Trent's Last Ride
Trent's Last Supper
Five days of oysters, scotch, and Uncle Trent wisdom — Savannah style
Home Base
Historic District House with Pool & Hot Tub
Luxury Airbnb — Restored Victorian mansion
This is HQ for five days. A restored Victorian with pool, hot tub, open kitchen, and multiple bathrooms means Trent and the crew have space to breathe, cook together, and enjoy downtime without feeling cramped. Historic District location puts you steps from dive bars, restaurants, and the river — no 30-minute Ubers. Pricing is estimated based on Savannah's April market rates for luxury 4-5 bedroom properties.
$1,800–$2,200/night (estimated for 8-person capacity, April rates)/nightDay 1 — Wheels Down, Uncle Trent Arrives
Arrive at Savannah/Hilton Head International Airport (SAV)
Group meets at baggage claim. Arrange one Uber XL or two rideshares to the historic district house (20-min drive). Settle in, unpack, grab the welcome kit from the kitchen.
Tip: Assign one person to pick up ice, mixers, and a case of Trent's favorite beer on the way to the house.
Settle in at the house — pool & hot tub time
Get comfortable, change into swim gear, crack open cold beers on the deck. This is HQ for five days — no rush, no schedule. Trent sets the pace.
Tip: Take a group photo by the pool for the trip album.
Fly Fishing Charter (Coastal Marshes)
Meet your guide at the dock (15-min drive from the house). 4-hour guided fly-fishing trip through Savannah's marshes — scenic, chill, and perfect for Trent's fly-fishing obsession. Back by 9 PM.
Tip: Bring sunscreen and a light jacket — April evenings can be cool on the water.
Casual dinner at the house
Order takeout from a local spot (Mrs. Wilkes or Zunzi's) or prep a simple pasta dinner at the house. Keep it low-key — everyone's tired from travel and fishing.
Tip: Save energy for the next two days.
Day 2 — Trent's Taste of Savannah
Breakfast at the house
Stock the kitchen with eggs, bacon, fresh fruit, and good coffee. Crew cooks together, eats on the deck. No rush — this is how 40+ guys do mornings.
Tip: Have someone make a killer bloody mary bar with Trent's favorite hot sauce.
Downtime at the house — pool, cards, porch drinks
Three-hour unstructured block. Pool time, poker at the kitchen table, cigars on the porch, cold beers. This is the crew's rhythm — no agenda, just hanging with Uncle Trent.
Tip: Set up a card game with a low buy-in ($20–$50 max) — keeps it fun, not serious.
Savannah Taste Experience (Food Tour)
2.5-hour guided walking tour through the historic district hitting 6+ tastings — oysters, low-country boil samples, craft beverages, local specialties. Trent's in his element. Tour ends near River Street.
Tip: Eat a light lunch before the tour so you can taste everything without getting too full.
Private Oyster Shucking Lesson at the house
A local oyster shucker arrives with a bushel of fresh raw oysters, teaches proper technique, and the crew eats oysters with cold beer on the deck. This is the moment Trent talks about for years — 'Uncle Trent's oyster night.' Pair with Lagavulin 16 for the true experience.
Tip: Have the shucker bring extra lemon and hot sauce — let Trent customize his oysters.
Dive bar crawl — Night 1
Three-bar crawl through historic district dive bars: (1) Barrelhouse South (Congress St, cheap drinks, college vibe), (2) Treylor Park (quirky cocktails, late-night food), (3) Alley Cat Lounge (speakeasy, wind down). Start at Barrelhouse, move to Treylor by 10:30 PM, finish at Alley Cat by 11:30 PM. Keep it chill — no clubs, no bottle service, just good drinks and good company.
Tip: Barrelhouse has pool tables — grab one if available. Alley Cat is small, so arrive before midnight or you'll wait.
Day 3 — Spirits & Recovery
Breakfast at the house
Eggs, bacon, fresh juice, strong coffee. Crew recovers from the oyster night. Trent's pace — no rush.
Tip: Have Gatorade and electrolyte packets on hand for anyone who needs it.
Ghost Coast Distillery Tour & Tasting
1-hour guided tour of Savannah's first post-Prohibition distillery. Tastings of craft spirits, history lesson, and a chance to appreciate single-malt and bourbon. Perfect for Trent's scotch appreciation. Tour ends by 1:30 PM.
Tip: Buy a bottle of their flagship spirit to take home — Trent will appreciate the souvenir.
Downtime at the house — pool, hot tub, cigars
Three-hour recovery block. Pool time, hot tub soaks, cigars on the deck, cold beers. This is the pace Trent wants — no agenda, just crew time.
Tip: Have Club Habana-style cigars on hand (order ahead or grab from a local shop). Pair with Lagavulin neat.
Private Chef Dinner at the house
A local private chef arrives and prepares a multi-course low-country dinner: oyster appetizers, shrimp and grits, local fish, sides. Crew eats together at the house table. This is THE dinner — elevated, personal, and Trent-focused. Chef handles cleanup.
Tip: Request the chef prepare a signature cocktail featuring Lagavulin or a local bourbon to start the meal.
Quiet evening at the house — poker, cigars, whiskey
After the chef dinner, the crew stays at the house. Low-key poker tournament, cigars on the porch, Lagavulin neat, Van Morrison or Willie Nelson on the speakers. This is the honoring moment setup — intimate, no distractions.
Tip: Have the best man prepare his toast notes during this time.
Day 4 — The Main Event (Golf & Steakhouse)
Breakfast at the house
Light breakfast — eggs, toast, fruit, coffee. Fuel up for golf.
Tip: Have everyone hydrate well before heading to the course.
Forsyth Park Golf Club — 18 Holes
Trent and the crew play 18 holes at a solid Savannah course. Carts included, pace is relaxed, and you're back by 5 PM. This is Trent's golf fix — no pressure, just good golf and crew time.
Tip: Book a cart with a cooler — cold beers on the course make it better.
Downtime at the house — shower, rest, get ready
Crew showers, changes, and relaxes before the big steakhouse dinner. Pool time if anyone wants it. This is the calm before the evening.
Tip: Remind everyone to dress nice — steakhouse has a smart-casual dress code.
The Olde Pink House (Steakhouse Dinner)
Fine Southern dining in a 1789 mansion on Reynolds Square. Prime steaks, low-country sides, excellent wine list. This is the tradition — the final big dinner. Trent sits at the head of the table. Book a private dining room if possible for the toast round.
Tip: Reserve the private dining room 3+ weeks ahead. Request a wine pairing or bourbon selection for Trent.
Toast Round (Honoring Moment)
In the private dining room at The Olde Pink House, each groomsman stands and shares one specific memory of Trent + one wish for his marriage. Keep it to 90 seconds each. The best man goes last. This is intimate, meaningful, and captures why Uncle Trent matters to this crew.
Tip: Have the best man text attendees 48 hours ahead asking them to pre-think their memory. Bring tissues — this gets emotional.
Quiet nightcap at the house
Crew returns to the house. Whiskey, cigars, porch time. Keep it low-key — the steakhouse and toast round are the peak. Wrap by midnight.
Tip: Have Lagavulin 16 and good cigars waiting on the porch.
Day 5 — Recovery Brunch & Departure
Recovery Brunch at The Collins Quarter
Melbourne-inspired brunch with lavender lattes, eggs, pastries, and fresh juice. Crew recovers, swaps favorite moments from the trip, and takes a final group photo. No rush — flights are booked for 3 PM or later.
Tip: Order the Eggs Benedict and a bloody mary — it's the perfect recovery meal.
Depart for airport
Arrange one Uber XL or two rideshares to SAV airport (20-min drive). Crew says goodbye, exchanges final hugs, and heads home with stories.
Tip: Have everyone exchange contact info and commit to a group text check-in in a week.
The Bars
Barrelhouse South
College-meets-party dive bar with cheap drinks and pool tables
Congress Street institution with a rowdy-but-fun crowd, cheap beer, and pool tables. This is where the dive bar crawl starts — casual, unpretentious, and perfect for Trent's crew. No dress code.
Treylor Park
Quirky trailer-park-themed bar with creative cocktails and late-night food
Eclectic, fun vibe with craft cocktails, late-night food, and a weird-in-a-good-way atmosphere. Second stop on the crawl — more refined than Barrelhouse, still casual. Try their signature cocktails.
Alley Cat Lounge
Underground speakeasy with craft cocktails and intimate vibe
Hidden speakeasy beneath Broughton Street with craft cocktails, dim lighting, and an intimate crowd. Perfect for winding down the night — small space, so arrive before midnight. This is where the crawl ends.
Rocks on the Roof (Bohemian Hotel)
Rooftop cocktail bar with river views and smart-casual dress code
Riverfront rooftop overlooking the Savannah River and cargo ships. Great for a pre-dinner cocktail or a quiet evening drink. Smart casual dress code. This is a backup option if the crew wants something more upscale than the dive crawl.
Club Habana Cigar Lounge
Downtown cigar lounge with leather chairs, bourbon, and old-school charm
Leather chairs, local bourbon selection, and a relaxed vibe perfect for cigars and whiskey. This is where Trent and the crew hang on Day 3 evening — no nightlife agenda, just cigars, Lagavulin, and crew time.
Where to Eat
The Olde Pink House
Fine Southern Steakhouse • $65–$85/person (with wine pairing)
1789 mansion on Reynolds Square serving prime steaks, low-country sides, and an excellent wine/bourbon list. This is the tradition — the final big dinner where Trent sits at the head of the table. Private dining room available for the toast round.
Private Chef Dinner at the House
Multi-Course Low-Country Cuisine • $60–$75/person (includes chef, ingredients, service)
A local private chef arrives on Day 3 and prepares a multi-course dinner: oyster appetizers, shrimp and grits, local fish, sides. Crew eats together at the house table. Elevated, personal, and Trent-focused. Chef handles all prep and cleanup.
The Collins Quarter
Melbourne-Inspired Brunch • $25–$35/person
Lavender lattes, eggs, pastries, fresh juice, and a relaxed vibe. Perfect recovery brunch on Day 5. No wait on Sundays if you arrive by 11 AM.
Mrs. Wilkes Dining Room
Southern Family-Style Lunch • $18–$25/person
Legendary communal Southern lunch — fried chicken, mac and cheese, collard greens, cornbread. Get in line early (opens at 11 AM). This is Savannah institution food, perfect for a casual crew lunch.
Zunzi's
South African Sandwiches • $12–$18/person
Cult-favorite South African sandwiches — the Conquistador is legendary. Quick, casual, and perfect for a grab-and-go lunch or late-night food after bars.
Budget Breakdown
Pack This
- - Golf shoes and golf clothes (Forsyth Park course)
- - Fly-fishing gear or rental-ready clothes (charter provides rods, bring polarized sunglasses)
- - Smart-casual dinner clothes (steakhouse dress code — no jeans, collared shirt or blazer)
- - Swim trunks and pool shoes (hot tub and pool time every day)
- - Comfortable walking shoes (historic district is walkable, food tour involves 2.5 hours on foot)
- - Light jacket or sweater (April evenings can be cool, especially on the water)
- - Sunscreen and sunglasses (April sun is strong, especially on the golf course and fishing charter)
- - Cigars or cigar preference list (Club Habana has options, but bring your favorite if you have one)
- - Lagavulin 16 or favorite scotch (optional — house will stock basics, but Trent's drink should be there)
Pro Tips
- - Book The Olde Pink House private dining room 3+ weeks ahead — it's essential for the toast round and keeps the crew focused on Trent.
- - Arrange the private chef dinner 2 weeks ahead — request low-country specialties and a Lagavulin-friendly cocktail to start.
- - Have the oyster shucker arrive by 7 PM on Day 2 — this is the blow-your-mind moment for Uncle Trent, so timing matters.
- - Savannah in April is perfect weather (70–75°F) — no extreme heat, azaleas in bloom, and outdoor dining is ideal.
- - The historic district is walkable — park the car at the house and use rideshare for nightlife. Saves money and keeps everyone safe.
- - Trent's pace is chill — build 3+ hours of unstructured downtime into every day. Pool time, cards, cigars, and porch drinks are the real memories.
- - Stock the house with Lagavulin 16, cold beer, good cigars, and quality bourbon — Uncle Trent appreciates the details.
- - Assign one person as the 'treasurer' to track group Venmo splits — keeps the money stress off Trent.
- - Take photos at the oyster shucking lesson and the steakhouse toast round — these are the moments that matter five years later.
- - Wrap nightlife by midnight on Days 2 and 4 — this crew is 40+, and recovery time is sacred.
Group Logistics
Transport: Rideshare (Uber XL or two standard Ubers) for airport transfers (SAV to house, ~20 min, $35–$50 total). Rideshare for nightlife crawls ($8–$15 per ride within historic district). No party bus needed — group is chill, and the historic district is walkable. Budget $50–$75/person for all transport over 5 days.
Nightlife Strategy: Two dive bar crawls (Day 2 and Day 4 optional). Day 2 crawl: Start at Barrelhouse South (9 PM, cheap drinks, pool tables) → Treylor Park (10:30 PM, cocktails, food) → Alley Cat Lounge (11:30 PM, speakeasy, wind down). No cover charges, budget $40–$60/person for drinks across all three bars. Day 4 is the steakhouse + toast round, so nightlife is minimal (quiet nightcap at the house by midnight). No bottle service, no clubs — this is Trent's crew, and they prefer good drinks in character bars over VIP tables.