Small Group 5-Day Tour Vacation Package in Vermont

Exploring Vermont in Style: A Deep Dive into the 5-Day Small Group Tour

If you’re considering a way to see Vermont beyond just a weekend getaway, this small group 5-day tour might be exactly what you’re looking for. Designed for up to six people, it promises an intimate vibe, personalized attention, and a chance to really soak in the sights, flavors, and stories of this picturesque state. While I haven’t taken this exact trip myself, I’ve looked into it thoroughly—and it sounds like a well-rounded experience that balances natural beauty, history, and local culture.

What I particularly appreciate is the focus on small groups — meaning you’re not just another face in a crowd, but part of a cozy, friendly crew. The inclusion of hotel pickup and admission to key attractions simplifies the logistics, so you can focus on enjoying Vermont’s scenic and cultural highlights. However, the cost of about $2,495 per person does put this experience into a more premium category, so it’s worth thinking about whether the tailor-made, guided approach aligns with your travel style.

One thing to note is that the tour is non-refundable—a standard policy for many guided experiences, but it’s good to be aware of before booking. This tour seems ideal for those who love a blend of nature, history, and local flavor without the hassle of planning every stop themselves. Whether you’re a Vermont virgin or a repeat visitor, there’s likely something here to pique your interest.

Key Points

• Intimate group size ensures personalized attention and a laid-back vibe
• Diverse itinerary covers scenic drives, historic sites, and local artisans
• Comfortable transportation and lodging included, with some flexibility on room arrangements
• Expert guides enrich the experience with stories and background info
• Focus on Vermont highlights like Stowe, Woodstock, Plymouth, Montpelier, and Shelburne
• Price includes attraction admissions and breakfasts, offering good value for a guided tour

A Closer Look at the Vermont Tour Experience

When thinking about a multi-day guided tour, what matters most is how well it balances carefully curated stops with a relaxed flow. From what I’ve seen of this tour, it manages to do that pretty well, taking you through a mix of Vermont’s most iconic spots and some lesser-known gems. Let’s break down each day and see what makes this experience stand out—and what might be a bit less ideal.

Day 1: From Burlington to Waterbury and Stowe

Starting bright and early, the tour kicks off with a pickup in Burlington, giving you a smooth start without the stress of driving. By heading to Waterbury and Stowe, you get to indulge in some classic Vermont experiences. First stop: the Ben & Jerry’s Ice Cream Factory—a must for anyone with even a passing interest in ice cream. The factory tour, while not detailed here, is usually a fun way to learn about how those famous pints are made, and it’s a treat to sample some flavors.

Next, the Cold Hollow Cider Mill offers a taste of Vermont’s apple harvest traditions—fresh cider, donuts, and local products. These stops highlight Vermont’s agricultural roots and give you a real sense of local craftsmanship. Then there’s the Trapp Family Lodge, inspired by the family that inspired “The Sound of Music.” This place isn’t just about the views but also about the story behind it, giving a cozy, alpine feel with its scenic surroundings.

Driving up to Smugglers Notch State Park offers a chance to see some of Vermont’s most stunning mountain scenery—narrow, winding roads that snake through impressive rock formations. The day ends in Killington, where you’ll stay overnight. This first day, which lasts about 7 hours including stops, is packed but manageable, especially since it’s tailored for small groups who appreciate flexibility.

Day 2: Exploring Woodstock and Quechee

On day two, the focus shifts to historic Woodstock, a charming Vermont town full of classic architecture and small-town charm. The Marsh-Billings-Rockefeller Mansion is a standout, offering insight into both the history and conservation efforts of the area. A guided tour here is perfect for history buffs and art lovers alike, thanks to its collection of Hudson River School paintings.

After lunch in downtown Woodstock, you’ll have free time for wandering art galleries, historic houses, and a picturesque covered bridge—ideal for those who enjoy exploring at their own pace. The afternoon visits the Simon Pearce glassblowing studio, where craftsmanship meets artistry. Watching artisans create stunning glassware and pottery is not only fascinating but also offers a glimpse into Vermont’s thriving arts scene.

This day emphasizes cultural depth and artisan craftsmanship, making it a good choice if you love seeing local talent in action. Many reviews mention how knowledgeable and passionate guides elevate the experience—”Natalia had each day planned with a nice balance of history, nature and background information,” one reviewer notes.

Day 3: Plymouth and Plymouth Cheese Factory

Day three immerses you in Plymouth, the birthplace of President Calvin Coolidge. Here, you can tour the Coolidge Homestead, taking a step back in time to see the home where the 30th President grew up. It’s a rare chance to see a preserved historic village that remains largely unchanged since the early 1900s.

Adjacent to the homestead is the Plymouth Cheese Factory, offering locally produced cheeses that you can buy and take home. The stop provides a taste of Vermont’s dairy culture and local food scene. The overall pace remains relaxed, with about 7 hours dedicated to this day’s adventures.

Day 4: Montpelier and Warren

The state capital, Montpelier, is a perfect blend of political history and scenic beauty. The State House tour gives you a behind-the-scenes look at a building that’s both historic and still in active use today. From there, a drive along VT RT 100 reveals Vermont’s quintessential mountain vistas, culminating at Appalachian Gap and Moss Glen Falls.

Lunch at the Warren Store offers a quintessential Vermont experience—local food in a cozy setting. The day’s highlights are scenic drives and natural beauty, appealing to those who love outdoor landscapes and photogenic stops. The roughly 7-hour day keeps the pace comfortable and engaging.

Day 5: Shelburne Museums and Farms

For the grand finale, the tour heads north to Shelburne, a hub of arts, history, and farming. The Shelburne Museum is a true highlight, with 39 buildings, over 150,000 works of art, and historic boats like the Steamboat Ticonderoga—an impressive sight that captures life on the water in 1923.

Following the museum visit, Shelburne Farms offers a look into Vermont’s agricultural and conservation efforts. It’s a fitting way to wrap up a week of diverse experiences—combining art, history, and sustainable farming—all at a relaxed pace. Lunch here is also available for purchase, giving you time to reflect on your trip.

Why This Tour Might Be Just Right for You

This 5-day Vermont tour offers a carefully curated itinerary that balances natural beauty, history, arts, and local flavors. What makes it stand out are the intimate group size, knowledgeable guides, and thoughtfully chosen stops. The reviews consistently praise the guides’ passion and knowledge, which adds depth to each visit.

The inclusion of admission fees and breakfasts helps you understand the value—especially compared to the hassle of planning your own trip. The lodging at the Snowed Inn in Killington offers a cozy base, though it’s worth noting that if you have specific room preferences, you should inquire ahead of time.

However, the cost might be a consideration for some. At nearly $2,500 a person, it’s a premium experience, but many reviewers felt the value was justified given the personalized service and curated stops. If you prefer a self-guided trip, you might find this tour a tad more expensive but also more convenient and relaxing.

Who Should Consider This Tour?

This experience is best suited for travelers who value guided expertise, want to see Vermont without the stress of driving or planning, and appreciate small, friendly groups. It’s perfect for those who enjoy a mix of outdoor scenery, cultural exploration, and local artisan experiences.

If you’re traveling with someone who loves history, art, or scenic drives, this tour offers something for all. It’s also a good fit if you prefer a structured itinerary with the flexibility of a small group rather than navigating Vermont on your own.

FAQs

Is transportation included?
Yes, the tour provides an air-conditioned vehicle for all days, making the journey comfortable and stress-free.

What is the lodging like?
You will stay four nights at the Snowed Inn in Killington, Vermont, which offers cozy accommodations. If you need two beds in one room, it’s best to inquire before booking.

Are meals included?
Breakfasts are included for four days, but lunch and dinner are on your own—there are plenty of restaurants nearby for each meal.

Can I join if I arrive late?
The tour begins with a pickup at 9:00 AM in Burlington. It’s advised to arrive the night before if flying into Burlington International Airport to ensure you’re there on time.

What attractions are covered?
Stops include Waterbury, Stowe, Woodstock, Plymouth, Montpelier, and Shelburne, covering scenic drives, museums, historic sites, and artisan studios.

Is this tour suitable for families?
While not specifically marketed as family-friendly, the stops are generally suitable for most ages, especially those interested in history and scenic views.

What about gratuities?
Guide gratuities are not included, so if you feel the guides added extra value, a tip would be appreciated.

How far in advance should I book?
Given the intimate size and popularity, booking early is recommended, especially during peak seasons like summer and fall.

In essence, this Vermont tour offers a practical, engaging way to see the state’s highlights with knowledgeable guides and a small group. It’s an experience for those who truly want to immerse themselves without the stress of planning each detail and prefer meaningful connections over rushes through sights.