Day 1 : Fly to Boston

Upon arrival, we check in to our hotel in Boston.

Day 2 : The Puritan City

A local guide joins us this morning for a comprehensive Boston city tour to witness some of the city’s oldest buildings and neighborhoods as well as its most iconic contemporary features. View Old North Church, Boston’s oldest surviving church that’s famous for its role in Paul Revere’s midnight ride of 1775. Our city tour concludes at the historic Faneuil Hall Marketplace with leisure time for lunch. We then depart The Puritan City and take an immersive tour of a family-owned dairy farm. Our travels continue into Plymouth, where we follow in the footsteps of the first settlers with visits to a reproduction of the Mayflower and Plymouth Rock. Later, get settled into tonight’s accommodations before we enjoy an included dinner near the beautiful waterfront.

Day 3 : Plymouth

Our day kicks off with a visit to the Plimoth Patuxet Museums, where we encounter the Wampanoag People and recreated colonial communities of the 1600s. Listen to surprising stories about the relationships between English and Indigenous cultures of the 17th century, including historical events and their ways of life. Immerse yourself in these two cultures’ pasts as we commemorate the famous feast of 1621 with an included "Eat like a Pilgrim" lunch featuring turkey, sweet Indian corn pudding, pompion (squash), fruit, cheese, and apple cider. Afterwards, spend time exploring the Pilgrim Hall Museum, the oldest continuously operating public museum in the country. Browse an extraordinary collection of 17th-century artifacts, some from the actual Mayflower. Before dinner we stop at Plimoth Grist Mill, where the milling process for various grains is a public spectacle.

Day 4 : Martha’s Vineyard

This morning we travel to Cape Cod and catch the ferry to Martha’s Vineyard, an affluent summer colony. Our time here begins with meeting the diverse herd of charming alpacas at Island Alpaca Company while learning about their selective breeding program. Next, a local guide joins us for a tour of the island’s colorful gingerbread houses, coastal communities, and breathtaking Aquinnah cliffs. Later, we return to Cape Cod and check in to our accommodations for the next three nights.

Day 5 : Provincetown

Today we visit Provincetown for time at leisure. Explore the downtown area, shop, and grab a bite to eat, then use the provided tickets to visit the Pilgrim Monument and Provincetown Museum, honoring the Pilgrim’s first landing in the city. At this site in the 17th century, Pilgrims explored the tip of Cape Cod for five weeks and established rules for the “new” land in the Mayflower Compact. This evening has us rolling through the wavy, oceanfront dunes of the Peaked Hill Bars Historic District where artists have famously found inspiration since the 1920s. Catch sights of Pilgrim Lake and watch for the historic dune shack homes of American writers and artists. We ride in a roomy SUV to our dinner destination for a real treat: your choice of a classic New England clambake or barbecue dinner on the beach (weather permitting).

Day 6 : Nantucket

Board the ferry this morning to explore the quaint, timeless island of Nantucket. This tiny coastal town preserves its aesthetic down to its signature New England cottages and manicured beaches. Capture the full Nantucket experience with a guided tour of the island, then visit the Whaling Museum, featuring nine galleries filled with artifacts that tell a story spanning four centuries. Enjoy time to walk the cobblestone streets, shop for souvenirs, or explore sights on your own before we ferry back to the cape for dinner together.

Day 7 : Cranberry Bog Tour

Our last day begins with an intriguing visit to a working cranberry bog. Get an up-close view of the bog area and meet one of the farmers, who teaches us the life cycle of this fruit from seed to harvest. We then travel into Rhode Island to take a tour of The Breakers mansion, the original Newport summer house of Cornelius Vanderbilt II. Take time to peruse through the 70-room 125,000+ square foot “cottage” that perfectly embodies the iconic Vanderbilt family’s massive social and financial influence at the turn of the last century. Tonight, we celebrate our travels with a Farewell Dinner in Providence.

Day 8 : Fly Home

We fly home today with fond memories of our time exploring history and agricultural highlights in this charming region of the United States.