Tour begins: 5:00 PM. Transfers are included upon arrival from Boston's Logan Airport or Boston's Back Bay, North and South train stations to the Fairmont Copley Plaza, a landmark hotel since 1912 and ideally located in historic Back Bay, in the city known as the birthplace of the American Revolution. Join us tonight for a welcome reception and dinner at the hotel.

Leave the city behind as you drive to Cape Cod, stopping en route for a guided visit at the Heritage Museum & Gardens in Sandwich, Massachusetts. It is set amidst 100 acres of flower-filled gardens and exhibits showcasing the history of the region, from antique automobiles to folk art and vintage memorabilia including a carousel built in 1908. Enjoy lunch in the town of Sandwich, the oldest town on the Cape and settled in 1637. While its name suggests a popular noonday meal, Sandwich is famous for the glassware produced here in the 1800s. Continue on to the southern coast of Cape Cod and West Harwich, where you'll spend two nights at The Pelham on Cape Cod – a charming, family-founded retreat in that effortlessly blends coastal charm and relaxed sophistication. 

Embark this morning on an exciting whale watching cruise in the nearby town of Provincetown, keeping your eyes peeled at all times for a glimpse of the giant marine mammals who frequent the waters here. It was the hunt for the whale that largely built Provincetown. By 1870, largely due to its whaling activities, Provincetown was one of the richest towns in Massachusetts. As Provincetown went from a whaling town to a Portuguese fishing village to the artsy town it is today, whales are now playing a part in its important conservation efforts to help prevent the whales' extinction. You may spot a variety of marine life during your whale watching cruise, from humpback, fin and right whales to dolphins, seals and sea turtles who may happen by. You'll have free time to explore the town of Provincetown as you wish before heading back to the hotel this afternoon. Dinner is at leisure tonight at your hotel.

This morning, board a ferry bound for the summer resort island of Martha's Vineyard for a guided sightseeing drive around the island and its towns. From Victorian-inspired Oak Bluffs to charming Vineyard Haven and West Tisbury, the island's agricultural center, and Aquinnah, home to the Wampanoag Indian tribe and clay cliffs, your tour is followed by a free afternoon in Edgartown, a quintessential New England town where hydrangeas line white picket fences in the summer and trees display red and orange in the autumn. Explore its many boutiques, whaling history, and Jaws filming locations as you please. Late this afternoon, arrive at the iconic Harbor View Hotel for a two-night stay in the center of Edgartown. Dine at your leisure tonight at your hotel.

Island hop from Martha's Vineyard to Nantucket this morning, boarding a fast ferry to an island once known as the whaling capital of the world. This compact island is renowned as a getaway for captains of industry who relish its endless beaches, rose-covered shingled homes, and the cobblestoned charms of its historic harborside town. Enjoy a guided orientation tour before free time to explore as you please. Return to Martha's Vineyard this afternoon for an optional private visit to The Carnegie Museum. Join a docent for a tour of the museum, learning about its start as a free library inspired by Andrew Carnegie, and viewing its collection of artifacts and photos of island landscapes and landmarks. An optional walking tour takes you to the Chappy Ferry Line, the Old Sculpin Gallery, the Norton Boat House, and the Edgartown Memorial Wharf. For those who don't wish to join the private tour of The Carnegie Museum, the evening is free to enjoy as you like.

Board a ferry bound for Woods Hole, Massachusetts, disembarking for lunch and a guided tour of the New Bedford Whaling Museum, recalling the town's heyday as a whaling port. Surrounded by cobblestone streets once strolled by Frederick Douglass and Herman Melville, the museum is located in the New Bedford Whaling National Historical Park. Inside you'll find a 66 ft. skeleton of a blue whale and a smaller skeleton of a sperm whale for an up-close look at the whales that are found in the oceans nearby, as well as a fully rigged, half-size replica of an actual whaling ship. Learn about the history of whaling and view paintings by famous maritime artists during your visit. The museum showcases the world's largest collections of scrimshaw, whaling logbooks, and journals, chronicling just about everything you wanted to know about whales in visually engaging displays. Drive to Newport, Rhode Island; your hotel is centrally located on the waterfront, an easy stroll from dining venues, shops and more. 

Wake up in Newport, where wealthy Gilded Age families, including the Vanderbilts, Astors, and Morgans, spent their summers at their "cottages." Explore one of these grand homes during a self-guided visit to The Breakers. Built between 1893 and 1895 by Cornelius Vanderbilt II, this 70-room Renaissance Revival estate is one of the most magnificent of Newport's opulent mansions. Spend the afternoon exploring Newport as you wish, and join us tonight for a farewell reception and dinner at 41° North.

Tour ends: Boston. Depart Newport after breakfast and drive to Boston's Logan International Airport, a distance of 73 miles, for your flight home. Flights should be scheduled after 2:30 PM. Guests staying an additional night in Boston will be transported to Fairmont Copley Plaza.