Chesapeake Bay Private Cruise
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
Meeting Location
453 Deale Road
Deale, MD 20751, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
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
- 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.
Frequently Asked Questions (9)
Q: Will I get seasick on Chesapeake Bay Private Cruise?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-107044P3
Traveler Photos
Reviews
Average 5.00 out of 5 stars based on 6 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor
Additional Info
Similar Tours & Activities
Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...
$75
Ocean City Daytime Party Cruise
Sunshine, Good Vibes, and Island Beats—All Aboard! Get ready to cruise into the day aboard your custom-built party boat! This 90-minute daytime escape is all...
$53
Explore Baltimore's Inner Harbor on a captivating 45-minute narrated sightseeing cruise. This journey unveils the rich history and vibrant culture of Charm City while gliding...
$34
Mount Vernon Place: Considered the most beautiful of Baltimore neighborhoods, Mount Vernon Place was once home the more millionaire philanthropists than any other city in...
$30
Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...
$75
Sunshine, Good Vibes, and Island Beats—All Aboard! Get ready to cruise into the day aboard your custom-built party boat! This 90-minute daytime escape is all...
$53
Explore Baltimore's Inner Harbor on a captivating 45-minute narrated sightseeing cruise. This journey unveils the rich history and vibrant culture of Charm City while gliding...
$34
Mount Vernon Place: Considered the most beautiful of Baltimore neighborhoods, Mount Vernon Place was once home the more millionaire philanthropists than any other city in...
$30
Travelers Who Bought This Tour Also Bought
Baltimore's Historical Sightseeing Tour
We Start from the Baltimore Visitors Center lobby (please arrive 15 minutes before tour starts); Our Baltimore Sightseeing Tour, gives guest the opportunity to visit...
$48
Embark on a spine-chilling journey through Baltimore's shadowy streets with our captivating walking ghost tour, where history and hauntings converge. Guided by an experienced local,...
$26
Embark on this Annapolis ghost tour and step back in time as you stroll through the historic district. Your guide will share chilling tales of...
$26
Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...
$65
We Start from the Baltimore Visitors Center lobby (please arrive 15 minutes before tour starts); Our Baltimore Sightseeing Tour, gives guest the opportunity to visit...
$48
Embark on a spine-chilling journey through Baltimore's shadowy streets with our captivating walking ghost tour, where history and hauntings converge. Guided by an experienced local,...
$26
Embark on this Annapolis ghost tour and step back in time as you stroll through the historic district. Your guide will share chilling tales of...
$26
Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...
$65
Frequently Asked Questions (9)
The answers provided below were previously given in response to questions from City Sky Diving customers.
Filter by:
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- 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 (EST).
- water and snacks.
- USCG Captain and a First Mate.
- Food.
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 2025There is no minimum age for this tour, so bring your wee one along for an adventure..
Apr 2025If 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 2025Accessibility 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
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 City Sky Diving. 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 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Water and snacks
- USCG Captain and a First Mate
- Food
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
- 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.
