traveling to the edge

Vacation where you Live, Travel for a Living

How I Planned a Vacation to Napa Valley for $500

I travel for work on a weekly basis but given it is the holiday season I have an obscene amount of time off, so I decided I needed to go on a vacation! Most people would not think that having three weeks off in a row would be a problem but me being the crazy person that I am I can not stay in one place for 25 days in a row. Instead I picked up a shift at work for the weekend before Christmas and I planned an amazing trip up to Napa Valley for New Year’s Eve. Why would I rest up at home when I can be sipping wine, cuddled up by a roaring fire in Napa. Seems like a pretty obvious choice to me.  

I have been to Napa a couple times before on business. I have planned a couple weddings up there and have driven through but I have never stayed and done the whole Napa Valley wine tasting experience. This past month I have worked up in San Francisco and Oakland and both trips I complained the whole time that I was so close but I could not find enough time in those trips to fit it in. I guess all of my complaining paid off because a coworker and I decided to go up and spend some time relaxing and enjoying the beautiful country air for New Year’s Eve. Since we will be driving we also decided to stop in Santa Barbara on the way back down to see one of our friends that lives there.

What is on the Agenda?

We will be driving from San Diego to Napa Valley. When planning out our route I wanted to make sure that at least one of the ways we took the scenic route. AKA the longer route but I know that stopping in Big Sur for lunch and Half Moon Bay to see the whales will be so worth the extra 80 miles it ends up putting on the whole trip.  Plus you get to look out at the ocean when you drive instead of cow fields. Not that there is anything wrong with cow fields. I actually love driving in the country and seeing all the animals. 

After getting some suggestions from my coworker Greg who has done this drive  many times I heard it would be best to do Big Sur on the way back down to Santa Barbara so we have more time to enjoy it. (These are some of my coworker’s photos that he took when he drove back down the coast after we worked our event in San Francisco.)

On the way up to Napa I know we will be excited to get there and have our first wine tasting so we are going to go the shortest route, which is up the middle of California next to all cow fields. (Happy cows come from California) We are going to drive up from San Diego super early on the morning of December 30th. I am anticipating we should leave San Diego around 4:30AM so we can get on the road and hit Los Angeles around 6:30AM and make it through just as the morning traffic is starting.  If we were to leave around 6AM it would put us in LA at rush hour and that would ultimately tack on another hour and a half to the trip, so leaving super early really is the best option, even though I am sure I will be super tired. If we are on schedule that will mean that we hit Bakersfield around 9AM. This is a great pit-stop town: bathroom, fuel and quick bite to eat. After that we are pretty much smooth sailing all the way up the great state of California. We can stop for lunch along the way but I also have ideas for a packed cooler lunch. This will put us into Napa at the latest 2:30 PM. That is perfect timing to rest up, go the grocery store, check out downtown and go to dinner. 

 Route on the way up to Napa

Route on the way up to Napa

 Route on the way back down from Napa stopping in Half Moon Bay, Big Sur and Santa Barbara

Route on the way back down from Napa stopping in Half Moon Bay, Big Sur and Santa Barbara

Once we get up to Napa we will be staying three nights. During our stay there we will spend one full day doing a bus wine tour tasting at several of the valley’s best local vineyards and one day relaxing getting a massage, going on a hike, sight seeing and shopping. 

On the 31st we will be doing the wine tour. I have done a wine tour before in Santa Barbara wine country and it was amazing! You have a local driver that takes you around to four different wineries. It is very educational and informative. They provide lunch at one of the wineries and have plenty of water to keep you hydrated in between tastings. It is great to have the local knowledge going into the wineries and you don’t have to worry about how many tastings you have since you have your own personal driver.  (I was with a large group when I did it in Santa Barbara and we had our own private shuttle. I recommend this for larger groups.)

Since it will just be the two of us, a join-in wine tour is going to be the best, most affordable and most fun option. This is a tour with mixed groups that range usually from 6-18 people. The great part is you get a chance to know other wine-lovers on the drive too and from wineries but also have the chance to go off and do your own thing once you reach your destination.  After researching many tour companies in the area I have narrowed it down to these two options:



1. Provides daily tours and they meet in a very central location of downtown Napa. They rotate their wineries every other day so that you could return a second day and go to different wineries. I like how this company has premium join-in options for more exclusive tours to higher end wineries. (Only the basic tour is offered on the 31st).

2. Provides daily tours and they pick you up at your hotel as well as drop you back off. This company has no set schedule of which wineries you go too each day. You and your driver pick it out that morning based on the group’s preferences. This gamble could really work out in your favor or it could end up being a flop if you had specific wineries you wanted to visit. This option ensures that you have a unique tour.

Both tours are on trolley type vehicles, which in it of itself is an experience. There are plenty of tour companies that use sprinter vans but they are a tab bit more expensive. Both companies have daily tours that run for $99 a person. The pick up or meet-up time is around 10AM and the drop-off time is between 5 and 5:30PM. So it is a full day of tasting and enjoying.

Please please note: When doing my research I found in the very small print that tastings at each individual winery was not included in this price. I found that surprising since they were included when I was in Santa Barbara. Napa Valley does everything a la carte. Napa winery tastings range from $10-$20. So what this means that at the most expensive it would be an additional $80. However when I was talking to the tour operator companies they said because of their great relationships with the wineries they usually discount tastings depending on the size of the group. Also if a bottle of your favorite wine is purchased or a wine-club is joined then tasting fees are waived. I also found out that most of the hotels have relationships with various wineries and usually have discount cards. This would be difficult to match up with the exact wineries you will be attending unless you go with Option 1 where you know which wineries you will go too that day. I found a few Groupons for discounted wine tastings, so with a little bit of extra effort and planning you could get a great deal.  Also keep in mind it is customary to tip your driver at the end of the day if you feel they provided exceptional service to you.

Note: Saturdays are popular in Napa all year round even in the off-season. High season is March to October. If you are planning a trip during these months and want to do a wine tour on a Saturday make sure to book far in advance for the company you would like. For off-season the tour companies said I would be fine booking about 5 days in advance.

Also keep in mind if you are planning a trip up to Napa for New Year’s Eve like we are you will find it more difficult to find companies who actually run tours on these days. Since it is a very slow time of year a lot of the companies take the opportunity to take a few days off. I also found out that most of the wineries are closed on New Year’s Day January 1st so that is why our only option for a tour was the 31st. I also saw some deals on Groupon for discounted wine tours for about $65 dollars per person but that company was not running tours during our stay.

I have been running into the same problem with booking massages on New Year’s Day but I have confidence that we will be able to find them. I budgeted $70 for a Groupon massage. I plan on us taking it easy on New Year’s Day and just enjoy exploring around the town of Napa or venturing out to Sonoma or Petaluma for lunch or dinner.

On New Year’s Eve there is plenty to do in Napa to ring in the New Year. I have found several parties at some of the wineries and hotels. They even have a party that is hosted on a train. Most of these parties are very formal affairs. Tickets should be purchased in advance and usually include dinner, open bar, live music and dancing all bundled into the ticket price. However since we will have been doing a wine tour all day I think the open bar might go to waste if we attended one of these parties. Our plan right now is to go to one of the local downtown bars and ring in the New Year in a more casual manor. Champagne I am sure will still be enjoyed. 


So now for the good part. How did I plan such an amazing trip for only $500?

The key word here is leverage. Since I travel a lot and even if you don’t you want to make sure that you are always maximizing your opportunity for future travel. This goes without saying but every time you travel you want to make sure you are apart of every single rewards program that you run into: Airlines, Rental Cars, Hotels, Restaurants, EVERYTHING! Because you will accumulate points and those points can be used for future vacations; for example Napa Valley trip.

So how did I really get up and back to one of the most expense places in California for my screaming deal of $510 dollars? This includes gas money, hotel accommodations, activities (wine tasting and massage), food and alcohol. I even made my food budget on the high side so that if I had left over money I could use it for shopping or bringing a bottle of my favorite tastings home with me.

So lets break it down. Accommodations are usually the most expensive part of any travel. The cheapest hotel I could find in Napa was right around the $200 dollar per night mark. Of course we would have been staying in a darling little bed and breakfast but since we are in our mid-twenties we don’t have that kind of budget yet.  You get what you pay for most of the time, unless you know how to leverage.

Since I am traveling with a coworker, he also travels for a living so we were able to leverage some of his hotel points as well as mine. I found a Hilton Garden Inn that was 2 miles from the heart of downtown Napa. Since we have my car it wasn’t a problem that we are staying just slightly off the main drag. We ended up using a total of 90,000 points and spending $170 for 3 nights. The cherry on top of all of this is because we have status with Hilton not only will we stay for practically nothing we will be upgraded to a suite the whole time. (The forth night we will be staying at our friend’s house in Santa Barbara so that doesn’t cost us anything.)

As mentioned we chose to drive which was more affordable than flying into San Francisco and getting a rental car. (Event though we could have used points and gotten that for free also, the road trip sounded like more of an adventure.) Total budgeted gas money for there and back is $120. (Perks of driving a Camry with good gas mileage.) Total miles will be close to 1200.

For the food budget I thought $50 a day would be more than sufficient. We are going to go to the grocery store when we first get there and pick up snacks. Breakfast is included with our stay since we have status with Hilton, and for dinner I already have some Groupons in my basket for really nice restaurants we can eat at for a fraction of the price.

Accommodations: $170

Transportation: $120

Food/Alcohol: $400

Activities: $330

Total: Divided by 2= $510 a person

I hope this information was helpful for you if you are trying to plan a trip up to Napa Valley on the more affordable side. Stay tuned for the blog that goes over what we actually did and spent compared to how I planned it out. I did a lot more research about where to stay and what to do so please feel free to reach out to me with any questions or comments.