Sail away in Class w/ Chessie on the Chesapeake Bay from Eastport!⛵️

(8 bookings)
40 ft
Boat length
Up to 6
This boat is rented with a captain
Owner’s response rate

The boat

Chessie is currently in Eastport... close to Annapolis & the Chesapeake Bay for a Beautiful day of Sailing & Sightseeing! 🌞⛵️📸

Meticulously maintained 2017 Jeanneau Sun Odyssey 389 offering Luxury & Comfort for you and your guests!

Enjoy the quaint area of to Annapolis or explore other sites all along the Chesapeake Bay.

We will make every effort to help you create your most memorable experience! ⛵️😃📸🌅📷

We even offer sailing & racing instruction! Sailing lessons are available by a Licensed Captain. You can select specific areas you are interested in such as the basics of sailing, advanced sailing, reading the wind, racing tactics, how to fly a spinnaker, etc.

Ask us today about our many options!!

Charter price includes the use of one inflatable kayak, one inflatable paddleboard, and photos throughout your trip. Please wear comfortable white soft non-marking soled shoes.

The boat may be in various locations of Eastport, Annapolis, the Severn River and all along the Chesapeake Bay based on it's last charter. Please verify current boat location before booking charter. Chessie will be at the Eastport Yacht Center after Aug 6th.

If Bareboat chartering, please arrive 1 hour prior to scheduled departure for proper vetting and an overview of boat details and safety items. Also, please bring your driver's license with you as a picture of it will be taken per ...

Be sure to book the boat during a time period where it is back at the slip by sunset at the latest.

Additional fees collected separately:

NOTE: 'Fuel Reimbursement' bill from Boatsetter to include:

$25 fuel fee:

There will be a $25 min charge for fuel/pump-out which is collected separately prior to cruise.

Amusement tax & MD sales tax:

There is a mandatory MD sales & amusement tax of 10% for Captained charter and 11% for Bareboat charter added to the booking fee and is collected separately by boatsetter under "Fuel Reimbursement" or will be collected prior to cruise.

$200 check-in/check-out/cleaning fee (Bareboat ONLY):

Bareboat charters ONLY will incur a $200 fee and will be collected, separately, prior to arrival for cruise. There will be a $100 fee if you are unable to dock the boat at the assigned slip and it has to be moved there by the Captain.

All bareboat charters require 25 yrs or older, current captains license / ASA104 certification or equivalent and extensive sailing experience on a similar sized sailboat.

Verify the Captain's rate before booking.

Tipping your Captain and crew appropriately as you typically would in any service industry is appreciated.

*Chessie is NOT to be subleased whatsoever.*


*Pictures / videos may be taken throughout your cruise and may be shared with you, as well as may be posted on our site, the boatsetter site and other public sites for public viewing. You acknowledge & agree to this, unless otherwise stated, as well as a written request is submitted to us prior to your cruise stating that you do not accept pictures/videos taken of you and/or your guests and/or such pictures/videos shared publically prior to, during or following your cruise.

Options include:

• 3 Cabins & 1 Electric Head (Fresh water flush)

• Furling Jib & Electric Winch on coachroof

• Furling main

• WiFi on-board

• Flatscreen Smart Wi-Fi connected (Netflix, Hulu, etc.) TV in Salon

• TV soundbar

• Microwave

• Oven

• Digitally controlled refrigerator with largest freezer size available for its class

• Hot/cold shower

• Hot/cold cockpit shower for after swimming

• Swimming platform

• Saltwater wash-down for anchor

• Electric Windlass for anchor

• Auto-pilot

• AC/Heat at dock

• Solar Panel to recharge batteries

• Propane BBQ grill (optional - ask owner to install if you want to use the grill)

• Bluetooth Radio

• Handheld comms at cockpit

• Dodger & Bimini

Technical Details

LOA: 39′.6″

Beam: 12′.4″

Draft: 4′ 11″ (shoal keel)

Engine: Yanmar 29 HP

Fuel: 34 gal

Water: 53 gal

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Owned by
(3 ratings)


Bluetooth audio
Inflatable toys
Cooler / Ice chest
Air conditioning
Swim ladder
Snorkeling gear
Deck shower
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40 ft.
Sun Odyssey 389
See all


Explore optional add-ons to tailor your booking at checkout.
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Ratings & reviews

(0 rating)

Boat location

Exact location information is provided after a booking is confirmed.

Your crew

Boat owner
(3 bookings)
35+ years sailing experience, ASA101 through 104 and ASA114 certified. Raced with Round Bay Sailing Association and J World Annapolis J/24 Series for several years.
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  • Response rate: 100%
  • Avg. response time: < 12 hours

Things to know

Allowed on boat

kids under 12

  • Free cancellations until 5 days before the booking start time.
  • 50% refund for cancellations between 3-5 days before the booking start time.
  • Cancellations within 2 days of the booking start time are non-refundable.
See policy

A security deposit hold (not a charge) will be placed on your credit card 48 hours before your booking starts to cover any incidental damage that may occur during your rental. This hold is released 48 hours after the booking is complete, if no claims are made. The security deposit amount for the boat you are booking will be outlined during the check-out process.

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