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 sailboat and powerboat private 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!'

We're the perfect venue for hot summer days, or cool Spring and Fall adventures! Chose our 43'-sailboat (Therapy), or either our 34-foot (Irie Vibes) or 20-foot (Tallawah) powerboats. You'll enjoy Chesapeake Bay cruising, sight-seeing along South River creeks or besides Rhode River islands. At anchor (powerboat; sailboat by request), enjoy swimming, aquatic toys, paddle boards and floating lily pad; call to add kayak or fishing options too (powerboat).

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 (each with add-on Decoration Package options). 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). 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 offer exciting 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 - on the Chesapeake Bay!' 

Welcome Aboard!


  • Irie Vibes34-ft Powerboat, for Up to 6-Guests
  • Therapy43-ft Sailboat, for Up to 6-Guests
  • Tallawah: 20-ft Powerboat 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)