Tour Highlights:

· Stay at the von Trapp Family Lodge and Resort, inspired by the famous musical family

· Brilliant fall foliage of Vermont and New Hampshire

· Grand elegance of the Omni Mount Washington Resort

· Scenic journey along the Kancamagus Highway

· Top notch views from Bretton Woods Scenic Skyway Gondola

· Sweet stop at Ben & Jerry’s Factory

· Stroll the charming streets of Historic Stowe Downtown

· Explore quaint shops and history in Historic Woodstock Downtown

· Natural beauty of New Hampshire’s White Mountains

Tour Includes:

· Five nights in carefully selected, premium hotels

· Most meals included, featuring regional flavors and memorable dining experiences

· All sightseeing admissions and guided tours

· Tips and taxes on included meals

· Baggage handling for ease and convenience

· Experienced Travel Host

· Workman Bus & Driver in New England

Hotels:

Hyatt Regency Boston, Omni Mount Washington, von Trapp Lodge & Resort

Itinerary:

Day 1 – Sunday, October 4: Arrival in Boston

Your journey begins with a group flight from Orlando to Boston. Upon arrival, you will transfer to the Hyatt Regency Boston Harbor, located right on the waterfront with beautiful skyline views. Enjoy a Welcome Reception at the hotel after check-in and meet fellow travelers and preview the week ahead.

Overnight: Hyatt Regency Boston Harbor

Day 2 – Monday, October 5: Exploring Historic Boston

Start the day with breakfast at the hotel. After breakfast, depart for a guided walk along the Freedom Trail, beginning near Boston Common. Enjoy time in Boston Common for lunch before continuing with an afternoon Boston city tour by motorcoach. In the evening, enjoy a classic New England seafood dinner at Legal Sea Foods – Harborside, or similar.

Overnight: Hyatt Regency Boston Harbor

Day 3 – Tuesday, October 6: Scenic Route to the White Mountains

After breakfast at the Hyatt Regency Boston Harbor, depart toward New Hampshire. Enjoy a rest stop at the Hooksett Welcome Center, followed by free time for lunch and shopping at Mills Marketplace in Lincoln. In the afternoon, experience one of New England’s most iconic drives—the Kancamagus Highway—with photo stops to take in the fall foliage.  Arrive at the Omni Mount Washington Resort around in the early evening with dinner served on the hotel terrace, offering spectacular mountain views.

Overnight: Omni Mount Washington Resort

Day 4 – Wednesday, October 7: Gondola Ride & Vermont Countryside

Begin with breakfast at the resort, followed by a ride on the Bretton Woods Skyway Gondola for panoramic mountain vistas. Enjoy lunch at the top at Switchback Grille. After lunch we depart for Vermont. Arrive at the von Trapp Family Lodge in the afternoon and start with a guided history tour. Check into your room and enjoy dinner at von Trapp Brewing & Bierhall.

Overnight: von Trapp Family Lodge

Day 5 – Thursday, October 8: Classic Vermont Experiences

Enjoy breakfast before departing for the Cold Hollow Cider Mill.

Next, spend time exploring Historic Downtown Stowe before touring the Ben & Jerry’s Factory. Return to the lodge for rest and resort time, followed by a special dinner in the Mozart Room.

Overnight: von Trapp Family Lodge

Day 6 – Friday, October 9: Woodstock & Return Home

After breakfast, depart the lodge at and travel to the beautiful town of Woodstock, Vermont, known for its covered bridges, village green, and charming local shops. Continue south to the Hooksett Welcome Center before arriving at Boston Logan International Airport for your early evening flight to Orlando. Arrive at MCO, then transfer back to The Villages, concluding your New England fall adventure.

Airport Transportation: Group transportation is provided:

You may leave your car at The Workman Transportation & Travel office, 761 Hoopfer Way in The Villages. We will travel by motorcoach to/ from the Orlando International Airport.

PRICING:

Optional Group Flight: $497 per person (separate from tour cost)

$3,599.00 per person, Double Occupancy

$3,199.00 per person, Triple Occupancy

$4,900.00 per person, Single Occupancy

• A $600 deposit (per person) is required upon booking. Deposit is refundable until Friday, July 31 ,2026, less a $150.00 per person cancellation fee.

• Final payment is due Friday, July 31, 2026. Entire cost is non-refundable after this date.

Travel Insurance is strongly recommended and can be purchased through Travel Insured (outside company-separate from Workman). To purchase, click here: TRAVEL INSURED / WORKMAN TRAVEL INSURANCE | or call, 1-855-752-8303. Our agency # is 53258. Mention our Name & Number to receive the best rate.

Meet & Greet: TBA. Wildwood Community Center. (6500 Powell Rd. Wildwood, FL 34785) *If you cannot attend, that is not a problem, but please send an email to let us know.

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Workman Transportation uses their own deluxe motor coaches. They are driven by drivers certified and licensed for motor coach transportation. Our motor coaches are air conditioned, equipped with Wi-Fi, video monitors, on-board restroom, and reclining seats.

Our hosts are experienced and will help make your trip enjoyable. They will give you lots of information along the way to make the traveling time fun and interesting. We will strive to keep you comfortable by having rest stops every two to two and 1/2 hours in the schedule.

All tours require some walking and the ability to embark/disembark a motor-coach without assistance. Advance notice is required for special dietary requests and handicap seating.

Prices are per person. Rates and space are subject to availability. A minimum number of people is required for the trip to commence. Specified inclusions i.e. hotels, restaurants, shows, etc. are subject to change. Cancellation penalties will apply. Bus driver and Host gratuities are not included. Itinerary subject to modification based on host discretion and unforeseeable circumstances such as inclement weather.

Workman Transportation / Workman Travel is not responsible for errors and omissions in our print ads.