A 5-Day Vermont Experience: Small Group Tours with Personal Touches
If you’re after an authentic Vermont adventure that balances scenic beauty, local history, and charming towns, this small group 5-day tour offers just that. For $2,495 per person, you get a well-curated itinerary that hits the highlights—think waterfalls, historic farms, and artisan studios—with a maximum of six travelers. Guided by a knowledgeable host, Natalia, this trip feels more like exploring with new friends than a typical bus tour.
We love how this experience combines personalized service, with pickup at your hotel and a cozy group size that encourages genuine connection. The inclusion of admission to key attractions and a comfortable vehicle means you’ll focus on enjoying Vermont, not how to navigate it. Plus, the itinerary balances nature, history, and local culture — perfect for those who want a well-rounded taste of the Green Mountain State.
One thing to consider: meals outside of breakfast are not included. You’ll need to budget for lunch and dinner, but with plenty of great Vermont eateries nearby, that’s part of the fun. This tour is ideal for travelers who love small-group intimacy, flexible exploration, and authentic experiences—perfect if you want to avoid the crowds and enjoy Vermont’s quieter, scenic spots.
Key Points
- Intimate Group Size: Only 2 to 6 travelers ensure personalized attention and meaningful conversations.
- Diverse Itinerary: Combines scenic drives, historic sites, artisan studios, and charming towns.
- Expert Guide: Natalia’s passion and knowledge shine through, making each stop lively and insightful.
- Comfort & Convenience: Air-conditioned transportation, hotel accommodations, and breakfast included add ease to your trip.
- Value for Money: Admission fees and multiple attractions included, making it a well-priced way to see Vermont.
- Flexible, Authentic Experience: Small group, local insights, and a focus on genuine Vermont culture.
Exploring Vermont on a 5-Day Small Group Tour
Vermont is a state that whispers stories through its mountain peaks, historic villages, and artisanal crafts—this tour captures that essence without rushing or sacrificing depth. It’s perfect for those who want a personalized, in-depth look at what makes Vermont special, all while traveling comfortably with like-minded explorers.
Planning more time in Burlington? We've covered other experiences worth considering.
Day 1: From Burlington to Stowe via Waterbury
Your journey begins with a hotel pickup in Burlington, where Natalia greets you with a warm smile and a shared excitement for Vermont. First stop is Waterbury, home to the famous Ben & Jerry’s Ice Cream Factory and Cold Hollow Cider Mill. Here, your sweet tooth will thank you; the tours are fun and give you a taste of Vermont’s dairy and cider traditions. Ben & Jerry’s is a classic, but the Cold Hollow Cider Mill offers a genuine glimpse into the region’s apple-growing heritage.
Next, the group heads to the Trapp Family Lodge in Stowe. This former residence of the Von Trapp family (who inspired The Sound of Music) offers a mix of historical charm and stunning mountain views. A scenic drive through Smugglers Notch State Park provides a chance to marvel at Vermont’s rugged beauty—expect tight curves and lush vistas that make for memorable photos.
You’ll have time to explore Stowe village, renowned for its cozy shops and welcoming atmosphere. Lunch options are available for purchase, giving you a chance to try local fare. The day concludes with a drop-off at your Killington hotel, setting the tone for relaxed exploration.
Day 2: A Taste of Historic Woodstock and Artistic Quechee
Day 2 takes you to Woodstock, one of Vermont’s most picturesque towns. The highlight is a guided tour of the Marsh-Billings-Rockefeller Mansion, led by a National Park Service ranger. The house’s architecture and art collection—including Hudson River School paintings—offer a window into the region’s cultural history. Reviewers say, “All we had to do was show up,” which speaks to the thoughtful planning and ease of the experience.
After lunch in Woodstock’s downtown, known for its galleries and charming covered bridges, you’ll visit Simon Pearce, a renowned glassblowing studio in nearby Quechee. Watching artisans craft crystal glassware and pottery is mesmerizing, and you can purchase unique handcrafted pieces to take home.
Day 3: Plymouth’s President Calvin Coolidge
Vermont’s history takes center stage on Day 3 with a visit to Plymouth, home of President Calvin Coolidge. You’ll tour his childhood home, barns, and local sites—a rare chance to step into the life of a U.S. president’s early years. It’s a quiet, almost untouched slice of Vermont life, described in reviews as “virtually unchanged since the 1900s.”
Just up the road, the Plymouth Cheese Factory offers a chance to sample and buy some of Vermont’s best cheeses—locally made and full of character. It’s a day that combines history and local flavors, appealing to those who enjoy learning about political roots and tasting regional specialties.
Day 4: Montpelier, Warren, and Scenic Vistas
On Day 4, you’ll explore Montpelier, Vermont’s capital. The State House tour highlights Vermont’s early government buildings, and guides are on hand to answer questions—adding depth to the visit. From there, a scenic drive along Vermont RT 100 takes you to Warren, with stops at Appalachian Gap and Moss Glen Falls. Both spots are praised for their breathtaking views and photo opportunities.
Lunch at The Warren Store offers authentic Vermont fare—think hearty sandwiches, local cheeses, and homemade pies. The day balances government, nature, and small-town charm, catering to those who love diverse experiences.
Day 5: Shelburne’s Art, History, and Agriculture
Your Vermont tour culminates in Shelburne. The Shelburne Museum is a highlight, with 39 buildings and over 150,000 works of art—including the iconic Steamboat Ticonderoga, which transports visitors back to 1923. The museum’s self-guided format, paired with ample free time, allows you to explore at your own pace, making it ideal for art lovers.
Later, you’ll visit Shelburne Farms, an organization dedicated to education and sustainable farming. It’s a perfect spot to wrap up your Vermont adventure—combining visual beauty, local food, and a sense of place.
What Makes This Tour Special?
Natalia’s guides are highlighted repeatedly in reviews for their passion and deep knowledge, making every stop engaging. Travelers mention how she personalizes the experience, sharing insider tips and stories that bring Vermont’s history and culture alive. The small group setting ensures plenty of interaction and a relaxed pace—no feeling rushed or overwhelmed.
The choice of locations is thoughtfully curated. From the historic homes and farms to artisan studios and scenic viewpoints, you’ll see a variety of Vermont’s highlights without feeling like you’re ticking boxes. The inclusion of admission fees helps you focus on exploring, not budgeting on the spot, which adds to the value.
The hotel stay at Snowed Inn in Killington is comfortable and conveniently located, providing a cozy base for your adventures. Breakfasts are included, giving you a good start each day, while the flexibility for lunch and dinner allows you to sample Vermont’s local cuisine at your leisure.
Who Is This Tour Best Suited For?
This tour appeals to travelers seeking a personalized experience with a guide who knows Vermont inside and out. If you love history, scenic drives, artisan crafts, and local food, this is an excellent choice. It’s perfect for those who prefer small groups over large tours, craving authentic encounters rather than cookie-cutter attractions.
It’s also suitable for those comfortable with a flexible schedule and willing to explore at a relaxed pace. If you’re visiting Vermont for the first time and want a comprehensive, engaging overview covering the state’s best bits, this tour will serve you well.
FAQ
Does the tour include transportation?
Yes, an air-conditioned vehicle is provided for all the drives, making it easy to relax and enjoy the scenery without worrying about navigating Vermont’s winding roads.
What’s the group size?
The maximum is six travelers, ensuring a small, intimate experience. Most groups will be between two and six people.
Are meals included?
Breakfast is included for four mornings, but lunch and dinner are not. There are plenty of nearby restaurants and cafes at each stop to choose from.
Is the tour suitable for children or older travelers?
Most travelers can participate, but consider individual mobility and stamina, especially for scenic drives and walking around towns.
What are the accommodations like?
You’ll stay four nights at the Snowed Inn in Killington, a comfortable hotel with easy access to the tour’s destinations. Rooms with two beds are available upon request.
How far in advance should I book?
Availability is limited because of the small group size. Confirmations are sent within 48 hours of booking, so early booking is recommended.
Can I customize or extend my stay?
Since accommodations are included, extending your trip at the Snowed Inn might be possible—just ask before booking.
To sum it up, this small-group Vermont tour offers a thoughtfully curated, enriching experience that balances scenic beauty, history, and local craftsmanship. With knowledgeable guides, comfortable transportation, and a flexible schedule, it’s perfect for travelers who want to see Vermont without feeling rushed or lost in crowds. Whether you’re a history buff, a nature lover, or an appreciator of artisanal food, this tour provides a genuine window into Vermont’s soul. It’s best suited for those who value personal contact and authentic experiences over cookie-cutter sightseeing—an adventure that leaves you with memories to cherish.