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Private tour in Boston Sasha G
New England in Four Acts
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4 days
1
Tour date
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4 days
1
Sasha G.
4.7
Guide rating
40
Reviews
Tours delivered
4 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.
Four Days. Four States. One Unforgettable Road Trip.
Overview of your Boston tour
Discover New England in Four Acts - four days, four states, and four very different sides of this beautiful region. From the Massachusetts and Maine coast to New Hampshire's lakes and White Mountains, and Vermont's country roads, farms, and small towns, this private road trip goes beyond the usual highlights. Travel with up to three guests, with flexibility for scenic stops, villages, local tastings, and different mobility levels, including limited mobility. Transportation, gas, private guide/driver, water, snacks, planned admissions, tickets, and tastings are included. Hotels and regular meals are extra. Guests must provide and pay for the guide's separate room at the same hotel for all 3 nights. Expect beautiful scenery, local flavors, history, hidden corners, and plenty of New England character.
Your Boston tour itinerary
Day 1 - Cape Ann & the Maine Coast: Travel through Cape Ann, Rockport, and Gloucester, then follow the coast north to Nubble Lighthouse and Kennebunkport, Maine. Overnight in Kennebunkport. Day 2 - Country Roads & the Lakes Region: Head inland through scenic New Hampshire, with Canterbury Shaker Village, Lake Winnipesaukee, country roads, and, depending on season and schedule, a scenic train or boat ride. Overnight in North Conway. Day 3 - White Mountains & Kancamagus Highway: Explore the White Mountains and drive the spectacular Kancamagus Highway, with scenic overlooks and short stops. Continue through Lincoln into Vermont. Overnight in Stowe. Day 4 - Vermont Country Roads: Explore Stowe and scenic Route 100, with farms, small towns, and stops for local cider, maple products, cheese, and other Vermont specialties before returning to Massachusetts. Specific stops may vary based on guests' interests, mobility, weather, and seasonal availability.
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
BMW X3 Private transportation is provided throughout the entire 4-day tour in a comfortable, air-conditioned vehicle. I will be your private guide and driver, so we can keep the itinerary flexible and add scenic or photo stops along the way when time permits. Gas and driving-related expenses are included in the tour price. The tour is designed for up to 3 guests. Because this is a multi-day road trip and all luggage travels with us, luggage is limited to 3 carry-on-size bags total. Please contact me in advance if you plan to travel with larger luggage.
What's included
Meeting location
Boston, MA, USA
Hotel/accomodation, seaport, South Station, a private house within 25 miles of Boston. I do not pick up from the airport. Other-please ask first.
- You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
Tour reference number
Languages
English
RussianActivity level
Accessibility
FAQs
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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?
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How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?
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AI-generated. Please confirm details with your guide
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4 days
1
Tour date
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4 days
1
Tour date
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Book with a deposit
If your tour is valued over $200 USD and booked at least 45 days before the tour date, you can book with a 20% deposit!
How it works
- Your credit card will be authorized only for the deposit amount.
- Funds will not be withdrawn until your tour booking is fully processed.
- The remaining balance will automatically be charged to your credit card 30 days before your tour date.