Private Sunset Cruise on Chesapeake Bay with Snacks and Drinks

Imagine gliding across the calm waters of Chesapeake Bay as the sun begins to dip, casting a warm glow over the shimmering surface. For a truly personalized experience, the Private Sunset Cruise offers an intimate voyage designed for up to six guests, making it perfect for a romantic evening, a family outing, or close friends wanting to celebrate together. Priced at $705 per group, this 2.5-hour adventure includes complimentary sparkling cider, light snacks, and refreshing water, creating a laid-back, luxurious atmosphere.

If you’re someone who loves stunning vistas and enjoys a more private, relaxed setting rather than crowded tours, this cruise might just be your ideal way to wind down the day. We particularly appreciate the personalized nature of the experience, allowing time to enjoy the scenery without the hustle and bustle of larger groups. Plus, the chance to spot dolphins and learn about the local Twin Beaches adds a touch of local flavor and wildlife excitement.

One thing to keep in mind is that the tour operates weather-dependent—if the forecast isn’t cooperating, you might need to reschedule. Also, since food isn’t included beyond snacks you bring yourself, those with specific culinary cravings might want to plan ahead.

This experience suits travelers who enjoy quiet, scenic moments, appreciate customized experiences, and are comfortable with a moderate price point for a private outing. If you’re traveling with loved ones looking for a memorable evening on the water, this cruise checks many boxes.

Key Points

• Exclusive Privacy: The entire boat is reserved for your group, making for a relaxed, intimate experience.
• Stunning Views: Enjoy the sunset over Chesapeake Bay, with ample opportunities for photo-taking and wildlife spotting.
• Educational Stops: Learn about Chesapeake Bay, the Twin Beaches, and scenic landmarks like the Cliffs of Calvert.
• Wildlife Sightings: Keep an eye out for dolphins and local birdlife, which can add excitement to your cruise.
• Flexible Snacks: Bring your own food or order at your own expense, though light snacks and drinks are provided.
• Weather Flexibility: Cancellations due to poor weather are fully refundable or can be rescheduled, adding peace of mind.

The Experience in Detail

Setting off from Chesapeake Beach

Your adventure begins at the Chesapeake Windsail Cruises dock at 4160 Mears Avenue, where you’ll meet your captain. The small, friendly dock feels inviting, and the private nature of the cruise means you won’t be jostling with strangers—just your group and the calming sound of water. The boat itself is equipped with a restroom, so you won’t have to worry about comfort during the cruise.

The Itinerary: A Relaxed, Scenic Journey

The cruise’s main highlight is, of course, the sunset over Chesapeake Bay. As the boat gently glides along, you’ll see the Twin Beaches (Chesapeake Beach and North Beach) from a unique vantage point—this is your chance to appreciate their charm away from the hustle of land-based visits. The guide (if you’re lucky, it’s a friendly crew member who’s passionate about local history) will share intriguing facts about the area, adding depth to your experience.

One of the stops involves discussing the Cliffs of Calvert, a natural formation that adds to the area’s scenic diversity. As the boat moves, you might also spot local wildlife—herons, egrets, and if luck is on your side, a pod of dolphins playing nearby. The guides often mention seeing dolphins, and many guests have noted the thrill of spotting these intelligent creatures in their natural habitat.

Scenic Highlights and Wildlife

The beauty of the cruise is that it’s not overly structured, allowing you to simply enjoy the panoramic views. The sunset’s colors reflect beautifully on the water, creating picture-perfect moments. The calm and quiet of the bay enhances the experience, letting you feel fully immersed in nature.

Guests commonly appreciate the informative narration about Chesapeake Bay’s ecosystem and history, which enriches the visual feast. This stops just short of being a full educational tour but offers enough context to deepen your appreciation for the region.

Food and Drinks

Included are sparkling cider, light snacks, and water. You’re welcome to bring along your own snacks or order from the menu at your expense—this flexibility allows you to tailor the experience to your tastes. Imagine sipping cider as the sky turns hues of pink and orange, a moment of quiet celebration or romantic connection.

Duration and Comfort

The 2.5-hour cruise is a perfect length—long enough to unwind and enjoy the scenery without feeling rushed. The boat’s limited capacity (up to 6 guests) ensures a comfortable, uncrowded environment. The relaxed pace makes it ideal for those who prefer a more personal, less hurried experience.

Practical Considerations

Because the tour is weather-dependent, it’s wise to check the forecast beforehand and be flexible with your plans. Cancellation due to weather is fully refundable or can be rescheduled, which adds a layer of security for your investment.

You should also note that food isn’t included beyond snacks, so if you’re coming with specific dietary needs or preferences, plan accordingly. The meeting point is accessible nearby public transportation, making it easy to reach without a car.

Who Will Love This Tour?

This cruise is best suited for travelers seeking a peaceful, scenic, and private experience on Chesapeake Bay. It’s ideal for couples celebrating a special occasion, small families wanting a memorable outing, or friends wanting an authentic, personalized water adventure. The emphasis on scenic beauty, wildlife, and flexibility makes it particularly appealing to those who appreciate nature and quiet reflection.

If you’re someone who enjoys luxury with a personal touch—and you’re willing to pay a bit extra for exclusivity—you’ll find this cruise well worth the price. On the other hand, if you’re looking for a fast-paced tour or a large-group experience, this may not be the best fit.

The Sum Up

The Private Sunset Cruise on Chesapeake Bay provides a special way to unwind at the end of the day, with the water, sky, and wildlife forming a perfect backdrop. The personalized setting makes it a flexible, intimate experience that feels like a gift to yourself. You’ll love the stunning views, the opportunity to spot dolphins, and the comfort of having your own space to relax and chat.

While the price might seem high, the focus on quality, privacy, and scenic beauty offers good value for a memorable, stress-free evening. It’s a fantastic choice for those wanting a gentle, authentic slice of Chesapeake Bay life—away from busy tourist spots but close enough to enjoy local sights and wildlife.

If you’re after a relaxed, scenic outing that leaves you with beautiful memories and maybe some great photos, this cruise is definitely worth considering. Just remember to check the weather, bring your favorite snacks, and prepare for a peaceful voyage into the sunset.

FAQ

Is this tour private?
Yes, this is a completely private experience for your group of up to 6 people.

How long does the cruise last?
The cruise runs for approximately 2 hours and 30 minutes, giving you plenty of time to relax and enjoy the scenery.

What’s included in the price?
You’ll receive light snacks, sparkling cider, and water. The restroom is also on board for comfort.

Can I bring my own food?
Absolutely. You’re welcome to bring your own snacks or order food separately at your expense.

What if the weather is bad?
If the weather isn’t cooperating, the tour can be canceled for a full refund or rescheduled. The policy covers cancellations due to poor weather.

Where do we meet?
The meeting point is Chesapeake Windsail Cruises, 4160 Mears Avenue, Dock X, Slip 15. It’s accessible by public transportation.

Is there a minimum age or special requirements?
Most travelers can participate, and no specific age restrictions are noted. Just ensure everyone is comfortable on a boat for the duration.

What kind of wildlife might we see?
Dolphins are a possibility, along with local bird species such as herons and egrets.

Enjoy your trip into Chesapeake Bay’s sunset—an experience that’s as peaceful and beautiful as it is private and personal.