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.

Set out this morning for a guided exploration of Boston with a local guide, discovering the city's historic neighborhoods and distinctive character. Travel through Back Bay's tree-lined streets and Victorian brownstones, the North End's deep-rooted Italian heritage, Charlestown's connections to the American Revolution, and the waterfront at Long Wharf, where Boston's maritime history comes into view. Along the way, gain insight into the people, architecture, and events that have shaped one of America's oldest cities. The afternoon and evening are yours to explore as you wish. Perhaps enjoy lunch along the harbor, visit one of the city's renowned museums, or spend time browsing shops and cafés in nearby neighborhoods. Later, a narrated harbor cruise offers a different perspective on Boston, with views of the skyline, historic landmarks, and the working waterfront from the water, adding another layer to your understanding of the city.

Leave the city behind as you drive to Cape Cod, stopping en route in Sandwich, Massachusetts, 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 a scenic drive to Provincetown, at the tip of Cape Cod, where the maritime traditions of the region remain an essential part of daily life. Once one of the richest towns in Massachusetts during the height of the whaling era, Provincetown has evolved over time—from a Portuguese fishing village to the vibrant, artistic community it is today—while maintaining its deep connection to the sea. From here, choose how you'd like to experience the Cape. You may opt for an exciting whale watching cruise, keeping your eyes peeled for a glimpse of the giant marine mammals who frequent these waters. Whales, once central to the town's livelihood, are now at the heart of conservation efforts, and sightings may include humpback, fin, and right whales, along with dolphins, seals, and sea turtles. Alternatively, explore the unique coastal landscape on a guided dune tour, or enjoy free time to discover Provincetown's galleries, shops, and waterfront as you wish. Later, continue to a local shellfish farm for a private oyster shucking demonstration and tasting, where you'll learn about the Cape's oyster harvest and its connection to the region's culinary traditions. Return to your hotel in the afternoon, with dinner at leisure this evening.

You have a choice today: remain on Cape Cod to enjoy its coastal towns and relaxed pace, or join us for a ferry ride to Nantucket, 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. Spend time on Nantucket experiencing the island's distinctive character and coastal setting before returning to Cape Cod, where the remainder of the day is free to explore as you wish.

Travel to New Bedford and 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-foot skeleton of a blue whale and a smaller skeleton of a sperm whale for an up-close look at the marine life found in nearby waters, along with a fully rigged, half-size replica of an actual whaling ship. Learn about the history of whaling and view paintings by renowned maritime artists, as well as one of the world's largest collections of scrimshaw, whaling logbooks, and journals presented in engaging displays. After your visit, enjoy lunch at a local restaurant before continuing on to Newport, Rhode Island. If time permits, your drive includes scenic stretches along the coast, offering views of the Atlantic and the grand estates that line the shoreline. On arrival, gain an introduction to Newport's historic character before a special after-hours guided visit to The Breakers, the Vanderbilt family's Gilded Age summer "cottage," where ornate interiors and oceanfront setting reflect the opulence of the era. The evening is free to explore Newport at your leisure, with its waterfront setting, shops, and dining options all within easy reach of your hotel.

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.