Itineraries
For most trips I’ve taken, I made a note on my phone, in a proper notebook, on post-its, or scribbled on hotel notepads with each day’s activities. For years, when recounting my tales and recommendations, I promised to write them down. I’m finally making good on that promise, one by one, detailing where I went in each city, in the hope that it inspires your future trips (and saves me from struggling to remember the order of events each time I share my stories.)
Austin
The drive from Dallas to Austin was a journey of its own. Texans like their trucks big, stacked high with loosely-secured piles of furniture and other paraphernalia. Buc-ee’s sold everything from bedazzled cattle skulls (faux or real, I couldn’t tell you) to the biggest sodas I’ve seen outside a 7/11.
With 19 hours in Austin, I had enough time for only a couple of meals. Everyone will argue over the best taco place to choose in that time frame. Although I had multiple recommendations for breakfast taco’s at Torchy’s, friends will still roll their eyes when I tell them my choice. As an out of towner, I think it’s hard to make a bad choice - so Torchy’s or not, enjoy those breakfast tacos to the fullest.
Save 6th Street for an evening because going during the day felt out of place. The State Capital was an impulse visit that I’m glad I did - it was both a beautiful building and an informative tour.
Drive from Dallas to Austin
Czech Stop
Buc-ees
Day 1 & only
Lady Bird Lake
South Congress Ave
Torchy’s Tacos
Amy’s Ice Cream
6th Street
Texas State Capital
2nd Street Shopping District
Toronto
I don’t know how others feel about this analogy: I consider Toronto the NYC of Canada. It has a downtown that feels a bit more like the financial district of New York, and fashion comes before function. The style is clearly a step up from San Francisco: dress shirts on every man, pumps on every woman. I felt consistently on the cusp of underdressed in most neighborhoods and much more significantly so when window shopping among serious shoppers in Yorkville.
Type Books has to be one of the prettiest bookstores I’ve seen with a great selection of super books that fly just under the radar on the best sellers list, yet very much deserve to top it. Pizzeria Libretto was a gem of an upscale pizza shop that came at the suggestion of my pizza-snob colleague and friend. I loved the Anndore House, even if I only stayed for 1 night.
If I’d have done anything differently, I’d have gone to Casa Loma sooner - there is a castle in Toronto! And the Almond Butterfly was a superb café with a range of allergy-friendly options that I’m so glad I skipped out on a top-ranked place for when the line was too long.
Day 1
Queen Street West
Type Books
The Chase Toronto
Day 2
CN Tower
Pizzeria Libretto
St. Lawrence Market
The Distillery Historic District
Toronto Maple Leafs game
Day 3
Toronto Islands
The Anndore House
Royal Ontario Museum
Shopping in Yorkville
Summer’s Ice Cream
Sabai Sabai Kitchen & Baro
Day 4
Breakfast at Almond Butterfly Cafe & Restaurant
Casa Loma mansion
Vancouver
3 days did not do this city justice. The surrounding mountains bring a humility to the city, where function defines fashion. The laid-back vibe combined with the enthusiasm of sunny days reminds me of the best parts of the west coast combined with the jubilance and appreciation of fair weather from the east coast. Had I budgeted more time, Vancouver Island definitely would have been my next stop.
3 days did not do this city justice. The surrounding mountains bring a humility to the city, where function defines fashion. The laid-back vibe combined with the enthusiasm of sunny days reminds me of the best parts of the west coast married with the jubilance and appreciation of fair weather from the east coast. Had I budgeted more time, Vancouver Island definitely would have been my next stop.
Saturday
Lynn Canyon and its suspension bridge
Grouse Mountain and its Grouse Grind Hike
Revel Room Jazzy Bar
Sunday
Ferry to & from Granville Public Market
Railspur District
Sunset Beach
La Belle Patate for poutine
Biked the perimeter of Stanley Park
Window shopped on Robson Street
Dinner at Alibi Room
Monday
Brunch at Jam Cafe
The Paper Hound Bookshop
MacLeod’s Books
Shopping in Granville on Alexandra Street
Museum of Anthropology
Funny story to conclude: On last-minute shopping trip on Alexandra Street, I picked up a beautiful sweater at Oak and Fort. It wasn’t until I was in a taxi en route to the Museum of Anthropology that I realized I bought it in an XL, not an XS by mistake. The store has locations in both the US and Canada, only with different inventory. A creative solution: a friend was traveling to Vancouver the very next week and made the return for me.
SF -> LA -> NYC Itineraries
Cliffnotes:
15-day trip to 3 cities and staying at friend’s houses in SF/LA
Skip Pier 39 altogether, there is always better food elsewhere in the city
Biking on the beach at sunset with a friend was a highlight in LA
Packed 1 suitcase and did laundry halfway through trip
6 days in SF, 6 days in LA, 3 days in NYC
Trip started in early November and ended in mid November
Saturday - day with friends
Drive SF to Sonoma
Cine for zinfandel
Domaine Carneros for champagne
Gott's burgers
Off to a friend of a friend’s birthday party
Sunday - day with friends
Breakfast at Lemonade
Turo rental
49ers game at Levi Stadium
Dinner at friend’s family
Monday - morning and evening with friends, Alcatraz was solo adventure
Drive to UC Berkeley for the views
Acai bowl at Vitality Bowls
Alcatraz
Lunch at Hook's in Pier 39
Walked through Nob Hill and Union Square
Golden State Warriors at their Oakland arena
Tuesday - solo adventure day until dinner
Muni to Golden Gate Park
Conservatory of Flowers
Academy of Science
Hellman Hollow
de Young tower & museum
Haight Ashbury
Sweater at Crossroads
Dinner at Otoro for sushi
Ice cream at Smitten
T-shirt vending machine at Marine Layers
Wednesday - solo adventure day until dinner
Hayes Valley
The Boulangerie
Alamo Square
Painted Ladies
Exploratorium
Aquarium
Sushirito
111 Minna Gallery
Union Square
Cable car ride (2 or 3 times)
Lombard street
North beach
City Lights Bookstore
Hayes Valley
The Grove for dinner
Thursday - day with friends
SOMA
Acai bowl'd food truck
Rented another Turo
Palace of Fine Arts
Sol Food
Muir Woods & Muir Beach
Twin Peaks
Upper Douglas dog park
Everlane
Tour of Lyft with friend of friend
Tour of Stripe & dinner there with roommate of friend
Friday - afternoon with friends
Fly SF to LA
Rental car pickup at Midway Car Rental LA
Stop at USC
The Grove & Original Farmer's Market
Dinner at Hugo's
Ice cream shakes at Swinger’s
Saturday - day with friends
Hiked from Griffith Observatory to Hollywood Hills. Ate at Griffith Observatory (yum). Total trip 6 hours, about 5 hours of hiking
Dinner in Sherbourne Oaks at On the Thirty
Ice cream in Studio City at Salt and Straw
Sunday - day with friends
Smorgasborg (acai bowl, taco, mofongo)
Last Bookstore
Hermosa Beach
Rented bikes at sunset
Dinner at Mercado in Santa Monica. Amazing! Elote, guac, carnitas, flan 👌
Monday - solo day
Laundry
Warner Bros studio tour (dobby's animation was the favorite)
Lunch at Tender Greens near ELA
Melrose shopping
Dash (store owned by Kardashians)
Google popup shop
Restoration hardware rooftop with views of downtown
Urth Cafe for quick dinner
Clippers vs 76ers - 😍 Blake Griffin
Tuesday - solo day until dinner
Spin & yoga at YAS with a fellow Amanda leading the class
Breakfast at Village Bakery near Glendale
LACMA
Falafel food truck
Dinner at Americana at Brand
Wednesday - day with family
Flower market
Getty Museum & Restaurant with family
Thursday - solo day of travel
Grand central market
LA 🛫🛬NYC
Stay at Pod51 in Hell’s Kitchen
Friday - solo day until Smogasborg, hanging out with friends afternoon and evening
Taping of “Live with Kelly & Ryan” with Reba McEntire as guest
Columbus Circle
5th avenue window shopping
Smorgasborg - mozz sticks & tacos & cider
Moleskine store
Strand bookstore
Union Square market
Eileen's Cheesecake
Little Italy
Chinatown
SoHo
Saturday - friends in morning, solo in afternoon
Observation session of coaching program
Grand Central Station
Market - Ceviche
Chelsea, Chelsea Market, and the Highline
Shopping in West Broadway
Morgenstern's Ice Cream - Black Shaved Coconut with toasted coconut
Roasted almonds
Rockette's (AMAZING!)
Vinyl diner (met mosaic Beyoncé in the bathroom)
Sunday - solo day from NYC to Boston
SoHo
Chobani & Joe's Juice
Everlane Store
Washington Square Park
Stationary Store
Times Square
To Boston
What I still had on my list for the next trip:
SF
Legion of honor
Rolled ice cream
MOMA
The Mission
The Castro
LA
Santa Monica/del Rey
Runyon
Old Pasadena
NYC
The Rooftop at 50 Bowery
Aladdin
Washington Square Park (more time there)
Stacked Ice Cream
Montreal Itinerary
Takeaways:
Great food in Old Montreal
Mount Royal offers superb views of the city
The cocktails are weak but the beer is strong
The young men at clubs acted like middle schoolers at a dance, hanging out around the perimeter of the dance floor, only to bop a friend on the head as their way of flirting ¯\_(ツ)_/¯
Day 1 - Drive from Massachusetts to Montreal
The GPS was misinformed, there was no Atwater exit
Payment for food is given at table
Fiddler's Green was empty and went to another bar with fantastic blueberry beer
Day 2
Selfie Stick Prank: 2 old women as part of the Canadian equivalent of Off Their Rockers asked to take a selfie with the 4 of us, using their selfie stick that had to be at least 6 feet long. I have no idea if we made it on TV.
Metro passes - public transit was the easiest and fastest way to explore the city
Botanical gardens - we visited on the last free day
Old Montreal
Dine at Jardin Nelson, order the Cartier Salad and sangria
Basilica de Notre Dame
Old Port
Went to Electric Blue and did the grandma dance: we didn’t know when it said 80s music online, everyone would be 50+
Proceeded to bar instead
Day 3
Mount Royal
St-Viateur Bagel
Little Italy
Poutine at La Banquise
Apt. 200 too exclusive, headed to Tokyo club
Learned clubs are empty before midnight
Left for McKibbin’s Irish Pub and West Point boys chatted up the one friend who didn’t like boys
Returned to Tokyo bar
Day 4 - Drive from Montreal to Massachusetts
Crepes and waffles for breakfast
A bridge closure caused us to be rerouted and spend 3 hours in the car before we even got out of the city
Chicago Itinerary
5-day, 6-night stay in the Windy City in the summer.
Context: 2 friends, 5-day, 6-night trip to Chicago in July 2017
Airline: Jetblue
Hotel: Autograph Collection, Chicago
Takeaway: Downtown Chicago is a fun city where the attractions live up to the hype.
Fave spots:
Wabash Arts Corridor
Improv show
Taste of Chicago Food Festival - only for 1 week in the summer if you time it right
Wrigley
Jeni’s Ice Cream
Thursday
Flight
Friday
Brunch at Eggy's
Planetarium
Aquarium
Deep dish at original Uno's
Willis/Sears Tower
Saturday
Brunch at Grand Lux Cafe
Museum of Contemporary Art
Art Institute of Chicago
Taste of Chicago
Architecture Tour
Ferries Wheel & spinning ride
Fireworks
Dinner at Tiny Tavern
Sunday
Brunch at Yolk
Cubs v Pirates
Jeni's Ice Cream
Shopping
Cloud gate
Bub City BBQ for dinner
Monday
Brunch at Nookies in Old Town Triangle
Lincoln Park Zoo
Magnificent Mile
Steak dinner at Wildfire
"Having it all" improv show
Drinks & guac at John Hancock 96th floor
Tuesday
Breakfast at Goddess & the Baker
Wabash street art
Old Town
Sushi
Shopping
Ride the brown line loop for the picture
Donuts
Back to Boston!