Guanajuato, San Miguel de Allende and Oaxaca, Mexico Itinerary
- Brooke
- Aug 5, 2021
- 4 min read

(This post is an itinerary post to help those looking for advice on how to spend their time in certain locations. For more detailed information about the destinations, look for postings about the individual places listed below).
In June 2021, Ben and I decided to spend our belated 40th birthdays in Mexico, one of the few countries that were allowing Americans to visit during COVID-19 without a quarantine. Having been vaccinated, and knowing our own feelings about visitors to Hawai‘i during the pandemic who did not follow the rules to keep our islands safe, we thought we might be the type of visitors who could enjoy Mexico while keeping ourselves, as well as the locals, safe from the virus. We invited my mother, who I had not seen in over a year and a half due to the pandemic, to join us for the second half of the trip.
Our original plan, though, was to go to Africa for our 40th birthdays and do a safari. However, even with vaccines, the idea of traveling so far away with so many unknowns due to the pandemic did not seem like a wise idea. Therefore, we elected to choose a destination with fewer variables, and much closer to home. We had been talking about going to San Miguel de Allende for a few years, coupled with a trip to Mexico City. However, we wanted to go to places where it wouldn't be necessary to use public transportation, and Oaxaca, also on our ever expanding list of must-sees, seemed like an ideal second choice.
So the two of us, then the three of us, set out to explore colonial Mexico. Below, I share our itinerary, in case you ever want to enjoy these beautiful cities for yourself (pro tip: you should).
Itinerary
Day 1, June 3, 2021
Depart Kona, Hawaii for León, Mexico (Guanajuato)
To maximize our time off, we took a red eye from Kona to Dallas (DFW), and Dallas on to León, Mexico, arriving the following morning on American Airlines.
Day 2, June 4, 2021
Arrive in León, Mexico, drive to Guanajuato and explore
Hotel: Casa del Rector
Lunch: Los Huacales
Sightseeing:
Plaza de la Paz and Basílica Colegiata de Nuestra Señora de Guanajuato
Dinner: Casa Valadez
Sightseeing:
Teatro Juárez
El Jardín de la Unión
Day 3, June 5, 2021
Sightsee around Guanajuato, Arrive San Miguel de Allende
Sightseeing:
Funicular to Monumento al Pípila Statue
Stroll to Plaza de San Fernando
Transportation: Car and driver arranged through our upcoming hotel

Dining: 1826 Restaurant at the Rosewood
Day 4, June 6, 2021
San Miguel de Allende
Lunch: Andanza at Casa de Sierra Nevada a Belmond Hotel
Dinner: La Unica
Sightseeing: Stroll around the city center, including Parroquia de San Miguel Arcángel, El Jardín, and surrounding streets.

Day 5, June 7, 2021
San Miguel de Allende
Lunch: Luna Rooftop Tapas Bar at Rosewood San Miguel de Allende
Dinner: Orquídia Thai
After dinner exploration of the Rosewood's gardens.
Day 6, June 8, 2021
San Miguel de Allende
Lunch: Agua (Rosewood's pool bar/restaurant)
Dinner: Zibu Allende
Day 7, June 9, 2021
San Miguel de Allende
Activity: Cooking class with Chef Gaby Green with market tour
Dinner: The Restaurant
Day 8, June 10, 2021
San Miguel de Allende
Activity: Visit Fabrica La Aurora
Shop at Mercado de Artesanías
Dinner: Bovine
Day 9, June 11, 2021
San Miguel de Allende
Visit: Luna de Queso
Lunch: Turk
Shop at Casa Armida
Dinner: Zumo
Day 10, June 12, 2021
San Miguel de Allende
Activity: Wander up to the laundry building, relax in Benito Juarez Park
Lunch: Restaurante del Parque
Dinner: Áperi
Day 11, June 13, 2021
Depart San Miguel de Allende, Arrive in Oaxaca (and pick up my mother)
Stay: Casa Mulata Airbnb
Dinner: El Olivo Gastrobar (take out)
Day 12, June 14, 2021
Monte Alban and artist villages with guide Gabriel Sanchez
Visit: Monte Alban with tour guide Gabriel Sanchez (who we highly recommend!)
Lunch: Azucena Zapotea
Visit: Taller Daniel Hernandez (Alebrijes)
Dinner: Casa Oaxaca El Restaurante
Day 13, June 15, 2021
Cooking class with Reina in Teotitlán del Valle
Cooking Class with Reyna Mendoza at El Sabor Zapoteca in Teotitlan del Valle
Dinner: Los Danzantes
Day 14, June 16, 2021
Oaxaca city tour with Gabriel Sanchez
Walking Tour of Oaxaca City
Lunch: Ni Hao Asian Bistro
Dinner: McCarthy's Irish Pub
Day 15, June 17, 2021
Oaxaca and Cooking Class at Casa Crespo
Breakfast: Tierra del Sol
Dinner: Casa Crespo pre-Hispanic cooking class
Day 16, June 18, 2021
Market Tour with Gabriel Sanchez, Textile Visit and Mezcal
Tour and Tasting
Market: Mercado Morelos
Visit: Taller Nelson Perez Mendoza
Dinner: La Matatena Pizzaria
Day 17, June 19, 2021
Oaxaca
Relaxing
Breakfast: Bolenc
Dinner: Las Quince Letras
Day 18, June 20, 2021
Oaxaca
Running Errands and Last Minute Shopping
Breakfast: Tierra del Sol

Shopping Marias Arte & Diseño to buy glassware from Xaquixe Glass Studio
Shopping at MisMezcales

Dinner: Sur a Norte
Ben finally gets his street corn!
Day 19, June 21, 2021
Depart Oaxaca (and Mexico) and Return to USA; Overnight in
Los Angeles
Flight: OAX - to Dallas/Forth Worth (DFW) ; DFW to Los Angeles (LAX)
Stay: Los Angeles Airport Marriott (our go-to hotel for layovers in LAX)
Dinner: Wallflower in Venice, CA
Day 20, June 22, 2021
Depart Los Angeles, and return to Kona, HI
American Airlines direct flight from LAX to KOA
Fin!
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