Private Catamaran Weekday Sail

100% (1) Saint Michaels, MD 1 - 12 People 2 - 7 Hours From $1,195 Trip #11489
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

About Your Trip

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Enjoy a two-hour cruise with knowledgeable, first-class captains and a friendly crew dedicated to creating an unforgettable experience.

Out on the open water, our spacious and modern 2016 44-foot Leopard catamaran offers your choice of a public or private cruise in one of the most beautiful places to sail. Chesapeake Bay sailing is renowned for its stunning scenery and unforgettable sunsets. Your charter begins with a peaceful glide through the harbor before heading out into...

About Your Trip

Enjoy a two-hour cruise with knowledgeable, first-class captains and a friendly crew dedicated to creating an unforgettable experience.

Out on the open water, our spacious and modern 2016 44-foot Leopard catamaran offers your choice of a public or private cruise in one of the most beautiful places to sail. Chesapeake Bay sailing is renowned for its stunning scenery and unforgettable sunsets. Your charter begins with a peaceful glide through the harbor before heading out into the Miles River, where you’ll enjoy sweeping views and, if you’re lucky, wildlife sightings like osprey and bald eagles. Several years, we have even spotted dolphins!

More about the vessel:

She offers a modern, luxurious and spacious sailing experience aboard a wide and stable catamaran intended for charter guest comfort and guest entertainment. Designed for easy single handed operation, the captain operates the vessel from the helm station allowing the mate to focus most of their time on enhancing the guests experience while aboard. There is ample cushioned seating for all guests including choices between trampoline, bow pulpit seats, beanbag chairs, captains chairs, built-in shaded cushioned cockpit seating with pillows, inside salon seating, multiple tables and counters for drinks and food, and modern kitchen amenities.

She is docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland—a charming Eastern Shore town known for its incredible seafood and inviting small-town atmosphere. Whether you’re planning a day trip to St. Michaels or seeking a sailing charter on the Eastern Shore of the Chesapeake Bay, our relaxing sailboat excursions are conveniently located just 90 minutes from Philadelphia, Baltimore, and Washington, D.C., and only an hour from Annapolis.

You are welcome to participate as a working crew member or simply sit back and relax; we’re here to help you complete your Chesapeake Bay sailing experience!
Amenities

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Boat Restroom

This boat has a restroom.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 7 days before the trip.

Lunch

Lunch / light snacks are available for an additional fee.

Physicality

This trip requires an average level of physical activity.

Disability Friendly

This trip is not suited for those with disabilities.

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Pricing Matrix

2 hours 4 hours 7 hours
1 Person
$1,195.00
$2,245.00
$3,295.00
2 People
$1,195.00
$2,245.00
$3,295.00
3 People
$1,195.00
$2,245.00
$3,295.00
4 People
$1,195.00
$2,245.00
$3,295.00
5 People
$1,195.00
$2,245.00
$3,295.00
6 People
$1,195.00
$2,245.00
$3,295.00
7 People (two boats)
$2,390.00
$4,490.00
$6,590.00
8 People (two boats)
$2,390.00
$4,490.00
$6,590.00
9 People (two boats)
$2,390.00
$4,490.00
$6,590.00
10 People (two boats)
$2,390.00
$4,490.00
$6,590.00
11 People (two boats)
$2,390.00
$4,490.00
$6,590.00
12 People (two boats)
$2,390.00
$4,490.00
$6,590.00
Pay 100% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Profile photo of Captain Experiences guide Gerald

Gerald B.

Independent Guide
Laid-back
Comfortable
Quality
Ahoy from the crew! Delivering the most personalized and enjoyable boat tours on the Eastern Shore of the Chesapeake Bay is always the top priority.

The owners, GM and Laura, both grew up sailing and bring a lifetime of experience to every trip. GM has been on the water since childhood and previously taught sailing in St. Michaels, Maryland. His adventures have taken him across the Mediterranean, Mexico, Hawaii, California, the U.S. East Coast, the...

About Your Guide

Profile photo of Captain Experiences guide Gerald

Gerald B.

Independent Guide
Ahoy from the crew! Delivering the most personalized and enjoyable boat tours on the Eastern Shore of the Chesapeake Bay is always the top priority.

The owners, GM and Laura, both grew up sailing and bring a lifetime of experience to every trip. GM has been on the water since childhood and previously taught sailing in St. Michaels, Maryland. His adventures have taken him across the Mediterranean, Mexico, Hawaii, California, the U.S. East Coast, the Delaware River, the Bahamas, and throughout the Chesapeake Bay. He has held a U.S. Coast Guard captain’s license since 2014. Laura also grew up sailing on monohull sailboats with her family and now has years of experience along the East Coast and in the Bahamas. She is also a professional photographer with a passion for capturing life on the water.

GM spent several summers serving as first mate aboard a historic Chesapeake vessel, gaining valuable experience that helped shape the style of tours offered today. After several successful seasons operating on Broad Creek, the operation will move across the harbor for the 2026 season and beyond, departing from the same marina dock that was once home to that iconic vessel.

Guests can choose between two unique sailing experiences: a historic 1935 ketch rich with Chesapeake heritage or a modern 44-foot luxury catamaran. Both vessels can comfortably accommodate up to 13 guests.

One of the highlights of the fleet is a beautifully preserved Maryland-built sailboat from 1935, bringing nearly a century of maritime history back to life on the Chesapeake Bay.
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Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
Huge lobster in Bahamas
If you were cooking for all your friends what would you cook?
Fish or seafood of some sort

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
Huge lobster in Bahamas
If you were cooking for all your friends what would you cook?
Fish or seafood of some sort
What’s your favorite band?
BB King
What’s your favorite movie?
Nacho Libre
What’s your favorite sports team?
SailGP
What’s your drink of choice?
Red wine
What was your last halloween costume?
Top Gun
What do you want for Christmas this year?
Sailing in the Bahamas
How did you get started guiding?
Decided to charter our personal boat in 2018
What makes you different from other guides?
We want a relaxing experience with your guests, not a stiff tour situation.
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Start Location & Lodging Options

Saint Michaels, Maryland

About Your Boat

Boat photo for Private Catamaran Weekday Sail
1/3
Boat Type
Catamaran
Boat Manufacturer
Leopard
Boat Length
44'
Boat Restroom
Yes

About Your Boat

Boat Type
Catamaran
Boat Manufacturer
Leopard
Boat Length
44'
Boat Restroom
Yes
Additional Amenities
Our boat offers a modern, luxurious and spacious sailing experience aboard a wide and stable catamaran intended for charter guest comfort and guest entertainment. Designed for easy single handed operation, the captain operates the vessel from the helm station allowing the mate to focus most of their time on enhancing the guests experience while aboard. There is ample cushioned seating for all guests including choices between trampoline, bow pulpit seats, beanbag chairs, captains chairs, built-in shaded cushioned cockpit seating with pillows, inside salon seating, multiple tables and counters for drinks and food, and modern kitchen amenities.
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Trip Details & Amenities

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Boat Restroom

This boat has a restroom.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 7 days before the trip.

Lunch

Lunch / light snacks are available for an additional fee.

Physicality

This trip requires an average level of physical activity.

Disability Friendly

This trip is not suited for those with disabilities.

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip. Guests are welcome to bring whatever food they want; alcohol is purchased from us (no BYOB). Water is complementary, and non-alcoholic beverages are available for purchase, but if you want to bring your own non-alcoholic beverages, that is fine also.
We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).
Cancel for free up to 7 days before the trip and receive credit back to your account. Cancelling within 7 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.
In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.
We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.
Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.
Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.
After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.
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