Day 1 : Fly to Boston

Upon arrival, we check in to our hotel in Boston and enjoy an included Holiday Vacations Welcome Dinner at Dryft, located across the street from our hotel.

Day 2 : The Puritan City

We start the morning with a tour of Fenway Park where we learn about the Boston Red Sox, the ballpark, and player history. A local guide joins us for a comprehensive Boston city tour as we witness some of the city’s oldest buildings and neighborhoods as well as its most iconic contemporary features. Our city tour concludes at the historic Faneuil Hall Marketplace where we stop for lunch. After, we depart The Puritan City and travel to Plymouth where we follow in the footsteps of the first settlers with visits to a reproduction of the Mayflower and Plymouth Rock.

Day 3 : Plymouth

This morning we kick off our day with a visit to the Plimoth Patuxet Museums, where we encounter the Wampanoag People and Colonial communities of the 1600s, telling surprising stories that educate us about the relationships between English and Indigenous cultures of the 17th century. Immerse yourself in "The Museum of Thanksgiving" as we all 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. After lunch, spend time exploring the Pilgrim Hall Museum, the oldest continuously operating public museum in the country. This museum houses an extraordinary collection of 17th-century artifacts, some from the actual Mayflower. Before dinner we stop at the Plimoth Grist Mill where the milling process for various grains is a public spectacle.

Day 4 : Martha’s Vineyard

Today, we travel to Cape Cod to catch the ferry to Martha’s Vineyard and tour the affluent summer colony with its colorful gingerbread houses, coastal communities, and breathtaking Aquinnah cliffs. After a lovely day on the island, we return to Cape Cod to check in to our accommodations for the next three nights.

Day 5 : Provincetown

After breakfast, we head to the northern tip of the cape for an exciting day in Provincetown. Go on a whale watching cruise for glimpses of humpbacks and other whales as well as birds, dolphins, and sharks. After lunch, we visit the Pilgrim Monument and Provincetown Museum which honors the Pilgrims’ 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 where we get a real treat: a classic New England Clambake and beach BBQ (weather permitting). Our beautiful sunset dune tour with dinner makes for a memorable adventure!

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 Nantucket Whaling Museum, featuring nine galleries filled with artifacts that tell a story spanning four centuries. There is time to have lunch and explore Nantucket on our own before we ferry back to the cape.

Day 7 : Providence

Our last full day together takes us across the border to Rhode Island where we begin the day with a visit to The Breakers Mansion, the original Newport summer house of Cornelius Vanderbilt II. Take time to venture 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. Enjoy lunch on your own in Newport before we travel to Providence and embark on a leisurely, educational, and fun exploration of the city’s waterways. Tonight, we come together for a Holiday Vacations Farewell Dinner.

Day 8 : Fly Home