Boston is the capital of and largest city in Massachusetts, and is one of the oldest cities in the United States. The largest city in New England, Boston is regarded as the unofficial "Capital of New England" for its economic and cultural impact on the entire "New England" region. The city proper had a 2009 estimated population of 645,169, making it the twentieth largest in the country. It is also the anchor of a substantially larger metropolitan area called  "Greater Boston", home to 4.5 million people and the tenth-largest metropolitan area in the country. Greater Boston as a commuting region includes six Massachusetts counties:  "Essex", "Middlesex","Norfolk", "Suffolk", "Plymouth", "Worcester", northern "Bristol" County, all of "Rhode Island" and parts of "New Hampshire"; it is home to 7.6 million people, making it the fifth-largest Combined Statistical Area in the United States.

Sydney is a Canadian urban community in the province of Nova Scotia. It is situated on the east coast of Cape Breton Island and is administratively part of the Cape Breton Regional Municipality. Sydney was incorporated in 1904 and dissolved on August 1, 1995, when it was merged into the regional municipality. It is the largest urban centre on Cape Breton Island. Together with Sydney Mines, North Sydney, New Waterford and Glace Bay it forms the Industrial Cape Breton region. Sydney is located on east bank of the Sydney River where it discharges into South Arm of Sydney Harbour.

Halifax, legally known as the Halifax Regional Municipality (HRM), is the capital of the province of Nova Scotia, Canada. It is a major economic centre in Atlantic Canada with a large concentration of government services and private sector companies. Major employers and economic generators include the Department of National Defence, Dalhousie University,Saint Mary's University, the Halifax Shipyard, various levels of government, and the Port of Halifax. Agriculture, fishing, mining, forestry and natural gas extraction are major resource industries found in the rural areas of the municipality. Halifax was ranked as the fourth best place to live in Canada for 2012, placed first on a list of "large cities by quality of life" and placed second in a list of "large cities of the future''. Additionally, Halifax has consistently placed in the top 10 for business friendliness of North and South American cities. Waterfront warehouses known as the Historic Properties recall Halifax’s days as a trading hub for privateers, notably during the War of 1812.

Acadia National Park is a national park located in the U.S. state of Maine. It reserves much of Mount Desert Island, and associated smaller islands, off the Atlantic coast. Initially created as the Sieur de Monts National Monument in 1916, the park was renamed Lafayette National Park in 1919, and was given its current name of Acadia in 1929. The oldest American national park east of the Mississippi River, its landscape is marked by woodland, rocky beaches and glacier-scoured granite peaks such as Cadillac Mountain, the highest point on the United States’ East Coast. The bayside town of Bar Harbor, with restaurants and shops, is a popular gateway.  

Montreal is the largest city in the province of Quebec and the second-largest city in Canada. Originally called Ville-Marie, or City of Mary, the city takes its present name from Mont Royal, the triple-peaked hill located in the heart of the city, whose name was also initially given to the island on which the city is located, or Mont Real as it was spelled in Middle French, Mont Royal in present french.

Charlottetown is a Canadian city. It is both the largest city on and the provincial capital of Prince Edward Island, and the county seat of Queens County. Named after Queen Charlotte, the wife of George III, Charlottetown was first incorporated as a town in 1855 and designated as a city in 1885. It was most famously the site of the Charlottetown Conference in 1864, the first gathering of Canadian statesmen to debate the proposed Canadian Confederation. From this, the city adopted as its motto  "Cunabula Foederis" – "Birthplace of Confederation".

Havana, officially Ciudad de La Habana, is the capital city, major port, and leading commercial centre of Cuba. The city is one of the 15 Cuban provinces. The city/province has 2.1 million inhabitants, the largest city in Cuba and the second largest in the Caribbean region, after Santo Domingo. The city extends mostly westward and southward from the bay, which is entered through a narrow inlet and which divides into three main harbours: Marimelena, Guanabacoa, and Atarés. The sluggish Almendares River traverses the city from south to north, entering the Straits of Florida a few miles west of the bay.

Key West is an island in the Straits of Florida on the North American continent at the southernmost tip of the Florida Keys. It is considered the southernmost city in the continental United States. The city also occupies nearby islands and portions of nearby islands. It’s popularly known for its stunning beaches, coral reefs – destinations for diving and snorkeling.

Ocho Rios (Spanish for "Eight Rivers") is a town in the parish of Saint Ann on the north coast of Jamaica. Just outside the city, travelers and residents can visit Columbus Park, where Columbus supposedly first came on land, and see maritime artifacts and Spanish colonial buildings. Ocho Rios was once a fishing village but it’s now a resort with a cruise ship harbor and a busy bay beach that’s lined with hotels. Scuba diving and other water sports are offered in the town's vicinity. The name "Ocho Rios" is a misnomer because there are not eight rivers in the area. It is most likely a British corruption of the original Spanish name "Las Chorreras" ("the waterfalls"), a name given to the village because of the nearby Dunn's River Falls - (a famous waterfall and a major Caribbean tourist attraction that receives thousands of visitors each year).

Grand Cayman is the largest of the Cayman Islands, a British Overseas Territory in the Caribbean. George Town, its capital, is home to the Cayman Islands National Museum, dedicated to Caymanian heritage.  There are fast food restaurants, night clubs, and resorts on the western side of the island down to George Town. The eastern districts have more restaurants specialising in native Caymanian cuisine. Because of its clubs, resorts, and hotels, Seven Mile Beach has the largest concentration of visitors and tourists on the island. Watersports such as scuba diving and snorkeling are among the most popular activities on Grand Cayman as the island is known for its coral reefs and underwater sea walls along with a number of shipwrecks.

Little San Salvador Island, also known as Half Moon Cay, is one of about 700 islands that make up the archipelago of The Bahamas. It is a private island, owned by Holland America Line, which uses it as a port of call for the cruise ships it operates in the region. Prior to being owned by HAL, Little San Salvador was the private island of Norwegian Cruise Line. The island is also a significant nesting area for waterfowl. Activities offered on the island include swimming, sunbathing, scuba diving, jet-skiing, cycling, and snorkeling. Deep-sea fishing, parasailing, glass-bottom boat rides, and nature walks also are available. A variety of water toys are available for rent, including Hobie catamarans, Sunfish sailboats, windsurfing sailboards, and kayaks.

Quebec, also Québec, City of Québec, Quebec City, or Québec City is the capital of the province of Quebec in Canada. Founded in 1608 by Samuel de Champlain, Quebec City is one of the oldest cities in North America. The ramparts surrounding Old Quebec (Vieux-Québec) are the only fortified city walls remaining in the Americas north of Mexico, and were declared a World Heritage Site by UNESCO in 1985 as the 'Historic District of Old Québec'. The city's famous landmarks include the Château Frontenac, a hotel which dominates the skyline, and La Citadelle, an intact fortress that forms the centre-piece of the ramparts surrounding the old city. The National Assembly of Quebec (provincial legislature), the Musée national des beaux-arts du Québec (National Museum of Fine Arts of Quebec), and the Musée de la civilisation (Museum of Civilization) are found within or near Vieux-Québec.