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Duration: 2 hours

Overview

Get out on the water with Sail the Chesapeake on a Catamaran in St. Michaels, Maryland, a relaxed sailing experience featuring open bay views, a smooth ride, and plenty of space to unwind along the Chesapeake Bay.

⛵ Cruise through St. Michaels Harbor and out onto the Miles River for a scenic Chesapeake Bay sail

🛋 Choose between shaded seating, front deck lounging, or open space to stretch out during the ride

🦅 Look out for local wildlife like osprey and bald eagles while gliding across the water

💬 Chat with the captain and crew to learn about sailing, the bay, and the surrounding area

Enjoy a laid back escape with Sail the Chesapeake on a Catamaran in St. Michaels, Maryland, a two hour sailing experience that focuses on comfort, scenery, and time on the water. The modern catamaran offers a smooth, stable ride with plenty of space to spread out, from shaded seating areas with tables to open lounging spots at the front of the boat.

The sail begins in the harbor of St. Michaels before moving onto the Miles River and into the wider Chesapeake Bay. Along the way, views shift between historic waterfront landmarks, open water, and passing boats, with the chance to spot wildlife like osprey or eagles overhead.

Enjoy a laid back escape with Sail the Chesapeake on a Catamaran in St. Michaels, Maryland, a two hour sailing experience that focuses on comfort, scenery, and time on the water. The modern catamaran offers a smooth, stable ride with plenty of space to spread out, from shaded seating areas with tables to open lounging spots at the front of the boat.

The sail begins in the harbor of St. Michaels before moving onto the Miles River and into the wider Chesapeake Bay. Along the way, views shift between historic waterfront landmarks, open water, and passing boats, with the chance to spot wildlife like osprey or eagles overhead.

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.

Year-Round,
Daily (excluding holidays)

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.

Year-Round,
Daily (excluding holidays)

Any restrictions to participate?

  • Age: All age groups are welcome.
  • Health limitations: Guests should be comfortable on the water. Those prone to motion sickness should plan accordingly.

Who can you accommodate for?

  • Children: All participants must have a valid ticket, including children. Life jackets are available in infant, toddler, and youth sizes.
  • Individuals with disabilities: Accessibility may be limited due to boarding steps and vessel layout. The catamaran is not wheelchair accessible.
  • Pets: Pets are not permitted.

What to expect on the day of the experience?

  • Duration: Approximately 2 hours.
  • What’s included:
    • A Chesapeake Bay sailing experience aboard a modern catamaran (Epiphany)
    • Complimentary bottled water
  • Who will be present: A licensed captain and experienced crew will operate the vessel. Up to 6 guests may be onboard for shared sails.
  • Spectators: No spectators are allowed; all guests must have a reservation.
  • Photo/ video: Photos and videos are encouraged.
  • Specific rules to follow: Guests must follow all crew instructions for safety. Shoes may need to be removed depending on conditions; high heels are discouraged.

How to prepare?

  • Weather dependency: The experience operates in most conditions but may be canceled for safety due to weather. If canceled, a full refund or rescheduling option will be provided.
  • Arrival: Plan to arrive 15 minutes prior to departure at the dock behind Harbour Inn & Marina, 101 N Harbor Road, St. Michaels, MD.
  • Parking: Parking is available in the Harbour Inn lot or along Harbor Road near the waterfront.
  • What to wear: Comfortable clothing with layers; it can be cooler on the water. Flat, non-slip shoes are recommended, and high heels should be avoided.
  • What to bring:
    • Light jacket or sweater
    • Sunglasses and sunscreen (apply spray sunscreen before boarding)
    • Camera or phone
  • Restrooms/ lockers/ changing rooms: A private onboard marine restroom is available; guests are encouraged to use the Harbour Inn facilities prior to boarding.

Anything else I should know before going on this experience?

  • Guests are encouraged to arrive early to explore the town of St. Michaels before departure.

Any restrictions to participate?

  • Age: All age groups are welcome.
  • Health limitations: Guests should be comfortable on the water. Those prone to motion sickness should plan accordingly.

Who can you accommodate for?

  • Children: All participants must have a valid ticket, including children. Life jackets are available in infant, toddler, and youth sizes.
  • Individuals with disabilities: Accessibility may be limited due to boarding steps and vessel layout. The catamaran is not wheelchair accessible.
  • Pets: Pets are not permitted.

What to expect on the day of the experience?

  • Duration: Approximately 2 hours.
  • What’s included:
    • A Chesapeake Bay sailing experience aboard a modern catamaran (Epiphany)
    • Complimentary bottled water
  • Who will be present: A licensed captain and experienced crew will operate the vessel. Up to 6 guests may be onboard for shared sails.
  • Spectators: No spectators are allowed; all guests must have a reservation.
  • Photo/ video: Photos and videos are encouraged.
  • Specific rules to follow: Guests must follow all crew instructions for safety. Shoes may need to be removed depending on conditions; high heels are discouraged.

How to prepare?

  • Weather dependency: The experience operates in most conditions but may be canceled for safety due to weather. If canceled, a full refund or rescheduling option will be provided.
  • Arrival: Plan to arrive 15 minutes prior to departure at the dock behind Harbour Inn & Marina, 101 N Harbor Road, St. Michaels, MD.
  • Parking: Parking is available in the Harbour Inn lot or along Harbor Road near the waterfront.
  • What to wear: Comfortable clothing with layers; it can be cooler on the water. Flat, non-slip shoes are recommended, and high heels should be avoided.
  • What to bring:
    • Light jacket or sweater
    • Sunglasses and sunscreen (apply spray sunscreen before boarding)
    • Camera or phone
  • Restrooms/ lockers/ changing rooms: A private onboard marine restroom is available; guests are encouraged to use the Harbour Inn facilities prior to boarding.

Anything else I should know before going on this experience?

  • Guests are encouraged to arrive early to explore the town of St. Michaels before departure.

Unused Experience Vouchers can be returned within 14 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 72 hours 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 72 hours in advance means losing the value of your experience.

Unused Experience Vouchers can be returned within 14 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 72 hours 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 72 hours in advance means losing the value of your experience.

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