, and knowledgeable. If we get the chance we will definitely come back and hire them again!

  3. EB

    Ernest

    Private Yacht Charter: On 40ft Regal Commodore

    GREAT experience!!! Captain Dennis was terrific. He was professional, yet fun & extremely well prepared. The yacht was clean & well maintained with all the amenities that we could ask for. Our only regret is that we did not book a longer cruise on Seas the Day.

  4. Abigail

    Abigail

    Private Yacht Charter: On 40ft Regal Commodore

    Captain Dennis was exceptional—punctual, professional, and allowed us to have a great time. The boat itself was in perfect condition, with all the necessary equipment and some luxurious extras, like the floating 🏝️, that made the day truly enjoyable. The excellent service and the beautiful setting made it an unforgettable birthday party. I highly recommend Captain Dennis for anyone looking to host a memorable and top-notch maritime event.

  5. AL

    Ayodele

    Enjoy a Day on the Bay and Cruise the South River

    Alan was great from the start! Very communicative and accommodating. Booking process was smooth. Our ride was super relaxing as we all felt safe with Alan as our captain! He took great photos of us to capture the memories! 10/10 recommend! Thanks Alan ✨

  6. SW

    Stacie

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Our sailing trip exceeded our expectations! Captain Alberto is a complete treasure: he shared his sailing knowledge and involved us in the sail as much as we wanted - The boat was clean and comfortable with space to enjoy the trip both above and below deck. We only had 2 in our party, but 6 people would absolutely be comfortable given the space. We hope to book a trip with Capt. Alberto again!