Shyla Bryant

TryShy Travel LLC

Napa Valley: Relax & Re-Wine

Sep 3, 2026 to Sep 8, 2026
Napa Valley & San Francisco

 

Luxury Small-Group Tour of Napa Valley & San Francisco

When

Thursday, September 3 - Tuesday, September 8, 2026

 
  
 
 

Highlights 

 

  • Dress to impress for themed events during the trip
  • Free breakfast is available each day to fuel up for the day ahead
  • Enjoy three unique experiences at premier wineries in Napa
  • Tour Castello di Amorosa’s medieval castle
  • Learn from knowledgeable wine-enthusiast guides
  • Enjoy a relaxing lunch in charming Calistoga (meal not included)
  • Enjoy photo opps at the famous Napa Valley Welcome sign and the Golden Gate Bridge in San Francisco
  • Make lifelong connections with a fun, like-minded small group

  • Delight in ample free time to enjoy Napa on your own terms outside of the group

 

Package Pricing Per Person

Package prices are inclusive of all items listed below, and is based on the number of guests in each room. If you'd like to skip any activity or winery visit, please let us know (or do not choose the winery during booking), and we will adjust your package rate.

Quad Occupany (4 people in a room) $1,392
Triple Occupancy (3 people in a room)
$1,561
Double Occupancy (2 people in a room) $1,897
Single Occupancy (1 person in a room) $2,840

Includes

  •  4-star accommodations in Napa Valley and San Francisco offering daily breakfast 
  • Free glass of wine at check-in
  • 1-hour professional photo session at a winery
  • Private roundtrip transfers for select activities in luxury vehicles including airport transfers
  • Gratuities for select transfers
  • Dinner credit at a specialty restaurant (separate checks provided)
  • Exclusive TryShy Travel Napa Valley & San Francisco travel guide and map
  • Three wine-tasting experience fees and winery tours of Castello di Amorosa, Jarvis Winery, and V. Sattui (meals not included)
  • Signature welcome gift bag
  • Knowledgeable and on-site travel host

 

Not Included

  • Airfare
  • Travel insurance (Highly recommended. Choose at checkout or ask us for another quote.)
  • Items of a personal nature
  • Meals or drinks not  stated as "included"
  • Rideshare costs during your free time

 

Important Information

  • A non-refundable deposit of $150 per person secures your spot.
  • Due to the nature of activities and winery visits, this experience is for adults aged 21 and over.
  • This trip is limited to 12 guests. Act fast to reserve your spot(s).
  • When making your flight arrangements, please plan to arrive at San Francisco International Airport (SFO) no later than 11:30am on 9/3/26.
  • Flexible payment plans are available during registration.
  • Final package rates may vary due to hotel or winery conditions that we have no control over. If conditions or events cause a hotel or winery to be unavailable, we will substitute it with a comparable experience.
  • When booking, select the total number of people in your room as well as the wineries and tours you'd like to participate in.
  • A non-refundable credit card convenience fee of 3.5% + $0.30 is included in your online payments. This fee is collected by the card processor, not TryShy Travel.
  • A smaller, non-refundable 1.5% convenience fee is available for ACH (bank transfer) payments. This fee is collected by the processor, not TryShy Travel.
  • Other deposit payment methods are available upon request.
  • Light to moderate activity level should be expected.
  • Contact us if you have any questions. 

Our 3-day hold option offers a one (1) time complimentary 72-hour hold while you finalize your decision to join the group. No payment is required to hold, but spots are limited, so act fast! After 3 days, you will receive an invoice for your deposit. If not paid, your spot will be released. Each person in your party opting for a 3-day hold must complete a separate sign up form.

SIGN UP FOR TRIP UPDATES

 

Cancellation Policy & Terms:

 
This trip includes a 7-day cancellation window after your deposit is paid. If you choose to cancel within that period, your deposit will be refunded minus a $25 cancellation fee and any bank processing fees. After the 7-day window, all deposits become 100% non-refundable. Please allow up to 2 weeks (14 days) for your refund to process.
 
See full Terms and Conditions HERE.
 
TryShy Travel LLC | Palmetto, FL

941- 557- 9757

Email: info@tryshytravel.com

Website: www.tryshytravel.com

 
Business Hours:

Available Packages

Hampton Inn & Suites Napa | Room, 2 Queen Beds, Non Smoking, Refrigerator
Available until May 22, 2026

Starting At: $1,392.00
Deposit: $150.00 per person

This room offers a comfortable and convenient stay for up to four guests. Spanning approximately 342 square feet, this non-smoking room features two queen beds adorned with premium bedding, ensuring a restful night's sleep. 

Room Features:

  • Size: Approximately 342 sq ft

  • Beds: 2 queen beds

  • Amenities: Air conditioning, ceiling fan, flat-screen satellite TV, free Wi-Fi, coffee/tea maker, in-room safe, iron and ironing board and fitness center. Free daily breakfast included.

 

Hampton Inn & Suites Napa | Room, 1 King Bed, Non Smoking, Refrigerator
Available until May 22, 2026

Starting At: $1,897.00
Deposit: $150.00 per person

This room offers a comfortable and convenient stay for up to four guests. Spanning approximately 342 square feet, this non-smoking room features two queen beds adorned with premium bedding, ensuring a restful night's sleep. 

Room Features:

  • Size: Approximately 336 sq ft

  • Beds: 1 King Bed

  • Amenities: Air conditioning, ceiling fan, flat-screen satellite TV, free Wi-Fi, coffee/tea maker, in-room safe, iron and ironing board and fitness center. Free daily breakfast included.

 
 

Extra Options

Hot Air Balloon Ride- 1 Hour
Available until February 6, 2026

$280.00

Embark on a breathtaking hot air balloon adventure over the iconic Napa Valley, where rolling vineyards, lush landscapes, and the majestic Mount Saint Helena await. Begin your day with the soft, golden light of sunrise as you lift off from the charming village of Yountville, known for its world-class dining and wineries.

After meeting your certified pilot, you'll gently ascend above the valley, where panoramic views stretch as far as the eye can see. On clear mornings, you might even catch a glimpse of the San Francisco skyline to the west and the snow-capped Sierras to the east. Soar between 1,000 and 3,000 feet (300 to 900 meters) above the valley floor, taking in a bird’s-eye view of one of the world’s most renowned wine regions.

As your journey winds down, you’ll slowly descend back to the valley floor—your final chance to soak in the serene beauty of Napa from above.

 
Media collage
 
 
 

Jarvis Winery - Included
Available until July 9, 2026

$0.00

Jarvis Estate Winery is a true hidden gem, nestled in a 45,000-square-foot cave deep within the Vaca Mountains. Known for its luxurious underground setting and exceptional small-batch wines, this exclusive Napa experience blends innovation with old-world charm.
 
 

V. Sattui Winery Tasting - Included
Available until July 9, 2026

$0.00

Nestled in the heart of Napa Valley, V. Sattui Winery offers an unforgettable experience with award-winning wines, lush picnic grounds, and a charming marketplace. Sip, savor, and soak in the vineyard views at this iconic destination.
 

Castello di Amorosa Tasting - Included
Available until July 9, 2026

$0.00

Step into a stunning medieval-style castle in Napa Valley for a premium wine tasting experience. Castello di Amorosa offers exquisite wines, grand architecture, and unforgettable views—truly a tasting like no other.
 

1-Night Stay in San Francisco - Included
Available until July 9, 2026

$0.00

Hotel is currently TBD. Multiple people sharing a room can spilt the cost equally. Hotel will be located near Fisherman's Wharf/ Pier 39. 
 

San Francisco Golden Gate To Sausalito Bike Tour - 1-3 hours
Available until July 9, 2026

$75.00

Pedal your way from San Francisco to Sausalito on this scenic bike tour that takes you across the iconic Golden Gate Bridge. Enjoy stunning views of the bay as you ride along a mostly flat route with a knowledgeable guide. Once in the charming, artsy town of Sausalito, you'll have free time to explore on your own. Afterward, return to San Francisco whenever you’re ready—either by biking back or hopping on a ferry (ticket available for purchase). You'll have full-day access to a classic or electric bike and gear.

Tour highlights:

  • Ride with a guide across the Golden Gate Bridge to Sausalito

  • Cruise a mostly flat path along San Francisco’s beautiful waterfront

  • Enjoy full-day use of your bike and equipment

  • Choose to upgrade to an electric bike for a more relaxed ride

  • Tour starts at $75 per person. Price is $105 per person for an electric bike
 
Gallery picture 9 (from the experience provider)