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Penelope the Pineapple's Charleston Itinerary
John Rutledge House Inn is one of Penelope the Pineapple's Charleston Itinerary.

1. John Rutledge House Inn

8.3
116 Broad Street, Charleston, SC
Bed and Breakfast · Harleston Village · 10 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Accommodations for week one of Penelope's vacation. Perfect location for exploring Charleston's Museum Mile and other historic landmarks. The piazza is a great place to relax with a tea and a book.

The Old Exchange & Provost Dungeon is one of Penelope the Pineapple's Charleston Itinerary.

2. The Old Exchange & Provost Dungeon

8.1
122 E Bay St (at Broad St), Charleston, SC
Historic and Protected Site · Charlestowne · 17 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Beautiful with a fascinating history. This site played a pivotal role America establishing itself as a free and independent nation. John Rutledge was sworn in as the first President of SC here.

Gibbes Museum Of Art is one of Penelope the Pineapple's Charleston Itinerary.

3. Gibbes Museum Of Art

7.8
135 Meeting St, Charleston, SC
Art Museum · Downtown Charleston · 12 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: The traveling exhibits are amazing. Penelope arrived in time to see this summer's Mary White "Working South" watercolor show and returned for the fall's "Rock and Roll Photography" exhibit.

Wentworth Mansion is one of Penelope the Pineapple's Charleston Itinerary.

4. Wentworth Mansion

8.3
149 Wentworth St (Smith Street), Charleston, SC
Hotel · Harleston Village · 10 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Penelope checked in to relax, restore and enjoy a luxurious week-long stay. She fell in love with the view from its 360-degree cupola: the clear view of steeples, especially. Read more.

Middleton Place is one of Penelope the Pineapple's Charleston Itinerary.

5. Middleton Place

8.6
4300 Ashley River Rd, Charleston, SC
Historic and Protected Site · west of the Ashley · 22 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Charleston has a rich culinary history and it all began here! Penelope visited on Rice Harvest Day, a celebration that happens each year in September. The gardens here are beau-ti-ful!

Circa 1886 Restaurant is one of Penelope the Pineapple's Charleston Itinerary.

6. Circa 1886 Restaurant

8.8
149 Wentworth St, Charleston, SC
Southern Food Restaurant · Harleston Village · 27 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: After visiting Middleton Place, Penelope went to Circa 1886 for Plantation Rice Rolls. A nod to Charleston's past, made from rice flour & served with whipped olive oil. A delicious starter.

St. Philip's Church is one of Penelope the Pineapple's Charleston Itinerary.

7. St. Philip's Church

7.8
142 Church St (at Queen St), Charleston, SC
Church · French Quarter · 9 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: One of many steeples visible from the Wentworth Mansion cupola. Home to the city's oldest congregation. The church and its building have many incredible stories to tell. Read more.

St. Michael’s Church is one of Penelope the Pineapple's Charleston Itinerary.

8. St. Michael’s Church

71 Broad St (at Meeting St), Charleston, SC
Church · Charlestowne · 11 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Steeple visible from the Wentworth Mansion cupola. Built on St. Philip’s original land plot. President George Washington and Oprah worshiped here. John Rutledge is buried in the graveyard. Read more.

The Cathedral of Saint John The Baptist is one of Penelope the Pineapple's Charleston Itinerary.

9. The Cathedral of Saint John The Baptist

120 Broad St (at Legare St), Charleston, SC
Church · Harleston Village · 8 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Steeple is visible from the Wentworth Mansion. Such a majestic site to see from inside and out. Read more.

Kings Courtyard Inn is one of Penelope the Pineapple's Charleston Itinerary.

10. Kings Courtyard Inn

8.5
198 King St, Charleston, SC
Bed and Breakfast · Downtown Charleston · 10 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Penelope had the perfect balance: peaceful relaxation in the center of downtown Charleston. She loved its hidden courtyards and fountains - and afternoon wine and cheese. Read more.

11. Cannon Park

7.6
131 Rutledge Ave, Charleston, SC
Park · Harleston Village · 5 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Original site of the Charleston Museum before it was taken down in flames. If you brought your dog along for a Charleston vacation, they'll love this spot's charming little dog park. Read more.

Hampton Park is one of Penelope the Pineapple's Charleston Itinerary.

12. Hampton Park

9.3
30 Mary Murray Dr (at Cleveland St), Charleston, SC
Park · Downtown Charleston · 25 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Worth the trip! Bring a picnic and sprawl out beside the beautiful gardens. Sit near the fountain and wait for a breeze. Jog around its 1-mile perimeter/original race track. Read more.

Cistern Yard is one of Penelope the Pineapple's Charleston Itinerary.

13. Cistern Yard

66 George St (at Saint Phillip St), Charleston, SC
College Quad · Harleston Village · 7 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: Short walk from Kings Courtyard Inn. A green space in the center of downtown, its home base is the College of Charleston! Claim a spot on a bench and wait for passing time. The energy is inspiring. Read more.

Fulton Lane Inn is one of Penelope the Pineapple's Charleston Itinerary.

14. Fulton Lane Inn

8.6
202 King Street, Charleston, SC
Bed and Breakfast · Downtown Charleston · 12 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: The last inn on Penelope's itinerary, on King Street, but accessed by a charming little alleyway. The Fulton Lane Inn gave Penelope almost instant access to the sites left on her itinerary. Read more.

Philadelphia Alley is one of Penelope the Pineapple's Charleston Itinerary.

15. Philadelphia Alley

Charleston, SC
Garden · French Quarter · 4 tips and reviews

Charming Inns of CharlestonCharming Inns of Charleston: A narrow cobblestone passageway. So pretty. Our homegrown musical artist Darius Rucker (from Hootie and the Blowfish fame) strolled down this alley in his latest music video “Come Back." Read more.