These itineraries are from our 2018, 2017, and 2012 trips. 

January 15, 2018: After months of talking about it and browsing guidebooks and doing nothing, we finally arrange one way reward tickets to Mexico City, for us to leave in 3 weeks and 1 day (we’re good at the last minute thing…)

February 6, 2018: Depart Boston, layover in Dallas, before a short flight to Mexico City.

February 6, 2018:  Land in Mexico City, the capital of Mexico, at 7:30pm local time. Get our bearings in the Spanish-speaking country, go on a food tour, and generally stuff our faces. Enjoy this world-class city for a bit, including a trip to Teotihuacan, before heading out to explore other areas.

That’s actually the only part of the itinerary that’s really planned as of January 18. But below is what we intend to plan & do. See links for pictures of Mexico and Costa Rica.

Take a 4-5 hour bus ride to the colonial UNESCO World Heritage city of Guanajuato. Enjoy the sites, maybe hang out there for a while. On the way to or from, visit San Miguel de Allende, which has been described as a Disney World for American adults – a huge ex-pat scene, tons of restaurants, and arts, and abnormally perfect architecture.

Fly to Merida, the capital city of the state of Yucatan. Enjoy the beautiful colonial city and rich Mayan history. Possibly meet up with some friends of friends/bloggers. Day trip out to some beaches and Chichen Itza, a Mayan city that’s full of tourists from Cancuun but still awesome.

Maybe go to other parts of Mexico, depending on our timing and what not. Then fly to San Jose, Costa Rica.

The itinerary for Costa Rica is pretty open-ended right now as we’ve been focusing our initial planning on Mexico, but we’re definitely planning for some hiking and beach time, and seeing awesome volcanoes and wildlife.

Have suggestions for Costa Rica or Mexico? Places to go, things to see, places to stay, people to meet, food to eat? Please please, send them our way!!


Itinerary/Timelines for 2017 Traveling Adventure

December 20, 2016: After months of talking about it and browsing guidebooks, we finally arrange one way reward tickets to South America, for us to leave in exactly 5 weeks, almost to the minute.

January 24, 2017: Depart Boston, layover in Miami, before a 9 hour flight to Buenos Aires.

January 25, 2017: Land in Buenos Aires, the capital of Argentina, in a sweltering hot summer. Get our bearings in the Spanish-speaking country, exploring the European-seeming city for a few days, most likely by bike. Head out shortly after to escape the heat and go south while it’s still warm.

That’s actually the only part of the itinerary that’s planned as of January 2. But below is what we intend to plan & do. See this link for pictures of Argentina.

Fly south to the very tip of the continent, to Ushuaia in Tierra del Fuego. Stare hard at the ocean to see if we can see Antartica, and enjoy seeing sea life, mountains, and very long days.

Fly to El Calafate, which is on the doorsteps to Patagonia. Go see glaciers and do some hiking. Do some more Patagonia exploring, crossing into Chile, visiting 2-3 jaw-dropping national parks.

Make our way to Bariloche, Argentina which is a beautiful lakes region, likened to the Swiss alps. Go hiking, swimming, fishing, biking, and take a lot of pictures.

Head to Santiago, the cosmopolitan capital of Chile. Take a trip out to Valparaiso, which is a port town on the Pacific described as quirky and known for colorful buildings and amazing graffiti. Possibly head to the beach.

Take a bus back to Argentina to the region of Mendoza, which is wine country. Do the wine country thing for a while.

Make our way further north to the region of Salta, which has crazy rock formations/colorful sand canyons and a desert. Explore the scenery & villages.

Return back to Buenos Aires and actually enjoy it now that it’s not so hot. See the sights, dance the tango, live the porteno lifestyle.

Fly back to Boston when winter is over. We don’t have tickets back yet, but we anticipate going back in March or April.

Here is a rough map to get an idea of the itinerary:

Note: While we anticipate being there for at least 2 months and South America is a big continent with a lot of countries, we intend to only visit Argentina & Chile, with a possible quick trip over to Uruguay. We are doing this intentionally because we feel like those countries are so big with so much to offer and we’d rather travel slowly than collect countries.

Itinerary/Timelines for 2012 Traveling Adventures

December 26, 2011: After weeks (months) of friends and family asking if we’ve gotten our tickets yet or not, we finally arrange reward tickets for us to leave the country in less than 4 weeks.


Jan 21, 2012: Depart Boston, layover Dallas, arrive in San Francisco to visit friends for a few days.


Jan 23: Spend 24+ straight hours in either an airport or airplane, with a 16 hour flight to Hong Kong, 1 hour layover, then 3 hour flight to Singapore.

Jan 24, 2012: Arrive in Singapore, be really hot, enjoy the zoo, acclimate to Asia.


Jan 28, 2012: Head to the northern, mountainous area of Chiang Mai, Thailand. Ride elephants, take cooking classes, go ziplining, make new friends.


Jan 29-March 22: Enjoy about 3 weeks in Chiang Mai, then head to Luang Prabang (Laos) for about 8 days, Siem Reap (Cambodia) for about 8 days, Krabi Province (Thailand) for about 2 weeks, and Bangkok for 4 days. Time spent in each location was determined at time of travel and we flew between each location.

March 22: Travel back in time (without Marty McFly), leaving Bangkok on March 22 at 4p and arriving in Los Angeles on Mar 22 at 2p.


March 22-26: After a few days of being confused about what day and time it is, enjoy a visit in Los Angeles with Jenny’s college roommate.




March 27: After a red-eye, stumble into Boston at 6:30AM, thankful to be back on the East Coast (love that dirty water, Boston you’re my home!).


April, May, June: Live and work in Boston in order to make enough money for the next adventure. Jenny gets hired to work as the program manager for Boston Bikes, with the caveat that she is going on a two month trip.




July 9: Head to Jenny’s motherland (Sao Miguel, Acores, Portugal).



July 19: After a week with the family, fly to Lisbon (visiting nearby Sintra & Belem) then bus down to the Algarve (specifically, Salema & Lagos – southern Portugal). Bus to Coimbra, then trained our way to Porto  – spending just about 3.5 weeks total in Portugal.

We then flew to Pisa, Italy, traveling by train and bus to Cinque Terre, Florence, Siena, Certaldo, for a total of just under 2 weeks in Italy. We flew to Spain, visiting Santander, San Sebastian, Barcelona, Valencia, and Bilbao, for about 3 weeks.

September 6: Fly from Bilboa, Spain, to Frankfurt, Germany, onward to Boston.

September 8: Move back to South Boston. Jenny starts back at work that Monday. “Normal” life resumes, until we scheme up the next adventure! (see above for South America 2017!)

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