Annapolis is a city built for boat lovers. Its scenic harbor, historic waterfront, and proximity to Chesapeake Bay make it an ideal place to explore by water. Whether you’re after a quick glimpse of the Naval Academy, a relaxing afternoon on an electric boat, or a full-day trip to St. Michaels, Annapolis offers options for all tastes and budgets. We especially like the Annapolis Harbor and U.S. Naval Academy Cruise, which combines history, scenic views, and a friendly recorded narration—all in just 40 minutes. It’s a great way to get your bearings and see the city’s iconic sights without breaking the bank.
If you’re craving a more immersive experience, the Round Trip Cruise to St. Michaels takes you across Chesapeake Bay to explore a charming Eastern Shore village. Or, if a private and tranquil outing appeals, the Electric Boat Rental – Duffy Sun Cruiser offers a peaceful glide through the waterways, perfect for a sunset or special celebration. Each of these options showcases different ways to enjoy the water, making Annapolis a true water lover’s destination.
1. Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
This 40-minute cruise is a perfect introduction to Annapolis and its famous Naval Academy. For just $30 per person, you’ll enjoy a narrated journey around the harbor, with views of historic buildings, elegant sailboats, and the lively waterfront. The recorded narration provides interesting insights into the history of the Naval Academy and the city itself, making the experience both relaxing and educational.
What makes this cruise stand out is its combination of affordability, brevity, and content. You won’t spend hours on the water, but you’ll still get a solid sense of what makes Annapolis special. The boat’s route focuses on the U.S. Naval Academy, allowing you to snap photos of the iconic 270-foot sails and the historic campus. The commentary shares fun facts like the Academy’s founding in 1845 and its role in shaping naval officers. Reviewers often mention how this tour offers “a quick but comprehensive look at Annapolis,” especially when time or budget are limited.
Bottom Line: Ideal for first-timers or those with limited time, this cruise offers a scenic, informative taste of Annapolis Harbor without the hefty price tag.
2. Annapolis: Round Trip Cruise to St. Michaels
Spanning approximately 7.5 hours, this full-day cruise takes you across Chesapeake Bay to the historic town of St. Michaels. For $157 per person, you’ll enjoy a scenic ride and ample time to explore at your own pace. The boat provides a complimentary non-alcoholic beverage during the ride, making the journey comfortable and refreshing.
Once in St. Michaels, you can wander through its charming streets, lined with boutique shops, cafes, and historic sites. A highlight is the Chesapeake Bay Maritime Museum, where you can learn about the area’s maritime heritage through engaging exhibits. The cruise itself offers stunning views of the bay, with the chance to spot waterfowl and perhaps even dolphins. Travelers often comment on the “peaceful ride across the bay” and how the town of St. Michaels is worth a full visit, not just a quick stop.
This tour is best suited for those who enjoy a full day of water and exploring a quaint town without the hassle of planning. Keep in mind, the price reflects the longer duration and the included museum visit, offering good value for those looking for a mix of scenery and cultural experience.
Bottom Line: Perfect for travelers who want a leisurely day combining scenic cruising with discovering a delightful Eastern Shore village.
3. Annapolis: Electric Boat Rental – Duffy Sun Cruiser – 10ppl
For those seeking a private, eco-friendly way to explore Annapolis waterways, this electric boat rental is a hidden gem. Costing $212 for up to 10 people, the Duffy Sun Cruiser provides 1 to 2 hours of silent cruising—perfect for a sunset, special occasion, or just a peaceful day on the water. The boat cruises at a leisurely 5 MPH, giving you plenty of time to soak in the scenery.
This electric boat is exceptionally quiet and emission-free, letting you glide past waterfront homes, marinas, and natural scenery without noise or fumes. It’s easy to operate, making it ideal for families, couples, or small groups who want control over their route. Many enjoy catching a sunset or celebrating a birthday on this vessel. Its size fits a small group comfortably, and there’s the flexibility to stop and take photos or enjoy a picnic onboard.
Guests often mention how relaxing and intimate this experience feels, especially compared to larger tour boats. It’s great for those who prefer a more personalized adventure or want to avoid crowds. One reviewer summed it up as “the most peaceful way to enjoy Annapolis’s waterways,” perfect for a memorable, quiet escape.
Bottom Line: A fantastic choice for small groups or couples wanting a private, eco-conscious water adventure, especially around sunset or special celebrations.
$212 per group up to 10
How to Choose Your Perfect Annapolis Water Experience
When deciding which boat tour suits you best, consider your interests, budget, and available time. If you’re after a quick, budget-friendly overview, go for the Harbor and Naval Academy Cruise. If you want a full day of exploration and culture, the St. Michaels cruise provides a scenic trip plus time to wander a charming town. For a personalized and quiet adventure, the Electric Boat Rental is unbeatable.
Think about how much time you want to spend on the water, your budget, and whether you’re traveling solo, as a couple, or with family. Booking early is recommended, especially for the longer cruises or private rentals, to ensure availability during peak visiting seasons. Also, consider the weather—summer months see more sailboats and vibrant waterfront life, but spring and fall offer quieter, more relaxed experiences.
Annapolis’s waterways offer a variety of ways to experience this historic city from the water. Whether you prefer a quick harbor cruise, a full-day exploration of the Chesapeake Bay and St. Michaels, or a private electric boat ride, there’s something to fit your style and schedule. For a first visit, the harbor cruise offers a great starting point. For more time and discovery, the St. Michaels trip adds a charming town and maritime museum. And for those seeking serenity and privacy, the electric boat provides a peaceful escape.
No matter which you choose, be sure to book in advance, dress appropriately for the weather, and prepare to enjoy some of the best water views Maryland has to offer. Enjoy your time on the water in Annapolis, a city where sailing isn’t just a sport—it’s a way of life.