Windrush Adventures

Frequently Asked Questions

Please reach us at sailingrocksteady@gmail.com if you cannot find an answer to your question.

What is Sailing Rocksteady?

Sailing Rocksteady offers private and semi-private day charters aboard our beautiful sailing vessel, perfect for sunset cruises, celebrations, or simply a relaxing day on the water.

How long are the charters?

Charters typically run between 3-5 hours, longer if you wish. We offer customizable experiences for you and your guest.

Where do we depart from?

Our hailing port is Westport, MA, and we depart from F.L. Tripps Marina. You will have to take a water taxi to and from Rocksteady. The cost of your charter will cover the fee for the water taxi.

What should I bring?

We recommend sunscreen, sunglasses, a hat, light layers (it can get breezy), a reusable water bottle.

What should I wear?

Casual, comfortable clothing and non-marking shoes are best. A light jacket or sweatshirt is recommended to bring with you.

Can we bring our own food and drinks?

You're welcome to bring your beverages (including alcohol), soft drinks, and water. We offer charcuterie boards and lunch options with advance notice. Options are discussed before your charter and catered to your liking.

Is there a bathroom on board?

Yes, there is a clean and private marine toilet available for guest use.

Will we be sailing or motoring?

Our goal is to sail as much as possible, but sometimes we may motor depending on wind and weather conditions.

Weather and cancellations! What if it rains?

We sail rain or shine, but in the event of severe weather or unsafe conditions, we may reschedule or offer you a full refund. We will monitor the weather leading up to your charter.

What is your cancellation policy?

Cancellations made 72 hours in advance receive a full refund. Within 72 hours, we offer rescheduling, a credit towards a future sail, or 50% refund.

Are children allowed?

Yes! Children are welcome, but must be supervised by an adult at all times. Children under 13 must have a Type 1 life vest on at all times. Children under 13 are not allowed to roam the decks.

Can I book for a special occassion?

Absolutely! We love hosting birthdays, anniversaries, proposals, and more. Let us know what you're celebrating, and we'll help make it memorable.

Is gratuity included in pricing?

No, we do not include gratuity in our pricing.

What forms of payment do we accept?

We accept cash, Venmo, and Zelle.

What payment is required to book?

We require a 50% deposit upon booking your charter and the remainder at the start of your charter.

Contact Us

Are you ready to go sailing?

If you are interested in booking a charter on Sailing Rocksteady, please contact us with the number of guests (six max) and preferred date and time. We will then review the weather forecast details and be in touch!

All trips are subject to change due to weather.

F L Tripp & Sons Inc, Cherry and Webb Lane, Westport Point, MA, USA

Set Sail for an Adventure!

Set Sail for an Adventure!

Sailing Rocksteady

Our Passion

time on the water

Price List

Sailing + Good Eats!

Day of sailing

Include lunch

See What Our Guests Are Saying!

FAQ's

Frequently Asked Questions

Contact Us

Get in Touch!

Are you ready to go sailing?

All trips are subject to change due to weather.

book at stay at the elinor house

The Elinor House

Set Sail for an Adventure!

Set Sail for an Adventure!

Sailing Rocksteady

Our Passion

time on the water

Price List

Sailing + Good Eats!

Day of sailing

Include lunch

See What Our Guests Are Saying!

Connect With Us on social!

FAQ's

Frequently Asked Questions

Contact Us

Get in Touch!

Are you ready to go sailing?

All trips are subject to change due to weather.

book at stay at the elinor house

The Elinor House

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