May 1–5, 2026

Napa Valley

A Wine Country Escape

Kevin & Lex • Katie & Joe

Trip Overview

Sacramento → Calistoga → Wine Country

Base Camp

Calistoga – Hot springs, spas & northern Napa charm

Duration

5 Days / 4 Nights
May 1–5, 2026

Travelers

Kevin & Lex (Austin)
Katie & Joe (New Orleans)

Wineries

9 Tastings across 2 days + Spa Day

Quick Glance

Day by Day

Thursday, May 1

Arrival Day

Land in Sacramento → Drive to Calistoga (1.5 hrs) → Check-in & explore downtown

Friday, May 2

South Napa Wine Tour

Hendry → Ashes & Diamonds → Trefethen or Matthiasson

Private Driver

Saturday, May 3

Icons & Art Tour

Domaine Carneros → Hess Persson Estates → Merryvale or Caymus

Private Driver

Sunday, May 4

Castle & Spa Day

Morning: Castello di Amorosa | Afternoon: Indian Springs Spa

Must Do Spa Day

Monday, May 5

Departure

Check-out → Drive to Sacramento → Depart

Flight Options

Coordinating arrivals for both couples

Strategy: Prioritizing Katie & Joe's flights since their route (MSY→SMF) is more expensive. Kevin & Lex match their arrival time within ±2 hours.

✈️ Option 1: Cheapest Overall

K&J's lowest fare • Arrive ~4:00 PM • More time in Calistoga evening

Kevin & Lex (Austin)

Southwest 12:40 PM → 4:05 PM

1 stop LAX • $110/person • $440/couple RT

Katie & Joe (New Orleans)

Alaska 10:30 AM → 4:09 PM

1 stop PDX • $206/person • $664/couple RT

Arrival gap: 4 minutes • Combined total: $1,104

✈️ Option 2: Earlier Arrival

Arrive ~1:30 PM • 2.5 hrs more to enjoy Day 1 • +$33 total

Kevin & Lex (Austin)

Southwest 11:40 AM → 1:30 PM

Nonstop • $130/person • $500/couple RT

Katie & Joe (New Orleans)

Southwest 8:15 AM → 1:30 PM

1 stop AUS • $219/person • $690/couple RT

Arrival gap: Same time! • Combined total: $1,137

Austin → Sacramento

Kevin & Lex

Search on Google Flights →

Outbound: Friday, May 1 (AUS → SMF)

Flight Times Duration Stops Cash Price Points + Cash
Southwest 12:40 PM – 4:05 PM 5h 25m 1 (LAX) $110 —
Southwest 11:40 AM – 1:30 PM 3h 50m Nonstop $130 —
Delta 6:50 PM – 11:35 PM 6h 45m 1 (SLC) $108 8,000 pts + $6
Delta 1:20 PM – 7:06 PM 7h 46m 1 (LAX) $108–109 8,000 pts + $6
Southwest 4:05 PM – 7:40 PM 5h 35m 1 (PHX) $110 —

Return: Tuesday, May 5 (SMF → AUS)

Flight Times Duration Stops Cash Price Points + Cash
Southwest 11:35 AM – 6:20 PM 4h 45m 1 (ONT) $110 —
United 11:28 AM – 7:27 PM 5h 59m 1 (IAH) $120 —
Southwest 12:45 PM – 8:35 PM 5h 50m 1 (SAN) $110 —
American 1:03 PM – 8:12 PM 5h 9m 1 (PHX) $137 —
Delta 1:05 PM – 9:15 PM 6h 10m 1 (SLC) $159 13,000 pts + $6
American 1:03 PM – 8:12 PM 5h 9m 1 (PHX) $176 15,000 pts + $36
💡 Kevin & Lex Best Value: Southwest 12:40 PM ($110) arrives at 4:05 PM – just 4 minutes before Katie & Joe land. Cheapest option that syncs arrivals perfectly. Return on the 11:35 AM Southwest ($110) for $220/person roundtrip.

New Orleans → Sacramento

Katie & Joe

Search on Google Flights →

Outbound: Friday, May 1 (MSY → SMF)

Flight Times Duration Stops Cash Price Points + Cash
Alaska 10:30 AM – 4:09 PM 7h 39m 1 (PDX) $206 15,000 pts + $39
American 9:18 AM – 1:36 PM 6h 18m 1 (DFW) $262 —
Southwest 8:15 AM – 1:30 PM 7h 15m 1 (AUS) $219 —
Southwest 5:30 AM – 10:00 AM 6h 30m 1 (DAL) $219 —
United 10:20 AM – 8:42 PM 12h 22m 2 (DEN, LAX) $467 10,900 pts + $58
United 12:13 PM – 8:42 PM 10h 29m 2 (ORD, LAX) $583 10,900 pts + $58

Return: Tuesday, May 5 (SMF → MSY)

Flight Times Duration Stops Cash Price Points + Cash
Alaska 11:50 AM – 9:24 PM 7h 34m 1 (PDX) $126 —
American 1:03 PM – 8:36 PM 5h 33m 1 (PHX) $139 —
United 5:00 AM – 1:29 PM 6h 29m 1 (DEN) $139 —
Delta 6:00 AM – 1:39 PM 5h 39m 1 (SLC) $139 —
United 11:28 AM – 7:42 PM 6h 14m 1 (IAH) $183 10,900 pts + $6
Southwest 3:15 PM – 11:05 PM 5h 50m 1 (PHX) $178 14,000 pts + $6
💡 Katie & Joe Best Value: Alaska 10:30 AM ($206) arrives at 4:09 PM – just 4 minutes after Kevin & Lex! It's cheaper than the American option and the timing works perfectly. For return, Alaska 11:50 AM ($126) is cheapest. Total ~$332/person roundtrip.

Summary

Flight Cost Comparison

Option 1: Cheapest Overall — $1,104 total

Travelers Outbound (May 1) Return (May 5) Per Couple
Kevin & Lex SW 12:40→4:05 PM ($110) SW 11:35 AM ($110) $440
Katie & Joe Alaska 10:30→4:09 PM ($206) Alaska 11:50 AM ($126) $664

Option 2: Earlier Arrival — $1,190 total (+$86)

Travelers Outbound (May 1) Return (May 5) Per Couple
Kevin & Lex SW 11:40→1:30 PM Nonstop ($130) SW 11:35 AM ($110) $480
Katie & Joe SW 8:15→1:30 PM ($219) Alaska 11:50 AM ($126) $690

Option 1 Timing

Arrive: ~4:05 PM (4 min gap)
Depart: ~11:35 AM (15 min gap)
In Calistoga by ~6:30 PM

Option 2 Timing

Arrive: 1:30 PM (same time!)
Depart: ~11:35 AM (15 min gap)
In Calistoga by ~4:00 PM

🎯 Recommendation: Option 2 gets you to Calistoga 2.5 hours earlier for just $86 more total – worth it if you want to explore downtown Calistoga or grab an early dinner on Day 1. Plus Kevin & Lex get a nonstop flight.

Transportation

Rental Car

Hertz @ Sacramento Airport

Compact SUV – Chevrolet Trax

Vehicle Chevrolet Trax or similar
Capacity 5 passengers, 2 bags
Features Automatic, A/C, Unlimited miles
Pick-up Fri, May 1 @ 5:00 PM
Drop-off Tue, May 5 @ 11:00 AM
Location 6327 Aviation Drive (SMF)
Total (4 days) $228.11
Per person (split 4 ways) ~$57

✓ Free airport shuttle to pick-up location
✓ Free cancellation until Apr 29

💳 Credit Card Benefits

By booking with Capital One Venture X, you can decline Hertz's expensive add-ons and save significantly:

Hertz LDW/CDW $45/day × 4 = $180
Personal Accident Insurance ~$12/day × 4 = $48
You Save ~$228

💎 Capital One Venture X

  • PRIMARY rental car insurance (up to $75,000)
  • Hertz President's Circle status – skip the counter
  • Free additional driver (spouse/partner)

PRIMARY insurance means: If the car is damaged, file directly with Capital One – your personal auto insurance is never involved.

⚡ At the Counter: Decline Hertz's LDW/CDW (say "I have coverage through my credit card"), pay with Venture X, and keep a copy of your card's benefits guide just in case.

Accommodations

Calistoga lodging options for 4 nights

Accommodation Options (2 rooms needed for hotels)

VRBO Vineyard Guest House

Best for Group

Total (4 nights) $3,047
Per Couple $1,524
Type Entire Home
Amenities Pool, hot tub, 2BR/2BA
View on VRBO →

Calistoga Spa Hot Springs

Built-in Spa Day

Total (2 rooms) $3,192
Per Couple $1,596
Type Hotel + Spa
Perk Spa on-site!
View Website →

Dr. Wilkinson's Resort

4-Star • Design Hotels

Total (2 rooms) $3,360
Per Couple $1,680
Type Boutique Resort
Perk Mineral springs
View Website →

Calistoga Motor Lodge

4-Star • Modern

Total (2 rooms) $3,380
Per Couple $1,690
Type Boutique Hotel
Perk Pool, modern vibe
View Website →

Mount View Hotel & Spa

3-Star • Full Spa

Total (2 rooms) $2,568
Per Couple $1,284
Type Hotel + Spa
Perk Free cancellation
View Website →

The Bergson

Best Value Hotel

Total (2 rooms) $2,052
Per Couple $1,026
Type 3-Star Hotel
Perk Great reviews, parking
View Website →

Calistoga Inn & Brewery

Budget Pick

Total (2 rooms) $1,526
Per Couple $763
Type Inn + Brewery
Perk On-site brewery!
View Website →

Cottage Grove Inn

3-Star • Cozy

Total (2 rooms) $3,496
Per Couple $1,748
Type Private Cottages
Perk Romantic, private
View Website →
💡 Note: VRBO has free cancellation before Apr 1. Hotel prices are for 2 separate rooms (one per couple). If you stay at Calistoga Spa Hot Springs, you can skip booking a separate spa day!

Day 1 — Arrival

Thursday, May 1, 2026

Theme

Sacramento to Calistoga

Travel & Settle In

Afternoon

Arrive Sacramento (SMF)

Pick up rental car at airport

~1.5 Hour Drive

Drive to Calistoga

Scenic Route: I-80 W → CA-29 N through Napa Valley

Beautiful drive through the valley – consider stopping in Yountville for a quick coffee

Late Afternoon

Check into Accommodation

Calistoga area – still need to book!

To Do

Evening

Explore Downtown Calistoga

Casual dinner, stroll Lincoln Avenue, early night before wine days

Day 2 — South Napa Tour

Friday, May 2, 2026

Theme

The "Insider" Tour

Educational, Modern & Family-Owned

10:00 AM

Hendry Winery

Book the "Long Tour" – their famous experience

~$75/person • Family estate since 1939 • Appointment-only

Book First

12:30 PM

Ashes & Diamonds

A&D Wines + Cheese pairing (doubles as lunch)

$60–95/person • Mid-century modern aesthetic • Lighter wines

2:30 PM

Matthiasson Wines

Extremely limited seating – book well in advance

~$75/person • Organic farming pioneers • Appointment-only

Critical Booking

4:00 PM

Option A: Trefethen or Option B: Matthiasson

A: Historic estate, standard flight • B: Organic pioneers, very limited seating

Trefethen ~$45/person • Matthiasson ~$75/person (appointment only!)

Pick One

Evening

Return to Calistoga

Driver drops you off • Dinner in town • Rest up!

Day 2 Wineries

Hendry Winery

Napa

Tasting Fee ~$75
Experience Long Tour
Booking Appointment Only
Known For Estate wines, education

Ashes & Diamonds

Napa

Tasting Fee $60–95
Experience Wines + Cheese
Vibe Mid-century modern
Known For Lighter, fresher wines

Option A: Trefethen

Oak Knoll District

Tasting Fee ~$45
Experience Standard flight
Vibe Historic, elegant
Known For Chardonnay, Cabernet

Option B: Matthiasson

Napa

Tasting Fee ~$75
Experience Intimate tasting
Booking Very Limited!
Known For Organic, terroir-driven

Day 3 — Icons & Art Tour

Saturday, May 3, 2026

Theme

Grand Estates & Views

Sparkling, Art & Cabernet

10:00 AM

Domaine Carneros

Sparkling flight on the terrace

~$50/person • French château • Stunning views

12:30 PM

Hess Persson Estates

Tour the Art Museum + Estate Tasting

$65–125/person • World-class contemporary art • Mountain wines

Art Museum

3:00 PM

Option A: Merryvale or Option B: Caymus

A: Historic Cask Room tasting • B: Famous Cabernet, books up fast

Merryvale ~$50/person (St. Helena) • Caymus ~$50/person (Rutherford)

Pick One

Evening

Return to Calistoga

Nice dinner to celebrate • Maybe Solbar or Sam's Social Club

Day 3 Wineries

Domaine Carneros

Carneros

Tasting Fee ~$50
Experience Terrace sparkling
Vibe French château
Known For Sparkling wine, views

Hess Persson Estates

Mt. Veeder

Tasting Fee $65–125
Experience Art + Wine tour
Special Art Museum (free)
Known For Mountain Cab, art

Option A: Merryvale

St. Helena

Tasting Fee ~$50
Experience Cask Room tasting
Vibe Historic, elegant
Known For Bordeaux blends

Option B: Caymus

Rutherford

Tasting Fee ~$50
Experience Famous Cab tasting
Booking Books up fast!
Known For Cabernet Sauvignon

Day 4 — Castle & Spa

Sunday, May 4, 2026

Theme

Castle & Relaxation

The Must-Do Day

10:00 AM

Castello di Amorosa

13th-century Tuscan castle – 8 levels, 107 rooms

Book a tour + tasting • Wine caves, great hall, torture chamber • ~$50-85/person

Must Do

12:30 PM

Lunch in Calistoga

Casual lunch before spa – Café Sarafornia, Calistoga Inn, or Buster's BBQ

2:00 PM onwards

Spa Afternoon

Indian Springs Resort or Calistoga Hot Springs

Mud baths, mineral pools, massages • Book treatments in advance • Perfect recovery day

Spa Day

Evening

Nice Dinner Out

Special night before departure – Evangeline, Solbar, or Sam's Social Club

Castello di Amorosa

Authentic 13th-century Tuscan castle with drawbridge, moat, and torture chamber. Italian varietals in an unforgettable setting.

Indian Springs Resort

Historic spa since 1862. Famous mud baths, Olympic-size mineral pool fed by natural geysers, world-class treatments.

Calistoga Hot Springs

Four mineral pools at different temps, mud baths, and affordable day passes. More casual, local vibe.

Day 5 — Departure

Monday, May 5, 2026

Theme

Farewell to Wine Country

Calistoga → Sacramento

Morning

Leisurely Breakfast

No rush – enjoy Calistoga one more time. Café Sarafornia has great breakfast.

Late Morning

Check Out

Pack up any wine you've purchased – might need to ship larger orders

~1.5 Hour Drive

Drive to Sacramento

CA-29 S → I-80 E • Option to stop in Davis for lunch

Afternoon

Depart Sacramento (SMF)

Return rental car • Still need to book flights!

To Do

Cost Breakdown

Estimated Per Person (4 Travelers)

Budget

Wine Tasting & Transport

Expense Estimated Cost Notes
Flights (Kevin & Lex) $220/person Southwest RT from Austin
Flights (Katie & Joe) $332/person Alaska RT from New Orleans
Rental Car (Hertz) $57/person Compact SUV, 4 days, split 4 ways
Day 2 Tastings $255–290 Hendry, A&D, Matthiasson, Trefethen
Day 3 Tastings $165–225 Domaine Carneros, Hess, Merryvale or Caymus
Day 4 – Castello $50–85 Tour + tasting experience
Day 4 – Spa $100–200 Treatments vary widely
Private Driver (1 day) $75–90 6-hr charter split 4 ways (~$300-360 total)
Lunches (2 days) $80–150 A&D + casual stop
Kevin & Lex (per couple) $1,540–1,880 — Flights $440 + Car $114 + Wine/Driver ~$986-1,326
Katie & Joe (per couple) $1,724–2,064 — Flights $664 + Car $114 + Wine/Driver ~$986-1,326
Not Included: Accommodation (4 nights for 4 people), dinners, wine purchases to take home.

Private Driver – 6-Hour Charter

Designated Driver for Your Rental Car

$50–60/hour

Hire a driver who drives YOUR rental car so everyone can taste. This is the most cost-effective option.

Services: Napa Valley Designated Drivers, My Private Driver

Why this works: Public buses/trolleys run fixed routes and never visit appointment-only spots like Matthiasson or Hendry. A private driver gives you the flexibility to hit your specific list.

Booking Checklist

Click to mark as complete

🍷 Pro Tip: Book Hendry first – they have the strictest schedule. If you choose Matthiasson (Option B), book that early too as seating is very limited. The driver will build the route once you confirm all reservations.