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Browse Annapolis Boat Rentals

Page 1 of 17 listings

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
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
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$450/hour
Instant Book
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
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
Instant Book
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
$94+/hour
Instant Book
2022 Sea Ray SDX Boat with Captain Included!
Powerboats in Edgewater · 6 guests

2022 Sea Ray SDX Boat with Captain Included!

New
Snoozed - Active 02 Aug 2025

Annapolis Reviews

  1. David

    David

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

    Couldn’t have asked for a better experience with Robert (Scott)! He was so nice to me and my family, the boat was wonderful, and my family had an absolutely wonderful time on the water. He was super flexible, helped us get underway, and get back to the dock at the end of the day. His trustworthiness and kindness didn’t go unnoticed. Couldn’t recommend him enough to others and hope to rent from him again soon!

  2. ST

    Sherzod

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Great experience, it was my first time boat sailing and Alberto and his wife were great. My fiance and I had a great time. Highly recommend!

  3. BF

    Bruce

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

  4. SW

    Stacie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    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!

  5. Cliff

    Cliff

    38-ft Hunter 376 Sailing Adventure in Annapolis

    I found Captain Alberto and his first mate lovely wife were the ultimate hosts and storytellers. What I didn't expect, was to get impromptu sailing lessons. It was a beautiful day on the Chesapeake and I would highly recommend this to anyone who wants to truly appreciate the beauty and magnificence and physics of sailing

  6. AM

    Aleisha

    38-ft Hunter 376 Sailing Adventure in Annapolis

    BOOK WITH CAPTAIN ALBERTO!! I mean this was the BEST thing experience I had all summer. He accommodated our needs, let us have fun, and taught us soo much during the process. Captain Alberto just had the best hospitality that I’ve seen in a long time. As a first-time boat goer, he made me feel so comfortable and welcomed! I will definitely be back and will rebook with captain Alberto. I mf you are looking through boat options and stumble on this, this is your sign to book with him!