Sunset on the Chesapeake Bay
Sunset on the Chesapeake Bay Sunset near Blackwater National Wildlife Refuge on Maryland's Eastern Shore. © Matt Kane/TNC

Legacy Journeys

Chesapeake Bay

Take in stunning scenery, incredible wildlife and the maritime culture of the largest estuary in the U.S.

2024 departure is full. Wait list space is available!

Explore the Journey

May 12-17, 2024

Full Itinerary

May 12-17, 2024

Experience the Chesapeake Bay, a national treasure that attracts travelers from around the world for its serene beauty and rich glimpse into our American heritage. This journey stretches from the nation’s capital to quiet, historic towns steeped in maritime culture along Maryland’s Eastern Shore. Our trip begins in Washington, D.C., where a boat ride along the Anacostia River reveals a river revived and teeming with returning wildlife, including bald eagles. From there, we follow the water to tranquil creeks, quaint fishing towns, oyster reefs and out on the open bay.


  • Hoist the sails and cruise across the waters of the Chesapeake Bay on a sailboat.
  • Bike along the trails of Blackwater National Wildlife Refuge, a prime spot for viewing bald eagles and other birds.
  • Visit Horn Point Laboratory, one of the largest oyster hatcheries on the East Coast.

Explore our Work in this Region

Wait list space is available!

Our 2024 departure to the Chesapeake Bay is full. Trip specialists at Iconic Adventures are maintaining a wait list. We often have space open on our departures, please call to add your name to the wait list if you have an interest in traveling on this Legacy Journey with The Legacy Club in 2024.

Information & Reservations

Reservations for all trips will open on Tuesday, August 29 at 2 p.m. ET/11 a.m. PT and can be made with the trip specialist listed below.

Iconic Adventures
Phone: (800) 329-4930

We recommend adding your name to the waiting list for the Journey if it fills up. We often have space open on our departures.

Please Note

Registration inquiry calls may direct to voicemail. Iconic Adventures will organize all inquiries received by phone or email in order of time of receipt and fill trips on a first come, first served basis. 

Traveling with TNC means showing respect for each other, respect for the world around us and acting with integrity. Before signing up for TNC Travel, please review and familiarize yourself with TNC’s Traveler Expectations.