Great Lighthouses of the Chesapeake Bay

Sorry, This Trip Has Already Passed. Click Here to View Our Upcoming Trips

The Chesapeake Bay in the heart and soul of Maryland, famous for blue crabs, sandy shores, lighthouses and centures-old seafaring heritage. Join us for a quick escape to start off your summer!

Day 1 – Mary, Mary, Maryland (D)
Meet your fellow travelers as we motor to Maryland, arriving at the famous Calvert Marine Museum. Learn about the ecology of the Bay from a museum biologist and tour the unique “screw-pile” lighthouse at Drum Point. Celebrate the start of your trip in style with a welcome dinner at Reynolds Tavern. Settle in to the Country Inn & Suites, your home for the next two nights.

Day 2 – Keepers of the Light (B, L)
Take to the bay on lighthouse cruise hosted by a turn-of-the-century lighthouse keeper. With multiple decks and a climate controlled cabin, you’ll have the perfect view of the famous Lights of the Chesapeake! Glide by three lighthouses and pass under the twin spans of the Chesapeake Bay Bridge, a stunning experience. Enjoy sandwiches on board before docking back in the heart of downtown Annapolis. The rest of the day is yours to enjoy this bustling city with great sightseeing, shopping and dinner on your own. Ask your Tour Director for their favorite recommendations!

Optional VIP Tour
Be a VIP tonight with an optional addition to enhance your trip. Go behind the scenes at the Naval Academy with a VIP Tour and dinner at the Officer’s Club.
This tour will feature many areas that are not open to the public!

Day 3 – Taste the Bay (B, L)
Savor a taste of the bay on a guided tour with craving stops along the way! With your colonial guide, roll through the city on a driving tour of Annapolis and visit the Maryland State House. Slurp the award winning crab soup at historic Rams Head Tavern, tuck into your bay inspired entrée at Blackwall Hitch Restaurant and delight in the official state cake at the William Paca House.

With full bellies, fun memories and new friends, head home happy and ready for the rest of the summer!

Book Now

Sorry, this trip has already passed.

Please click here to view our upcoming trips.


  • $529 Triple
  • $549 Double
  • $679 Single
  • Travel Protection 10%


  • Chesapeake Bay Lighthouse Cruise
  • Annapolis City
  • Taste of the Bay Tour
  • 2 nights hotel, 5 meals
  • Upper Class Tour Director, All Taxes and Gratuities


Wednesday June 28th, 2017

  • Mamaroneck 6:00 am
  • Yonkers 7:00 am


Friday June 30th, 2017

  • Yonkers 7:45 pm
  • Mamaroneck 8:30 pm