Explore and wander at leisure through Key West’s colorful history along the charming streets of Old Town.

[click here for printable version] You may make one copy for your personal use, or pick one up at the Oldest House (address on the right side of this page).  This walking tour is recommended on PreservationDirectory.com under self-guided tours in Florida.

The tour takes 1 to 2 hours


Walk the length of Mallory Square; the freestanding walls around the restrooms were once cisterns to collect rainwater for passing ships and the Waterfront Playhouse was originally built as a warehouse. The various masonry-built structures in this area were used for storage of salvage from ships wrecked on the reef, ice brought to the island by steamships from New England and for storing Cuban tobacco when Key West was the cigar-making capital of the world in the 19th century.

1. WALL & COMPANY WAREHOUSE/Waterfront Playhouse, Mallory Square, built in 1879 by the descendants of William H. Wall, an Englishman shipwrecked here in 1824 who started the cigar-making industry in 1831. By 1900, the island had 200 cigar factories, half the population was Cuban and we produced more cigars than anywhere else in the world. In front of the Waterfront Playhouse is the Key West Historic Memorial Sculpture Garden.


2. COAST GUARD BUILDING/Clinton Square Market, Front St. Built in 1856 by the Navy for storage of coal, this building served as headquarters of the East Coast Blockade Squadron in 1861 when Key West was one of the only portions of the South to be in Union soldiers’ control throughout the Civil War. It later served as the Naval Administration Building until 1932, the Coast Guard Headquarters until the 1970s and now has been cleverly adapted to a shopping mall.

3. THE CUSTOMS HOUSE/Key West Art and Historical Museum, Front & Greene Sts. Designed by H. H. Richardson in the Romanesque style for all such Federal buildings (thus the inclusion of fireplaces!) the 1891 landmark was built at a cost of $107,956 and required almost one million bricks. It served as housing for Navy offices, the Post Office and U.S. District Courts. After a $9 million restoration, the building now serves as the Museum of Art and History at the Customs House.


4. GEIGER HOME/Audubon House, 205 Whitehead St. Captain John Geiger and his heirs occupied this home for over 120 years. In 1958, this handsome structure was slated for demolition to make room for a filling station; saving this property from that fate sparked the restoration movement in Key West, led by the Old Island Restoration Foundation. After careful restoration supported by the Mitchell Wolfson family, the home was opened as a museum in1960 to commemorate the1832 visit of John James Audubon and the 19 new species he discovered here for his monumental work, Birds of America. This property, with nearly an acre of lush gardens, is maintained by the Mitchell Wolfson Family Foundation, heirs of the man who saved it.


5. PRESIDENTIAL GATES, Whitehead at Caroline Sts. Installed in 1906 as the ceremonial entrance into the Navy base beyond and only opened for visiting dignitaries. This 40 acre parcel was deactivated in 1974 and was purchased by a developer in 1987 for $17.5 million, and a residential community, called Truman Annex, was built on the old base. The Gates maintain the tradition of opening only for dignitaries. Former presidents Jimmy Carter and Bill Clinton (as well as Colin Powell) have been through these gates in recent years.


6. HARRY S TRUMAN LITTLE WHITE HOUSE, 111 Front St. Built in 1890 by the Navy as a duplex for the commandant and paymaster, it was transformed into a vacation home for President Truman in 1948. President Eisenhower also made use of this retreat while he was in office. It is Florida’s only presidential home site and is presented by Historic Tours of America as a commemoration of the Truman years.


7. AERO-MARINE AIRWAYS/ Kelly’s, 301 Whitehead St. Originally built on the Porter Docks at the foot of Duval St. on the Gulf where sea planes took off and the first international air mail route to Cuba began in 1920. In 1927, Pan American World Airways was created to offer the first international flight service ever for passengers, a 90 mile/1 hour and 20-minute journey from Key West to Havana. Jessie Porter Newton moved this building to its present location when her family sold their waterfront property. She and a partner established the Old Island Trading Post in this building, a shop offering local crafts. Now called Kelly’s, a restaurant and micro-brewery bar once owned by actress Kelly McGillis.


8. CAPT. GEORGE CAREY HOME/Jessie Porter’s Heritage House & Robert Frost Cottage, 410 Caroline St. The original 2-room cottage Carey built here in 1834 was expanded toward the street and to the present 2- story height in 1844 as his family grew. Jessie Porter, the 5th generation of prominent early settlers on the island, purchased the neglected property in 1934, restored and enlarged it and filled it with extraordinary treasures handed down through her family. A popular hostess, Jessie Porter entertained many famous people in the literary and entertainment world including poet laureate Robert Frost, who wintered here from the 1940s until 1960.

9. W. HUNT HARRIS HOUSE, 425 Caroline St. Built about 1900, with unusual double round columns and arched entrance, it was home to Judge Harris who was president of the Florida Senate 1907-09, and later the Lt. Governor of Florida.

10. J. Y. PORTER HOUSE, 429 Caroline St. Built in 1838 with later addition of rare mansard roof and gabled dormers to create a spacious third floor, J. Y. Porter was born here in 1847 and died in the room of his birth 80 years later. Dr. Porter, grandfather of Jessie Porter, was a contributor to yellow fever research and became Florida’s first Public Health Officer. Note hand-wrought iron balconies on the sides.


11. OLDEST HOUSE IN SOUTH FLORIDA, ca. 1829, 322 Duval St. The home of Captain Francis Watlington, his wife and nine daughters for decades, incorporates the influences of colonial architecture found in the Caribbean and New England. Watlington was a Customs Inspector, Lightship Captain and harbor pilot. Of particular note is the only surviving Cook House in South Florida located in the spacious rear garden. It’s currently operated as a non-profit museum by Old Island Restoration Foundation with original furnishings and maritime artifacts.

12. MARTIN HELLINGS HOUSE/Woman’s Club, 319 Duval St. This unusual brick home was built in 1892 by the manager of the International Ocean Telegraph Company. The first public library in South Florida was housed here; since 1941 it has been home to the Key West Woman’s Club. The original carriage house at the rear was cleverly transformed into the Red Barn Theater decades ago.

13. PATTERSON HOUSE/Prudential Knight Realty, 336 Duval St. In 1842,Mrs. Passalogue, a French lady of rare attainments, opened a school here that lasted about two years; note the school bell still hanging on second floor porch. Later inhabitants were the Henry Baldwins, an aristocratic British family who traced their ancestry to Lord Nelson and Sir Robert Walpole. Annie Baldwin and her three daughters taught music here.


14. ST. PAUL’S CHURCH, 401 Duval St. The first Episcopal Church in South Florida was established here with a Christmas Day service in 1832. Early structures on this site were lost to fire and hurricanes. The present church is the fourth built on this corner; it dates from 1916 and incorporates stained glass saved from the earlier structures.

15. WARREN HOUSE/ Old Town Manor, 511 Eaton St. This classical revival home was built in 1886 by Sam Otis Johnson; he had a general store to the right of the house, which was moved to the rear of the property in the early 1900s for garage use. By then this property had became the home and office of Dr. Richard William Warren and remained in the family until his widow’s death in the early 1970s. The tallest cistern in the Keys, 3-stories for gravity fed rainwater into the home, survives at the rear of the property.

16. ALVEREZ HOUSE/The Carriage Trade, 523 Eaton St. Judge Alverez was married to one of the Watlington sisters, daughter of Captain Francis Watlington (see #11 above).

17. OTTO HOUSE/The Artist House, 534 Eaton St. Built by Thomas Osgood Otto in the 1890s in the popular late Victorian style of the period, this home was occupied by his descendent, Eugene Otto, an accomplished artist, until the late 1970s. The painter used the turreted room at the top of the house, with light from all sides through the shuttered windows, as his working studio. As a child, Eugene owned the notorious Robert, the haunted doll, who now resides in the Fort East Martello Museum.

18. UNITED (formerly OLD STONE) METHODIST CHURCH, 600 Eaton St. This handsome structure was built of two-foot thick limestone quarried in the Keys during the 1870s and is the oldest standing religious building on the island. The robust construction withstood the 1886 fire and early 20th century hurricanes. It is shaded by a Spanish Laurel, a ficus variety related to the Banyan.

19. PETER A. WILLIAMS HOUSE/Donkey Milk House, 613 Eaton St. Built in 1866, this home remained in the same family for over 120 years. U.S. Marshall Williams saved his home by dynamiting along Eaton St. during the 1859 fire. As a man of considerable means, his home incorporates a black walnut staircase, Spanish floor tiles and hand-decorated ceilings created by an Italian artist. The large clay pot in front, a “tinajone,” dates from the 1800s, made in Cuba to collect rainwater. Donkey Milk Alley, at the back of this home, was created for the 19th century milkmen who delivered containers of cow’s milk in carts pulled by donkeys.

20. GEORGE H. CURRY HOUSE, 620 Eaton St. This handsome mansion was built after the 1886 fire in grand Classical Revival style. The large trees at the front are Canary Island Date Palms. This property encompassed several of the narrow plots that were originally platted along this street; the home to the right of the main house (#616) was the original carriage house.

EATON STREET was originally known as Church Street due to the three religious structures within one block of each other. The current name comes from John Henry Eaton, U.S. Senator (Tennessee) and member of President Andrew Jackson’s Cabinet. Jackson appointed Eaton to the governorship of Florida.

21. WILLIAM URIAH SAUNDERS HOUSE, 709 Eaton St. Saunders and his wife came from Green Turtle Key, Bahamas and incorporated Bahamian influences in the design of their 1853 home. The central doorway with sidelights and heavy surround mouldings is unusual in Key West.

22. RICHARD PEACON HOUSE, 712 Eaton St. Peacon, owner of the town’s largest grocery store, built this house in the 1890s. Often referred to as the “Octagon House”, it is actually a rectangular structure incorporating a multi-sided front. This once neglected home was restored by the famous designer Angelo Donghia in the 1970s and sold to Calvin Klein in the 1980s for a record price at the time of nearly $1 million.

23. FILER HOUSE, 724 Eaton St. Built in 1885, this unusual home incorporates Victorian fashion of the time with classic Bahamian design. Samuel Filer, who built this house for himself, was a lumber merchant apparently wanting to display extravagant use of wood embellishments know locally as “gingerbread”. Note the etched cranberry glass transom window.

24. JOHN BARTLUM HOUSE/Bahama House #1, 730 Eaton St. This home was built on Green Turtle Cay in the Bahamas in the early 1800s. After losing his Key West residence in the 1846 hurricane, Bartlum dismantled this structure, put it onto a barge in the Bahamas and brought it to this site where it was reassembled in 1847. Bartlum built a famous ship, the Stephen R. Mallory, believed to be the only clipper ship ever built in Florida.


25. RICHARD ROBERTS HOUSE/Bahama House, #2, 408 William St. Brother-in-law of John Bartlum (#24), Roberts also dismantled this Bahamas-built house and reassembled it here in 1847. Low ceiling/porch heights are common to both. Note the hand-planed pine siding of varying widths with unique beading on the lower edges and the exterior stairs on the deep veranda.

26. GIDEON LOWE HOUSE, 409 William St. Recently renovated, the rear portion of this home was originally built in the early 1840s and enlarged toward the street in the 1870s. It is an outstanding example of Classical Revival proportions and detailing.

27. ISLAND CITY HOUSE, 411 William St. Built in the late 1800s as a private home for a wealthy Charleston merchant family, it was converted into a hotel by its owners in anticipation of the railroad’s arrival in 1912. By the late 1940s this enormous structure had fallen upon hard times, and was condemned by the City. The neglected building, with distinctive 3-story wrap-around verandas, underwent a massive restoration in the late 1970s when the tourist industry was just beginning to revitalize after the Navy down-sized heavily.

28. WILLIAM RUSSELL HOUSE/Key West Bed and Breakfast, 415 William St. This turn-of-the-century home incorporates unusual double/triple columns adorned by ornamental trim across the front porch.

29. SHORT JACKET METHODIST CHURCH/Southernmost Prayer & Faith Center Church, Corner of William & Fleming Sts. The unusual name comes from the many members who were seamen and traditionally wore short jackets. First established on this corner in 1884, the original structure was destroyed in the 1909 hurricane. The present concrete building was completed in 1912.

FLEMING STREET is named for John W. C. Fleeming, an Englishman and business partner of John Simonton (the New Jersey gentleman who bought the island for $2,000 in 1822). Fleeming saw the potential for a salt industry on the island.


30. THE ROBERTS HOMES, 512 & 516 William St. The graceful “eyebrow” house at #512, a style unique to Key West (named for upper windows shaded by roof overhang) was built by Charles Roberts in the 1890s. His brother, John Samuel Roberts, constructed the Classical Revival home at #516 at the same time. Lowered capitals on the columns allowed for the late Victorian fashion of “gingerbread” embellishments on porches.

31. WILLIAM ALBURY HOUSE, Corner of William & Fleming Sts. One of the earliest homes built in this area; it incorporates the mid-19th century preference of simplified detailing on the 3-sided wrap-around porches and a fine example of the “widow’s walk,” the lofty perch crowning the roof for the sighting of ships approaching the island.

32. Restorations by Jerry Herman, 626 & 628 William St. The well-known lyricist and composer of Hello Dolly and Mame brought these neglected 19th century homes into good order during the years he lived here in the 1980s and 1990s. Herman was responsible for several handsome refurbishments on the island, such as the “twin” houses opposite the library on Fleming Street.

33. EDWARDS ROBERTS HOUSE, 643 William St. This nicely-detailed and proportioned “eyebrow” home was built at the end of the 1800s. Roberts, who was born in Ireland, worked as a ship builder and stone mason in Key West. He worked on the construction of the Old Stone Church in the 1870s (#18).


KEY WEST CEMETERY. The island’s original burial ground, along the southern edge of the island, was badly damaged by the 1846 hurricane. The City established these 16 acres of “high ground” (10’ above sea level) as the new cemetery in 1847. The late poet James Merrill, a writer and Key West resident for many years, described the unique above-ground vaults as “white-washed hope chests.” Numerous family plots contain open roof structures, and some even incorporate masonry buildings. Tours of the cemetery are offered to guide those interested around the many eccentric delights, such as hand-carved angels, pet burials and the headstone proclaiming “I Told You I Was Sick.”


34. WINDSOR VILLAGE/ Writers’ Compound, 713-727 Windsor Lane. Behind the stucco wall and double gates is a Key West phenomenon where numerous small original plots are joined together, some old houses retained, some newer ones added, and a “common” garden area with pool is formed in the center. This is one of the earliest compounds on the island, originally built in the 1950s. After the writers John Hersey, John Ciardi, Richard Wilbur and Ralph Ellison bought winter homes here in 1976 the place became known as The Writer’s Compound, though none of the writers still live here.


35. BENJAMIN BAKER HOUSE, 615 Elizabeth St. Possibly the most “decorated” house in Old Town, this substantial home was built by entrepreneur Baker in 1872 as a wedding gift for his daughter. This house displayed the strength of structures built by ship carpenters when a 1972 “hurricane-spawned tornado” shifted this massive bulk 8’ off its supporting piers; the home was jacked up and returned to its foundations with no structural damage or cracked window panes.


36. JOHN LOWE JR. HOUSE, 620 Southard St. Lowe owned one of the largest sponging fleets in Florida and, as a lumber merchant, had the first sawmill on the island. Construction of his enormous villa, with enclosed “widow’s walk”, or belvedere, took years to build and was completed in 1865.

37. BENJAMIN CURRY HOUSE, 610 Southard St. Curry originally bought the plot for $200. The home was completed in 1856 and remains in the Curry family, now seven generations after Benjamin moved here from the Bahamas.


FREE SCHOOL LANE (Between Southard & Fleming Sts) This lane gave access to one of the first “free”, or public, schools on the island. The 3-story building, built in 1874 and called the Sears school, was demolished in 1909 with the completion of the new Harris School on Southard and Margaret Sts. Nancy Forrester’s Secret Garden, an acre of rare, tropical rainforest, is at the end of this lane. Within it is an 1880s Bahama house and cook house.

38. DR. JOHN MALONEY BUILDING, 500 Simonton St. Commercial buildings favored non-combustible construction after the devastating 1886 fire. Dr. Maloney established his Key West Drug Company in this brick structure. In 1908 Maloney connected this building to the houses adjoining on Fleming St. and established the Louise B. Maloney Hospital, the first private hospital. As surgeon to the Overseas Railway, he treated Henry Flagler’s crew working on the “railway that went to sea” during the years of this massive bridge construction and rail laying.

39. JOHN HASKINS BUILDING/Marquesa Hotel, Simonton & Fleming Sts. Built in 1884, and narrowly missing destruction by the 1886 fire, this commercial building with residential attachment has seen various businesses. A “Gent’s Goods” operation was one of the earliest. Later it was used as a drug store, the Key West Gas Company, a car dealership and the second home of Fausto’s Food Palace. The property underwent a large refurbishment and enlargement in the 1980s to create the present hotel and restaurant.

40. WILLIAM R. KERR HOUSE, 410 Simonton St. Architect Kerr designed this home for himself about 1880, employing lessons learned from the then fashionable Downing’s Carpenter Gothic style; the heavy ornamentation, decorative bargeboards and jerkinhead roof distinguish this cottage style. Kerr designed several brick or masonry commercial structures in Key West.

41. DANE ALLEY/Simonton Court, 320 Simonton St. The 2-story building on the street was a cigar factory in the late 19th century. Walk down the lane to the left to see the “cigar-makers cottages” behind that were built by the factory owner for employee housing. At the end of the attractively landscaped lane is an unusual pool created from an old cistern. The historic structures on this 2-acre compound now offer a variety of guest accommodations.

42. THE TREV-MOR/Casa Antigua, 314 Simonton St. This early 1900s building was the first Ford dealership on the island, with two floors of a residential hotel above, run by Messrs. Trevor & Morris. Ernest Hemingway and his second wife, Pauline, stayed here on their first visit to Key West in April 1928. Hemingway fished and worked on the draft of A Farewell to Arms while awaiting delivery of his new Model A. This Mediterranean Revival building has been transformed into a private residence with an extraordinary atrium garden.

43. RICHARD KEMP HOUSE/Cypress House, Simonton & Caroline Sts. The Kemp family moved to Key West from the Bahamas in the early 19th century. William Kemp, brother of Richard, introduced the sponge industry to Key West, from which they prospered. Note the third floor eyebrow-style windows tucked under the roof overhang of this Bahamian-influenced home built after the 1886 fire. The pine and cypress used in the 1800s for construction did not require a protective coat of paint.


44. GEORGE BARTLUM HOUSE, 531 Caroline St. Bartlum, a successful sponge merchant, completed this New England style house in 1888. For many years this was the home of Florida State Senator John Spottswood and his wife Mary. Harry and Bess Truman considered the Spottswoods as their closest friends in Key West and were frequently entertained in this home.

45. MILTON CURRY HOUSE/Curry Mansion Bed and Breakfast, Caroline & Ann Sts. Milton Curry’s father, William, came to Key West from the Bahamas in the 1834. William established a lucrative ship’s chandlery, served as mayor and became Florida’s first millionaire in the late 1800s. His son, Milton, built this exact replica of a 22-room Newport, RI “cottage” in 1905. He was also famous for his extravagant 18K gold flatware, trays, and tea/coffee service/napkin rings created by Tiffany & Company in New York.


46. OLD CITY HALL, 510 Greene St. This 1891 brick structure replaced the original wood City Hall that was destroyed in the 1886 fire. The building was designed by William Kerr (# 40). A market, the jail and the fire department occupied the lower level, with city offices and local courts on the floor above. City Commission meetings, open to the public on a weekly basis, now take place in the spacious second floor chamber, and the Key West Chamber of Commerce and Visitor’s Center is housed on the first floor.


DUVAL STREET evolved as the main thoroughfare for Old Town with shopping and entertainment. It was named for Florida’s first Territorial Governor, William Pope Duval, when Key West was the largest and richest city in the state.

47. OLD CUSTOM HOUSE, 124 Duval St. This mid-1800s building, with distinctive dormers in the mansard roof, was the processing center for the thousands of Cuban and Bahamian immigrants entering the United States in the 1800s. The very profitable cigar-making and salvage industries in Key West were the obvious draw. It was also to this building that wreckers brought their salvage claims for processing. The building was moved to Duval St when the new Custom House was built in 1891 (#3).

48. CLAUDE ROBERTS HOUSE/ Bagatelle, 115 Duval St. Roberts was foreman to the Cortez Cigar Factory. His gracious home, with an unusual curve on the wrap-around porch, had been built on Fleming St. To enable expansion of the Monroe County Public Library in the 1970s, this home was placed on rollers and brought down Duval St. to this new location.


49. FORMER FLORIDA FIRST NATIONAL BANK, (established 1891) Front & Duval Sts. By the late 1800s, with half of the Key West population being Cuban, it should not come as a surprise that this 1897 red and yellow brick building, with heavy Spanish influence, was financed by a group of wealthy cigar manufacturers. The carved balcony along the Duval side, with finely detailed column capitals, and the tower on the corner are particularly noteworthy.

50. BANK OF KEY WEST/ Harbour House, 423 Front St. After destruction by the Great Fire of 1886 the bank was rebuilt in brick, as dictated by City ordinance after the fire, an attempt to make commercial structures more fire resistant. Note the upper balcony, reminiscent of the architecture of New Orleans.

51. JOHN W. SAWYER BUILDING, 400 Front St. Sawyer was a Bahamian-born merchant. After the loss of the 1868 building in the 1886 fire, Sawyer imported Irish bricklayers to construct his new “fancy clothing emporium.”