1. The Island Princess (Large Group Charters & Events)
Our flagship vessel, the Island Princess, is built to host large groups, corporate gatherings, and grand celebrations. Designed with a climate-controlled, enclosed main salon and a spacious, open-air upper deck, it delivers maximum comfort in any weather.
- Capacity: Accommodates large groups up to 32+ guests.
- Key Features: Full 360-degree viewing decks, comfortable seating, climate control, Bluetooth sound system, onboard restroom, and large coolers for your BYOB refreshments.
- Ideal For: Corporate outings, bachelorette parties, family reunions, live music cruises, and special event views like the 4th of July fireworks.
2. Shannon Brendan (Intimate Luxury Powerboat Charters)
The Shannon Brendan is a refined 32-foot flybridge powerboat operated by Chesapeake Nautical Cruises. It offers an exclusive, high-end private charter experience for small groups looking to explore tranquil creeks and islands in relaxed luxury.
- Capacity: Up to 6 guests (VIP Private Charter).
- Key Features: Elevated flybridge seating for panoramic views, comfortable cabin amenities, swim platform access, and smooth navigation through shallow tributaries.
- Ideal For: Romantic date nights, intimate family outings, small business meetings, and quiet anchor-and-swim trips in local coves.
Signature Annapolis Tour Boat Routes & Sightseeing Options With Our Annapolis Charter Boats
When you reserve an Annapolis charter boat with us, you aren't stuck on a generic route. We tailor our cruises around four signature water routes depending on your vessel choice and preferred experience:
Please Note: All cruise routes, itineraries, and destinations are subject to change at the captain's discretion based on weather conditions, tidal shifts, Coast Guard advisories, river traffic, or safety considerations.
1. Scenic Severn River & Naval Academy Circuit
- Vessels: Island Princess & Shannon Brendan
- What You’ll See: Depart from Back Creek and cruise along the historic seawalls bordering the U.S. Naval Academy (USNA). You'll get clear views of Bancroft Hall and the iconic Naval Academy Chapel dome. As we move further up the Severn River, you'll pass under the sweeping Naval Academy Bridge and cruise along protected shorelines rich with native wildlife, including nesting ospreys, great blue herons, and bald eagles.
2. Annapolis Harbor, Ego Alley & Spa Creek Loop
- Vessels: Island Princess & Shannon Brendan
- What You’ll See: Perfect for taking in the city's charm, this route winds through the historic downtown waterfront. We navigate right through Ego Alley and City Dock, giving you front-row views of the bustling harbor and the Maryland State House dome towering above the trees. We then loop through picturesque Spa Creek, cruising past historic waterfront estates and Eastport marinas.
3. South River Creeks & Rhode River Islands Escape
- Vessel: Shannon Brendan
- What You’ll See: For those seeking peace away from harbor traffic, this route explores the tranquil tributaries southwest of Annapolis. Cruise deep into Harness Creek along Quiet Waters Park, or anchor off the secluded islands of the Rhode River for a swimming and lounge break.
