Mexico: Oaxaca, San Miguel de Allende and Mexico City 

April 26 to May 4, 2019  |  9 days / 8 nights |  $2,695

Share with Friends: 

This trip is full, but check out other adventures, request early notification for adventures on the horizon, or we can work together to design your own adventure!

Growing up in the West, taking quick trips to Mexico to visit Cabo San Lucas, Puerto Vallarta and Mazatlan were relatively quick trips to find the sun and sand. But I didn’t make it inland until much later in life, and now I realize just how much I’ve been missing out on. The cities we’ll visit on this trip: Oaxaca, San Miguel de Allende and Mexico City, are overflowing with kindness, culture, charm and tradition. They’re full of vibrancy and energy, and not just in the bright colors but how they live their daily lives. There’s a lot to experience and learn from our neighbor to our south; consider this trip just the beginning.”—— Mary, Living Big trip host for this adventure.

Trip Agenda

Day 1 – Friday, April 26

Oaxaca is known for its mole, epic celebrations around Dia de los Muertos (any Coco movie fans?) artisans, large markets, street art, mezcal and more. It’s the kind of city you can just see yourself settling into for a while 🙂 On this first day your Trip Host will meet you at the airport, and once we’re all gathered at our boutique hotel, we’ll head to a local roof top restaurant for margaritas, guacamole and dinner, with epic views of the beautiful Church of Santo Domingo de Guzmán in the background. After dinner we’ll stroll the streets and start soaking up all that Oaxaca has to offer. Meals included: dinner
Arrival Airport: Oaxaca International Airport, OAX — flights should arrive by 3PM

Day 2 – Saturday, April 27

There is a local organization in Oaxaca, En Via, that has been helping female entrepreneurs with their unique approach to micro lending. Today we’re going to not only learn about En Via’s, work, but meet some of the women that have benefited from their zero-interest loans, educational opportunities and mentorship programs. Our visit will take us out to Teotitlan del Valle, which is known around the world for their hand-crafted textile production. Many of these textile houses are led by women who have started, and grown their business, as a result of En Via’s programs. Plan on a day of inspiration, service, purchasing a textile if it’s on your wish list, and connecting with other women who are doing their best to support their family and advance their life, business and career — just like we are 🙂 All meals included

Day 3 – Sunday, April 28

To really experience Oaxaca, you need to experience the food. And on this day we’re heading to a local market to shop for, and learn about, the local produce, vegetables, flowers and ingredients that are unique to us, but staples of the Oaxacan cuisine. After a visit to the market we’ll roll-up our sleeves and learn to cook from one of the best. On the menu: mole, a few fresh appetizers, tortillas, salsas, mezcal cocktails and more. The rest of the late afternoon and evening are your own to shop, explore and soak up what makes Oaxaca such a special place. Meals included: breakfast and lunch

Day 4 – Monday, April 29

We’ll say goodbye to Oaxaca, and make our way up north by plane to the beautiful town of San Miguel de Allende, which feels like a bit of Tuscany in the middle of Mexico. It won’t take long for you to fall in love with the cobble stone streets, brightly painted buildings, stunning Parroquia de San Miguel Arcángel Church and lively jardin, which together make-up the living room of this charming city. In 2017 San Miguel de Allende was named the ‘Best City in the World‘ by Travel and Leisure Magazine, and you’ll immediately see and feel why. On this first day we’ll spend time leisurely soaking up the city, walking through the streets, enjoying the live music that surrounds the jardin and having a wonderful dinner with the spires of the Parroquia in view. We’ll start to slow down in San Miguel de Allende; if you go too fast, you’ll miss its magic. Meals included: breakfast and dinner

Day 5 – Tuesday, April 30

After a hearty breakfast at our boutique hotel (which will feel like a Mexican folk art museum!) we’ll join a local guide to explore the city, but go beyond its beautiful surface to understand its place in history and role in the present day. After the walking tour the afternoon is your own to shop at the local artisans market, visit the local food market, enjoy a gelato around the jardin or anything in between. We’ll gather in the early evening to learn about (in a hands-on kind of way) the local art scene. We’ll all learn how to paint, and take home a piece of our own artwork. In the artists studio we’ll be working from, we’ll sip, nosh and paint our way through a fun night. Meals included: breakfast and dinner

Day 6 – Wednesday, May 1

San Miguel de Allende, as beautiful and pristine as it is, also has a cowboy culture. And today we’re going to dive into that side of the culture. We’re heading to a family-run ranch about an hour outside the city. Here we’ll saddle up and enjoy a few hours on the back of a horse as we explore the hills, valley, water, and vistas of this beautiful area. After the ride we’ll enjoy lunch with the family that will be hosting us on their ranch, and then head back to the city for a quiet evening. Meals included: breakfast and lunch

Day 7 – Thursday, May 2

This will be an early morning, but don’t worry – it’s all in the name of adventure 🙂 We’ll travel to Mexico City by bus (about 4-5 hours) to join a local guide that will introduce us to Mexico City. The city is cosmopolitan, rich in culture, innovative, creative and historic all at the same time. Many say it takes years to really understand and see the city, but today we’ll see/learn/eat as much as we can on two wheels. We’ll go by bike to check out the local neighborhoods, learn about the history, see some of Freda Kahlo’s work and explore Chapultepec park, which is right in the heart of the city and nearly 3X the size of Central Park. All meals included.

Day 8 – Friday, May 3

Eat light this morning, because this afternoon we’ll join a local chef who will show us some of her favorite hole-in-the-way taco stands, street-side taco counters and the food market loved by chefs. Stretchy pants are highly advised. We’ll take a few hours to rest after the tour, and to prep for the night ahead. It’s Friday night and we’re heading to watch a local ‘lucha libre’ wresting match. We’ll choose our favorite wrestler, cheer like heck, maybe wear masks, and join for one of Mexico City’s loved traditions. Meals included: breakfast

Day 9 – Saturday, May 4

On this final day we’ll enjoy breakfast, and then you can start the next leg of your journey or head back home. Meals included: breakfast
Departing Airport: Mexico City International Airport, MEX — flights can depart at any time


Trip itinerary is subject to change but will always maintain a spirit of adventure and diverse activities. 

Questions? Check out the FAQ section for more information about this adventure!

Frequently Asked Questions

Who is going on the trip?

This trip is made up of 12 women: 11 guests and your Trip Host. A major tenet of Living Big Travel is to make international travel more accessible to women who don’t want to go at it alone. To learn more about the philosophy, click here.

Can I join the trip solo? Or can I invite a few of my friends to join me on the trip?

Yes and yes to both questions! Some women join Living Big trips on their own; there to make friends and see the world, and others join Living Big trips because they want to share the experience with their friends, sisters, mothers or daughters and don’t want to do any of the planning!

You’ll find that the trips are structured in a way that you’ll have a good amount of group time, but also a fair amount of independent time to explore on your own, with new friends you met in the group, or with the friends joining you on the trip.

Who is the Trip Host? And what is her role?

On this trip your Trip Host is Mary. To learn more about Mary, click here.

The role of the Trip Host is to be there to make sure everything goes as smooth as possible, even when the inevitable travel bumps come our way – such as an unexpected rainy afternoon, traffic, missing luggage, etc. But more importantly, to be a resource that will give you the space you need to really enjoy the experience. So if throughout the trip there is something your Trip Host can do to support you in this regard – please let her know. For example, if you’re not feeling well, having trouble sleeping, not getting along with someone, not satisfied with something, etc. please please share these concerns. No one needs a ‘Mother’ on this trip – that’s not our intention, but if there are small adjustments that can be made to create more space for you to enjoy the experience —- the Trip Host will see what she can do!

How much does the trip cost? And what is included/excluded in this price?

The total price per person is $2,695. This includes the following:

  • Planning: all trip logistics, including pre-trip negotiations with all hotels and vendors, onsite coordination, useful information leading up to your trip such as advice on what to pack, how much to budget for spending money, a cheat sheet for learning the local language, advice on local currency, etc.
  • Hotels: 8 nights accommodation based on a shared room
  • Flight between Oaxaca and San Miguel de Allende
  • Meals: see the daily itinerary for meals included each day. Dinners generally include a limited amount of hosted beer and wine
  • Transport: all ground transportation, including airport transfers if you arrive on the stated start and end dates, and hired ground transportation throughout the trip, are included.
  • Activities: all activities, unless specified in the itinerary, are included.
  • Gratuities for local guides and partners.

The following are not included in the trip fee:

  • Round-trip airfare is not included, but gives you flexibility in using airline reward miles or extending your trip as you wish. Each guest is responsible for organizing their own airfare and transportation to the stated start and end cities.
  • A set amount of wine and beer will be purchased with each hosted dinner, but each guest will be responsible for alcoholic beverages beyond this amount
  • While not required, each guest is encouraged to consult their existing insurance policy to determine what is covered while on the trip, and if needed, secure an individual insurance policy for the trip.
  • Any additional activities you want to book along the way: spa visits, private tours, cooking classes, etc.
  • Spending money, additional tips for your Trip Host and excess luggage fees.

What are the health and physical fitness requirements to join on the trip?

Guests should take personal responsibility to ensure they are physically able and healthy to participate in all group trip activities, such as hiking at elevations and in conditions outlined in the trip itinerary, walking on uneven surfaces, carrying luggage in/out of vehicles, on uneven surfaces and up stairs, riding in a van for up to 5 hours, riding a horse with instructions/supervision, riding a bike through a city with instruction/supervision and being active in potentially hot and humid conditions. The trip is physically strenuous and best enjoyed by anyone who is physically fit and enjoys very active days. You should consult with a medical doctor to determine if you are healthy and physically able to participate.

Is there a minimum/maximum age to participate?

Women over the age of 21, that are physically able to participate in the trip itinerary, are welcome to join for this adventure. Please see the detailed itinerary and FAQ on minimum physical fitness requirements to learn more.

What should I do to secure my spot on the trip?

The first step is to request a spot, which you can do online (click here.) Once you request a spot, we’ll reach out to you to schedule a call to review the trip details, get to know you, give you a chance to ask questions about Living Big, etc. If after this conversation you’re on board to join for the adventure, you’ll receive a link to the registration page where you can formally register, submit your first payment and sign the trip waiver. Please note: registration is taken on a first-come, first-serve basis.

Is airfare included in the trip fee? What do I need to know before I book my flight?

Round-trip airfare is not included in the trip fee, but this gives you flexibility in using airline reward miles, to extend your trip any way you like, and to select the routes and airlines you prefer. Each guest is responsible for organizing their own airfare and transportation to the stated start and end cities.

  • Inbound flights should arrive into Oaxaca International Airport (code: OAX) on April 26 by 3PM local time
  • Outbound flights should depart from Mexico City International Airport (code: MEX) on May 4 anytime

You will be required to share flight details at least eight weeks before the adventure commences.

Will I be sharing a hotel room? Can I choose my roommate?

Yes, everyone will be sharing a room with at least one other person, but you will have your own bed. You can request a roommate preference, and share sleeping preferences, on forms that you’ll be asked to fill out 10-12 weeks before your adventure begins.

There is not an opportunity for women to pay a single supplement in order to secure a private room. Here’s why: single supplements, while convenient for some willing to pay the fee, often prevent many single women from traveling because the cost is just too high, so the decision was made early on to not go down that path as a means to encourage more women to travel. And we find that sharing a room with another woman, and having an opportunity to connect with other women and learn about their lives in this way, contributes to what makes these trips very special.

Can you tell me about the type of accommodations we'll be staying at?

You betcha! In Oaxaca and San Miguel de Allende we’ll be staying at boutique hotels, and our group will be the majority of guests at the property during our stay. In Mexico City we’re staying at a medium-size hotel that’s right next to the Zócolo.

What kind of ground transportation will we use?

In Oaxaca we’ll be traveling by local taxi’s, hired shuttle drivers and on foot. We’ll take a flight from Oaxaca to San Miguel de Allende (flight is included in your trip) and then once we’re in San Miguel de Allende, we’ll travel by local taxi’s, hired shuttle drivers and on foot. We’ll travel on a coach bus between San Miguel de Allende and Mexico City, and then once we’re in the city we’ll travel by local taxi’s, hired shuttle drivers, the subway, by bike and on foot.

What should I pack?

About 10-12 weeks before the trip you’ll receive a detailed packing checklist and advised on what type of clothes and supplies you’ll need.

Do I need to carry my luggage?

Yes, plan on carrying your bags to/from the airport, on/off the vans and other forms of transportation and in/out of lodging.

What will the weather be like?

The weather in late April/early May will vary depending on the city we’re in, but plan on temperatures averaging between 65 degrees and 85 degrees fahrenheit.There might be occasional light rain and winds, and you should expect some humidity. The temperature will also vary depending on the elevation and time of day.

What if I don't need every hotel/activity/etc. on my trip?

Unfortunately, refunds aren’t possible for unused hotel rooms, meals or activities. The total trip price is a package deal; credits are not given for services not used. Please contact Living Big if you have questions or concerns about any trip activities due to a physical condition. If there is a reasonable alternative, we can explore it.

How do I communicate information like allergies, injuries, etc?

About 10-12 weeks before we begin our adventure, you’ll receive a pre-trip packet of information. This includes forms, questionnaires and waivers that you’ll need to submit no later than 8 weeks before the trip begins. These forms allow you to share these important details. Living Big will provide meals as outlined in the official trip itinerary and will work with you to try and accommodate special dietary requirements; however, Living Big is not required to provide such meals, supplements and/or any special requests beyond what is outlined in official trip itinerary.

Do I need a U.S. Passport or Visa for this trip?

Yes, a U.S. Passport is required to visit Mexico. Your U.S. Passport must be valid at the time of entry and you need one blank page for an entry stamp. A Visa is not required. Entry requirements may change. While your Trip Host will keep you informed of changes, you should take personal responsibility to ensure you can satisfy entry requirements. Click here to learn more about entering Mexico with a U.S. Passport. If you plan to visit another country before or after your Living Big trip, contact your Trip Host to discuss any additional entry requirements.

Is it safe to travel to Mexico?

Mexico, like all countries, has its fair share of crime. We probably hear of the crime in Mexico more than other countries because it’s our neighbor, and a place frequently visited by US citizens. But in our experience, the cities of Oaxaca City and San Miguel de Allende, and the areas we’ve spent time (and will spend time as a group) in Mexico City did not feel dangerous or threatening. As with all travels, tourists need to exercise caution, be aware of their surroundings and do not attempt to engage in any unlawful activities while traveling. To read the official advisory from the US Department of State click here and reference the following states that we’ll be visiting on this trip: Oaxaca (Oaxaca City;) Guanajuato (San Miguel de Allende;) and Ciudad de México (Mexico City.) All three states have a “Level 2” security warming, which indicates that tourists should exercise caution.

Do I have to pay for the entire trip up front or can I make payments?

No, you do not need to pay for the entire trip up front. (Although you can, if you prefer.) Check out the Pricing, Payment and Reservation tab for payment details.

What is Living Big's policy on non-discrimination and violence?

Please take a moment to review the Living Big policy towards anti-discrimination and violence. Click here to review.

If you’re on board with this philosophy, and can join us in creating a safe, comfortable and judgment-free zone, then we’d love to have you join for an adventure!

What if I need to cancel the trip?

If you decide you need to cancel your trip the following refund schedule applies upon written notice of your cancellation:

  • Cancellations made on or before Jan 2, 2019:
    • Your trip deposit is nonrefundable. If you paid in full for the trip the deposit is $500.
    • You will be reimbursed 50% of what you have paid to date, less the nonrefundable deposit.
    • As an example, if you made a $500 deposit, then made two additional payments each for $250 (total paid = $1,000) then the amount you would receive back is $250.
  • Cancellations made on or after Jan. 3, 2019:
    • All payments made to date are nonrefundable.

Travel insurance helps protect against last-minute cancellation, trip interruption, and to cover medical treatment or emergency medical evacuation during your trip. We strongly recommend you purchase travel insurance and flight cancellation insurance in advance of your trip. To learn about travel insurance, click here for a quick lesson!

What if the trip doesn't fill up or is cancelled?

The trip requires a minimum number of participants in order to take place at the stated price, since it takes into account group discounts, shared accommodations and other factors that create cost efficiencies. Once an adequate number of participants sign up for the trip, you will be notified. If a trip does not have enough participants, or if someone unexpectedly cancels, you will be refunded your deposit or you will be given the option to pay a trip supplement to continue the trip with fewer participants. Should additional participants sign-up after you have paid the trip supplement, this fee will be refunded. Your air travel itinerary is yours to decide, and we recommend you purchase flight cancellation insurance. Living Big is not responsible for additional expenses incurred by you in preparing for the trip including non-refundable air tickets, gear, medical equipment or travelers insurance.

What if I can't make payments according to the payment schedule?

If unusual circumstances arise and you can’t make payments on time please contact Living Big to discuss. Generally speaking, failure to make payments according to the schedule may result in losing your spot on the trip.

Trip Pricing

This trip is nearly all-inclusive of meals, all lodging, all ground transportation, and all activities outlined in the itinerary, all the planning and booking (so you don’t have to do ANY work but show up!) and advice on what to pack, tips on international travel and a go-to resource who is here to answer any questions you have leading up to the trip, and on the trip, to help ensure that you have an amazing experience! Trip Fee: $2,695.

Payment Options

There are two options for payment:

  1. Pay the full amount by credit card or by check.
  2. Break your payments into equal monthly installments. Make a deposit of $500 to formally register for your spot, and then on the first of each month (following the month you made your deposit payment) your credit card will be automatically charged a set amount, so that the final payment is applied on February 1, 2019. If you decide to make monthly installment payments, you will receive a payment schedule based on when you register.

Requesting a Spot

If you’re interested in requesting a spot on this trip please make note of the following booking process and payment terms:

  • The first step is to request a spot, which you can do online. Once you request your spot, we’ll reach out to you to schedule a call to review the trip details, get to know you, give you a chance to ask questions about Living Big, etc. provided there are spots available on the trip.
  • If after this conversation you’re on board to join for the adventure, you’ll receive a link to the registration page where you can formally register, submit your first payment and sign the trip waiver.

Ready to request a spot on this adventure? Click here to get started!

If you're thinking
FOMO is real.
We get it.

Be the first to receive notifications of new adventures, travel tips and special offers right in your inbox.