Private tour in Boston Sasha G

Connecticut Travel – A Full Day of Adventure Awaits!

-
Hours icon 10 hours
Private transportation
Private tour for 1-4 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 10 hours
Private transportation
Private tour for 1-4 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later

Sasha G.

4.7

Guide rating

35

Reviews

Tours delivered

5 hrs

Avg. response time

🌟 Meet Your Private Tour Guide – Sasha G. Customized Private Tours of Boston, New England & Beyond 🚗📷 Hi! I’m Sasha — an avid nature photographer, storyteller, and passionate private tour guide who believes travel should be meaningful, personal, and joyful. Whether you're exploring Boston for the first time or returning to uncover hidden New England gems, I create one-of-a-kind driving and walking tours tailored just for you. I don’t just guide in Boston. I offer private tours across all five New England states — and even further! From the scenic coasts of Maine to the mountains of Vermont, from charming Connecticut villages to Upstate New York and even Pennsylvania — if we can drive there, I’ll take you. 💡 What Makes My Tours Different? ✨ Every tour is custom-built – Based on your group, your interests, and your pace (families, couples, solo travelers, seniors, teens, or kids). 📸 You’ll always get great photo stops – As an amateur photographer, I know the most scenic and peaceful spots in every season. 🧭 Flexible and guest-centered – Stop where you want, skip what you don’t care for, extend time in places you love — you’re in charge. 🏛️ Not licensed for interior monument guiding, but I’ll always make sure you have what you need: → A real on-site guide when available, or → A downloadable app or handheld device for self-guided touring inside. 🌈 Fun over facts – Instead of overwhelming you with dates and names, I point out unique details and local stories. ❤️ Every tour is prepared with love and care – I don’t just run tours—I design experiences that reflect you. 🌄 Tour Types I Offer: 🏙️ Boston City Highlights and Hidden Gems 🕍 Jewish Heritage Tours (Boston + Beyond) 🍷 Food, Wine and Coastal Culinary Escapes 🌳 Nature, Lakes, Waterfalls & Wildlife Drives 🎒 Kid-Friendly & Teen-Focused Explorations 📷 Scenic Photography Outings (All Seasons) 🛍️ Real Estate, Shopping, and Neighborhood Tours 🏰 Multi-State Trips (MA, ME, VT, NH, RI, CT, NY, PA) 🔔 Please Note: 🗣️ I’m not a native English speaker, so I do speak with an accent — but I always communicate clearly and kindly 😊 🚙 My car is not handicap accessible 🚫 No smoking, alcohol, or recreational drugs in the vehicle (prescriptions okay) 🩺 CPR and AED certified by the American Heart Association 📬 Let’s Go on an Adventure! If you’re looking for a guide with a beautiful soul, a love for people, and a passion for showing you more than just the usual sights, I’m your guide. Let’s plan a tour that matches your mood, your group, and your dreams. One that feels relaxed, exciting, and just right for you. 📆 Reach out to book your unforgettable journey through Boston and beyond. 👉 Explore New England with someone who truly cares. Let me show you the places I love — and help you fall in love with them too. 💛

Have a question or want to customize this tour? Message Sasha G.

Overview of your Boston tour

Enjoy a full day in our neighboring state of Connecticut, filled with history, scenery, and fun! Begin at Gillette Castle and State Park, where the whimsical architecture and river views will amaze you. Continue with a boat or ferry ride for a refreshing perspective of the castle from the water, and if available, enjoy a nostalgic trip on the historic Essex Steam Train. Afterward, savor a delicious lunch and wine tasting at a charming local winery. End the day with a stroll along the famous Connecticut Antiques Trail, where hidden treasures and unique finds await. Please note that during the summer, these visits can be arranged daily; however, after Labor Day, many attractions are open only on weekends and holidays. Fall, Winter, and Spring itineraries may be adjusted to accommodate all-season travel. Join us for a day of exploration, culture, and discovery—just a short trip away!

Your Boston tour itinerary

Start your adventure at Gillette Castle and State Park, exploring William Gillette’s whimsical mansion and scenic river views. Continue with a boat or ferry ride for a refreshing perspective of the castle from the water. Depending on availability, enjoy a ride on the historic Essex Steam Train for a nostalgic touch. Afterward, relax at a local winery with a delicious lunch and wine tasting, savoring Connecticut’s regional flavors. Conclude your day along the famous Connecticut Antiques Trail, where hidden treasures and unique finds await. Please note that while summer programs run daily, many attractions operate only on weekends and holidays after Labor Day. Our Fall, Winter, and Spring itineraries will be adjusted accordingly to ensure a fulfilling experience throughout the year. Join us for a day of history, culture, and fun—just across the border!

Want to customize this tour?

Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.

Transport details
Type: Private Transportation / Category: Suv

2019 BMW X3 SUV

What's included
Private Guide
Tickets: most admissions, but not the train
Private Transportation
Other: Tastings, simple lunch (a soup and a toast or similar)
What's not included
Tickets: Scenic Historical Train Ride is extra and based on availability
Meeting location

Boston, Massachusetts, United States

I can meet you anywhere in Boston or West of Boston. At your hotel, in your private residence, and so on. I will not be able to meet you at the airport (any airport), but other locations are fine

  • You can request a different meeting location (for example, your hotel) during the checkout process.
Other details
Tour categories
History
Day Trip
Nature Wildlife And Safaris
Food And Drink
Boat
Architecture
Tour reference number
1437900
Languages
English
Russian
Activity level
Moderate
Accessibility
Kid Friendly

Frequently asked questions

Who is this private tour in Boston best suited for?

This private tour is perfect for travellers who want to explore Connecticut's rich history, scenic beauty, and local flavours in a single day. It's ideal for those looking to connect with a local guide like Sasha G. for deeper insights into the area. The tour is also kid-friendly, making it suitable for families.

What should I bring or wear?

Can this private tour in Boston be customized to focus on what I want to see and skip places I've already visited?

How long is the tour, and can the start time or duration be adjusted?

Where does the tour start and end?

Is transportation included?

How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?

What languages is this tour offered in?

What's included in this private tour, and what should I budget for separately?

Is this a private tour? What is the maximum group size and the starting price?

AI-generated. Please confirm details with your guide

-
Hours icon 10 hours
Private transportation
Private tour for 1-4 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 10 hours
Private transportation
Private tour for 1-4 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
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