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Phone: 508-457-7461
Toll Free: 866-518-6877

Stars and Stripes and Chesapeake Delights

Stars and Stripes and Chesapeake Delights

Travel to the Chesapeake Bay for a taste of all Baltimore & Annapolis have to offer!

Stars and Stripes and Chesapeake Delights

Sunday, October 16 - Wednesday, October 19


Travel to the Chesapeake Bay for a taste of all Baltimore & Annapolis have to offer! We’ll enjoy a full day culinary tour, a visit to the Annapolis Naval Academy, and more!


DAY 1 – Arrive in Baltimore for a narrated cruise on Baltimore Harbor, where we will sail past Federal hill, Under Armour, Fell’s Point, Ft. McHenry, and the Key Bridge. After our cruise, we will enjoy a delicious meal at Dalesio’s of Little Italy. Then, we’ll travel to Annapolis where we will check into our hotel, Hampton Inn, Annapolis. (D)


DAY 2 - Enjoy a full day of Chesapeake Bay culinary tidbits, traditions and history. Start the day at the historic Ram’s Head Tavern for some Maryland Crab Soup and tales of the area. Then take a guided tour of the Maryland State House before enjoying a Chesapeake inspired lunch at a local restaurant. We’ll end the day with a visit to Historic Londontown - a “lost” colonial town and garden sanctuary on the South River – site of the Historic William Brown House, where we will indulge in the Maryland State Dessert, Smith Island Cake. (B, L)


DAY 3 – We’ll visit the Annapolis Naval Academy, home to over 4,000 midshipmen (photo ID required). We’ll see the US Naval Academy Chapel and Crypt of John Paul Jones, Bancroft Hall (building interiors if available), and hear stories of years past and current education, service and leadership requirements of today’s future officers on our walking tour of the yard. After our tour, we’ll sit down for a lunch at the Officers Club. Then, we’ll head to Annapolis’ historic district for a tour of the Paca House & Gardens, a Georgian Mansion built in 1760 by William Paca, the 3rd Governor of Maryland and a signer of the Declaration of Independence. (B,L)


DAY 4 – Enjoy a self-guided tour of Fort McHenry, the site of the Battle of Baltimore that inspired Francis Scott Key to write the words that became the U.S. national anthem, before we depart for the Cape. 


$ 1,099 per person, double occupancy, $ 1,289 single occupancy


Dennis - 6:40 AM
Barnstable: 6:55 AM
Sagamore - 7:05 AM



Sagamore - 6:30 PM
Barnstable - 6:50 PM
Dennis - 7:05 PM


B=Breakfast included, D=Dinner included

Package Includes:

3 nights stay at Hampton Inn Annapolis

3 breakfasts, 2 lunches, 1 dinner

Self-Guided Tour of Fort McHenry

Culinary tour of Annapolis

Guided tour of Maryland State House

Walking tour of Annapolis Naval Academy

Tour of Paca House & Gardens

Cruise on Baltimore Harbor

Deluxe Motorcoach Transportation

Tour Guide, Driver, and Meal gratuities


Payments and Cancellations

Cash, personal checks & money orders accepted

Visa & MasterCard payments accepted via phone.


$75 per person deposit due upon booking, balance due 45 days prior to tour.  Refundable up to 30 days prior to tour.

Insurance is available for this trip

Below is a list of pick-up points available on this tour.

Below is a list of pick-up points available on this tour.

Name Address Contact Details
1 - Dennis Patriots Square, Route 134, South Dennis
On Stop & Shop side, park in lot closest to Rt 134
2 - Barnstable Barnstable Exit 6 Commuter Lot - behind
Burger King, wait at enclosures
3 - Sagamore Sagamore Commuter Lot at base of bridge
on NON Cape side, wait at enclosures
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15 Mill Pond Way, East Falmouth, MA 02536 | Phone: 508-457-7461 | Toll-Free: 866-518-6877