Couple’s Getaway

Romantic Cruise Getaway For Couples

Cruise with us and enjoy a Full- or Half-Day private and all-inclusive romantic getaway on the Chesapeake Bay!

You'll enjoy an exciting tour of the South River aboard either 43' sailboat Therapy or 34' powerboat Irie Vibes and into the Chesapeake Bay by the Thomas Point Lighthouse while you enjoy our delicious lightfare food and drinks. We'll anchor in a tributary of the South River where you can relax in comfort to enjoy each other's company, or choose a more active time together with out water sport fun toys. Endless entertainment. You also have the option of ordering our delectable meals or sleeping overnight. Your Island Chill sales agent will help you choose the perfect accompaniment for you both.


♦  Captain & Crew  ♦  Watersports 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.

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Sail-A-Brate With Us!


Optional Gourmet Cuisine 

Succulent appetizers-Buffet meals

Sunset-Full Moon Cruise

Daily Sunset - 5:30-8:30p

Add Massage - Call for Pricing


Special Events - Call for Pricing

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

Overnight Boat & Breakfast

Truly Romantic...

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.

Sailboat Charters

Exciting cruiser-Take the helm

Power Charters



'After 15-years of marriage, we got away from the kids and enjoyed each others company. That simple. That lovely. Must do Boat-and-Breakfast next year. Thanks!'  Carrie.  Read reviews


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