DAYS 1 – 2

Lenox, MA

“Autumn…the year’s last, loveliest smile” - William Cullen Bryant

We begin our adventure in the Berkshires, quintessential of New England and everything Autumn. The advent of Fall Foliage in Massachusetts brings a landscape of roads and meadows lined with trees ablaze with color, and invigorating cool, crisp air that makes you want to breathe deeply and enjoy the splendor of the season. For many in the Northeast, Fall is the most anticipated time of the year, bringing Fall Festivals, apple and pumpkin picking, an excuse to sit by the fire drinking hot cider and eating apple doughnuts, and spontaneous day trips for leaf peeping.

Upon arrival at Pittsfield Municipal (KPSF), make your way to the nearby town of Lenox, MA, where we will be staying for 2 nights. Take a few moments to relax, breathe the fresh air, and take in the beauty of our surroundings before meeting the group for our Opening Night Dinner. We will use this opportunity to get to know our fellow travelers while enjoying good food and conversation.

On day two, we will take a trip to a nearby Orchard and Winery, where we will spend the day partaking in traditional Fall activities- apple picking and wine tasting. Walk between the rows of trees, choosing the fruit that catches your fancy, and breathe in the fresh New England air. Stop by the store to indulge in fresh apple cider doughnuts, or buy some house made jam. Then come in to warm up and enjoy a wine tasting around the cozy fireplace.

After our outing, we will head back to the hotel, where you will have time to relax before we gather to enjoy a delicious meal together. Tonight and tomorrow morning we will discuss the route and weather for the next leg of our trip into Canada, and go over the intricacies of international flying.


DAYS 3 – 4


North to Canada!

We begin the day with breakfast at the hotel and a weather and route briefing, and a discussion of international flight planning and filing, and customs procedures.

We’ll then begin our excursion up to Canada, travelling over the scenic mountains of the Northeastern US, across the border and up to Quebec City, where we will clear customs and head to our hotel.

Quebec City is the capital city of Quebec, and has a distinct four-season continental climate, with warm summers and snowy winters. Old Quebec is the only walled city north of Mexico and has a uniquely European flavor, with narrow, winding streets and an extensive array of boutiques, museums and attractions. As the cradle of French civilization in North America, it’s a living history lesson with a remarkable mix of architecture, heritage, art, and culture.

After checking into the hotel, you will have free time to relax or even venture out along the waterfront, taking in Old Port and the incredible views of the St Lawrence River, before our group dinner, where you can relax, enjoy, and share stories about the day of flying.

The next day will begin with breakfast at the hotel, followed by a walk through the city and a cooking class.After the class the rest of your day will be free to explore parts of the city that we didn’t see or that you’d like to view in more depth.Quebec City has much to offer, including the Chateau Frotenac, Place Royale, Old Port, and Parliament Hill.Immerse yourself in Old Quebec, where the historical districts are all within walking distance from each other. Have dinner at your leisure and relax before the next leg of the trip.


DAYS 5 – 6


We’ll start day five with breakfast and a route and weather briefing for the final leg of our trip. After breakfast we’ll depart Quebec City, flying over the scenic landscape of northern Maine, stopping to clear customs in Bangor. From Bangor, we’ll continue to take in the magic of New England in the Fall as we turn south along the coast to our final destination- Martha’s Vineyard.

Martha’s Vineyard is an island south of Cape Cod in Massachusetts. It has a land area of 100 square miles and is the third largest on the East Coast of the US (and 58thin the US). The Vineyard is primarily a summer colony and only accessible by boat and air. It is a popular tourist destination because of its pleasant summer weather and beautiful beaches.

Take the time to relax and enjoy the view after checking into the hotel. Spend your free time before dinner exploring Edgartown.

Day six will be an opportunity for you to relax, shop, tour the island, or even just stay in enjoying the view with a good book.We will also set up a group outing for those that would like to participate.After the activities of the day, relax until our final group dinner, where we can share a last meal together and enjoy the company of fellow aviators.




Our final day will begin with breakfast, and a weather and route briefing. We will depart Martha’s Vineyard to fly over Block Island, East Hampton, and Long Island, towards the Statue of Liberty. We will then turn north up the Hudson River Corridor, with amazing views of NYC on our right. We will land at Essex County Airport (KCDW) and from there say our final goodbyes and make our departures from this adventure.



  • Two guests

  • 6 Nights Accommodations

    • 2 nights in the Berkshires

    • 2 nights Quebec City

    • 2 nights Martha’s Vineyard

  • Breakfast each morning

  • Dinner each evening (day 4 exception)

  • Ground transportation during trip

  • Planned Group activities in the Berkshires, Quebec City, and Martha’s Vineyard

  • Instructor in your aircraft (if requested- must request in advance)

  • Aircraft tiedown fees

  • Additional activities are available



The Flight Academy will not fly or sanction flight in weather that is unsafe or for which the Cirrus is not rated. The weather at our departure location and our destination must be above published minimums in order for us to launch.

In the event weather does not permit a flight to take place as scheduled, the Flight Academy will attempt to find an alternate route that allows for a safe execution of the flight. If the weather causes the trip to be cancelled, no refund will be offered. Any additional expenses incurred during the trip due to foul weather will be the responsibility of the customer.