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Martha’s Vineyard
Colonial History
Sand Dunes Adventure
Pilgrim Hall Museum
Providence Boat Tour
Erin Davisson
Erin Davisson
Erin is the former anchor of Local 5 News at 5, 6 and 10 p.m. with Tom Zalaski. She has been at Local 5 News since 1988. Erin has won numerous reporting and anchoring awards and has consistently been voted Best Anchor in newspaper polls in the…
Discover quintessential charm and rich history within the breathtaking region off the Atlantic Coast where Pilgrims landed 400 years ago. Begin with a Boston city tour including Fenway Park, then head south towards Plymouth to learn about its past of Indigenous and colonial settlements. Become immersed in life during the 1600s while visiting enriching sites at Plimoth Patuxet Museums, featuring a full-scale reproduction of the Mayflower, a historic homesite, a recreated 17th-century English village, and a grain mill. Enjoy ferry rides to Martha’s Vineyard and Nantucket with a guided tour and ample time at leisure. Head to the tip of the cape, Provincetown, for a whale-watching cruise and time to explore before embarking on a sand dunes adventure, complete with a mouthwatering dinner. Our journey concludes in Rhode Island with a fascinating tour of The Breakers mansion in Newport and a boat ride in Providence.
Trip overview may vary by departure.
Highlights
Following in Footsteps of Colonists
Plimoth Patuxet Museums brings the history of Plymouth Colony and the Indigenous homeland to life with expansive museum exhibits. Journey back to the early 1600s and see the famous Plymouth Rock nestled along the shore of Plymouth Harbor, then behold the Mayflower II, an impressive replica of the original Mayflower. Help costumed staff playing an actual inhabitant pound corn in the 17th-century English Village, and learn about the Wampanoag culture at the Historic Patuxet Homesite. We also enjoy a traditional “Eat like a Pilgrim” lunch featuring authentic 17th-century recipes.
Nantucket Island
Enjoy a narrated motorcoach tour of all six charming towns to learn about the island’s fascinating history and famous residents. We make a stop to see the Aquinnah Cliffs and lighthouse, plus spend some leisure time in Edgartown. Experience tranquil, timeless beauty with an island tour and time at leisure to wander the cobblestone streets and shop for souvenirs, eat fresh seafood, relax on picturesque beaches, or visit the immersive Whaling Museum.
The Breakers Mansion
Visit Rhode Island’s most popular attraction, originally a summer home to the wealthy Vanderbilt family who ran one of the greatest railroad empires of the Gilded Age. Constructed in 1895, the massive mansion and grounds were inspired by Italian Renaissance Villas. Hear about the family’s legacy on a self-guided tour of several rooms, including the Great Hall, Music Room, bedrooms, and more. Admire the gold accents, crystal chandeliers, marble mosaics, and other opulent designs found throughout.
Whale-Watching Excursion
Cruise into the open waters of Stellwagen Bank National Marine Sanctuary, enjoying the crisp sea breeze as we watch closely for majestic marine life, including the world’s largest mammals. Listen to fascinating narration of our experienced naturalist and learn how to spot the telltale signs of a whale’s presence. Sightings may include a variety of whale species – humpback, finback, minke, sei, and North Atlantic – as well as birds, dolphins, and sharks.
- Day 1: Fly to MassachusettsUpon arriving in Boston, we take a short drive to our wonderful hotel and have a restful evening at leisure.
- Day 2: The Puritan CityOur adventure begins with an exclusive tour of Fenway Park to learn about the Boston Red Sox, the famed ballpark, and iconic moments in baseball history. Next, a local guide boards our motorcoach for a comprehensive city tour with views of historic buildings, impressive contemporary architecture, and iconic neighborhoods, such as Harvard Square. We step off the coach for a short stroll to see the Paul Revere statue, Old North Church, and Freedom Trail. Our city tour concludes at Faneuil Hall Marketplace, where we have time to grab lunch from the country’s largest and oldest food hall, Quincy Market. Afterwards, we travel to Plymouth and follow in the footsteps of the first settlers. Climb aboard a full-scale reproduction of the Mayflower and see legendary Plymouth Rock! We then check in to our accommodations for the next two evenings before enjoying dinner near the waterfront.
Meals Included: Breakfast, Dinner
- Day 3: PlymouthWe kick off our day with a visit to Plimoth Patuxet Museums, where we encounter the Wampanoag People and colonial communities of the 1600s. Walk through a recreated 17th-century village while listening to fascinating stories about the relationships between the English and Indigenous cultures. We then commemorate the famous feast of 1621 with an "Eat like a Pilgrim" lunch featuring traditional foods. Later, revel in a private visit to Pilgrim Hall Museum, the oldest continuously operating public museum in the country. Spend time exploring an extraordinary collection of 17th-century artifacts, some from the actual Mayflower!
Meals Included: Lunch
- Day 4: Martha’s VineyardAfter breakfast, we board our motorcoach for Cape Cod and catch the ferry to Martha’s Vineyard. A local guide joins us for an interesting tour of this affluent summer colony, known for its colorful gingerbread houses, coastal communities, and breathtaking Aquinnah Cliffs. The motorcoach takes us through all six charming towns with a stop in Aquinnah to see the lighthouse and clay cliffs, as well as time for lunch at leisure in Edgartown. After a lovely day on the island, we return to Cape Cod and settle into our accommodations for the next three nights.
Meals Included: Breakfast
- Day 5: ProvincetownToday is spent in beautiful and creative Provincetown, nestled on the northern tip of the cape. We embark on an exciting whale-watching cruise, hoping to catch glimpses of humpback whales, birds, dolphins, and sharks. The afternoon is at leisure to grab lunch, shop for souvenirs, explore local attractions, or use provided tickets to visit the Pilgrim Monument and Provincetown Museum. Marvel at the soaring 252-foot granite tower, which honors the Pilgrims’ first landing in the city, and see the Mayflower Compact in the museum, written by Pilgrims to establish rules in the "new" land. This evening, we board SUVs with experienced driver-guides to traverse the wavy, oceanfront dunes in Peaked Hill Bars Historic District, where artists have famously found inspiration since the 1920s. Our adventure concludes with a mouthwatering meal: your choice of a classic New England clambake or barbecue dinner.
Meals Included: Breakfast, Dinner
- Day 6: NantucketThis morning, we ride a ferry to the timeless island of Nantucket. This quaint coastal town preserves its aesthetic down to its signature New England cottages and manicured beaches. We take a bus tour to discover charm and history throughout the island, including sights of the oldest windmill in the country. Afterwards, enjoy an afternoon at leisure to have lunch and explore independently. Be sure to use your included tickets to visit the Whaling Museum, which features nine galleries filled with artifacts spanning four centuries! Upon returning to the mainland, we gather for another delicious dinner.
Meals Included: Breakfast, Dinner
- Day 7: ProvidenceOur last full day takes us across the border to Rhode Island for a morning at The Breakers mansion, the original Newport summer house of Cornelius Vanderbilt II. Enjoy time to venture through the 70-room “cottage” that spans 125,000+ square feet, perfectly embodying the iconic Vanderbilt family’s massive social and financial influence at the turn of the last century. We then have lunch at leisure in Newport before traveling to Providence. Enjoy a relaxing boat tour along the city’s waterways as our guide narrates historical, nautical, and architectural highlights. Later, we check in to our hotel and depart for an incredible Farewell Dinner to celebrate our adventures together.
Meals Included: Breakfast, Dinner
- Day 8: Fly HomeWe return home with incredible memories of our time soaking up rich history and coastal charm.
Sep 19-26, 2026
$6,849
per person
$5,599
per person
Jul 6, 2026
What's Included
All Accommodations
- 1 night at SpringHill Suites - Boston Logan Revere Beach
- 2 nights at Hotel 1620 in Plymouth
- 3 nights in South Yarmouth
- 1 night at Marriott Providence Downtown
Attractions & Highlights
- Mayflower II & Plymouth Rock
- Boston guided city tour feat. Faneuil Hall Marketplace
- Fenway Park guided tour
- Pilgrim Hall Museum
- Plimoth Patuxet Museums
- Ferry to Martha’s Vineyard feat. island tour
- Cape Cod National Seashore sand dunes adventure
- Pilgrim Monument & Provincetown Museum
- Whale-watching excursion
- Ferry to Nantucket feat. island tour & Whaling Museum
- Providence boat tour
- The Breakers mansion
10 Excellent Meals
- Welcome Dinner in Plymouth
- “Eat like a Pilgrim" lunch at Plimoth Patuxet Museums
- New England clambake or barbecue dinner
- Farewell Dinner in Providence
Learn more about what's included with the Holiday Advantage.
Chicago - O'Hare International Airport