It’s been 6 short years since our “200 Year Trip” to San Francisco and Pebble Beach and the golfing gang is interested in making another golfing trip. Here is a sample itinerary with a cost breakdown to get an idea of what is possible this time around if we were to try to recreate the magic of that trip. The first trip was done on a shoestring budget and with inflation, things will be more expensive this time. Plus we’re looking at staying a couple more nights than the first trip, but let’s see what we can do.
Note – All price estimates are in many cases guesstimates since many hotels and airlines aren’t selling tickets for the timeframe we’re looking at. They are used to find relative pricing between sample itineraries so we can best determine which trip to pursue and are just starting points for trip planning.
Sample Itinerary
Note – As with all sample itineraries in this series this assumes a Friday evening “getaway flight” and a Sunday evening “redeye return” 9 days later.
Day 1 (Friday)
- Early evening flight from BOS to SFO. Arrive around 9 or 10pm
- Pick up rental car and checkin to nearby Hyatt Regency SFO for 3 nights
- Possibility of paying cash and using Hyatt points to upgrade to a Premiere Suite for all of us to stay in.
Day 2 (Saturday)
- Up early to eat breakfast at the hotel (due to my Globalist Status)
- Drive south to San Jose area to play morning round at Cinnabar Hills
- Back to relax at the hotel
Day 3 (Sunday)
- Up and getting breakfast at the hotel
- Drive to play mid-morning round at Badlands Golf Links
- Back to relax at the hotel
Day 4 (Monday)
- Up early and getting breakfast at the hotel before checking out
- Fight traffic going north into the city to play Presidio
- After the round check in to Hyatt Regency San Francisco in the financial district for 2 nights. Use points to book a premium suite for all 4 of us
- Relax and explore the city
Day 5 (Tuesday)
- Up early and getting breakfast at the hotel (due to my Globalist Status) or locally
- Drive to play golf at TPC Harding Park
- Return to hotel and relax and explore the city
Day 6 (Wednesday)
- Up early and getting breakfast at the hotel before checking out
- Drive south along the Pacific Coast to Half Moon Bay to play the Old Course. We played the Ocean course here during our first trip
- Continue driving south to check in to the Hyatt Regency Monterey Hotel and Spa on Del Monte Golf Course for 2 nights. Booking two rooms with cash or one with cash upgrading to a premium suite on points that could hold us all.
Day 7 (Thursday)
- Up whenever and getting breakfast at the hotel (due to my Globalist Status)
- Rest day or optionally playing golf at the Del Monte course at the hotel
Day 8 (Friday)
- Up early and getting breakfast at the hotel before checking out
- Play Pebble Beach mid-morning
- Check into the Inn at Spanish Bay. Staying at the resort for a minimum of 2 nights is a requirement for getting a tee time at Pebble Beach. The Inn at Spanish Bay is the cheapest of the Pebble Beach Resorts (and is in no way actually cheap)
Day 9 (Saturday)
- Up whenever and play mid morning round at Spyglass Hill
- Enjoy the resort amenities the rest of the day (free practice range access/etc)
Day 10 (Sunday)
- Up early and checkout before golf
- Play early round at Links at Spanish Bay
- Drive north to eat dinner in San Francisco
- Drive back to airport to drop off car rental and take redeye overnight flight home
Day 11 (Monday)
- Land in Boston 5am(ish)
Cost Breakdown
Flights
Friday evening with Sunday redeye return (likely on JetBlue): 4 x 450 = $1900
Using JetBlue has several advantages. With the right credit card, we get one piece of checked luggage per person for free (i.e. our golf clubs) which saves us several hundred dollars. There is currently a JetBlue card with a 100,000 point bonus and JetBlue allows point sharing so potentially a couple of us could apply for the card and pool our points to offset this price entirely.
Hotels
Nights 1-3: Hyatt Regency SFO
$150/night + 9000 points for a premium suite upgrade -> $450 + 27000 Hyatt points
Since the nightly rate is so low it’s best to pay cash for the room and use points to upgrade to a premium suite. The premium suite is currently showing for around $650/night so those 9000 points are getting $500 points of value each night (more the 5.5 cents per point)
Nights 4-5: Hyatt Regency SFO
40,000 points per night for a premium suite -> 80,000 Hyatt Points
Cash rates are almost $1000/night for a standard room (non-suite). Spending double the points for a premium suite makes a lot of sense. This hotel is in a convenient part of town that I know well. We can easily walk or take public transport (or a Lyft) to any of the touristy places we want to visit.
Nights 6-7: Hyatt Regency Monterey Hotel and Spa on Del Monte Golf Course
$150/night x 2 rooms -> $600
As an alternative, I see the site lists the President’s House as a premium suite. If possible we would pay for only one room and use 9000 Hyatt Points a night to upgrade to that “room” which looks amazing!
Nights 8-9: The Inn at Spanish Bay
$870/night x 2 -> $3480
There is, unfortunately, no way around this if you want to play Pebble Beach, which we do. It’s “that good” of a course/experience but this “tax” of having to stay at the resort to have access still hurts the wallet. The hotel is beautiful and fully 5 stars and is in a beautiful location that matches the price. This price does NOT include the price of golf which is $575 per person at Pebble Beach. Be prepared to shell out.
Hotel Total: $4530
Golf
Day 1 – Travel, no golf
Day 2 – Cinnabar Hills: 150 x 4 = $600
Day 3 – Baylands Golf Links: 125 x 4 = $500
Day 4 – Presidio: 175 x 4 = $700
Day 5 – TPC Harding Park: 240 x 4 = $960
Day 6 – Half Moon Bay Old Course: 100 x 4 = $400
Day 7 – Rest day (or Del Monte: 110 x 4 = $440)
Day 8 – Pebble Beach: 575 x 4 = $2300
Day 9 – Spyglass Hill: 415 x 4 = $1660
Day 10 – Links at Spanish Bay: 295 x 4 = $1180
Total $8740 (includes Del Monte)
Food
We eat rather frugally though prices are quite high in San Francisco. Most breakfasts will be included with the hotel so we are looking at lunch dinner and snacks. Budgeting $250/day for the four of us:
250 * 9 = $2250
Car Rental
On our last trip, we had a minivan and it was perfect for what we needed for the trip. It was comfortable for longer drives and easily held our golf clubs. Last trip we somehow got a rate that was about $300 for the week. I’m doubtful we can match that again so budgeting slightly higher based on current rates:
Total: $550
Overall Total
Total: ~$18000 = $4500/person
If we use points for the flights, have a rest day, and can get a suite upgrade in Monterey, the total would be reduced by up to $2600. That would put the per person cost down to $3850.
Points Outlay:
- JetBlue points from credit card signup bonuses
- Up to 137,000 Hyatt points
Thoughts
This trip is much more luxurious than our last trip, but it closely mirrors the itinerary. It’s also much more expensive due to increased costs at Pebble Beach and extra/more expensive days of golf elsewhere.
This itinerary hits some major bucket-list courses, though. Every course on the list looks amazing. Since this trip closely models the first trip so there is a level of comfort with this itinerary. That is a positive but also a negative. Is the cost worth repeating the original magical trip that may not be as magical the second time? We’ll have to compare it with some of the other itineraries to figure out if it’s worthwhile.
Next up the Robert Trent Jones Golf Trail Itinerary.
Tomatico Travels 