top of page

Charms of the Chesapeake

September 13 - 19, 2026
$3,995 /double • $5,095 /single
Chesapeake.jpg

From colonial port towns and elegant waterfronts to wild barrier islands, this intimate journey reveals the heart and soul of the Chesapeake Bay. Explore historic Annapolis, sail aboard a classic schooner, trace the paths of Harriet Tubman and Frederick Douglass, and experience the quiet beauty of Maryland’s Eastern Shore before viewing the wild ponies of Assateague from the seas and strolling sandy beaches amidst island charm of Chincoteague.

 

Tour Includes

  • TOUR INCLUDES

  • Local home pick-up service and luggage handling

  • Fully escorted by Globe Treks tour manager

  • All meals, attractions, guides, and activities

  • Two-night stay at the Annapolis Waterfront Hotel

  • Guided tour of Maryland’s capital, including the U.S. Naval Academy and William Paca House

  • Sailing adventure aboard the 75-foot schooner Woodwind

  • Two-night stay at the luxurious Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina

  • Guided exploration of Easton, Oxford, and Cambridge

  • Visit to the Harriet Tubman Underground Railroad Visitor Center and Frederick Douglass Park

  • Two-night oceanfront stay on Chincoteague Island, Virginia

  • Cruise on the Assateague Explorer to view wild ponies

  • Delicious regional cuisine, from waterfront seafood feasts to elegant Chesapeake dining

  • Deluxe 14-passenger motorcoach with extra legroom, refreshments, and door-to-door pickup

We aim to provide the best travel experience possible. While we plan every detail meticulously, dates, itineraries and accommodations are subject to change as necessary to ensure your smooth and enjoyable journey.

Tour Updates, Every Sunday!
Book Now
828-692-1399

Thanks for submitting!

Join our email list to receive weekly updates

  • Instagram
  • Facebook

Office Location: 1605 Asheville Highway • Hendersonville, NC 28791

© 2025 by Globe Treks Tours & Cruises

bottom of page