Captivating Cape Cod

Day 1 : Fly to Boston

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

Day 2 : The Puritan City

We start the morning with a tour of Fenway Park. You’ll get to 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’ll stop for lunch.

We depart The Puritan City and make our way to Plymouth where we follow in the footsteps of the first settlers. To begin, we explore a reproduction of the Mayflower and see Plymouth Rock.

Enjoy an included dinner overlooking the waterfront and check-in for a two-night stay in Plymouth.

Day 3 : Plymouth

This morning we kick off our day with a visit to the Plimoth Plantation where we encounter the Wampanoag People and Colonial communities of the 1600s, providing us with engaging in-and-outdoor learning experiences to educate and tell surprising stories of the intersection between English and Indigenous cultures in the 17th century.

Immerse yourself in "The Museum of Thanksgiving" as we all commemorate the famous 1621 feast 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’ll return to Cape Cod where we’ll 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 Provincetown. 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 prepared by local Provincetown restaurants 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. We’ll visit the Nantucket Whaling Museum that showcases nine galleries filled with artifacts telling stories of the island’s past four centuries.

Following, we’ll go on an island tour and get the full Nantucket experience.

You will have time to explore on your own and grab lunch before we ferry back to the cape.

Enjoy an included dinner tonight as we gather at the Sea Dog Brew Pub.

Day 7 : Providence

Our last full day takes us across the border into 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 and status 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

Fly home with lovely memories from Boston, Cape Cod, and Rhode Island.