On The Wind Sailing.

On The Wind Sailing. welcome to On The Wind Sailing! Offering the finest private sailing charter experience in midcoast maine.

Formerly the highly regarded Calendar Islands Sailing co. Step aboard with us and experience sailing at its finest. We offer the finest, private charter sailing experience in Midcoast maine! Home ported out of Rockland Maine we also Offer pickup in rockport, Camden, as well as Vinalhaven, Northhaven and islesboro.

It’s wedding season! What does your perfect boat wedding look like?
06/07/2022

It’s wedding season! What does your perfect boat wedding look like?

to when came to visit. #
04/28/2022

to when came to visit.

#

Sometimes the winds are brisk and the sailing is spirited. Other times the winds are light and we quietly ghost among th...
04/03/2022

Sometimes the winds are brisk and the sailing is spirited. Other times the winds are light and we quietly ghost among the islands. What kind of sailing do you prefer?

Bookings are now open! Call us to book! 207-318-3025

04/01/2022

We are still looking for a full time deckhand for the summer sailing season beginning mid may and ending in early October. We operate a 60ft sailing yacht out of rockland running mostly day trips. This is fb way to spend tyr beautiful maine summer outdoors and on the water. We are looking for someone who has at least some basic sailing experience and good people skills are a must since we are a passenger vessel. please note that this is not a live aboard position so candidates should live somewhat nearby to rockland. Also please note that you must be able to pass a pre employment drug screen and will be enrolled in a random testing program for the duration of the sailing season.

Grab friend and let’s go sailing. 📸:
03/31/2022

Grab friend and let’s go sailing.
📸:

Sunsets on the water. Nothing finer. Step aboard and experience sailing at its finest.
03/02/2022

Sunsets on the water. Nothing finer. Step aboard and experience sailing at its finest.

We’ve been getting some questions about if we can pick you up guests in Camden. Fortunately the answer to those question...
02/25/2022

We’ve been getting some questions about if we can pick you up guests in Camden. Fortunately the answer to those questions is: YES! There are are 2 caveats however.
1. Charters from Camden have a minimum length of 4 hours.
2. Pickup and drop-offs in Camden will be from the Camden harbor courtesy launch, use of the launch of common for yachts of all sizes in Camden harbor but we like to make our guests aware that pickup and drop won’t be from a dock. we look forward to sailing with you!


Want to take the helm? Bookings are open now for our 2022 sailing season!
02/24/2022

Want to take the helm? Bookings are open now for our 2022 sailing season!

It may be snowing today but personally, we’re daydreaming about watching the sunset on warm summer evenings. ...
01/29/2022

It may be snowing today but personally, we’re daydreaming about watching the sunset on warm summer evenings.

Address

50 Tilson Avenue
Rockland, ME
04841

Opening Hours

Monday 9am - 8pm
Tuesday 9am - 8pm
Wednesday 9am - 8pm
Thursday 9am - 8pm
Friday 9am - 8pm
Saturday 9am - 8pm
Sunday 9am - 8pm

Telephone

(207) 318-3025

Website

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