Sail 250 America

Day 1: Connecticut – Williamsburg, Virginia

This morning we begin our fascinating journey to Williamsburg, Virginia—our home base for 3 nights. We will check into our hotel centrally located – The Courtyard by Marriott Busch Gardens Area. This evening dinner is included at The Jefferson. This popular restaurant has been serving locals and travelers from around the world for four generations. (Dinner included)

Day 2: The Parade of Sails – Hampton, Virginia

After breakfast we set out for Hampton, Virginia for an event of a lifetime---The Parade of Sails as part of Sail America250. From the historic Fort Monroe, you will witness international ships still under sail as they proceed into Hampton Roads Harbor on their way to Norfolk. Their majestic sails unfurl against the backdrop of Chesapeake Bay, a scene that evokes centuries of maritime tradition.

This afternoon there will be time to step back into history as we visit the Fort Monroe Visitor & Education Center, the nation’s largest stone fort. There will be time to enjoy Hampton’s Juneteenth festivities. Dinner is included at The Whaling Company serving delicious food in the cozy atmosphere of a replica of a New England Boathouse (Breakfast and dinner included)

Day 3: Colonial Williamsburg -Jamestown Settlement

After breakfast we are ready to step back into American history for the day! We begin with a guided walking tour through Colonial Williamsburg. Our guide will share the rich history, architecture and daily life of 18th century America. You will stroll past restored homes, see authentic trades in action, enjoy staged shows**, gardens and government buildings in this living history museum. (**subject to change)

Next, we head to nearby Jamestown Settlement, a 17th century Virginia living museum that depicts America’s first permanent English colony in 1607. Discover the story of America’s beginnings through immersive films, gallery exhibits and outdoor re-creations. You’ll learn about the Virginia Indians who occupied the landscape for centuries and the arrival of English colonists to Jamestown. After an exciting day, we return to Williamsburg for the evening with time for dinner and relaxation. (Breakfast included)

Day 4: Williamsburg- Home

After breakfast we return home with memories of our Parade of Sails adventure. (Breakfast included)

Photo credit Visit Williamsburg; Hampton CVB; Williamsburg photographers, Wayne Reynolds, Brendan Sostak, Brian Newson, the Colonial Williamsburg Foundation

For reservations, please go to the Book Now tab. When the trip code is requested, please insert the following: capecod24.

Deposit: $500 upon sign up of tour

Final Payment: Due by 50 days in advance

Deadline for Registration: May 15. After this date, please call our office directly to check availability.

Meal Selections: (Please select your entrée for the following restaurants when making reservations)

The Jefferson:

1. Baked Stuffed Pork Chops with cornbread dressing

2. Southern Fried Chicken and Baked Virginia Ham

3. Southern Fried Chicken and Barbeque Ribs

The Whaling Company:

1. Charbroiled Lemon Herb Chicken with rice

2. Baked Fresh Salmon with rice

3. Vegetarian (mushrooms, sundried tomatoes, asparagus and garlic butter served over linguini)

Cromwell: Commuter Lot Exit 21 off I-91 Departure: 615am

North Haven: Commuter Lot Exit 10 off I-91 Departure: 6:45am

Milford: Commuter Lot Exit 40 off I-95 Departure: 7:15am

Westport: Commuter Lot Exit 18 off I-95 Departure: 7:45

We strongly recommend the purchase of Trip Protection Coverage. To purchase your policy, please click on the link provided during your registration process and follow the steps to approve and purchase. There are 2 levels of insurance: Standard and Enhanced. You may purchase the Enhanced Trip Protection option (Cancel for Any Reason) up until 14 days from the time of making your reservation. If you have further questions on insurance coverage, please contact Trip Mate at 844-777-6856. Please make reference to plan #F5615.

If you choose to travel without adequate coverage, DK Tours, LLC will not be liable for any of your losses arising for which trip protection plan coverage would otherwise have been available.

Please see our Terms and Conditions page under Travel Protection.

*Please note the $10 discount per person is non-transferable if passenger cancels the tour. Discount applies only to overnight tours reserved by March 15, 2026.

Cancellations 50 days or more days ahead receive a full refund.

Cancellations 49-30 days ahead will be charged 50% of total tour cost.

Cancellations 29 days or less ahead of departure, no refunds.