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Captivating Cape Cod

Discover Cape Cod on a charming tour with stops in bustling Boston, colonial Plymouth, Martha’s Vineyard, quaint Nantucket Island, Newport, and Providence. Travel down from Boston to explore the cape, stopping at historic landmarks and museums and appreciating the rich history of this small geographic region off the Atlantic coast where the Pilgrims landed 400 years ago. Enjoy ferry rides to Martha’s Vineyard and Nantucket Island, taking full days to experience these distinct places and appreciate their natural beauty and legacies. During our visit to Newport, we tour the magnificent Breakers Mansion known for its Renaissance-style opulence.

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The Holiday Advantage
Airfare Included
Airfare Included
Exceptional Accommodations with Baggage Handling
Exceptional Accommodations with Baggage Handling
Premier Attractions
Premier Attractions
Professional Tour Directors
Professional Tour Directors
Motorcoach & Professional Driver
Motorcoach & Professional Driver
Low Deposit, Guaranteed Prices, & No Hidden Costs
Low Deposit, Guaranteed Prices, & No Hidden Costs
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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.

Breakfast, Dinner

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, 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.

Breakfast, Lunch

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

Tour a cranberry bog this morning, driving into the area and stepping out in several spots to get up-close looks of the unique produce operation.

Then, we head to the northern tip of the cape for an exciting day in Provincetown.

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!

Breakfast, Dinner

Day 6 : Nantucket

Board the ferry this morning to explore the quaint, timeless island of Nantucket.

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

Following, we’ll visit the Nantucket Whaling Museum that showcases nine galleries filled with artifacts telling stories of the island’s past four centuries.

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.

Breakfast, Dinner

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.

Breakfast, Dinner

Day 8 : Fly Home

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

Additional Tour Information

Your Holiday Vacations Experience Includes

  • All Transportation
  • Holiday Vacations Tour Director
  • Motorcoach & professional driver
  • Baggage handling at hotels
  • $100 Loyalty Credit for a future tour

All Accommodations Featuring

  • 1 night in Boston
  • 2 nights at Hotel 1620 Plymouth Harbor
  • 3 nights in Cape Cod
  • 1 night at the Providence Marriott Downtown

Attractions & Highlights

  • Fenway Park tour
  • Boston guided city tour
  • Faneuil Hall Marketplace
  • The Mayflower
  • Plymouth Rock
  • Plimoth Patuxet Museums
  • Pilgrim Hall Museum
  • Plimoth Grist Mill
  • Ferry to Martha's Vineyard
  • Martha's Vineyard tour
  • Cranberry bog tour
  • Pilgrim Monument and Provincetown Museum
  • Cape Cod Sand Dunes Adventure
  • Ferry to Nantucket
  • Nantucket Island tour
  • Nantucket Whaling Museum
  • The Breakers Mansion
  • Providence boat tour

11 Excellent Meals Featuring

  • Dinner at Tavern on the Wharf
  • “Eat like a Pilgrim" lunch at Plimoth Patuxet Museums
  • BBQ and Clambake Dinner on the beach in Cape Cod (weather permitting)
  • Dinner at the Sea Dog Brew Pub
  • Holiday Vacations Farewell Dinner

Tour Dates & Pricing


Price Per Person

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Final Payment Date: 07/26/2021

Tour Map for Captivating Cape Cod

Departure Cities

WSAW TV Pickup Locations:

Colby/Abbotsford, WI - Hardees/Shell Truck Stop

Marshfield, WI - Holiday Inn & Conv. Center

Merrill, WI - Walmart

Stevens Point, WI - Dunham's Sports

Wausau, WI - Walmart Supercenter

Wisconsin Rapids, WI - Walmart Supercenter

Minneapolis/St. Paul, MN - MSP International Airport

Mosinee, WI - Central Wisconsin Airport