Fly into Savannah/Hilton Head International Airport and plan on about a 20–25 minute ride into the Historic District, depending on traffic. For a girls trip, I’d aim for an Airbnb near Forsyth Park, Taylor Square, or one of the quieter residential blocks just off Bull Street so you can walk to dinner, parks, and shops without juggling cars all weekend. Expect check-in to take an hour or two once you arrive; if you’re landing before your place is ready, drop bags first and head out on foot. For a 5-bed setup, start looking early and filter for whole-home stays with at least 3 bathrooms if you can — the best spots here go fast, especially in October.
After settling in, make Forsyth Park your first real Savannah moment. It’s the city’s classic “okay, now we’re here” spot: the white fountain, the live oaks, the Spanish moss, and lots of easy photo ops without needing a big plan. It’s especially pretty in late afternoon when the light softens and the park feels alive but not packed. This is a free stop, and you only need about an hour; if you’re up for it, wander the surrounding streets a bit too, since the blocks around the park are some of the prettiest in town. From most Historic District Airbnbs, it’s an easy walk, but an Uber or quick drive is fine if you’re farther north.
From the park, head downtown to Leopold’s Ice Cream on Broughton Street for an easy first-night treat. It’s one of those Savannah institutions that actually lives up to the hype — old-school, a little nostalgic, and perfect when you don’t want anything too heavy before dinner. Expect around $8–15 per person, and if there’s a line, it usually moves reasonably well; give yourself about 45 minutes total. If you’re walking from the Historic District, it’s doable, but after sunset or if anyone’s in heels, I’d just Uber the short hop so you save your feet for later.
Make dinner reservations at The Olde Pink House well in advance — this is one of Savannah’s most iconic tables, and it books up fast, especially for groups. Plan for 1.5–2 hours and about $35–70 per person depending on cocktails, seafood, and whether everyone goes all in on dessert. It’s a very Savannah-first-night choice: historic, polished, a little special without feeling too formal. After dinner, walk or ride down to River Street for a relaxed end to the night — just enough time to browse the shops, hear the riverfront buzz, and take in the cobblestones and string lights. It’s an easy way to close out arrival day without overdoing it, and the walk back to the Historic District is short if you’re staying nearby; otherwise, grab a quick rideshare back to the Airbnb.
Get there early — this is one of those Savannah experiences where the line is part of the story. Mrs. Wilkes Dining Room is open for lunch only on weekdays, usually around 11:00 AM to 2:00 PM, and it’s cash-friendly, old-school, and worth the wait. Plan on about $25–40 per person depending on drinks and tip. Go as a group and don’t expect a fast meal: it’s family-style, so you’ll share fried chicken, collards, black-eyed peas, cornbread, mac and cheese, and whatever else the table keeps sending your way. From most Historic District Airbnbs, it’s an easy 5–10 minute rideshare or a pleasant walk if you’re staying nearby, but I’d still grab an Uber/Lyft so nobody has to think about parking.
After lunch, head over to the Owens-Thomas House & Slave Quarters, one of the most important historic sites in the city and a very different kind of Savannah stop. Reserve a ticket if you can, since tours typically run in timed slots and the visit takes about 1 to 1.5 hours. Expect around $15–25 per person depending on admission type. It’s thoughtful, guided, and intimate — a great contrast to the big, pretty mansion tours Savannah is known for. From there, it’s a short 5–10 minute rideshare or 15-minute walk to the Cathedral Basilica of St. John the Baptist in the Cathedral District. Even if you’re not religious, go for the architecture alone: the stained glass, the vaulted ceiling, and the front steps make it one of the prettiest photo stops in town. It’s usually free, though donations are appreciated, and a quick 30–45 minutes is plenty unless you want to linger.
By this point, give yourselves some breathing room and stroll Broughton Street. It’s Savannah’s easiest shopping strip for a girls trip: boutiques, jewelry stores, little home-goods shops, and a few good places to duck in for a drink or a snack. This is the time to wander, not rush — pop into the stores that catch your eye, grab iced coffee, and do your people-watching. Most of it is very walkable from the Cathedral District or a quick rideshare if your feet are tired. If you want to keep it practical, this is also the best window to head back to the Airbnb for a quick outfit change before dinner, since the evening gets more polished.
For dinner, book The Grey if you can — it’s one of the best special-occasion restaurants in town, set in a beautifully restored old Greyhound station with a refined but not stuffy vibe. Dinner is usually the splurge meal of the day, around $45–80 per person depending on what you order and whether you do cocktails. Make a reservation, aim for around 6:30 to 8:00 PM, and plan on 2 hours so you can actually enjoy it. From there, it’s an easy rideshare to Savannah Smiles Dueling Pianos in the City Market area for a fun, high-energy girls’ night finish. It’s loud, lively, and very much the kind of place where the whole room ends up singing along, so don’t go expecting a quiet cocktail bar. Cover is usually modest, drinks add up fast, and 2 hours is a good amount of time before calling it a night.
Start the day at Bonaventure Cemetery while it’s still quiet and the light is soft — that’s when it feels most Savannah. It’s about a 15–20 minute drive from the Historic District, and rideshare is the easiest move unless you’ve got a car. Plan for roughly $15–25 each way in an Uber/Lyft depending on where your Airbnb is. Give yourselves about 90 minutes to wander; the grounds are free to enter, though a guided tour or maps can make the history hit harder if you’re into the lore. Wear comfy shoes, bring water, and go early enough to avoid the heat if October still feels like summer.
Head back downtown for a reset at Savannah Coffee Roasters, which is one of the easier spots for a casual brunch/coffee break without overcomplicating the day. It’s a good place to grab sandwiches, pastries, and strong coffee; most people spend around $12–25 per person here. After that, walk or rideshare over to the Telfair Museums Jepson Center for a dose of modern art and air conditioning. The Jepson is right in the downtown core, so if you’re staying in the Historic District it’s usually a short 5–10 minute ride or a pleasant 15–20 minute walk depending on your starting point. Budget about an hour to an hour and a half, and check the current admission price before going — it’s usually in the moderate museum range, worth it if you want a stylish, low-key midday break.
Keep things relaxed with a wander through City Market, where you can browse shops, pick up little souvenirs, and snack as you go. It’s especially fun for a group because nobody has to commit to one plan; you can split up, shop a bit, and regroup for photos and drinks. From there, head to a popular seafood dinner spot near the riverfront — think oysters, shrimp and grits, crab, or a good Lowcountry boil at somewhere like Chive Sea Bar and Lounge, The Shrimp Factory, or A-J’s Dockside if you want the classic Savannah waterfront feel. Expect about $40–85 per person depending on drinks and how indulgent you get. After dinner, wrap the night at a Historic District cocktail lounge like Alley Cat Lounge, Artillery, or Peregrin if you want something a little more elevated and girls-trip friendly; cocktails usually run about $15–25 each, and the best move is to arrive before the late-night rush so you’re not waiting around.
Start your last Savannah morning at The Sentient Bean on Bull Street near Forsyth Park — it’s the kind of easy, unhurried coffee stop that works well before a checkout day. Expect strong espresso, solid breakfast sandwiches, pastries, and plenty of room to sit for a bit while everyone wakes up. Budget about $10–20 per person, and if you’re there on the weekend, plan for a little wait but nothing stressful. From most Historic District Airbnbs, it’s usually a quick 5–10 minute rideshare or walkable if you’re staying south side.
If it’s operating, swing by Forsyth Farmers’ Market around Forsyth Park for one last local loop before you pack up. It usually runs Saturday mornings, so this only works if your departure day lines up — but when it’s on, it’s one of the best ways to grab local snacks, small gifts, peaches, boiled peanuts, or a last coffee while soaking in the neighborhood feel. Give yourselves about an hour, then head a few minutes north into the Historic District for a final photo stop at Chippewa Square — it’s a fast, classic Savannah square and a good “we were really here” moment before everyone starts looking at bags and watches.
Plan on 45–60 minutes back at the Airbnb for packing, bathroom runs, charging phones, and doing one last sweep so nobody leaves a charger or makeup bag behind. If you’ve got a 5-bed Airbnb in the Historic District, this is also the time to load anything bulky and do a quick check of stairs, parking, and trash instructions so checkout doesn’t turn into a scramble. Most hosts in Savannah are pretty specific about trash and linens, and it’s worth following the rules closely to avoid extra fees. If you’re taking an Uber to Savannah/Hilton Head International Airport, leave the house with a cushion — the ride is usually 20–25 minutes, but give yourself a little more on a Sunday if you’re crossing town.
Head out with enough time to return keys, load luggage, and get through the airport without rushing. For a midday flight, I’d be in the car no later than 90 minutes before takeoff, and if you’re driving, leaving Savannah before the late-morning heat and beach traffic picks up is the move. If you end up with a few spare minutes on the way out, the route from the Historic District to the airport is straightforward, so there’s no need to overcomplicate it — just enjoy the last marshy, moss-draped views and start planning the next girls trip.