Charter a Boat

Spend multiple days and nights on-board your private yacht, or just a few hours to watch the sunset. Bring your own snacks & drinks or have a meal delivered or catered on-board. Arrive in style at your favorite dock bar. Go for a swim or just relax and enjoy the view.

We want you to have your perfect day on the Bay, whatever that means to you. That's why we've come up with a variety of itinerary options to choose from. Have something specific in mind? Just ask!

Charter Itineraries

sailboat in sunset

Annapolis Sunset Cruise

Catch the gorgeous Chesapeake Bay sunset aboard a luxury catamaran. Perfect for a romantic evening, cocktails with friends or a way to end a day exploring Annapolis.

family hanging out on boat deck

Mid-Week “3 Hour Tour”

“Just sit right back and…” feel the wind in your hair, go for a swim or just enjoy the views. Great for office outings and happy hour hangs.

friends celebrating on a boat

Celebrate Your Special Event

Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.

woman drinking wine with dinner

Annapolis Dinner Cruise

A romantic getaway or a casual evening with friends and family. We’ll serve dinner from a downtown restaurant or have your meal catered on-board.

couple on saba 50 boat

Half Day Sail

Only have time for a shorter day on the water? No problem! Plenty of time to fit in a swim, take in amazing views or enjoy a cocktail on-board or at your favorite dock bar.

saba 50 sailing

Full Day Sail

It’s the ultimate day on the water! Spend a full 8 hours exploring the northern Chesapeake Bay aboard one of our luxury catamarans.

sleeping cabin on boat

Chesapeake Overnight Sail

Get away for a night (or 2) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.

Ready to sail with us?

Get in touch to book one of our itineraries or discuss something special for your cruise.