Designated a UNESCO World Heritage site, the Old Town of Tallinn is one of the best-preserved medieval cities in Europe. An entire day can easily be spent exploring the churches, homes and public buildings constructed from the 13th to 16th centuries by wealthy German merchants of the Hanseatic League. Other periods of history are represented by the soaring spire of St. Olaf’s Church, dating to the 12th century and dedicated to the King of Norway, and the distinctive onion domes of Alexander Nevsky Cathedral, built in the late 19th century under the reign of the Russian Empire.

Once called Man-es-ayd'ik, or “clam-gathering place,” by the Wabanaki people, Bar Harbor is relaxed and fun but still retains an air of elegance from its history as an enclave for elites including the Morgans, Vanderbilts and Astors. It was the Rockefellers who convinced big landowners to donate the land to create Acadia National Park – over 50 square miles of mountains, lakes, hiking, biking, scenic vistas and dramatic coastline. The restaurants and boutiques of Main Street and the neighboring villages on Mount Desert Island offer the simple to the spectacular.

Founded in 1630, Boston is one of the oldest cities in the United States and arguably America's greatest walking city. Step along the cobblestones in any direction and you'll run into history. The Freedom Trail connects 16 significant sites, including the Paul Revere House, Boston Common and the USS Constitution. Once dubbed the “Athens of America,” this cultural capital is rich with museums, libraries, music venues and art galleries. The Isabella Stewart Gardner Museum houses a world-renowned art collection, famously heisted in 1990.

Breathtaking shorelines, gorgeous sunsets, sparkling waters, fresh seafood and world-famous sailing are the just the beginning of what's on tap in Newport. From the Cliff Walk to the Ten Mile Drive, there's no shortage of amazing experiences in the “City by the Sea,” but the opulent mansions built by wealthy industrialists must top the list. Gloriously styled after Italianate palazzi, French châteaux and Elizabethan manors, these impeccably restored homes, known as the summer “cottages” of the elite, are filled with priceless antiques and must be seen to be believed.

Established in 1633 as a fishing village, Portland grew to become not only the largest tonnage seaport in New England but also a charming destination of cobblestone streets, delectable seafood and history galore. The Old Port district is the center of it all with its restored brick warehouses bustling with shops, galleries, cafés, bars, and restaurants serving the freshest possible lobster. The Portland Museum of Art showcases works by Homer, Picasso, Matisse, Monet and more, while the views of the city from Portland Observatory are a work of art in their own right.

The Abenaki people once called this town Catawamteak, meaning “great landing place,” and Rockland certainly remains exactly that. This gateway to island-dotted Penobscot Bay is a thriving port of fishing boats and tall-masted sailing ships. Main Street is the hub with an array of specialty shops, antique stores, historic storefronts and the Center for Maine Contemporary Art. Other museum stops include the renowned Farnsworth Art Museum and the Maine Lighthouse Museum. The charming lighthouse and fascinating transportation museum in nearby Owls Head also merit a visit.

Few American cruise destinations have a past as engrained in popular culture as Salem. Settled by European fishermen in 1626 and named for the Hebrew word for peace – “shalom” – the seaport in 1692 was anything but peaceful. Multiple attractions harken back to the days of the witch trials, including the Witch House and the Trials Memorial. The Maritime National Historic Site comprises the Custom House, the enduring wharves and buildings along Derby Street and the Friendship of Salem, a replica of the East Indiaman tall ship launched in 1797.

St. Andrews by-the-Sea, as it is often called, has long been one of New Brunswick's premier vacation destinations. This pretty seaside town sits beside the U.S. border and has an old-fashioned charm. Once a hotspot for wealthy Americans who owned the lavish turn of the century homes that line the downtown core, it has a high-end feel but remains approachable and fun. From lobster rolls to chowder to fine dining, lovely eateries abound, many with a view of the harbor.

Founded in 1608 by Samuel de Champlain, known as the “Father of New France,” the grand provincial capital of Québec is one of the oldest European settlements in North America and blends past and present beautifully. The only walled city in the Americas north of Mexico, Old Québec is a UNESCO World Heritage treasure offering 400 years of history and evolution, and its aged cobblestones also feature the best of today's shopping, food and entertainment.

Percé is a small town near the tip of the Gaspé Peninsula in Québec, located within the traditional lands of the Mi'kmaq. These native people called the area Siscog, or “steep rocks,” an apt description of the dramatic landscape of rugged coastal cliffs and soaring mountains. One of the world's largest natural arches, striking Percé Rock looms just off the coast. On nearby Bonaventure Island, hiking trails wind through meadows and evergreen forests populated by large colonies of gannets, puffins, cormorants and murres.