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Experience Our Personalized Chesapeake Bay Sailing Charters

A fantastic opportunity to bolster your sailing experience!

Try Before You Buy


Starts @ $1,400

A Great Way to Relax!

Full Day Charter

$1,000


Anchor out for one or more evenings or visit a town

The

Sailing Channel Experience

Sailing Vacation Charter

Starts @ $1,400


The Type Trips Ohana Can Charter.

  • Experience a breathtaking anniversary celebration aboard Ohana on the Chesapeake Bay. Toast your love amidst stunning sunsets, gentle breezes, and panoramic views. Indulge in a romantic voyage, creating unforgettable memories surrounded by the beauty of the open water.

  • Indulge in a sophisticated bachelorette soirée aboard Ohana, steering clear of bachelor party frenzy. Delight in a serene evening on the water with fine wine, champagne, and delectable finger foods. This elegant affair offers a peaceful escape, creating cherished moments for the ladies amidst tranquil waters, fostering relaxation and a sense of refined celebration in a serene and picturesque setting.

  • Opt for an unforgettable overnight stay aboard Ohana—an affordable alternative to hotels, offering both accommodation and an enriching experience. Enjoy the tranquility of sailing coupled with a night's stay at a cost-effective rate. Embrace the adventure of daytime sailing activities, creating a unique and memorable getaway while avoiding the expenses of traditional lodging, providing both lodging and entertainment in one remarkable package.

  • Celebrate a birthday aboard a splendid sailing catamaran on the Chesapeake Bay. Enjoy a day of joy and adventure, surrounded by scenic vistas, salty breezes, and the thrill of sailing. Make unforgettable memories with friends and family amidst the beauty of this picturesque nautical setting.

  • Join us aboard Ohana for the annual Blue Angels flyover in Annapolis! Experience the spectacular show from the comfort of serene waters. Enjoy breathtaking views, camaraderie, and an unparalleled vantage point. Share this thrilling event with friends and family in an unforgettable nautical experience.

  • It’s always hard to find a new and unique venue for your management team. Ohana has ability to have a 50" monitor in the cockpit to do presentations…before everyone gets to relax out on the deck and network/build a team.

  • Groups of 4 or less. Pick crabs while anchored out on the water, jump in for a swim while you pick.

  • Gather for an intimate family reunion on Ohana, amidst the tranquil waters. Share cherished moments, bask in scenic views, and create lasting memories. With ample space and a serene ambiance, it's the perfect setting to bond, reconnect, and celebrate togetherness in an idyllic seafaring escape.

  • Commend your graduate's success with a memorable party on Ohana. Celebrate their achievements on serene waters, surrounded by elegance and joy. Create lasting memories in a unique setting, honoring their hard work and marking this milestone in style.

  • Invite your cherished parent to an exclusive celebration aboard Ohana for Mother's or Father's Day. Escape the ordinary and offer a unique experience on tranquil waters. Embrace luxury, stunning vistas, and attentive service. Encourage relaxation and joy in a serene setting, allowing them to unwind, celebrate, and create enduring memories on a special day away from the usual confines of home.

  • Midshipmen, share the Annapolis essence with your parents aboard Ohana for a unique Naval Academy Pre-Party/After-Party event! Experience authentic Annapolis living on serene waters, offering breathtaking views and genuine city vibes. Treat your parents to a memorable taste of Annapolis culture, creating lasting memories and showcasing the city's beauty from an unforgettable perspective.

  • Experience pure romance with Ohana's sailing package. Set sail on the tranquil waters, enveloped in luxury and serenity. Enjoy breathtaking sunsets, private moments, and attentive service, creating an idyllic ambiance for love to flourish—a perfect blend of intimacy and elegance, fostering cherished memories on the open sea.

  • Watched a few sailing channels on YouTube and now thinking to try this lifestyle?. What better way to try it out the do an overnight adventure or a week long trip.

  • Craft intimate, picturesque weddings or proposals aboard Ohana. Sail into a lifetime of love amidst stunning waters, creating magical moments. With its serene ambiance and breathtaking views, Ohana provides the perfect setting for unforgettable vows or a romantic proposal, ensuring cherished memories on the open seas

  • Embark on a sophisticated wine tasting journey aboard Ohana, curated by Mrs. Laurie. Delight in her expertise as she guides through exquisite selections, perfectly complemented by her expertly paired hors d'oeuvres. Enjoy this elegant experience amidst serene waters, savoring delightful flavors and fostering a deeper appreciation for wine, creating unforgettable moments in a picturesque setting.

  • Join us for a unique yoga experience on Ohana! Bring your yoga class to the serene waters in the tranquil early morning. Enjoy a peaceful practice on flat waters, surrounded by serenity and the beauty of the sea. Elevate your yoga routine with us for a special and rejuvenating session.

  • Come aboard Ohana for a spectacular 4th of July celebration in Annapolis! Watch fireworks dazzle over the water from the best seats. Enjoy a festive atmosphere, breathtaking views, and the company of friends. Experience an unforgettable Independence Day on serene waters with us!

Captain Dave’s Boat Delivery

Hiring a professional boat captain to deliver or relocate your personal yacht offers a range of benefits and solutions for various scenarios in the boating world.