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All listings in Annapolis

Search yacht rentals in Annapolis, Maryland.

Page 1 of 119 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
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
Catamaran in Maryland
Sailing in Annapolis · 12 guests

Catamaran in Maryland

5.0
Superowner
Best of 2023
$390/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
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
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
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
Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography
Events in Annapolis · 6 guests

Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography

New
$255/hour
Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
Events in North Beach · 8 guests

Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

5.0
$400/hour
45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity
Powerboats in Annapolis · 32 guests

45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

New
$55/person
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500+/hour
Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New
$400/hour
Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550/hour
New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland

New
$1,100/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
Snoozed - Active 02 May 2025

Motor Yacht Reviews in Annapolis

  1. 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.

  2. 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.

  3. MT

    Marija

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    We had a wonderful time at Captain McCoy’s boat. The boat is gorgeous, impeccably clean, and very spacious. The Captain played great music (we didn’t bring our own playlist). He found a great spot for our group to take a swim. It was a perfect balance of cruising and swimming and a perfect 2 hr cruise

  4. WS

    Wendy

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    Captain McCoy is the best. His boat was the perfect place to spend the morning on the water with my son and husband celebrating my 60th birthday! We had fun and felt safe and secure. Highly recommend the fabulous accommodations!

  5. Alex

    Alex

    43ft Cruiser Express Yacht for Daily Charter

    Captain Rob was flexible with our departure time to work around bad weather, which was awesome! His boat was beautiful and clean. He showed us some truly private quiet spots where we could swim and cool off. On the way back the winds and waves picked up, but Capt. Rob was able to “jake” this huge boat into the parking spot under pressure like a true boss. We will be back!!

  6. AS

    Abby

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    Captain McCoy and his boat were perfect for some time out on the water! The boat was very accommodating, especially the bean bag chairs to lounge on the front of the boat! Pick up / drop off and communication was seamless