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Browse Annapolis Boat Rentals

Page 3 of 354 listings

Cruising the South River. South of Annapolis.
Powerboats in Annapolis · 4 guests

Cruising the South River. South of Annapolis.

5.0
Snoozed - Active 04 Jul 2025
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
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
Snoozed - Active 04 Jul 2025
Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)
Powerboats in Pasadena · 10 guests

Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)

New
Snoozed - Active 02 Aug 2025
Watch the Blue Angels Annapolis 2025 May 20 practice & May 21 show.
Powerboats in Annapolis · 12 guests

Watch the Blue Angels Annapolis 2025 May 20 practice & May 21 show.

New
Snoozed - Active 04 Jul 2025
Enjoy the best views of Annapolis, MD aboard the Island Princess
Events in Annapolis · 128 guests

Enjoy the best views of Annapolis, MD aboard the Island Princess

New
Snoozed - Active 02 Aug 2025

Annapolis Reviews

  1. AL

    Ayodele

    Cruising the South River. South of Annapolis.

    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 ✨

  2. EG

    Erin

    Cruising the South River. South of Annapolis.

    Alan is amazing! We had such a wonderful time. He was really helpful and took us to great locations for our day out on the water. He was a superb host and we will definitely rent with him again! The boat was great and perfect for a day out on the water. Highly recommend him for all your boat adventures 😁

  3. LS

    Larissa

    Cruising the South River. South of Annapolis.

    Got together with family for a 4th of July morning boat ride and swim before fireworks. Alan was great, love his boat and all its amenities (kayaks, inner tube, paddle boards, on board head). Alan took us to a great swimming spot and allowed us some privacy with our guests. Highly recommend!

  4. SG

    Sara

    Cruising the South River. South of Annapolis.

    Alan was a great captain! Everything was smooth and easy. The boat was just what we needed for our family. He managed my husband, me and our 3 small boys really well. We had a great time out on the boat, swimming, tubing and fishing. Communication was great. We'd definitely do it again!

  5. Ally

    Ally

    Cruising the South River. South of Annapolis.

    Alan was very friendly, accommodating, thorough. He even had extra cups and napkins on hand for our small group. We really enjoyed the experience and look forward to a future excursion with Alan.

  6. FJ

    FLAVIA

    Cruising the South River. South of Annapolis.

    My family and I had a wonderful experience. The boat ride was clean and really enjoyable . Boat Captain was nice and very accommodating to our needs.