Orlando → Savannah, Georgia (Southern Charm Road Trip)

Trip Snapshot:

Distance & time: ~285 miles one-way (about 4.5 hours driving).
Best time: Spring (March–May, azaleas blooming) or fall (October–November, mild weather). Summers are hot/humid; winters are quiet and cooler.
Ideal for: History buffs, foodies, slow-strolling romantics.
Quick route: Orlando → I‑4 East to I‑95 North (past Jacksonville) → Savannah Historic District. (Add Tybee Island for the beach, about 18 miles further).
Top 3 highlights: Forsyth Park’s fountain • The 22 historic squares & cobbled streets • River Street along the Savannah River.

Route Overview: It’s a straight shot north on I‑95 once you get out of the Orlando area. The drive is roughly 4.5 hours, not counting stops consider a pit stop halfway in Jacksonville or St. Augustine. Savannah’s Historic District is the goal: it’s the largest National Historic Landmark district in the U.S., a grid of elegant squares, oak-lined avenues, and antebellum architecture. Once there, park the car (Savannah is very walkable) and explore on foot or via trolley tour. You might spend one night or the whole weekend you can also add nearby Tybee Island for a beachside bonus. This road trip is as much about the destination as the journey, but the ride up I‑95 is easy and gives you a taste of the Lowcountry scenery (pine forests, coastal marshes). Enjoy the contrast between Orlando’s theme-park vibe and Savannah’s stately, slow-paced charm.

Top Stops & Experiences:

Savannah Historic District(Family-friendly) The crown jewel of the trip. This roughly 2.5-square-mile district encompasses downtown Savannah’s famed 22 park-like squares, beautifully preserved homes, churches, and museums. Stroll down Jones Street (often called the most beautiful street in America) under moss-draped live oaks. Each square has its own character Chippewa Square is where Forrest Gump’s bench scene was filmed (the bench was a movie prop and has since been removed to a museum, but the square is still lovely for a sit-down). Don’t miss Monterey Square (site of Mercer House from Midnight in the Garden of Good and Evil) or Reynolds Square (with a monument to city founder Oglethorpe). The entire district oozes history and yes, it’s America’s largest urban historic landmark district, established in 1955. Simply wandering on foot or by trolley tour is the best way to soak it in.
Forsyth Park(Family-friendly) Savannah’s iconic 30-acre park at the southern end of downtown, famous for its enormous white fountain (dating to 1858). The fountain is one of Savannah’s most photographed spots a majestic centerpiece often surrounded by blooming azaleas in spring and framed by Spanish moss-laden oaks. There are playgrounds for kids, plenty of benches, and often you’ll catch a wedding or photoshoot happening. Tip: Each St. Patrick’s Day, they dye the fountain water green! The park is great for a picnic or just people-watching; you’ll often find art students sketching under a tree or a musician strumming on a bench.
River Street & Factors Walk(Family-friendly) Head down to the Savannah River waterfront, where old cotton warehouses have been converted into candy shops, pubs, galleries, and boutiques. River Street itself is cobblestoned (wear comfy shoes) with plenty of places to grab pralines or a drink and watch cargo ships glide by. You’ll see the Waving Girl statue at the riverfront a tribute to Florence Martus, who according to legend waved to every ship for 44 years. Along Factors Walk (above River Street) you can see iron bridges and old cotton factors’ offices reminders of Savannah’s cotton trading era. It’s touristy but charming, especially with a bag of fresh-made pecan pralines in hand from River Street Sweets or Savannah’s Candy Kitchen (free samples abound!). At night, the gas lamps and faint sounds of riverboat music give it a magical feel.
Bonaventure Cemetery(Family-friendly, for those who appreciate history/atmosphere) A short drive east of downtown (about 15 minutes) takes you to this world-famous Southern Gothic cemetery. Immortalized in Midnight in the Garden of Good and Evil, Bonaventure is hauntingly beautiful: moss-draped oaks over ornate headstones and statues, set along the Wilmington River. Even those who don’t usually visit cemeteries will find it captivating for a peaceful walk. Allow about an hour to wander the main lanes (a map from the visitor center can guide you to notable graves like lyricist Johnny Mercer or poet Conrad Aiken). It closes at 5 p.m. daily. The serene scenery and elaborate monuments make it a photographer’s dream (just be respectful it’s still an active cemetery).
Tybee Island Light Station & Museum(Family-friendly) If you crave some beach time, Tybee Island is Savannah’s beach town. The big attraction is the historic Tybee Lighthouse, Georgia’s oldest (first built in 1736, current structure 1867). You can climb its 178 steps to the top for sweeping Atlantic Ocean views a bit of a workout, but worth it for the breeze and scenery. Next door, the keeper’s cottages and a small museum give insight into Tybee’s maritime history. Afterwards, Tybee’s North Beach is a short walk from the lighthouse (less crowded than the main South Beach). Tybee has a quirky, laid-back vibe don’t expect luxury, but it’s perfect for a flip-flop afternoon.
Fort Pulaski National Monument(Family-friendly) History enthusiasts might detour on the way to Tybee to visit this Civil War-era brick fort. Fort Pulaski has a moat, drawbridges, and cannon display kids love exploring its tunnels and ramparts. It’s famous for the 1862 battle where Union rifled cannon forced a Confederate surrender, showing the obsolescence of masonry forts. You can walk the perimeter trail to see cannon damage still visible in the walls. It’s about 30 minutes from downtown Savannah, on the road toward Tybee. Bring bug spray (marshy environs = mosquitoes in warm months). The site offers a fascinating look at military history amid scenic coastal marshland.
Evening Ghost Tour (various)(Adults-only, PG-13) Savannah consistently ranks among America’s most haunted cities, and nighttime ghost tours are popular. You can choose from trolley ghost tours, walking tours with costumed guides, even pub crawl ghost tours. They’ll take you to eerie cemeteries, old mansions, and tell tales of restless spirits (many rooted in real history yellow fever epidemics, war, etc.). It’s a fun way to cap an evening, though younger kids might find it spooky. Popular options include the “Ghosts & Gravestones” trolley or Blue Orb’s walking tours. On weekends, book ahead as they do sell out.

Where to Eat & Stay:
– Food: Savannah is a foodie haven with a mix of old Southern and trendy new. For a quintessential experience, try Mrs. Wilkes Dining Room for a family-style Southern lunch (fried chicken, collards, biscuits people line up early; it’s cash only). The Olde Pink House offers upscale Southern cuisine in an elegant historic home (dine in a former mansion’s parlor by candlelight). Don’t miss sampling pralines on River Street or grabbing an icy Chatham Artillery Punch (local cocktail) if you imbibe. Other favorites: Leopold’s Ice Cream (since 1919, often a line out the door for flavors like Tutti Frutti) and Fox & Fig for a vegetarian twist on Southern comfort.
– Lodging: Staying in the Historic District is the way to go. Bed-and-breakfast inns are abundant think four-poster beds in restored Victorian homes. The Marshall House (1851) is a popular historic hotel rumored to have friendly ghosts. For river views, River Street Inn or Hotel Indigo put you by the water. Families might prefer mid-range hotels near Bay Street (Hyatt, DoubleTree) which are walkable to everything. If you desire oceanfront, Tybee Island has beach motels and rental cottages (just note you’ll be 30 minutes from downtown). Spring and fall weekends can book up quickly due to festivals and weddings, so reserve early.

Detours & Extensions:

St. Augustine, Florida (add 2–4 hours, on the way): If you have extra time en route, stop in St. Augustine the nation’s oldest city (founded 1565). It’s right off I‑95 about 1.5 hours from Orlando. Highlights include the Castillo de San Marcos (17th-century Spanish stone fort) and the charming Old Town streets like St. George Street. Even a lunch stop here is rewarding enjoy a Cuban sandwich at a sidewalk café or pop into the Pirate Museum. Then continue north to Savannah.
Wormsloe Historic Site (add 1–2 hours): Just 20 minutes southeast of Savannah’s center lies Wormsloe, famous for its dramatic oak avenue. Imagine a mile-long driveway canopied by live oaks and Spanish moss it’s an Instagram favorite. Wormsloe was a colonial estate; you can visit ruins of the old tabby house and a small museum. Closed on Tuesdays; modest entry fee. It’s a quick but unforgettable detour for that quintessential Savannah photo under the mossy oaks.

Practical Tips:

Parking: Savannah’s Historic District has mostly metered street parking (free nights & Sundays) and some garages. The Liberty Street Garage and Robinson Garage are centrally located options if you want to park once and forget it. Many B&Bs have limited parking included. Once parked, you really can walk everywhere or use the free DOT shuttle (runs around downtown). Tip: Don’t park facing the wrong direction on a street Savannah will ticket for that.
Weather: Spring and fall are delightful (60s-80s°F). Summer is hot, humid, and buggy tour indoors (museums, shops) during midday and enjoy squares in morning/evening. Afternoon thunderstorms are common in summer. Winters are generally mild (40s-60s°F), though a cold snap can occur. Dress in casual layers; even finer dining in Savannah doesn’t demand very formal attire (though some upscale places appreciate jackets for gentlemen). Comfortable walking shoes are a must on those brick sidewalks and cobblestones.
Dress & Etiquette: “Casual resort wear” is perfectly fine for most activities sundresses, khakis, shorts are all seen. If you plan a fancy dinner or night out at a rooftop bar (like The Peregrin or Ele and the Chef’s spots), smart casual works. Savannah is open-container in the Historic District you can carry a plastic cup of beer/wine on the street (no glass). It’s common to grab a to-go cocktail from a bar and wander, but of course, do so responsibly.
Safety: Savannah is generally safe in tourist areas, but some outskirts can be sketchy after dark. Stick to well-lit, populated streets at night (the walk along River Street and through the squares is active in evenings). Watch your step on uneven pavement, especially after a few Chatham Artillery Punches!

Rentals & Logistics: A midsize sedan or SUV is perfect for the I‑95 cruise good fuel economy and comfortable for the 4+ hour haul. You won’t need 4WD or anything special. If you’re a smaller party, even a compact car will do, but you might appreciate a bit more space for luggage and any antiques or goodies you buy in Savannah’s boutiques. Make sure your rental has cruise control for the long highway stretches. One consideration: if you plan to stay in Savannah’s historic inns, parking can be tight smaller vehicles fit easier in B&B lots or on narrow streets. Leaving Orlando, take I‑4 East to I‑95 North and just stay on 95 through Georgia exit 99A (I-16 East) which leads into downtown Savannah. It’s one of the easier navigation trips you’ll find. With your car sorted and sweet tea on your mind, you’re set to experience Spanish moss and Southern hospitality.

Orlando → Savannah, Georgia (Southern Charm Road Trip)

Trip Snapshot:

Distance & time: ~285 miles one-way (about 4.5 hours driving).
Best time: Spring (March–May, azaleas blooming) or fall (October–November, mild weather). Summers are hot/humid; winters are quiet and cooler.
Ideal for: History buffs, foodies, slow-strolling romantics.
Quick route: Orlando → I‑4 East to I‑95 North (past Jacksonville) → Savannah Historic District. (Add Tybee Island for the beach, about 18 miles further).
Top 3 highlights: Forsyth Park’s fountain • The 22 historic squares & cobbled streets • River Street along the Savannah River.

Top Stops & Experiences:

Savannah Historic District(Family-friendly) The crown jewel of the trip. This roughly 2.5-square-mile district encompasses downtown Savannah’s famed 22 park-like squares, beautifully preserved homes, churches, and museums. Stroll down Jones Street (often called the most beautiful street in America) under moss-draped live oaks. Each square has its own character Chippewa Square is where Forrest Gump’s bench scene was filmed (the bench was a movie prop and has since been removed to a museum, but the square is still lovely for a sit-down). Don’t miss Monterey Square (site of Mercer House from Midnight in the Garden of Good and Evil) or Reynolds Square (with a monument to city founder Oglethorpe). The entire district oozes history and yes, it’s America’s largest urban historic landmark district, established in 1955. Simply wandering on foot or by trolley tour is the best way to soak it in.
Forsyth Park(Family-friendly) Savannah’s iconic 30-acre park at the southern end of downtown, famous for its enormous white fountain (dating to 1858). The fountain is one of Savannah’s most photographed spots a majestic centerpiece often surrounded by blooming azaleas in spring and framed by Spanish moss-laden oaks. There are playgrounds for kids, plenty of benches, and often you’ll catch a wedding or photoshoot happening. Tip: Each St. Patrick’s Day, they dye the fountain water green! The park is great for a picnic or just people-watching; you’ll often find art students sketching under a tree or a musician strumming on a bench.
River Street & Factors Walk(Family-friendly) Head down to the Savannah River waterfront, where old cotton warehouses have been converted into candy shops, pubs, galleries, and boutiques. River Street itself is cobblestoned (wear comfy shoes) with plenty of places to grab pralines or a drink and watch cargo ships glide by. You’ll see the Waving Girl statue at the riverfront a tribute to Florence Martus, who according to legend waved to every ship for 44 years. Along Factors Walk (above River Street) you can see iron bridges and old cotton factors’ offices reminders of Savannah’s cotton trading era. It’s touristy but charming, especially with a bag of fresh-made pecan pralines in hand from River Street Sweets or Savannah’s Candy Kitchen (free samples abound!). At night, the gas lamps and faint sounds of riverboat music give it a magical feel.
Bonaventure Cemetery(Family-friendly, for those who appreciate history/atmosphere) A short drive east of downtown (about 15 minutes) takes you to this world-famous Southern Gothic cemetery. Immortalized in Midnight in the Garden of Good and Evil, Bonaventure is hauntingly beautiful: moss-draped oaks over ornate headstones and statues, set along the Wilmington River. Even those who don’t usually visit cemeteries will find it captivating for a peaceful walk. Allow about an hour to wander the main lanes (a map from the visitor center can guide you to notable graves like lyricist Johnny Mercer or poet Conrad Aiken). It closes at 5 p.m. daily. The serene scenery and elaborate monuments make it a photographer’s dream (just be respectful it’s still an active cemetery).
Tybee Island Light Station & Museum(Family-friendly) If you crave some beach time, Tybee Island is Savannah’s beach town. The big attraction is the historic Tybee Lighthouse, Georgia’s oldest (first built in 1736, current structure 1867). You can climb its 178 steps to the top for sweeping Atlantic Ocean views a bit of a workout, but worth it for the breeze and scenery. Next door, the keeper’s cottages and a small museum give insight into Tybee’s maritime history. Afterwards, Tybee’s North Beach is a short walk from the lighthouse (less crowded than the main South Beach). Tybee has a quirky, laid-back vibe don’t expect luxury, but it’s perfect for a flip-flop afternoon.
Fort Pulaski National Monument(Family-friendly) History enthusiasts might detour on the way to Tybee to visit this Civil War-era brick fort. Fort Pulaski has a moat, drawbridges, and cannon display kids love exploring its tunnels and ramparts. It’s famous for the 1862 battle where Union rifled cannon forced a Confederate surrender, showing the obsolescence of masonry forts. You can walk the perimeter trail to see cannon damage still visible in the walls. It’s about 30 minutes from downtown Savannah, on the road toward Tybee. Bring bug spray (marshy environs = mosquitoes in warm months). The site offers a fascinating look at military history amid scenic coastal marshland.
Evening Ghost Tour (various)(Adults-only, PG-13) Savannah consistently ranks among America’s most haunted cities, and nighttime ghost tours are popular. You can choose from trolley ghost tours, walking tours with costumed guides, even pub crawl ghost tours. They’ll take you to eerie cemeteries, old mansions, and tell tales of restless spirits (many rooted in real history yellow fever epidemics, war, etc.). It’s a fun way to cap an evening, though younger kids might find it spooky. Popular options include the “Ghosts & Gravestones” trolley or Blue Orb’s walking tours. On weekends, book ahead as they do sell out.

Detours & Extensions:

St. Augustine, Florida (add 2–4 hours, on the way): If you have extra time en route, stop in St. Augustine the nation’s oldest city (founded 1565). It’s right off I‑95 about 1.5 hours from Orlando. Highlights include the Castillo de San Marcos (17th-century Spanish stone fort) and the charming Old Town streets like St. George Street. Even a lunch stop here is rewarding enjoy a Cuban sandwich at a sidewalk café or pop into the Pirate Museum. Then continue north to Savannah.
Wormsloe Historic Site (add 1–2 hours): Just 20 minutes southeast of Savannah’s center lies Wormsloe, famous for its dramatic oak avenue. Imagine a mile-long driveway canopied by live oaks and Spanish moss it’s an Instagram favorite. Wormsloe was a colonial estate; you can visit ruins of the old tabby house and a small museum. Closed on Tuesdays; modest entry fee. It’s a quick but unforgettable detour for that quintessential Savannah photo under the mossy oaks.

Practical Tips:

Parking: Savannah’s Historic District has mostly metered street parking (free nights & Sundays) and some garages. The Liberty Street Garage and Robinson Garage are centrally located options if you want to park once and forget it. Many B&Bs have limited parking included. Once parked, you really can walk everywhere or use the free DOT shuttle (runs around downtown). Tip: Don’t park facing the wrong direction on a street Savannah will ticket for that.
Weather: Spring and fall are delightful (60s-80s°F). Summer is hot, humid, and buggy tour indoors (museums, shops) during midday and enjoy squares in morning/evening. Afternoon thunderstorms are common in summer. Winters are generally mild (40s-60s°F), though a cold snap can occur. Dress in casual layers; even finer dining in Savannah doesn’t demand very formal attire (though some upscale places appreciate jackets for gentlemen). Comfortable walking shoes are a must on those brick sidewalks and cobblestones.
Dress & Etiquette: “Casual resort wear” is perfectly fine for most activities sundresses, khakis, shorts are all seen. If you plan a fancy dinner or night out at a rooftop bar (like The Peregrin or Ele and the Chef’s spots), smart casual works. Savannah is open-container in the Historic District you can carry a plastic cup of beer/wine on the street (no glass). It’s common to grab a to-go cocktail from a bar and wander, but of course, do so responsibly.
Safety: Savannah is generally safe in tourist areas, but some outskirts can be sketchy after dark. Stick to well-lit, populated streets at night (the walk along River Street and through the squares is active in evenings). Watch your step on uneven pavement, especially after a few Chatham Artillery Punches!