Romantic Charters are our specialty!  Whether it's an engagement, anniversary, or date night ... we have you covered. If you are staying at The Ocean House, Capt. Jack will pick you up in his 1913 Model T Woody. By special request additional charge of $100.

Sunset and full moon charters are the most romantic! As you step aboard either Trim Again or Encore you will hear your favorite songs playing in the background (requires sending a play list ahead of time). As we push off you will enjoy your sparkling wine and cheese. If aboard Trim Again, once we set the sails, you will go forward and enjoy the privacy and sensual experience of the water under the stem of the boat with the wind in your hair.  If aboard Encore you will enjoy the privacy of sitting in the aft seating area enjoying the open air and beautiful sights.


Watch the sun set while classic love songs or your play list  fills the air. Sunsets are stunning in Watch Hill and on the water is a once in a lifetime experience.


We like to stay out past sunset to see the sky change colors.  As we drop sail or head home the music changes to entice you and your partner to dance as the lights ashore come up the sounds of the horns, whistles and bells are heard in the background and the wake grows ever darker as we dock.