Chesapeake Bay Sunset Sail

Unwind with a Chesapeake Bay Sunset Sail in charming Southern Maryland—an ideal way to end a warm summer day. This laid-back sailing experience offers stunning views of the twin beaches from the Western Shore, as the sky transforms into a canvas of soft pinks and golds. Whether it’s a romantic date night or a peaceful solo escape, this sail delivers quiet moments and sweeping coastal views without the crowds.

Settle in aboard Eternal Hope, where complimentary snacks and water keep things easy and relaxed. The breeze, the view, and the slow pace of the evening offer a refreshing reset—no agenda, just a beautiful sail into the sunset over Chesapeake Bay. A simple, scenic, and memorable way to cap off any visit to Southern Maryland.

Unwind with a Chesapeake Bay Sunset Sail in charming Southern Maryland—an ideal way to end a warm summer day. This laid-back sailing experience offers stunning views of the twin beaches from the Western Shore, as the sky transforms into a canvas of soft pinks and golds. Whether it’s a romantic date night or a peaceful solo escape, this sail delivers quiet moments and sweeping coastal views without the crowds.

Settle in aboard Eternal Hope, where complimentary snacks and water keep things easy and relaxed. The breeze, the view, and the slow pace of the evening offer a refreshing reset—no agenda, just a beautiful sail into the sunset over Chesapeake Bay. A simple, scenic, and memorable way to cap off any visit to Southern Maryland.

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Seasonal,
Mid-May -October,
Tuesday - Sunday 6:00pm

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Seasonal,
Mid-May -October,
Tuesday - Sunday 6:00pm

Any restrictions to participate?

Age: All age groups are welcome

Who can you accommodate for?

Children: All participants must pay to participate, children included
Individuals with disabilities: The vessel is not wheelchair accessible
Pets: Sorry, no pets allowed

What to expect on the day of the experience?

Duration: Approximately 1.5–2 hours. Tour may go slightly longer based on participant engagement throughout the sail
What’s included: Complimentary snacks and bottled water
Who will be present: A licensed captain and crew will be onboard at all times; other guests may be joining, with a maximum of 6 passengers total
Photo/video: Photos are encouraged—bring a camera or smartphone to capture the sunset
Specific rules to follow: No smoking is allowed on the vessel

How to prepare?

Weather dependency: This experience is weather-dependent and may be rescheduled in the event of inclement weather
Arrival: Plan to arrive at least 15 minutes before departure time
Parking: Free parking is available near the marina
What to wear: Dress in layers and wear flat, comfortable shoes
What to bring:
- Sunglasses, sunscreen, and a hat recommended
- Personal belongings may be brought aboard, but space is limited—small bags only
- Outside alcohol and large coolers are not allowed

Any restrictions to participate?

Age: All age groups are welcome

Who can you accommodate for?

Children: All participants must pay to participate, children included
Individuals with disabilities: The vessel is not wheelchair accessible
Pets: Sorry, no pets allowed

What to expect on the day of the experience?

Duration: Approximately 1.5–2 hours. Tour may go slightly longer based on participant engagement throughout the sail
What’s included: Complimentary snacks and bottled water
Who will be present: A licensed captain and crew will be onboard at all times; other guests may be joining, with a maximum of 6 passengers total
Photo/video: Photos are encouraged—bring a camera or smartphone to capture the sunset
Specific rules to follow: No smoking is allowed on the vessel

How to prepare?

Weather dependency: This experience is weather-dependent and may be rescheduled in the event of inclement weather
Arrival: Plan to arrive at least 15 minutes before departure time
Parking: Free parking is available near the marina
What to wear: Dress in layers and wear flat, comfortable shoes
What to bring:
- Sunglasses, sunscreen, and a hat recommended
- Personal belongings may be brought aboard, but space is limited—small bags only
- Outside alcohol and large coolers are not allowed

Unused Experience Vouchers can be returned within 15 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 7 days before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 7 days in advance means losing the value of your experience.

Unused Experience Vouchers can be returned within 15 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 7 days before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 7 days in advance means losing the value of your experience.