Bayside Bliss: A Cape Cod Getaway

Your journey begins with departures from New York and Mount Vernon, followed by a leisurely drive toward the timeless charm of Cape Cod. Upon arrival in Hyannis, you’ll be welcomed by a local guide for a scenic tour showcasing the area’s rich heritage — including the John F. Kennedy Memorial, the Korean War Memorial, picturesque Hyannisport, and St. Francis Xavier Church, the beloved summer parish of the Kennedy family. Afterward, check in to your thoughtfully selected hotel and unwind for the evening. A gracious dinner is included to complete the day.

Hotel: Holiday Inn Cape Cod – Hyannis, or similar
Meals: Dinner

Set out on a stunning journey along Cape Cod’s historic Route 6A — also known as the Old King’s Highway — lined with centuries-old homes and charming coastal scenery. Discover the natural beauty of the Cape Cod National Seashore, explore the historic Eastham Windmill, and snap photos at the iconic Nauset Lighthouse.

In Provincetown, soak in sweeping ocean views from the Province Lands Visitor Center, then buckle up for an unforgettable off-road adventure with Art’s Dune Tours, weaving through rolling dunes and past remote artist shacks.

After lunch and free time in Provincetown, head to the harbor for a thrilling whale watching cruise with Dolphin Fleet, where you might witness humpbacks, fin whales, and more in their natural habitat.

End the day with a relaxing dinner on your own along the vibrant Main Street in downtown Hyannis — home to over 40 family-run restaurants serving global cuisine — before returning to the hotel.

Hotel: Holiday Inn Cape Cod – Hyannis, or similar
Meals: Breakfast

Start your day with a scenic ferry ride across the waters to the enchanting island of Nantucket. Once ashore, enjoy a guided Signature Tour that reveals the island’s timeless beauty — from the historic Old Mill and Sconset Village to the dramatic Sankaty Head Lighthouse and some of the oldest homes in New England.

After the tour, take the afternoon to explore at your own pace. Wander cobblestone streets, browse boutiques, visit the Whaling Museum, or simply breathe in the sea air on a pristine beach — Nantucket is pure New England magic.

Back in Hyannis, dive into rich local heritage at the Zion Union Heritage Museum, where African American and Cape Verdean histories are brought to life through powerful exhibits on abolition, whaling, and cranberry farming.

That evening, gather with your fellow travelers for a memorable farewell dinner — a perfect opportunity to reflect, celebrate, and toast to an unforgettable journey through Cape Cod.

Hotel: Holiday Inn Cape Cod – Hyannis, or similar
Meals: Breakfast, Dinner

After hotel check-out, begin your final day on Cape Cod by stepping into presidential history at the John F. Kennedy Hyannis Museum. This immersive experience offers rare photographs, archival films, and touching tributes to the Kennedy family’s deep connection to the Cape.

Next, travel to Sandwich, the oldest town on Cape Cod, where colonial charm meets timeless beauty. Stroll past Shawme Pond, visit the historic Dexter Grist Mill, and maybe even sip from the town’s own “fountain of youth.” After lunch on your own, wrap up the day at the Sandwich Glass Museum, where molten glass is transformed into dazzling shapes during a live glassblowing demonstration — a hands-on display of artistry and innovation.

With hearts full and cameras loaded, begin the journey home with unforgettable memories of Cape Cod’s history, culture, and coastal charm.

Meals: Breakfast

Full Package Price

$2,599 per person
(double occupancy)

$2,999 per person 
(single occupancy)

Payment Schedule

• Deposit: Due at time of booking: $500 (non-refundable)
• October Payment: October 15, 2025
• November Payment: November 15, 2025
• December Payment: December 15, 2025
• January Payment: January 15, 2026
• February Payment: February 15, 2026
• March Payment: March 15, 2026
• April Payment: April 15, 2026
• Final Payment: May 15, 2026 Remaining Balance

CANCELLATION POLICY

• The deposit is non-refundable and non-transferrable
  • Cancellations must be submitted in writing to [email protected] on or before March 15, 2026. 
  • Cancellations submitted on or before March 15, 2026 the final payment date will be refunded the amount paid less the deposit and a $150 administration fee.
  • Cancellations submitted after the final payment date will forfeit all payments made and no refund will be provided.

• We encourage all travelers to purchase a travel protection plan at the time of initial trip deposit. 
• Overton Travel uses Travel Safe. Click here to review and purchase a travel protection plan from them: Travel Protection.
• You can purchase travel protection through the supplier used by Overton Travel or any other supplier you choose.