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04/19/2024  ± 2 days

Browse Annapolis Boat Rentals

Page 1 of 246 listings

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

4.8
Best of 2023
$225hour
41' Lagoon Catamaran in Maryland
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
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-$150hour
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
$120hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 12 guests

31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

5.0
$250hour
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
$150hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$165hour
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
$250hour
The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.
Sailing in Mayo · 6 guests

The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.

5.0
$175hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$450hour
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-$150hour
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-$160hour
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

4.5
$275-$375night
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

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

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425hour
Come take a cruise on the Annapolis Jet Boat
Powerboats in Annapolis · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$60person
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
$150hour
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
$300hour
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0
$400hour
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
$250hour
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
$325hour
Catalina 425 Sailing Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Catalina 425 Sailing Yacht in Rock Hall, Maryland

5.0
$160hour
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
$365hour
Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
Powerboats in Edgewater · 6 guests

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

New
$200hour

Annapolis Reviews

  1. DH

    Daniel

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    We had a great time with Alberto and Gracelia. The boat was well organized and well maintained. They walked us through the proposed route and adjusted it according to our interests. Because we were interested, Alberto was happy to explain all the elements of saling and let family members take the helm. Also, very nice that Alberto speaks English, Spanish and Portuguese. Parkin was clear and easy.

  2. WG

    William

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    Captain McCoy was an excellent guide of the Annapolis waters. It was an amazing experience from start to finish. Easy meeting spot and was fun sightseeing all of the houses along the water. We were even able to play our own music through the captains Bluetooth. We popped champagne and made mimosas while cruising the river for my wife’s birthday and I would highly recommend you do the same! Thanks Captain McCoy. Look forward to coming back and booking in the future!

  3. SM

    Stephanie

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    We chartered captain McCoy's boat to celebrate our friend's bachelorette party. We had the absolute best time. I have only positive things to say about the boat, the itinerary and the overall experience. Would highly recommend.

  4. CB

    Caprice

    41' Lagoon Catamaran in Maryland

    This was one of the best rides I’ve had in a while. Captain Jess is communicative, helpful and kind. We went out for 4 hours and had great weather. The boat is clean, he had 2 fridges for our food and drinks, it was nice and spacious, and there were floaties to get out on the water. It was a very enjoyable day.

  5. DA

    Dana

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    We cannot thank McCoy enough for this unbelievable experience watching the Blue Angels perform over the Annapolis skyline. McCoy and his wife did not miss a single detail, including making sure our kids had enough sunscreen on for the voyage! These were incredibly crowded and challenging areas to navigate during the show and McCoy did so with ease and grace. Thank you both for making amazing memories for us!

  6. DB

    Dan

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Capt Alberto and Grace were wonderful hosts. They were very flexible regarding the weather, great teachers of sailing, and were very hospitable and welcoming with their boat. We had an amazing time. Capt Alberto truly loves the sea.