Friends

Exclusive & All About You

Cruise with us and enjoy a private- all-inclusive getaway on the Chesapeake Bay. Our captain and crew are fun, entertaining and at your service! So, sit back and enjoy delicious light-fare meal, spectacular views and water fun activities.

Cruise with us and enjoy non-stop entertainment on your personalized yacht charter experience aboard our Therapy  43' sailboat or  Irie Vibes 34' powerboat. You also have the option of trying our delectable meals from our catered menu and sleeping aboard overnight. Your Island Chill sales agent will help you choose the perfect accompaniment for you and your friends.

Charter Inclusive:

♦ Captain & Crew  ♦ Watersport Equipment  ♦ All Fuel  ♦ Snacks & Beverages view menu

Combine With: 

Special Offer!

Enjoy 10% OFF Full day cruises on any of our boats. Enter CHILL19 at booking.

Testimonials 

'We had a blast - cruising - partying - anchoring - partying - swam - partied. Why did we have to go home...!' Read reviews

Sail-A-Brate With Us!

Birthday/Anniversary/Graduation

Gourmet Cuisine (optional) 

Succulent appetizers-Buffet meals

birthday bachelor anniversaries celebration Annapolis, Washington DC, Baltimore

Sunset-Full Moon Cruise

Daily Sunset - 5:30-8:30p

Overnight Boat & Breakfast

Sleep On-Deck or Down-Below!

Special Events - Call for rates

Blue Angels, July 4th, Memorial Day, Labor Day

Adventure Sail Cruise 

Exhilarating Sailboat Experience!

Our Yachts

Your crewed charter experience begins with your desired yacht. Each gives you a safe and exhilarating ride, comfortable spaces, and modern features to give you the best onboard experience. Click charter below and enjoy cruising with us!

Therapy Sail Charter

Relaxin cruiser-Enjoy the helm!

Irie Vibes Power Charter

Modern-Safe-Fun

water tube, waterski, kayak & paddle board rental Chesapeake bay Annapolis MD

Free Watersport Equipment

Paddle boards-Noodles...

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Click on booking link below and allow our crew to take you and your guests on a private Chesapeake Bay cruise to remember!