1. WEST STREET AND MARKET SQUARE

Stop Description: The centre of life in Port Antonio, West Street is always abuzz with activity as locals navigate its narrow sidewalks, sometimes spilling into the middle of the road. West Street runs along the northern side of Market Square. In the middle of the square, stands a white cenotaph, forever expressing Jamaica’s gratitude to the sons of Portland who died during World War I and II. Musgrave Market faces the cenotaph. Shops and stores offering a cornucopia of items for sale, including fresh produce and straw items, surround the market. 

Directions: Travel east along West Street, to the intersection with Harbour Street, and you will see a Victorian clock tower facing a two-storey redbrick building, which is the: 

2. PARISH COUNCIL BUILDING AND COURTHOUSE

Stop Description: Erected in 1895 on the order of the Colonial secretary, this Georgian building houses the parish courthouse, offices of the parish council and the post office. There are ornate metal verandas both at the front and back of the building. Atop of its pyramidal roof sits a white octagonal cupola. Inside the graceful structure is a plaque, dated November 16, 1918, given to the governor from the Secretary of State for the British Colonies. 

Directions: To your left you’ll see a colourful building with fantastic murals, painted on its outside walls. This is the Village of St George – now known as the Port Mall. It lies in front of the main entrance to the Port Antonio Marina. 

3. PORT MALL

Stop Description: This astounding complex will live on in your memory as a fabulous melange of architectural trends. Its design is a delightful combination of Elizabethan, Renaissance Tudor, Art Deco and Postmodern architectural styles with palladian columns, decorated cornices, gothic arches, and domed and vaulted ceilings. The mall also has lively mosaic patterns inlaid in its floors and walls, which are made from marble, redbrick or stone. At the mall’s centre, you’ll find a covered courtyard with impressive columns and an imposing statue of the Madonna. Built between 1995 and 1997, the four-storey building features a collection of small, local shops, a café, lounge and nightclub. 

Directions: Climb the spiral, wrought-iron staircase to the second floor where you’ll find The Gallery Café, a bright spacious spot that offers a birds-eye view of the Marina.

After you’ve explored the Port Mall, walk across to the entrance of the: 

4. PORT ANTONIO MARINA

Stop Description: This "brand spanking new" marina stretches for half a kilometre along the southern side of the West Harbour, and houses the Ken Wright Cruise Ship Pier, the Marine Police and Coast Guard stations, and the customs and immigration offices of Port Antonio. It also has berthing facilities for small yachts. Attractively landscaped with gazebos and a beautiful wooden promenade, the Marina is set to have a host of recreational activities, including boutiques and souvenir shops, a restaurant and bar, as well as a few swimming pools. 

Directions: From the Marina, you may hire a boat to the picturesque Navy Island. Originally called Lynch’s Island, after a former governor of Jamaica, the island was used by the British Navy in the 1700s as a place to careen and repair their ships. Once owned by Errol Flynn, Hollywood star and renowned playboy, Navy Island now belongs to the Port Authority of Jamaica.

Exit the Marina’s main entrance and turn left onto Fort George Street, heading up hill. This area is known as the Titchfield Peninsula, named after the former Duke of Portland, Marquis of Titchfield and Governor of Jamaica in 1723. Rising between Port Antonio’s twin harbours, the peninsula was once home to the town’s most wealthy residents. The Titchfield Hotel, the Caribbean’s first “big” resort with 400 luxury rooms, crowned the peninsula’s landscape until the 1930s, when it was destroyed by fire. Today, many tattered buildings still stand on the peninsula, as reminders of its glory days. As you walk along, look out for old wooden houses with delicate fretwork and charming balconies, reflecting architecture of a bygone era. About midway up the hill, you will see a wonderfully restored red-brick three-storey building with intricate white iron work. This is the: 

5. DeMONTEVIN LODGE

Stop Description: Built in the early 1900s, this Victorian-styled building was home to the then custos of Portland, David Gideon. It is thought that Gideon brought the elaborate ironwork, barley columns and veranda rails, which adorn the exterior of the house, from America. In recent years, DeMontevin Lodge has been extensively renovated and refurbished and has been declared a National Heritage site. The lodge operates as a guesthouse and restaurant, and is widely recognized for its comfortable accommodations and scrumptious local fares. On the ground floor, you’ll encounter numerous antique pieces, some of which are approximately 100 years old. 

Directions: Continue heading north along Fort George Street. At the tip of the of the peninsula, you’ll find the: 

6. TITCHFIELD HIGH SCHOOL AND FORT GEORGE

Stop Description: Fort George was constructed in 1729 to guard the twin harbours. Originally, the fort boasted twenty-two powerful cannon. Today, only two guns sit atop of the fort’s old walls, still guarding the entrance to the East Harbour.

Founded in 1785, the Titchfield High School was built around the ruins and buildings of the old fort. The school’s administrative buildings are housed in the fort’s barracks, while another of its old stone buildings, formerly the powder house, stands in the middle of the school yard. 

Directions: From the school’s gates, head south along Gideon Street, keeping the harbour to your left. Make a right pass the Port Mall and the Parish Council Building, and then turn left onto Harbour Street. Proceed in south-easterly direction along Harbour Street passing the Police Station, a restored old home, displaying the Jamaican-Vernacular style of architecture from the 19th century, and the beautiful Methodist Church, which was built over 175 years ago by Dutch Naval Officers. Eventually, you will see the Parish Church, towering above you from a small hill. 

7. THE PORTLAND PARISH CHURCH (CHRIST CHURCH)

Stop Description: Built during the late Georgian Period (in 1837-1840), this impressive red brick structure boasts a high, vaulted ceiling and a bell tower with a clock. From the church grounds, you are treated to a stunning view of the East Harbour, while inside the building, you’ll discover memorial plaques that offer an insight into 19th-century Jamaican life. 

Directions: You may end your walking tour here, or if you are feeling energetic continue to the Folly Estate, which lies about 1km from the church. Although it is a very pleasant walk along the harbour, you may opt to hire a taxicab to take you to Folly.

If you decide to continue on foot, from the church’s entrance gate, turn right, toward the harbour, onto Allen Avenue. Head east along Allan Avenue, away from the town centre, keeping the sea to your left. Along the way, you may pass fishermen tending their nets and canoes, or cleaning their latest catch. You may also stop and grab a bit to eat or a cool drink at one of the colourful shops and restaurants that line the seaward side of the road. Continuing on your walk, you will eventually see a large field, called the Folly Oval. If you’re in luck, you may find local men, donning white uniforms, playing cricket. Should you see a match being played, stop to catch your breath and watch the entertaining game! Just before the field, there is a stone gate leading to a dirt road. Head north along this road, following it as it curves to the right. At the end of the road, you’ll see the remnants of: 

8. FOLLY MANSION

Stop Description: Alfred Mitchell, an American millionaire, visited Port Antonio and fell under the town’s spell. In 1901, he bought a 90-acre estate and began constructing a grand two-storey mansion with 60 rooms, Doric columns, inner-courtyards and impressive stairways. Mitchell reportedly built the mansion as a home for his family. Some years after its construction, the mansion began to crumble and many fantastic stories now surround the house. Some Jamaicans will tell you that Mitchell’s wife, for whom he built the house, broke his heart and so the symbol of their love – the mansion –fell to pieces. Others may say that in his haste to build the house, Mitchell allowed saltwater (or sea-sand) to be used in the cement mixture, which compromised its strength. The most logical theory is, however, that the use of an ill-proportioned mixture of marl and cement, as well as the position of the house, facing the full brunt of the ocean breeze, caused it to fall into ruin. Today, what remains of the Folly Mansion offers a great tale of wealth, love and loss. 

Directions: Beside the mansion stands the Folly Point Lighthouse. To get to the lighthouse, retrace your steps along the dirt road. At the fork, continue north to the point or you may cut across the fields to the northwest of the mansion. 

9. FOLLY POINT LIGHTHOUSE

Stop Description: This Port Antonio landmark has lit the shoreline of the East Harbour since 1885. About 40 feet high, the red and white striped lighthouse stands proudly atop honeycombed limestone, overlooking the sparkling Caribbean Sea. Coconut trees, their bases uniformly painted white, adorn the immaculately manicured grounds, surrounding the lighthouse. Check in with the lighthouse keeper, and spend sometime exploring the limestone rocks and lawn around the tower. From these vantage points, you’ll see picturesque views of Port Antonio, Navy Island and Folly Mansion.