Maine Cruise from Portland to New York — 16 Days

Portland ME, USA

Portland follows the Willamette River, with the Columbia to its north and Mount Hood on the eastern horizon. Begin downtown at Powell’s City of Books, a landmark independent bookstore spanning an entire city block. Visit the Japanese American Historical Plaza beside the waterfront, or head to Washington Park’s International Rose Test Garden. Food carts, craft breweries and seasonal produce give the city its distinctive taste. Allow time for the Columbia River Gorge, whose waterfalls and trails lie east of town.

• Land Tour (Land Tour)
• Coastal Cruising (Coastal Cruising)

Bath ME, USA

Bath, Maine, sits on the Kennebec River, where shipbuilding has shaped this coastal city for generations. Its working waterfront and historic streets give the port a distinctly local character. Explore the Maine Maritime Museum for stories, vessels and skilled trades behind the state’s maritime heritage. Then stroll downtown, where independent shops, cafés and 19th-century architecture are close at hand. Bath suits travelers who prefer authentic history to a staged seaside scene.

Portsmouth NH, USA

Portsmouth is a New England port with a long maritime history and a lively, walkable center. From the waterfront, follow the streets to Market Square, where brick sidewalks, independent shops and cafés anchor downtown. At Strawbery Banke Museum, preserved homes trace four centuries of life in this former seaport. Across the Piscataqua River, the Portsmouth Naval Shipyard sits in Kittery, Maine—a reminder that this harbor remains working water.

Gloucester MA, USA

Gloucester is a working harbor with a history you can still see along its waterfront. Founded in 1623, this Cape Ann city built its fortunes on the sea, and fishing remains central to its identity. Visit Maritime Gloucester, watch boats return to port, or join a whale-watching trip into the Atlantic. Then explore nearby beaches, rocky headlands, and the artists’ colony of Rockport.

Boston, USA

Boston rewards visitors who like their history close at hand and their cities easy to explore. From the waterfront, follow the Freedom Trail to landmarks of the American Revolution, including Faneuil Hall. Beacon Hill’s brick streets, the Public Garden and North End cafés reveal distinct sides of the city. Make time for harbor views and New England seafood; Boston’s pleasures are as tangible as its past. Its museums and universities give the compact city a lively, modern edge.

Martha's Vineyard Island, USA

Martha’s Vineyard is more than a summer address. Its six distinct towns are reached by ferry from mainland Massachusetts. In Edgartown, white Greek Revival houses recall the whaling era. Oak Bluffs adds painted gingerbread cottages and a lively harborfront. On the western shore, Aquinnah’s clay cliffs frame broad Atlantic views. Make room for fresh seafood, independent shops, and the island’s easy pace.

Nantucket MA, USA

Nantucket is a small island 30 miles south of Cape Cod, where maritime history remains part of daily life. From the harbor, head for cobbled streets and handsome gray-shingled houses. The Whaling Museum traces the 19th-century trade that once made Nantucket one of America’s richest towns. Beyond town, lighthouses and broad Atlantic beaches reward a bicycle ride or a slower afternoon.

Newport RI, USA

Newport rewards visitors who look beyond its famous mansions. This Rhode Island harbor town pairs Gilded Age grandeur with working waterfronts, historic lanes and Atlantic views. Tour The Breakers, the Vanderbilt summer home, then follow the Cliff Walk past oceanfront estates and crashing surf. Downtown, independent shops and seafood restaurants line streets shaped by centuries of seafaring trade. Allow time for a harbor sail or a visit to Fort Adams, where the coastline opens wide.

Long Island New York, USA

Long Island stretches east from New York City, trading urban intensity for Atlantic beaches, quiet bays and village streets. On the North Fork, working farms and vineyards sit near seafood towns. Farther east, the Hamptons and Montauk offer Atlantic beaches, galleries and the Montauk Point Lighthouse. On the North Shore, grand Gold Coast estates reveal the island’s Gilded Age past. Choose a base carefully: distances are substantial, and summer traffic can slow journeys between communities.

New London CT, USA

New London rewards visitors who look beyond its working waterfront. Set at the mouth of the Thames River, this Connecticut port pairs maritime history with a lively downtown. Explore Fort Trumbull, where exhibits trace the city’s role in coastal defense, or visit the Custom House Maritime Museum. The U.S. Coast Guard Academy stands nearby, and ferries cross Long Island Sound. Leave time for waterfront dining or a short drive west to Mystic.

Sleepy Hollow NY, USA

Sleepy Hollow sits on the Hudson River, where broad water, wooded slopes and colonial history shape a quieter visit. Walk the grounds of Washington Irving’s Sunnyside, then see the Old Dutch Church and its 17th-century burial ground. At nearby Philipsburg Manor, costumed interpreters bring an 18th-century milling and farming estate to life. Come in autumn for crisp air and the legend that made this village famous; save time for Hudson River views.

New York, USA

New York does not ease you in; it arrives in a sweep of skyline, river and restless energy. From the harbor, Manhattan’s towers frame a city built for walking, looking up and changing plans. Spend time among Central Park’s paths, Fifth Avenue’s museums and the neighborhoods that give each block its own character. Allow room for a classic meal, a Broadway curtain and the simple pleasure of watching the city move.