The Chesapeake Bay - crab country and home to over 5,000 of protected coastline at our disposal to voyage onward through America’s sailing capital. With sprawling nature along the water’s edge, there are predictable winds and protected harbors within easy reach in nearly every corner of the Bay. We sail to historic and scenic ports, enjoy the nightlight of downtown Baltimore, enjoy some of the best seaside restaurants in North America, and best of all, the Chesapeake Bay is in our own backyard!

Beginning summer 2020, Sailing Collective has put the Chesapeake Bay as one of our top Journeys with dozen of quality sailboats options available at a variety of travel budgets. The Chesapeake Bay Journey is a perfect summer vacation perfect for families or a private group of friends.

Price range for a private crewed charter for 5 to 7 nights | $13,000 to $19,000 (all-inclusive)

The season begins July 1st and we will organize sailing charters in the Chesapeake Bay through September. Each journey is crewed by a Sailing Collective captain and chef who will adhere to all Covid-19 cautionary measures prior to and during the voyage. Please contact us for more information.


Boat Options:

• 40’ to 58’ monohull accomodating up to 6 guests in 3 private cabins | 40’ to 48’ catamarans accommodating up to 6 guests in 4 private cabins. If there are more than 6 people in your group, ask us about our Flotilla options - two or more boats sailing together during the itinerary. Cost for a private charte depends on the boat and availability.


Included in the total trip cost:

• Private captain and chef

• Travel support to help customize and guide your group's journey

• Delicious family style meals with breakfasts, 6 lunches, 3 dinners and snacks aboard, all prepared by your private chef

• Marina fees, dockage, and moorings for overnight anchorages

• Boat incidentals including fuel, water, local taxes, etc.

• And of course unabashed adventure and epic memories!


50% due at booking, remaining balance due 30 days prior to departure

Before booking, please review CANCELLATIONS/CHANGES, INSURANCE, AND CONDUCT policy on the booking page.

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