5 Days in Napa Valley: A Napa Valley Wine Train-Inspired Itinerary

Welcome to Napa Valley, where we invite you to slow down, sip, and savor life’s finest pleasures. Napa weaves together sky-high adventure, one-of-a-kind Wine Train dinners, and deeply restorative moments of calm. The most luxurious way to take in the region’s charm is aboard the iconic Napa Valley Wine Train, which offers sweeping vineyard views, delicious seasonal fare, and curated wines. 

This 5-day Napa itinerary is ideal if you want at least one day aboard the Napa Valley Wine Train, time for tastings in St. Helena, and a balance of culture, wellness, and riverside dining. It’s full of thoughtfully chosen experiences, much-deserved relaxation, and, of course, plenty of wine.

Day 1: Settle In and Savor Your Arrival in Downtown Napa

Day 1 At a Glance

• Check in at River Terrace Inn, your riverside home base in Downtown Napa

• Savor a Gourmet Express lunch aboard the Napa Valley Wine Train

• Stroll the Napa Riverfront, one of Fodor’s Best Riverwalks in the U.S.

• Indulge in a classic steakhouse dinner at Cole’s Chop House

Morning

Once you arrive, hand over your bags — and your stress. Your accommodations at the award-winning River Terrace Inn will be your home base and escape for the next five days. Overlooking the Napa River and nearby nature preserve, the Inn is located near Napa’s best tasting rooms, wine bars, fine-dining options, and downtown shopping. It’s the perfect place for you to unwind, refresh, and ease into the relaxed rhythm of Wine Country. 

Afternoon

For your first activity, indulge in the Napa Valley Wine Train’s Gourmet Express experience — a leisurely lunch paired with vineyard views drifting past your window. We’ll welcome you aboard this three-hour journey with a glass of sparkling wine. The journey continues with three courses of seasonal Wine Country cuisine, from fragrant starters to indulgent desserts. You’ll also receive a digital boarding photo keepsake to take home. This will set the tone for the rest of your stay in Napa: relaxed, luxurious, and elegant.

Evening

Your evening in Napa begins with a light walk along the Napa Riverfront, named one of Fodor’s 15 Best Riverwalks in the U.S. Stroll along the river to spot local wildlife, or pause for a fun photo-op at one of the various art displays, such as “The Big City Chair.” The Riverfront is home to award-winning restaurants, including Cole’s Chop House, named one of the best steakhouses in America by OpenTable. End your first day in Napa with one of their world-class dishes, paired with a robust list of wines, or indulge in one of their 175 hand-selected bourbons.

Day 2: Napa Valley Wine Tasting and Vista Dome Dinner on the Wine Train

Day 2 At a Glance

• Take a scenic drive along the Silverado Trail to Howell Mountain

• Hike at Moore Creek Park or head straight to a mountainside winery

• Enjoy a guided, wine-paired lunch at Joseph Phelps Vineyards

• Dine in style during a twilight Vista Dome Dinner on the Wine Train

Morning

Ease into your second day in Napa Valley with a scenic drive along the Silverado Trail up to Howell Mountain in St. Helena. Enjoy a hike with gorgeous valley views at Moore Creek Park on Lake Hennessey, or head straight to one of the mountainside wineries for a wine-tasting experience. Stags’ Leap Winery, Joseph Phelps Vineyards, and Amizetta Estate Vineyard are excellent options. If you prefer a slower pace, skip the hike and linger longer over your tasting and lunch instead. 

Afternoon

Stay a while and enjoy a wine-paired lunch at the historic Joseph Phelps Vineyards. A wine educator will guide you through a curated selection of estate wines paired with seasonal dishes, highlighting how each one enhances your meal.

Evening

A twilight dinner beneath the Napa sky awaits you aboard the Napa Valley Wine Train Vista Dome Dinner. A completely different experience from the lunchtime voyage, this immersive journey takes place in one of only ten 1952 Super Dome Pullman Railcars ever built. This fine-dining experience unfolds in the opulent, glass-domed observation-style dining car, where four courses are prepared and served on board during this two-and-a-half-hour ride through Napa Valley. 

Day 3: Culture, Craft, and Community 

Day 3 At a Glance

• Discover local art, culture, and history at the Napa Valley Museum

• Sample coffees, bites, and regional flavors at Oxbow Public Market

• Return to River Terrace Inn for riverside drinks at ALBA Bar + Café

• Cozy up by the fire pits and enjoy a relaxed dinner just steps from your room

Morning

Today is all about exploring the culture that surrounds the tracks. But first, fuel up with a delicious breakfast at Under-Study—whether it’s their overnight oats or French toast sticks, you’ll be ready for the exciting day ahead.  Immerse yourself in Napa Valley’s rich culture and history with a visit to the Napa Valley Museum. This vibrant cultural institution highlights the region’s history and artistic explorations through exhibitions, educational programs, and events that bring local stories and creativity to life. This day provides a thoughtful complement to your wine-filled adventures, enriching your experience with the context and stories behind the wines you’ve been savoring.

Afternoon

Head to the Oxbow Public Market for your afternoon pick-me-up. The market, situated along the Napa River, champions sustainable agriculture and features diverse local food vendors, artisan cafés, and an organic produce outlet from nearby farms. Stroll through the market for coffee, olive oil, donuts, and, of course, wine. For lunch, grab a bite from one of the local vendors, such as Hog Island Oyster Company or Bar Lucia,  and enjoy it while seated on the scenic outdoor deck overlooking the Napa River.

Evening

Enjoy a relaxing dinner at your accommodations, River Terrace Inn. ALBA Bar + Café offers casually elegant riverside dining just steps from your room. Take a seat by one of the outdoor fire pits while you choose a beverage from their list of wines, seasonal cocktails, and spirits. The menu ranges from burgers and seafood to flatbreads and wings – there’s truly something for everyone. Then turn in early — tomorrow begins with a sunrise adventure.

Day 4: Hot Air Balloons, Wellness, and Wine Elevated

Day 4 At a Glance

• Float above the vineyards on a sunrise hot air balloon ride

• Refuel with a gourmet breakfast for two at ALBA Bar + Café

• Choose your pace: Peloton ride, strength training, or riverside bike path

• Step into character for a Murder Mystery Dinner aboard the Wine Train

Morning

Begin your day with a sunrise hot air balloon ride with Napa Valley Balloons. This unforgettable experience offers rolling views of Napa Valley and its gorgeous vineyards. Watch the valley wake up below you — rows of vines catching the first light, mist lifting off the hills — from 5,000 feet up. Afterward, fuel up from your big morning adventure with a gourmet breakfast for two at ALBA Bar + Café. Sip your morning coffee or juice while savoring sandwiches, oats, yogurt, avocado toast, and all your classic breakfast favorites.

Afternoon

Wind down from your morning excursion with some leisure time. Head to the fitness center at the Inn for a Peloton class, or take advantage of their strength-training options, including dumbbells and TRX equipment. Looking for some outdoor activities? Enjoy a scenic bike ride along the Napa Riverfront. 

Evening

Tonight, there’s been a mysterious crime on the Wine Train! Search for the cunning killer (or conceal your role in the story) on the Murder Mystery Dinner journey — all while enjoying a three-course gourmet dinner during this two-and-a-half-hour fully immersive theatrical experience aboard our restored 1915 Pullman railcar.

Day 5: One Last Taste of Napa Valley

Day 5 At a Glance

• Take a final Napa Riverfront walk to a local café for coffee and brunch

• Squeeze in one last tasting at The Wine Thief or Gustavo Wine

• Toast to five days of Napa memories (and the wines heading home with you)

Morning

Take your final walk along the Napa Riverfront and stop at one of the local cafés along the way for coffee and brunch. With so many options to choose from, Winston’s Cafe is a great pick, and River Studio is perfect if you’re looking for a longer walk to start the day. Soak in the last morning in Napa Valley with every sip of coffee.

Afternoon

When in Napa Valley, why not enjoy one last tasting on the Riverfront? The Wine Thief offers tastings of wines that are rarely available anywhere else. Alternatively, experience a Gustavo Wine tasting featuring in-house wines crafted with a passion for winemaking and a focus on family values.

Evening

And just like that, your five days in Napa come to a close. We’re sure you will be leaving Napa Valley with cases of wine being shipped to your home (and maybe a few bottles packed in the suitcase), memories to last a lifetime, and plans for another vacation in Napa already swirling around your mind.

Ready for Your Napa Valley Wine Train Journey?

Five days in Napa can feel like a lifetime of indulgence — and still, leave you wanting more. Whether you ride the Wine Train once or more, it’s a core part of the Napa story: slow-paced and soul-filling. Explore Wine Train packages, special offers, and curated partner stays to make your dream itinerary effortless. Not sure where to begin? Explore our collection of Napa Valley Wine Train experiences and choose the journey that suits your travel style.