Imagine gliding smoothly across the calm waters of Chesapeake Bay aboard a 42-foot sailing yacht named Eternal Hope. For about 2 hours and 30 minutes, you’ll be out on the water with a small group—no more than six people—so it’s an experience that feels both personal and relaxed. The tour departs from Chesapeake Beach, Maryland, with prices at $102 per person. Whether you’re celebrating a special occasion or simply craving a quiet escape, this cruise offers a chance to slow down, enjoy nature, and see the bay from a different perspective.
What makes this tour stand out? First, the small-group size ensures plenty of space to breathe and chat with the crew, making it ideal for those who dislike the crowded feeling of larger excursions. Second, the chance to spot wildlife like dolphins and ospreys adds an exciting element that appeals to nature lovers and families alike. On the flip side, a consideration might be that the tour requires moderate physical fitness—you’ll be handling some sailing and standing on the boat, so if you’re less mobile, it’s worth noting.
This cruise suits travelers who value authentic, relaxed experiences over scripted tours. If you enjoy picturesque views, learning about local habitat and wildlife, and having a crew that genuinely cares, you’ll probably find this outing a highlight of your Chesapeake Bay visit.
Key Points

- Small-group intimacy provides a personalized experience on the water.
- Wildlife sightings like dolphins and ospreys boost the excitement and authenticity.
- Knowledgeable crew members enhance the experience with insights about the bay’s environment and history.
- Flexible start times make planning easier for your day.
- Weather-dependent nature means cancellations for poor conditions are possible, but full refunds or rescheduling are offered.
- Value for money given the personalized service and wildlife encounters.
What to Expect on This Chesapeake Bay Sailing Tour

This tour is designed to be a peaceful, scenic escape. The Eternal Hope, a 42-foot sailing yacht, provides a stable platform for enjoying the water. Once you meet your captain and crew at 4160 Mears Ave, you’ll quickly get aboard and set sail into the bay, heading toward sights like the Cliffs of Calvert—a striking shoreline feature. As you cruise, if the wind favors it, you might sail near the opposite side of the bay, which offers a different view and experience.
Planning more time in Washington DC? We've covered other experiences worth considering.
The Itinerary in Detail
The tour’s core attraction is heading out into the Chesapeake Bay, which offers a variety of sights. The Cliffs of Calvert are a highlight—imposing yet scenic, they mark a significant part of the shoreline. The voyage’s real charm is the opportunity to relax and take in the landscape from the water, which is quite different from land-based sightseeing.
Wildlife is a recurring theme with this cruise. Several reviews mention spotting dolphins and ospreys, which are common but exciting sightings. One guest mentioned seeing stingrays, fish, and even nettles, indicating the bay’s vibrant ecosystem. You’ll also cruise through a shipping channel, where large ships occasionally pass by—an impressive reminder of the bay’s role in commerce.
The Experience
Expect to enjoy soothing sea breezes and the gentle sway of the yacht. Some guests have said they loved “taking the wheel,” which adds an interactive element, making the trip more memorable. The crew, often praised for their attentiveness, will share insights about the bay’s natural environment and history, making this more than just a boat ride.
Practical Details
The meeting point is straightforward, and the tour operates with a mobile ticket for convenience. The cruise is capped at six travelers, ensuring a quiet, uncrowded environment. The price of $102 is quite competitive for an experience that combines scenic beauty, wildlife, and expert guidance in a personal setting.
Authentic Insights from Reviewers

Guests consistently highlight the knowledgeable crew and their efforts to ensure safety and comfort. One reviewer remarked, “Very attentive and safety was their first priority!” which reassures anyone worried about the safety of small boat excursions.
Many reviews emphasize the relaxing atmosphere and beautiful weather making the day perfect. A guest celebrating a birthday noted, “Great weather and a good sailing breeze,” adding that the crew was friendly and accommodating. Others enjoyed the chance to take the wheel themselves, making the outing both fun and engaging.
A common theme is the intimate, personalized feeling. With such small groups, you’re not just another passenger—you’re part of a relaxed, friendly crew who genuinely seem to love sharing Chesapeake Bay’s beauty.
- Arlington Cementary & Guard Ceremony with Iowa Jima Memorial
- Arlington National Cemetery: Guided Walking Tour
- African American Tour Of Annapolis From Washington DC
- Bike Tour: Capitol Hill, Lincoln Memorial, National Mall
- 2 For 1! DC Highlights & Arlington Cemetery Tour Bundle
- Washington DC: African American History Museum Private Tour
A Few Considerations
While most reviews praise the experience, one reviewer mentioned a booking mix-up and a slight delay. It’s important to call 24 hours in advance to confirm your reservation and ensure the minimum number of four guests is met. Weather can also impact operations; cancellations are fully refunded or rescheduled if the weather turns poor.
Who Is This Tour Best For?
If you appreciate small, personal outings and enjoy watching wildlife in a peaceful setting, this cruise is a natural choice. It’s ideal for nature lovers, couples celebrating special days, or families willing to handle some light sailing. Those seeking a more active or adventure-packed experience might find this too laid-back, but if your goal is to relax and unwind on the water, it’s perfect. It also suits travelers who value knowledgeable guides and want a real feel for Chesapeake Bay’s natural habitat.
The Sum Up

For anyone looking to escape the hustle and enjoy the serenity of Chesapeake Bay, this small-group sailing tour offers authentic, scenic, and wildlife-rich experiences. The personalized attention from the crew, combined with the chance to see dolphins and ospreys, makes it a memorable outing. It’s a great value for its intimate setting and the opportunity to learn about the local environment while enjoying smooth sailing.
This tour will delight nature enthusiasts and those who simply want a peaceful, scenic cruise with a touch of adventure. The flexible start times and small group size mean you can tailor your experience and truly savor the bay’s beauty. Whether celebrating a special occasion or just wanting a quiet day on the water, it’s a worthwhile choice for making genuine memories.
FAQs

How long is the cruise?
The tour lasts approximately 2 hours and 30 minutes, offering plenty of time to relax, take in the views, and enjoy the surroundings.
What is the group size?
This is a small-group experience capped at six guests, ensuring a personal, less crowded outing.
Do I need to call ahead?
Yes, it’s recommended to call 24 hours before your scheduled cruise to confirm that the minimum of four passengers has been met.
Are there any physical requirements?
The tour suggests a moderate physical fitness level. You should be comfortable standing and possibly handling some sailing tasks.
What should I wear?
Soft-bottom shoes are required, and no black-soled shoes are allowed. Dress comfortably for the weather, and consider bringing a jacket if it’s breezy.
What happens if the weather is bad?
Tours are weather-dependent. If weather conditions are poor, your cruise may be canceled, but you’ll be offered a rescheduled date or a full refund.
Embark on this peaceful, wildlife-filled sailing adventure and see Chesapeake Bay from a fresh perspective. It’s a meaningful way to connect with nature, learn about local habitat, and enjoy the gentle rhythm of the water.
More Tour Reviews in Washington DC
- Small-Group History Tour Pub Crawl of Washington, D.C.
- Arlington National Cemetery Guided Morning Walking Tour
- Family Friendly Smithsonian Air and Space Museum Private Tour
- Washington: VIP Private Tour of the U.S. Capitol & Library
- e-Scavenger hunt Washington: Explore the city at your own pace
- Washington DC: Grand Sightseeing Tour
More Washington DC experiences we've covered
- Small-Group History Tour Pub Crawl of Washington, D.C.
- Arlington National Cemetery Guided Morning Walking Tour
- Family Friendly Smithsonian Air and Space Museum Private Tour
- Washington: VIP Private Tour of the U.S. Capitol & Library
- e-Scavenger hunt Washington: Explore the city at your own pace
- Washington DC: Grand Sightseeing Tour
- U Street’s Jazzed Up Cocktail Tour
- Washington DC New York City Private Intercity Transfer JFK, LGA
- Sunset Cruise (Private) aboard Geronimo in DC – Reflections DC
- Private Departure to Ronald Reagan Airport DCA
- Washington DC:Sightseeing & Mount Vernon Admission Admission
- US Capitol visit Walking tour & Morning Tour Plus Arlington Tour
