Autumn Taste of New England

Join us on this fun and exciting New England Trip!

 

October 4-12, 2025

 

Day 1 Saturday, October 4

Depart pickup and head to pre night hotel in Chicago, IL.

 

Day 2 Sunday, October 5

Depart from Chicago and fly to Boston.

 

Welcome to New England! Arrive at Boston’s Logan International airport where our Timi's Tours motorcoach will meet the group. We will head to the Boston area hotel for the evening. Take time to relax and freshen up before gathering for a welcome dinner. (D)

 

Day 3 Monday, October 6

Historic Boston, Stockbridge, & the Berkshires

 

This morning, set out for a guided (driving) tour of historic Boston, the birthplace of American Freedom! Follow the famous Freedom Trail viewing many historic sites while hearing tales of the brave Bostonians and Colonialists who dared to challenge Britain and helped establish the greatest republic in the world. Enjoy free time for lunch on our own at Faneuil Hall Marketplace which is as alive today as it was in 1742 when our nation’s fathers proclaimed it “The Cradle of Liberty.” This afternoon, enjoy the beautiful colors of autumn as you travel through the Pioneer Valley to the Berkshires Hills! Enjoy a visit to the famous Norman Rockwell Museum found in the beautiful town of Stockbridge! This afternoon, arrive to your hotel and take some time to freshen up before enjoying a delicious dinner this evening. (B,D)

 

Day 4 Tuesday, October 7

Berkshire Cottage Tour, Hildene & Lincoln Family Home

 

Enjoy a ‘Cottage Tour’ through the Berkshires this morning, viewing magnificent Gilded Age Mansions. Travel north to the Green Mountains of Vermont, touring through historic Bennington, and visiting the Bennington Monument State Historic Site. Continue to the beautiful village of Manchester to visit the magnificent Hildene, the former summer home of Robert Todd Lincoln, son of Abraham Lincoln, and his wife Mary Harlan Lincoln. Tour the restored 24-room Georgian Revival mansion, hear the 1908 Aeolian Organ, and explore the magnificent gardens. This afternoon, sit back, relax, and take in the beautiful autumn scenery as we journey to our Vermont Resort for a relaxing two-night stay. This evening, gather for a delicious dinner together. (B,D)

 

Day 5 Wednesday, October 8

Maple Sugar Experience, Vermont State Capitol, Trapp Family Lodge History Tour & Stowe Village

 

Today explore Vermont’s splendid foliage and countryside, beginning with a visit to one of Vermont’s Family Maple Sugar farm! Tour the farm; enjoy a lively maple demonstration and sample syrups! Enjoy free time and lunch on own in Montpelier, Vermont’s state Capitol. Admire the majestic State House and explore this delightful town. This afternoon, the hills come alive with a special visit to the famous Trapp Family Lodge. As Maria von Trapp once said, “Our life is like a beautiful story that happens to be true.” Hear their story on this unique History Tour! Finish the day off with some free time in the charming village of Stowe. Enjoy a planned dinner this evening. (B,D)

 

Day 6 Thursday, October 9

Lake Winnipesaukee Cruise, Moulton Farm & Kancamagus Hwy

 

Enjoy another spectacular day of touring through the Lakes Region of New Hampshire! Start the day in the charming lakeside village of Wolfeboro, known as the oldest Summer Resort in America. Enjoy some free time to explore before boarding the M/S Mount Washington for a scenic cruise on Lake Winnipesaukee. While aboard, enjoy a buffet lunch. Disembark in Weirs Beach and venture to Moulton Farm, an authentic family-owned New England farm, for a fun wagon ride and tasty treats! Travel along the Kancamagus Highway, one of the country’s most scenic by-ways, viewing magnificent scenery and making picture stops. Check into your North Conway hotel for a two-night stay. This evening, gather for a delicious dinner at one of the area’s fine restaurants. (B,L,D)

 

Day 7 Friday, October 10

Mount Washington Hotel Tour & Luncheon and Mount Washington Cog Railway

 

This morning set off for the majestic White Mountains of New Hampshire and the historic Omni Mount Washington Hotel. A grand masterpiece of Spanish Renaissance architecture, The Mount Washington Hotel was a two-year labor of love for 250 master craftsmen. Conceived by industrialist Joseph Stickney, this National Historic Landmark opened in 1902 and at once became a favorite summer haunt for poets, presidents, and princes. Enjoy a self-guided tour of this magnificent hotel followed by a delicious luncheon in the grand dining room. Journey to the Mount Washington Cog Railway for an unforgettable and exciting “once in a lifetime” railing experience. In 1869, the Cog Railway was an engineering marvel, a technology of toothed cog gears, rack rails and tilted boilers. Enjoy a rare glimpse of this world gone by while enjoying spectacular views as we travel up some of the steepest railroad tracks in existence. before checking into your North Conway hotel for a two-night stay. This evening, dinner is on your own. (B,L)

 

Day 8 Saturday, October 11

Kennebunkport, Ogunquit, Lobster Cruise, & Nubble Lighthouse

 

Set off for the stunning coastline of “Down East” Maine, to the popular summer resort of Kennebunkport! Drive by Walker’s Point where the summer home of the 41st President of the United States George H. W. Bush. Enjoy free time in Dock Square to explore, shop and have lunch on own. Then continue to the seaside village of Ogunquit – named by the Abenaki Indians meaning, “Beautiful place by the sea” to board Finest Kind Cruises for a fun-filled lobster cruise experience! Enjoy the scenic beauty of Ogunquit’s shoreline, learn about lobsters and their habitat, and see traps hauled and lobsters caught by an authentic Maine lobsterman. Enjoy some free time in Perkin’s Cove before checking into your Resort. Tonight, enjoy a traditional down east meal for a chance to try succulent Maine lobster! (B, Lobster Dinner)

 

Day 9 Sunday, October 12

Depart for Home

 

This morning, we will head to Boston Logan International Airport , taking with you many treasured memories of your Autumn in New England vacation. (B)

 

Your trip includes luxury transportation, airfare, hotel rooms, included activities and 15 Meals (7 Breakfasts, 2 Lunches, 6 Dinners).

 

Starting May 7th, 2025 a REAL ID will be required to fly.

 

Occupancy	Due At Booking	Due 3/7/25	6/7/25
Double-$4,895	$1,995	$1,450	$1,450
Single-$6,095	$1,995	$2,050	$2,050
Triple-$4,695	$1,995	$1,350	$1,350
Quad-$4,495	$1,995	$1,250	$1,250

 

Timi's Tours offers Travel Protection through Trip Mate. The Pre-Existing Medical Condition Exclusion Waiver is available if Travel Protection is purchased at the same time you make your Timi's Tours deposit (or within 15 days). For questions about coverage please call our office.

 

Travel Insurance price per person:

Single: $549.77

Double: $441.53

Triple: $423.49

Quad: $405.45

 

Activity Level: 2

*Our Activity levels are a 1-4 scale. To view what each level includes, please go to the  “Policy” tab on the website*