7-Nights Boston, Cape Cod & The Islands - Classic Group from $5,050

Insight Vacations

OFFER ID 1556432

Boston, Cape Cod & The Islands - Classic Group
This 8-Day guided tour blends history with glamour as you travel from Massachusetts to Rhode Island. Follow the red-brick Freedom Trail in Boston to see where the U.S. took shape. On the shores of Cape Cod Bay, see Sandwich, a coastal town famous for its glassmakers; here, visit the Sandwich Glass Museum, where you can learn tricks of the trade. At Martha's Vineyard, a driver will take you past the former home of Jacqueline Kennedy Onassis and to Oak Bluffs, an idyllic town with gingerbread-like cottages. Indulge in a sea-to-table feast filled with fish caught from local fishermen, fresh produce from nearby farms and delicacies picked by foragers. In the seaside city of Newport, board an 80-foot schooner to cruise the coastline, taking in views of historical buildings and the homes of the rich and famous - and learn about the area’s past as a pirates’ haven.


Dining Summary

  • 4 Dinner with Wine (DW)
  • 7 Breakfast (B)
Authentic Dining
  • Boston: At 18:00, join your Travel Director for a dinner with wine and an opportunity to mingle with fellow guests.
  • Martha's Vineyard: Indulge in a locally sourced dinner in a private dining space in Bettini Restaurant.
  • Newport: Meet your new friends in the evening for a seafood dinner with wine, where you can share the highlights of your trip while savoring a freshly prepared meal.
Insight Experiences
  • Newport: Meet your captain and jump onboard the Adirondack II, an 80-foot schooner sailing ship and cruise around the coastline. You’ll sail out and pass nearby islands, old historical buildings and homes of the rich and famous, as you learn about the region’s exciting history, including its pirate activity.
  • Newport: Enjoy a visit to one of Newport's renowned landmarks, The Vanderbilt's Breakers Mansion.
Make Travel Matter
  • Plymouth: Visit the Plimoth Patuxet (Puh – tux- it) Museum – which is really more like a living memorial dedicated to the lifestyle of the first English settlers and the Wampanoag Indigenous community. Enjoy a guided journey to the early homesite of the Wompanoag people, a living version of the early English settlement village and a full scale replica of the Mayflower 2 – the ship that made the initial voyage in 1620. By visiting, we’re helping the museum preserve the histories and stories of the early inhabitants and the revitalization of pre-industrial crafts, trades, domestic skills, horticulture, and maritime arts.Your experience advances UN Global Goals 10 & 11: Reduced Inequalities & Sustainable Cities and Communities.
Top Rated Highlights
  • Plymouth: Visit Pilgrim Hall Museum, the oldest continuously operating public museum in the country and America’s museum of Pilgrim possessions. Meet a direct descendant of the Mayflower party that landed on America's shores in 1620 and hear their family stories.
  • Boston: Explore the great city of Boston, with your Travel Director and learn about its transformative past. You’ll follow part of the red-brick Freedom Trail that brings the story of the American Revolution to life. Journeying to other historically significant sights that include the Boston Common, the Old Corner Bookstore and the The Old State House.
  • Sandwich: View through the lens of the skilled craftsmen at the Sandwich Glass Museum, where you will learn the techniques of the English and Irish glass-makers developed during the early 19th century.
  • Cape Cod: Experience the natural wonder and human history emphasizing the cultural themes represented on Cape Cod, including the First People--the Wampanoag; European settlement culture; fishing, life-saving, and lighthouses; communication technology of Cape Cod's National Seashore.
  • Nantucket: Walk through historic downtown Nantucket and discover the unique history of the island. Journey through Nantucket’s past and hear about the rise and the fall of the whaling industry, the rise of tourism, and the impacts the island’s economy has had on social and racial development on Nantucket.
  • Martha's Vineyard: After disembarking from your ferry ride, visit the port neighborhood of Oak Bluffs and be transported to a different era. Known for its rainbow-colored, gingerbread-like cottages with Gothic storybook decorations, high-peaked roofs, and dainty verandas. You’ll also find the oldest operating platform carousel in America here.


7 nights from $5,050 per person

Black Friday Promotion: Save Up to 30% on Select “Business Class” Tours

Valid on new bookings deposited November 1, 2024 – December 5, 2024 for travel in 2025.  

*Discount may already be included in the displayed price. Promotion may not be combinable with any other offers, promotions, or discounts, and is subject to availability and airline booking guidelines. Other restrictions may apply.

Itinerary

Insight Vacations: Boston, Cape Cod & The Islands - Classic Group

Day 1 - Welcome to Boston
Boston, often described as America’s most European city, is a captivating blend of history, art, and culinary delights. Upon your arrival at the Hyatt Regency, nestled in the heart of downtown, you're just moments from sights such as the historic Faneuil Hall and the fashionable Newbury Street. Take a leisurely stroll through the charming South End or along the picturesque Charles River Esplanade. This evening, meet your Travel Director and fellow guests for a delightful dinner, marking the beginning of your unforgettable journey.
Accommodations: Hyatt Regency, Boston
Meals: Dinner with Wine

Day 2 - Exploring Plymouth's Past
Join your Travel Director for an enriching exploration of Boston’s storied past. Walk along the famous Freedom Trail, where each step brings the American Revolution to life. Visit landmarks like Boston Common, the Old Corner Bookstore, and the Old State House. Continue your historic exploration at the Pilgrim Hall Museum in Plymouth, hosted by a Mayflower descendant, offering personal stories tied to the museum’s fascinating collection of 17th-century artefacts. At the Plimoth Patuxet Museum, immerse yourself in the stories of early English settlers and the Wampanoag Indigenous community during a MAKE TRAVEL MATTER® Experience. From the replica Mayflower II to the recreated homesites, your visit contributes to preserving this vital heritage, supporting pre-industrial crafts, trades, and maritime traditions.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast

Day 3 - The Wonders of Cape Cod
The windswept shores and pristine landscapes of Cape Cod await as you embark on a journey through the heart of New England’s maritime history. The Cape’s rolling sand dunes, historic lighthouses, and timeless fishing villages set the stage for a day rich in cultural discovery. Explore Cape Cod’s National Seashore, where the stories of the Wampanoag people and European settlers converge against a backdrop of stunning coastal beauty. Later, visit the Sandwich Glass Museum, where you’ll witness demonstrations of glassblowing techniques pioneered by English and Irish craftspersons in the early 19th century. This captivating experience will leave you with a deeper appreciation of Cape Cod's art, history, and natural beauty.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast, Dinner with Wine

Day 4 - Nautical History in Nantucket
Set sail from Hyannis to the island of Nantucket, where cobblestone streets and preserved historic homes tell the story of a bygone whaling era. Stroll through the charming downtown, learning how the rise and fall of the whaling industry shaped Nantucket’s social fabric and economy. As you uncover tales of seafaring adventures, witness the island’s transformation into a beloved destination for visitors from across the globe. After a day steeped in maritime history, return to Hyannis by ferry for an evening at leisure.
Accommodations: Dan'l Webster Inn and Spa, Sandwich
Meals: Breakfast

Day 5 - The Charms of Martha’s Vineyard – An Island Escape
Board a morning ferry to Martha’s Vineyard, an island known for its pristine beaches, charming harbor towns, and storied visitors, including U.S. presidents. Explore Oak Bluffs with its gingerbread cottages, visit the Flying Horses Carousel and see State Beach, made famous by the film Jaws. Discover the island’s colorful past, from whaling to modern-day tourism, as you gain insights into the history of Edgartown harbor lighthouse. Later, enjoy island hospitality with seasonal offerings from local farms, fishing boats and foragers during a dining experience at Bettini, located in your elegant hotel.
Accommodations: Harbor View, Martha's Vineyard
Meals: Breakfast, Dinner with Wine

Day 6 - The Timeless Elegance of Newport Relaxed Start
Arrive in Newport, where over 95 years of hospitality and charm characterize the historic Hotel Viking. Set in the heart of this coastal city, your boutique accommodation offers luxurious rooms and stunning views. Enjoy complimentary bike rentals or relax in the hotel’s spa, pool, or café. This evening, take a leisurely stroll through Newport’s vibrant streets, where every corner reveals another piece of its storied past.
Accommodations: Viking, Newport
Meals: Breakfast

Day 7 - Newport, the Queen of Summer Resorts Relaxed Start
Your day begins with Newport’s famed Ten Mile Drive, a scenic route that hugs the coastline, showcasing public parks, historic landmarks and breathtaking ocean views. Afterwards, explore the grandeur of Newport’s "summer cottages" as you visit the Breakers, the grandest of them all. A symbol of the Vanderbilt family’s wealth and prominence, this opulent mansion offers a glimpse into the lavish lifestyle of America’s Gilded Age elite. Cap off the day with a sunset sail aboard the Adirondack II, gliding along Newport Harbor and Narragansett Bay.
Accommodations: Viking, Newport
Meals: Breakfast, Dinner with Wine

Day 8 - Farewell to Boston Relaxed Start
As your tour comes to a close, bid farewell to your fellow travelers and transfer to Logan International Airport for your onward journey. With memories of Boston’s historic charm, the beauty of Cape Cod, and the elegance of Newport, you leave with a deeper appreciation for this unique corner of New England.
Meals: Breakfast

Featured Destinations
Newport, RI
Martha's Vineyard
Sandwich
Boston

Vacation Details

Valid Date Ranges
05/15/2026 - 05/22/2026
from $5,050 per person
05/29/2026 - 06/05/2026
from $5,350 per person
06/12/2026 - 06/19/2026
from $5,350 per person
06/26/2026 - 07/03/2026
from $5,225 per person
07/09/2026 - 07/16/2026
from $5,295 per person
09/04/2026 - 09/11/2026
from $5,175 per person
09/11/2026 - 09/18/2026
from $5,175 per person
09/18/2026 - 09/25/2026
from $5,175 per person
09/25/2026 - 10/02/2026
from $5,175 per person
10/02/2026 - 10/09/2026
from $5,175 per person
10/09/2026 - 10/16/2026
from $5,175 per person


* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.
Prices Start At
from $5,050 per person
Length
7 Nights
Air City
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Vacation Rating
Deluxe
Fine dining, on-site bars or lounges and room service with extended hours are characteristic of deluxe establishments. Guest services usually include valet parking, concierge services, baggage assistance and laundry services. Other on-site facilities often include shops and boutiques, full service spas, full fitness facilities with pools and tennis courts. Business amenities may include available up-to-date technology and support staffs available for services. Attention to detail is apparent in the guestrooms which typically have stylish furnishings, quality bedding and bath products and often provide an evening turn down service.
Remarks
Trip prices are per person, land only, based on double occupancy and reflect applicable discounts. Trip prices and discounts are subject to change. Airfare is additional. Tour prices, dates and itineraries are correct at the time of the website going live, however are subject to confirmation at the time of booking. Other restrictions may apply.

All fares are quoted in US Dollars.

OFFER ID
1556432

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Rosenbluth Travel

610 W. Germantown Pike - Suite 180
Plymouth Meeting, PA 19462
USA

610-825-9010
800-233-3158