Maine · Hudson · Burlington · Montréal

	Transfer	Notes
May 22
	Flight ORD → PWM — United Airlines UA1401	✓ CONFIRMED — Departs Chicago O'Hare 6:18 PM · Arrives Portland 9:51 PM · Seats: James 11E · Debbie 11D · Conf: JM065Y
May 26
	Car Pick-Up — Portland International Jetport	✓ CONFIRMED — Dollar Car Rental · Nissan Rogue SUV (Intermediate) · 9:00 AM · Booking: 5086303019385350 · Driver: James Vincent Shine
	Hotel Check-In — Burlington, VT	✓ CONFIRMED — Hotel Vermont · 41 Cherry Street, Burlington · Conf: 6636.440.600 · PIN: 4833
May 28
	Hotel Check-In — Montréal, QC	✓ CONFIRMED — Hotel Gault · 449 Rue Sainte-Hélène, Vieux-Montréal · Conf: 5308.696.049 · PIN: 6794
Jun 1
	Car Drop-Off — Burlington International Airport	Dollar Car Rental · Burlington Airport · 12:30 PM · Booking: 5086303019385350
	Flight BTV → ORD — United Airlines UA329	Departs Burlington 4:42 PM · Arrives Chicago O'Hare 6:26 PM · Seats: James 10E · Debbie 10D · Conf: JM065Y

Who	Task	Notes
James	Confirm Dollar car rental	Verify booking 5086303019385350 — have driver's license and credit card ready at pick-up. Note: $650.26 due at counter (not prepaid)
—	Check travel insurance coverage for Canada	Confirm medical coverage is valid in Québec — consider trip cancellation/interruption cover for international portion
—	Ensure valid passport for Canada entry	Both travellers need valid passports or NEXUS cards — Canada border crossing between Burlington VT and Montréal QC
—	Research dining reservations — Burlington & Montréal	Burlington: Honey Road, Paradiso Hi-Fi · Montréal: Mon Lapin, Damas — book in advance as these are popular spots
—	Plan Day 1 driving stops	Route: Portland → North Conway (Diana's Baths waterfall) → Glover VT (Museum of Everyday Life, hours irregular) → optional Lake Willoughby detour → Stowe (lunch) → Smugglers' Notch → Burlington. Confirm Museum of Everyday Life is open before relying on it as a stop.
—	Note Hotel Gault damage deposit	CAD 250 damage deposit required at check-in — ensure credit card available. Free cancellation until May 25, 2026
—	Check in online for both United flights (24 hrs before)	UA1401 (May 22): check in May 21 after 6:18 PM · UA329 (Jun 1): check in May 31 after 4:42 PM · Conf: JM065Y · Passports required for both flights

Day 1 — Friday, May 22

Chicago → Portland · Arrival Evening

6:18 PM

Chicago O'Hare

ORD · Terminal

→

UA 1401 · Non-stop

9:51 PM

Portland, Maine

PWM · Portland Jetport

UA 1401

Conf: JM065Y

Seats: 11D & 11E

Accommodation Staying with friends in Portland · May 22–26 (4 nights)

Arrive late evening — flight lands at 9:51 PM. Easy first night settling in with friends after the flight.

Days 2–4 — Saturday–Monday, May 23–25

Portland with Friends

Accommodation Staying with friends in Portland · 3 full days

Portland Food Portland is one of the best food cities in New England — Duckfat (duck-fat fries & panini), Eventide Oyster Co., Fore Street, Honey Paw, Central Provisions

Portland Old Port Historic waterfront district — galleries, boutiques, cobblestone streets · Portland Museum of Art nearby

Day Trips Portland Head Light (Cape Elizabeth, 15 min) · Peaks Island ferry (20 min) · Cape Elizabeth shorepath

Car rental note: Rental car pick-up is on Tuesday, May 26 at 9:00 AM from Portland Jetport. No car needed for the Portland days.

Day 5 — Tuesday, May 26

Portland Jetport to Burlington via the White Mountains

Car Pick-Up Dollar Car Rental · Portland International Jetport (PWM) · 9:00 AM

Vehicle Nissan Rogue Intermediate SUV (or similar)

Booking 5086303019385350 · Driver: James Vincent Shine · $650.26 due at counter

Route Portland ME → North Conway NH → White Mountains → Northeast Kingdom VT → Stowe → Smugglers' Notch → Burlington · approx. 5.5–6 hrs driving (plus stops)

Stop 1 Diana's Baths — Near North Conway, NH · Easy waterfall walk (~½ mile) · Great for stretching after the drive · 20–40 min

Stop 2 (if open) Museum of Everyday Life — Glover, VT · Tiny barn museum devoted to ordinary objects; unusual, humorous, and thoughtful exhibits · 20–45 min · Hours irregular — treat as "stop if open"

Detour (optional) Lake Willoughby — ~20 min from Glover · Dramatic cliffs rising straight from the lake · No walking required for views · ~40 min round trip

Stop 3 — Lunch Stowe, VT — Just before Smugglers' Notch · Lunch: Butler's Pantry or Harrison's Restaurant & Bar · Optional quick art stop: Helen Day Art Center

Scenic Drive Smugglers' Notch — Huge glacial boulders, winding road, dense forest · One of Vermont's most dramatic mountain passes · Drive time: 25–30 min

Hotel Hotel Vermont · 41 Cherry Street, Burlington, VT 05401

Check-In From 4:00 PM · 2 nights

Room Standard King

Confirmation 6636.440.600 · PIN: 4833 · Free cancellation until May 24

Route highlights: The White Mountains deliver dramatic scenery before Vermont opens into the pastoral Northeast Kingdom. Smugglers' Notch — a narrow mountain pass famous for its massive glacial boulders — is one of Vermont's most memorable drives. Diana's Baths near North Conway is an ideal early stretch-and-walk stop. Aim to reach Stowe for lunch before tackling the pass in the afternoon. Cambridge pit stop: If passing through Cambridge (just north of Smugglers' Notch on the way to Burlington), Currier's Market is a local institution — great donuts and Vermont creamies worth stopping for.

Day 6 — Wednesday, May 27

Burlington — Shelburne Museum, Lake Champlain & the Arts

Hotel Hotel Vermont · 41 Cherry Street, Burlington, VT

Morning Shelburne Museum — 15 min drive from Burlington · Highlights: Steamboat Ticonderoga, American folk art galleries, Circus building, quilt collections · Allow 2–4 hours

Afternoon Waterfront Park — Views of Lake Champlain & the Adirondack Mountains · Burlington City Arts Center (BCA) · Optional: Fleming Museum of Art (contemporary & global art, 45–60 min)

Optional Shelburne Farms — ~10 min south of Burlington · 1,400-acre working farm on Lake Champlain · Guided farm tours, cheese-making, stunning grounds · 1.5–2 hours · A beautiful and distinctly Vermont experience

Optional Rokeby Museum — ~40 min south of Burlington · Underground Railroad history & abolitionist Robinson family farm · 1.5–2 hours

Dining Honey Road (Eastern Mediterranean) · Hen of the Wood (farm-to-table, reservation confirmed) · Paradiso Hi-Fi (coffee & cocktails)

Dinner Hen of the Wood · Reservation: Wed, May 27 · 7:30 PM · Hyper-seasonal Vermont farm-to-table — exceptional vegetable preparations, beautifully sourced meat and fish · One of the state's most acclaimed restaurants

Cocktail Bars The 126 — Speakeasy behind a deli door on College Street, live jazz, top pick for serious cocktails · Devil Takes a Holiday — Speakeasy-style, classics & creative twists · BKK in the Alley — Thai-influenced program down an alley near Church St · Hotel Vermont bar — Jazz on Wednesdays, polished and well-executed

Burlington bar scene: Burlington has one of the most active U.S. Bartenders Guild chapters — even incidental restaurant bars tend to be above average. The 126 (hidden behind a deli door on College Street — speakeasy, cozy, jazz that's never too loud) is consistently named the top craft cocktail destination in the city. Shelburne Museum has an outstanding collection of American folk art on a 45-acre campus — Steamboat Ticonderoga, the Circus building, and quilt galleries are the standouts.

Day 7 — Thursday, May 28

Burlington Check-Out → Montréal

Check-Out Hotel Vermont · By 11:00 AM · 41 Cherry Street, Burlington

Drive Burlington VT → Montréal QC · approx. 1.5–2 hrs · I-89 N across border

Border Highgate Springs/Frelighsburg crossing (US–Canada) · Have passports ready

Hotel Hotel Gault · 449 Rue Sainte-Hélène, Vieux-Montréal, QC H2Y 2L9

Check-In From 3:00 PM · 4 nights · Loft room, queen bed

Confirmation 5308.696.049 · PIN: 6794 · CAD 250 damage deposit at check-in · Free cancellation until May 25

Dinner Restaurant Candide · Reservation: Thu, May 28 · 6:30 PM · Seasonal French bistro in the Plateau-Mont-Royal — intimate, ingredient-driven cooking with a focus on Québec producers. Creative, carefully composed dishes from a tight market menu. One of Montréal's most quietly acclaimed neighbourhood restaurants.

Hotel Gault is set in a restored 1871 warehouse in the heart of Old Montréal — loft-style rooms with exposed brick and high ceilings. Walking distance to Old Port, Notre-Dame Basilica, and Vieux-Port.

Days 8–10 — Friday–Sunday, May 29–31

Montréal — Arts, Food & Old City

Hotel Hotel Gault · 449 Rue Sainte-Hélène, Vieux-Montréal

Arts & Culture Musée d'art contemporain de Montréal (MAC) · PHI Centre · Old Montréal walking tour · Old Port (Vieux-Port) · Notre-Dame Basilica · Mont Royal Park · Mile End neighbourhood

Dining Hoogan et Beaufort — Hyper-seasonal woodfire grill in converted warehouse; large wine list · Vin Papillon — No reservations; arrive at opening or be prepared to wait · Sushi Momo — All vegetarian · Cadet — Casual, market-forward, fresh ingredients · Le Petit Alep — Family-run Syrian & Armenian, mazza spread with Levant spices, one of the best wine lists in the city · Damas — Syrian fine dining (Outremont)

Cocktail Bars Cloakroom Bar — #2 in Canada & #31 in North America (50 Best Bars 2025); 25-seat intimate bar, no printed menu, personalized cocktails; reservations recommended · Atwater Cocktail Club — Graffiti-lined alleyway; Altos Bartenders' Bartender Award 2024 winner; walk-ins only · The Coldroom — Speakeasy in a 19th-century cold storage cellar, Old Montréal, unmarked black door with duck logo · Big in Japan — Whisky & bourbon focus, intimate candlelit atmosphere · Le Mal Nécessaire — Tiki-inspired, plush velvet banquettes, cocktails in hollowed-out fruit; Best of MTL 2025 · Foxy — Michelin Exceptional Cocktails Award winner; only bar in the city with that distinction

Cloakroom Bar (Golden Square Mile) is the serious craft cocktail destination — 25 seats, no printed menu, bartenders craft personalized cocktails using rare & vintage spirits based on what you tell them. Reservations strongly recommended. Vin Papillon does not take reservations — arrive at opening. Mon Lapin and Damas remain among the city's most sought-after restaurants — book well in advance for weekend evenings.

Day 11 — Monday, June 1

Montréal Check-Out → Burlington Airport → Chicago

Check-Out Hotel Gault · By 11:00 AM · 449 Rue Sainte-Hélène, Montréal

Drive Montréal QC → Burlington VT · approx. 1.5–2 hrs · Allow extra time for border crossing

Car Drop-Off Dollar Car Rental · Burlington International Airport (BTV) · By 12:30 PM

Booking 5086303019385350 · Return by 12:30 PM sharp

4:42 PM

Burlington

BTV · Burlington Intl

→

UA 329 · Non-stop

6:26 PM

Chicago O'Hare

ORD · Terminal

UA 329

Conf: JM065Y

Seats: 10D & 10E

Note: US Customs/border crossing can add 30–60 minutes — depart Montréal by 9:30 AM to comfortably make the 12:30 PM car drop-off and 4:42 PM departure at Burlington Airport.

Vendor	Description	Date	Amount	Status
United Airlines	ORD→PWM (May 22) & BTV→ORD (Jun 1) · 2 passengers · Conf: JM065Y	Prepaid	$1,511.75	PAID
Hotel Vermont · Burlington	Standard King · 2 nights · May 26–28 · Conf: 6636.440.600	Prepaid	$773.14	PAID
Hotel Gault · Montréal	Loft Room · 4 nights · May 28–Jun 1 · Conf: 5308.696.049	Prepaid	~$1,808 USD CAD 2,480.53	PAID
Dollar Car Rental	Nissan Rogue SUV · 7 days · Portland Jetport → Burlington Airport · Booking: 5086303019385350	At counter May 26	$650.26	DUE
Hotel Gault · Deposit	Damage deposit — refundable at check-out	At check-in May 28	CAD 250	DEPOSIT
Estimated Total (excl. deposit)			~$4,743 USD