National Holidays

Join us for a exciting cruise on a private yacht with your loved ones, cruising the Chesapeake and Annapolis & enjoying the fireworks and different attractions with a cold beverage and delicious catered treats, the Island Chill’s professional sales staff can help you plan every detail. Depart at Londontowne Marina on either Therapy - 43' sailboat or Irie Vibes - 34' powerboat seating up to 6 guests for a cruise that you'll memorable for a lifetime!

4th of July Fireworks Display
Join us for a exciting private cruise celebrating the 4th of July. Depart at Londontowne Marina 3:00 pm for a sunset cruise on either of our sail or powerboats (see boats). Anchor in downtown Annapolis and watch up-close view of fireworks. Cruise ends at 11:00pm. BOOK Fireworks Cruise.



Memorial Day

Monday, May 30, Celebrate Memorial Day with your loved ones cruising, sailing  the South River and Chesapeake Bay. We have lots of activities for us to do on the waters. Anchor, swim BBQ, listen music and enjoy the scenery. BOOK Memorial Day Cruise.


Labor Day

Monday, September 30, Celebrate Memorial Day with your loved ones cruising and sailing  along the South River, Chesapeake Bay & see the beautiful wild-life refuges. There are lots of activities to do on the water; swim, visit secluded creeks, anchor, BBQ, listen music and enjoy the scenery!


Watch The Blue Angels 

Wednesday, May 22 & 24th

The Blue Angels return to the skies over Annapolis in a spectacular and breath-taking flyby. Anchor in the Severn River right by the U.S. Naval Academy to watch the amazing Blue Angels perform during Commissioning Week on a private cruise experience. Learn more

Specifically for this cruise:

If the captain cancels the cruise due to unsafe conditions, a refund will be issued for the cost of the sail but not the catering, the box lunch will be available for pick up.

4th of July fireworks are subject to change. Please ask us about our special cancellation and refund policy for these charter packages.


AYE MATE! If you would like to celebrate your  special day cruising the Chesapeake Bay and South River, feel free to send us a message. We would love to celebrate with you! Send message...

International Holidays 

  • Mother's Day:
  • Father's Day: June 17th
  • Columbus Day: October 8th

International Holidays 

  • Jamaica Day: July 6th
  • Vincy Mas: July 7th
  • Trinidad Day: August 31st
  • Antiga Carnival: July 28