Four days, two Southern cities, real receipts — but the budget framing this trip usually gets is misleading, so let me put the honest numbers up front before the itinerary.
TL;DR — What This Costs
- ~$1,100/person if you split a room and Ubers with a friend (the version I actually did, with Kelsey).
- ~$800/person if you also cut the trolley tour and book in shoulder season (March-early April or November) when the Fairfield Savannah drops to ~$160/night.
- $2,194 total if one person eats the whole tab — that’s the receipt total below, before splitting.
Below is the line-by-line trip from NYC, the one day I’d script the exact same way next time, and the two I’d change.
The trip in one paragraph
My friend Kelsey and I flew into Savannah on a Thursday midday and flew home the following Monday evening. Three full days in between: Tybee Island the first afternoon, a walking day through the Savannah Historic District with a sunset riverboat cruise on day two, a Hilton Head day pass on day three, and a trolley tour + last meals on the way out Monday. Three nights at the Fairfield Savannah Downtown (Marriott property), American Airlines out of LGA.
Why Marriott + American Airlines, every trip
I fly American Airlines and stay Marriott on every trip — no exceptions. After a decade of stacking one hotel chain and one airline, the points unlock trips that would otherwise cost way more. The Fairfield Savannah is a Bonvoy property — it’s not fancy, but 3 nights got me Bonvoy elite-night credits and a mid-tier redemption on a future trip. Single-chain loyalty pays off slowly, then all at once.
The lesson, especially for a short trip like this: even when the budget hotel isn’t the absolute cheapest, staying in-chain on a property you’ll earn credits at is worth $20-40 of “price difference” I give up.
Best time to visit Savannah + Hilton Head
Late March to early April is the sweet spot: 70s during the day, azaleas blooming in Forsyth Park, restaurants not slammed. I went March 25-28 and hit it perfectly.
Avoid: June-August humidity, October Savannah Film Festival crowds, the St. Patrick’s Day weekend in Savannah (hotel rates 3x, city packed). The Hilton Head day pass in shoulder season (March-May, Oct-Nov) is wide open; in peak summer, Saturdays sell out 10+ days in advance.
What this trip actually cost (real line items, total before splitting)
| Line item | What I paid |
|---|---|
| Flight LGA ↔ SAV (American Airlines) | $576 |
| Fairfield Inn Savannah (3 nights) | $997 |
| Omni Hilton Head day pass (for 2) | $159 |
| Trolley tour | $79.22 |
| Sunset Riverboat Cruise (for 2) | $77.35 |
| Uber to Hilton Head (round trip) | $56 |
| Uber to Tybee | $31 |
| Crab Shack + misc dinners + Ubers | ~$218 |
| Trip total (before split) | $2,194.11 |
That total is for the whole trip. Split with a friend (one shared room, one shared rental of activities) it lands closer to $1,100/person. From NYC; if you’re driving or flying regional, subtract ~$400. The Fairfield was fine but if I were doing it again I’d price-compare a boutique Historic-District place for a small upgrade.
Day-by-day
Day 1 (Thursday): arrive + Tybee Island
7:10 AM LGA → 12:21 PM SAV. Uber to downtown, drop bags. Afternoon on Tybee Island — used the tybeeisland.com “10 things to do” list as our rough guide. Dinner at The Crab Shack.
Day 2 (Friday): the scripted walking day
This is the only day I actually scripted stop-by-stop, and it was the best day of the trip.
- Coffee at Sentient Bean right outside the hotel.
- Morning walk in Forsyth Park — the tunnel of trees. (Next time: earlier. Mid-morning it’s already busy; the shot is at sunrise.)
- Walk north on Bull Street → two blocks east to Lafayette Square → north on Abercorn to Colonial Park Cemetery → east to Chippewa Square.
- Owens-Thomas House & Slave Quarters — one of Savannah’s best historic-home tours and it doesn’t gloss over slavery. Worth the ticket.
- Leopold’s Ice Cream one block north of Owens-Thomas.
- City Market for lunch (Café at City Market or Wet Willie’s).
- River Street — pop into River Street Sweets for a warm praline sample.
- Sunset Riverboat Cruise on the Georgia Queen. $77 for two, ~2 hours. Best-value thing we did on the whole trip.
Day 3 (Saturday): Hilton Head day pass
Omni Hilton Head Oceanfront Resort day pass via ResortPass — $75/person. Pool, beach access, chair, towel, resort facilities. Ubered both ways (~$55 each way from Savannah). Book 7+ days out — Saturdays fill fast in peak season.
Day 4 (Sunday → Monday): last morning + fly home
- Trolley tour on Sunday. We paid $79 and I wouldn’t do it again — the Historic District is too walkable and a good podcast covers the same ground for free.
- Late check-out Monday, 18-minute Uber to airport, 6:07 PM flight home.
The food list (what I actually ate vs. what I’d eat next time)
These are the places I had written down going in. “Had” = actually ate there. Everything else is the next-time list.
- Sentient Bean — coffee (had)
- Leopold’s Ice Cream (had)
- River Street Sweets — warm pralines (had)
- Café at City Market or Wet Willie’s (had one)
- The Paris Market — on my list, missed it, don’t make my mistake
- Andaz for shrimp and grits — on my list
- Mint To Be Mojito — empanadas, on my list
- American Prohibition Museum — Chatham Artillery Punch cocktail
What I’d do differently
- Skip the trolley tour. $79 back in my pocket.
- Actually eat at The Paris Market. Wrote it down, didn’t go, regretted it on the flight home.
- Early-morning Forsyth Park — the tunnel of trees at sunrise is the shot.
- Consider a boutique Historic District hotel instead of the Fairfield, for a $50-100/night upgrade.
Getting around, at a glance
- SAV airport ↔ downtown: 18 min, Uber.
- Inside the Historic District: walk.
- To Tybee: Uber, ~$30 each way.
- To Hilton Head: Uber ~$55 each way. Rental car only if you’re doing Tybee + HHI on back-to-back days.
Want the full printable planner?
I packaged the exact itinerary — the walking-day script, the food list, the $2,194 budget, the Hilton Head day-pass tip — as a printable PDF + HTML + Google Maps KML. $9 for the planner, $14 with the map.
- Savannah + Hilton Head Real Travel Planner — $9 — PDF + HTML
- Savannah + Hilton Head Google My Maps — $5 — KML with every stop pinned
- US Long Weekend Bundle — $24 — Savannah + Pacific Coast products together (save $7)
Heading to the West Coast instead? Read my Pacific Coast 10-day post next — same honest, line-item format.
FAQ
Can you do Savannah + Hilton Head in less than 4 days?
Yes, but you’ll miss one of the three. My recommendation: drop the Hilton Head day pass if you’re cutting a day. The Savannah walking day + Tybee afternoon is the core; HHI is bonus.
Is $997 for 3 nights at the Fairfield a good price?
Peak spring weekend (March 25-28), so not bad. Off-season the same hotel would be $150-180/night. If you’re flexible on dates, early March or late November gets you into a boutique property for the same money.
Was the Omni day pass actually worth $75/person?
Yes — for a resort beach day without paying for a full stay, ResortPass is the right answer. Bring your own snacks; on-property food is a markup.
How many real flight miles did you earn?
~1,500 AAdvantage miles on a $576 ticket — not a big earn, but the Bonvoy elite-night credits from the Fairfield stay were the real multi-year win.
Written by Jenna Fattah
I have visited 25+ countries across 6 continents, attended 7 Formula 1 races, and spent 4 years writing about what actually works and what I would do differently. Every recommendation on this site comes from trips I planned and paid for myself. Read more about me