Romantic Couple’s Getaway

Special Offer!

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

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Enjoy a full or half day unforgettable and private romantic getaway on the Chesapeake Bay on either 43' sailboat Therapy or 34' powerboat Irie Vibes. We'll anchor in a tributary of the South River where you can enjoy our delicious free lightfare food and drinks, or choose a more active time together with water sport fun toys.

Cruise Inclusive:

♦ Captain & Crew  ♦ Watersports Equipment  ♦ Fuel  ♦ Snacks & Beverages view menu


Choose from any of our boats for a private 3h Sunset Cruise!

Our Other Products

Boat-and Breakfast

Comfortable Accommodations

1/2 Day, Full & Overnight

Crew the boat or Chill and Cruise

Catering Menu

Order from our delicious specialty buffet

Sail-A-Brate With Us!

Celebrate birthdays or anniversaries

Watersport Activities

For the couples that love a little adventure

Water taxi

To Annapolis' nice waterfront restaurants


Before You Book / Call...If you would like specialized package details...The friendly staff of ‘Island Chill Family’ will help you plan every detail of your next special day to make it extra special. Contact Us!