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Chesapeake Bay Private Cruise

6 Reviews 5.00 out of 5 stars Based on 6 traveler reviews collected by Cool Destinations and TripAdvisor |
Recommended by 100% of reviewers
100% of reviewers gave this experience a rating of 4 or higher.
| Maryland, USA
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from $746 per group (up to 6)

Lowest Price Guarantee
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On average, this is booked 31 (0) days in advance.
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2 hours 30 minutes (approx.)
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Instant confirmation
Offered in: English

Overview

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope, a 42 ft sailing yacht, as she glides through the waters of the Chesapeake Bay.

We are only a 42 minute drive from Washington DC, 30 minutes from Annapolis, MD and one hour from Baltimore, MD, so bring your own food or you can order food for this two and half hour cruise. The time and the boat are all yours. Complimentary snacks and water will be served.

What's Included

  • Water and snacks
  • USCG Captain and a First Mate
  • Food
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Meeting Location

Meeting point

453 Deale Road
Deale, MD 20751, USA

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

On your private cruise you can steer the boat, pull the sails or just set back and relax while your crew, the captain and first mate, sail the boat. Enjoy the wind, the sightseeing and the sounds as you sail the Chesapeake Bay aboard Eternal Hope, a 42 ft. sailing yacht. If you are lucky maybe you will see dolphins, ospreys and other amazing sights.

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • Travelers should have at least a moderate level of physical fitness
  • Infants are required to sit on an adult’s lap
  • Life jackets are available

Frequently Asked Questions

(8)

Q: Will I get seasick on Chesapeake Bay Private Cruise?

A: If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy. Read more Feb 2023

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-107044P3

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Reviews

5.00
6 reviews

Average 5.00 out of 5 stars based on 6 traveler reviews collected by Cool Destinations and partner sites such as Trustpilot, Viator, and TripAdvisor

5 stars
6
4 stars
0
3 stars
0
2 stars
0
1 star
0

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On average, this is booked 31 (0) days in advance.
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Frequently Asked Questions (8)

Activity name

The answers provided below were previously given in response to questions from Cool Destinations customers.

Filter by:

Q: Will I get seasick on Chesapeake Bay Private Cruise?
A:

If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.

Feb 2023
Q: What is the cancellation policy for the Chesapeake Bay Private Cruise?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (EDT).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • water and snacks.
  • USCG Captain and a First Mate.
The following is NOT included:
  • Food.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Chesapeake Bay Private Cruise is as follows:

  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • No Smoking
  • Travelers should have at least a moderate level of physical fitness
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chesapeake Bay Private Cruise will be included in your confirmation email from Cool Destinations. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024

What's Included

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  • Water and snacks
  • USCG Captain and a First Mate
  • Food

Additional Info

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  • Confirmation is instant and will be received at time of booking
  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • No Smoking
  • Travelers should have at least a moderate level of physical fitness
  • Infants are required to sit on an adult’s lap
  • Life jackets are available
  • Weight Limit - 250 lbs. Maximum per person.
  • Operated by a business

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For your protection and stress-free bookings, use our secure platform to pay for bookings. Chesapeake Windsail Cruises Corporation

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  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
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  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Destinations and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased tour into one or more parts sold separately.
  • Cool Destinations reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Destinations.
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Free Cancellation

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You can cancel up to 24 hours in advance of the tour for a full refund.

  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (EDT).
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

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Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

Miscellaneous

  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
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  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.