Welcome to Island Chill Yacht Charters, 2023!

'To Bring People Together to Create Memories and Strengthen Friendships & Family Connections'

Island Chill Yacht Charters creates the 'Relaxing Excitement of the Islands' on our Chesapeake Bay private sail and powerboat cruises (up to 6-Guests per boat). We're conveniently located close to Washington D.C. & Baltimore in Edgewater, just 6 miles south of Annapolis - the 'Sailing Capital of America!'. 

Our official 'ICYC 2023 Season' will begin on Friday, April 21st; we'll cruise until Tuesday, October 31st: A full Spring - Summer - Fall itinerary! Our Booking portal will be available on January 31st, but you can always call with questions, custom requests or reservations to (410) 212-4476, or email islandchillyachtcharters@gmail.com.

We're the perfect venue for hot summer days, or cool Spring and Fall adventures! Click the links in our menu above or underlined below to see cruise details and book our Half-Day, Full-day and Sunset cruises for Families, Kids, Friends and Special Occasions – Birthdays, Anniversaries, Bachelorette Parties and Graduations (with add-on Decoration Packages - call to add). We're a private and exclusive charter company, so we're happy to customize your cruise too! We celebrate National Holidays: Memorial and Labor Day, July 4th fireworks, Father's Day, Jamaica Day, Canada Day, and honor the Blue Angels display over the Naval Academy during Commencement Week in Annapolis in May. We also have Lighthouse visit tours and Chesapeake Storyteller featured excursions (full of history, ecology and wildlife); and Family Fishing Charters. There's Full Moon rising trips, and Corporate Retreats and Rewards cruises (call to book). You'll enjoy sight-seeing and anchoring in one of the South River’s creeks or besides Rhode River islands, with swimming, aquatic toys, paddle boards and/or floating lily pad; call to add kayak or fishing options too. We also have special 2-Boat combinations for up to 12-Guests (call to book), as well as Overnight Bed & Breakfast charters (call to book). We even opportunities to Crew on Therapy on Windy-Day sailboat expeditions (call to book)! No travel hassles, no airport chaos, no traffic, no lines, no exorbitant gas prices - just the 'Relaxing Excitement of the Islands!' 

Welcome Aboard!


  • Irie Vibes34-ft Powerboat, for Up to 6-Guests
  • Therapy43-ft Sailboat, for Up to 6-Guests


  • Half-Day: Morning (2 h or 3 h)
  • Half Day: Afternoon (3 h or 4 h)
  • Sunset (2.5 h)
  • All Day (Morning - Afternoon: 7.5 h)
  • All Day (Afternoon - Sunset 7.5 h)
  • 2-Boat Parties, Up to 12-Guests (Call to Book)
  • Overnight Boat and Breakfast: 22 h (Call to Book)

Special Occasions:

  • 'Just a Fun Get Together'
  • Birthday
  • Anniversary
  • Bachelorette
  • Graduation
  • Corporate Retreats
  • 2-Boat Parties, Up to 12-Guests (Call to Book)