Cape Cod and The Islands

After breakfast, we continue our travels to Cape Cod, known for its sandy shores, historic charm, and fresh sea air. Upon arrival, settle in for a four-night stay at the oceanfront Red Jacket Beach Resort, where you’ll have time to relax and unwind. Stroll the beach, take in the view of Nantucket Sound, or simply enjoy the coastal atmosphere before gathering for a group dinner to kick off our Cape Cod stay.

This morning after breakfast, board the ferry for the beautiful island of Martha’s Vineyard. On a guided tour, learn about the island’s diverse communities, whaling history, and cultural heritage. Highlights include Oak Bluffs, Edgartown, and the Federated Church where Frederick Douglass spoke in 1852. Enjoy free time to browse shops or relax with a view of the harbor before returning to the mainland for dinner with the group.

After breakfast, embark on another fun-filled day exploring the lower and outer Cape! Begin with a visit to an authentic 17-acre cranberry bog, where you’ll discover the fascinating annual cycle of America’s jewel-toned fruit. Learn how cranberries are planted, cultivated, and harvested, and meet friendly farm animals that help keep the bog healthy. Tour through the Cape Cod National Seashore, enjoying sweeping views of the Atlantic. Our journey continues to Provincetown, where you’ll enjoy free time browsing its eclectic shops, art galleries, and seafood cafés. Early afternoon, board the Dolphin Fleet for an exciting whale-watching cruise to Stellwagen Bank National Marine Sanctuary. The Dolphin Fleet whale watch is enrolled in WhaleSENSE, a voluntary educational and recognition program that recognizes companies committed to responsible whale-watching practices and ocean stewardship. Keep your camera ready for breaching humpbacks! Tonight, gather for a delicious lobster dinner with all the fixings!

After breakfast, we’ll board the high-speed ferry to picturesque Nantucket—affectionately dubbed “The Gray Lady” for its weathered shingles and enduring grace. Once the world’s whaling capital in the 1800s, today Nantucket delights with its cobblestone Main Street, winding lanes, and Quaker-style cottages nestled alongside elegant Federal-era homes. Enjoy a guided tour of the island’s storied past—discover hidden architectural gems and hear tales of mariners and merchants—before you enjoy leisure time to browse the quaint shops and galleries at your own pace. As the day winds down, we’ll return by ferry to the mainland, where a delicious, locally sourced dinner awaits you. Over this meal, a gifted storyteller will share an evening of history and mystery, bringing local legends vividly to life.

After breakfast, we’ll check out and enjoy a guided tour of Hyannisport, the summer home to the Kennedys. Enjoy a picture stop at the Kennedy Memorial and Korean War Memorial overlooking scenic Veterans’ Beach. Continue to Cape’s oldest town of Sandwich for a tour of the village, stroll around Shawme Pond, view the historic Dexter Grist Mill, take a sip out of the ‘fountain of youth’, before we bid farewell to Cape Cod. This afternoon, we’ll return to our Rochester, NY area hotel for the evening and enjoy a final dinner together, sharing all the wonderful stories of our Cape & Islands adventure!

After breakfast, we begin our final travel day, bringing home fond memories of Martha’s Vineyard, Nantucket, and Cape Cod’s coastal beauty. Take along stories of island adventures, ocean breezes, and the special moments shared with fellow travelers on this unforgettable tour.