Spain | May 22 - 31, 2026

I can’t believe it’s already been a month since I was sitting in Madrid with a glass of wine. Now I’m back home, still often with a glass of wine, but it’s not the same. 

Thursday, May 21

In terms of red-eye flights, this one was easy because it was direct to Madrid. We landed, made our way through Madrid customs (the hardest part of the day), and then hopped in some taxis to reach the Airbnb. 

Our Airbnb was excellent. The management company communicated through WhatsApp, making it very easy to meet up and collect the apartment keys. The apartment was huge, with four bedrooms and four bathrooms, allowing for minimal necessary sharing. The floors were a little creaky, but we were all up at the same time anyway, so that didn’t matter.

Once we got settled, we went outside to Plaza De Matute and had some tinto de verano at El Imperfecto before walking around the area and getting dinner at Lamucca de Prado. It was an early night after a long travel day.

Friday, May 22

We had to start our vacation off with an overview of the city, so we did the Madrid Private City Tour by Eco Tuk Tuk. We rode in Tuk Tuk 30 with Julian as our tour guide. We chose the 4-hour tour since we had no other plans for the day. We saw the Royal Palace of Madrid, the Cripta de Santa María la Real de la Almudena, El Retiro Park, the Iglesia de San Jerónimo el Real, the Plaza de Toros de Las Ventas, a Starbucks that let us see into Bernabéu, La Rosaleda del Parque del Oeste, and the Temple of Debod. Some locations we got to walk around and explore, while others we drove by, but Julian was very knowledgeable and able to answer any questions we had throughout the day. Sometimes it was hard to hear him in the Tuk Tuk because of the wind and city sounds around us, but he did have a microphone, and we were able to understand the important parts of the tour or ask for clarification when needed.

After the tour, we needed to find some food, so we made our way to Plaza Mayor and got lunch at Cafetería Magerit. Then, we toured some rooftop bars (Sky 44 Rooftop Terraza & Bar Madrid and Capitol Rooftop) before making our way back towards the Airbnb and grabbing dinner at O Cacho do José in Plaza de Santa Ana.

Saturday, May 23

Part of our group went to a wedding Friday night, and didn’t get home until after 4 am, so while they slept in, a smaller group of us went to breakfast at Brunchit, walked around, and then grabbed a drink at La Merecida.

Once the entire group was awake, we went to Hotel Riu Plaza España for lunch at El Edén Gastrobar and drinks at the Sky Bar 360°, which was definitely worth making a reservation for because the food was good and the views were even better.

From there, we walked to the Chamberí neighborhood in Madrid for a Non-touristy Tapas Tour. This ended up being the highlight of my trip because we never would have explored this part of the city on our own, and our guide, Raul, was phenomenal. He’s from the area and, after some time in a corporate job, decided he’d rather show people the highlights of his home. The stops we made were:

• Filito - Chamberí: Beer (I drank white wine), Payoyo cheese with asparagus sauce, and pork belly (my favorite of the day)
• Taberna Alipio Ramos: Sangría, tortilla española (Spanish omelette), and roasted ham
• Bar Restaurante Ponzano: Wine, Ibérico ham croquettes, jamón (ham), and extra virgin olive oil
• Los Arcos de Ponzano: Vermouth, deep fried calamari, and chorizo

After the tour, we ended up at Papaya Destilados Artesanales for drinks, drinks, and more drinks.

Sunday, May 24 

The calmest day of the trip. After taking the most unrelaxing walk through the crowds of El Rastro (Madrid’s most iconic and historic open-air flea market), we spent most of the day in El Retiro Park; food and drinks at Heladería El Ancla and Bar Mirador. 

After some souvenir shopping, we had dinner at Las Tapas de Juan in Plaza de Santa Ana.

Monday, May 25

Mission 1 of the day: figure out the location of Monasterio del Corpus Christi "Las Carboneras" so we could buy some “Nun Cookies”. Thanks to social media and maps, this was not a very difficult mission, and we purchased some Galletas (lemon-flavored biscuits), which were very good, but would have been better dipped in tea. 

We took a lap through Mercado de San Miguel before stopping for a drink at Cervecería Restaurante Plaza Mayor. While in Plaza Mayor, we took our time looking through the shops.

We had lunch reservations at La Terraza del Campo del Moro, which is in the gardens of the Royal Palace, meaning it is absolutely gorgeous. 

Before heading back to the apartment, we went to La Postalera to buy fun postcards, prints, and fans.

We had dinner at Las Tapas de Juan in Plaza de Santa Ana again.

Tuesday, May 26

Early morning because we needed to head to the airport! We flew from Madrid to Palma de Mallorca. 

We stayed at MHOUSE Hotel Palma, which was a lovely hotel and perfect for the one night we were there. We couldn’t check in right away, but we were able to drop off our bags and have some breakfast.

We spent the day at Anima Beach Palma, eating, drinking, sleeping, reading, and testing out the waters in the Bay of Palma. I had a delicious strawberry daiquiri.

By the time we were ready for dinner, we couldn’t find much open, but ended up at Mani Pizza & Cucina Palma De Mallorca, which was really good and had a kind staff.

Wednesday, May 27

To explore more of Plama, we did a bus tour to the other side of the island called Palma: Caves of Drach Entrance, Music Concert, and Boat Trip. We were on the 138 bus with Ester as our tour guide and Tony as our driver. We loved Ester, she ran a tight ship and shared a lot of interesting information without it feeling like she was lecturing us the whole trip to the cave. She also spoke multiple languages, which is always impressive.

The caves were really cool. We looked for shapes in the stalagmites. The concert they performed in the lake at the bottom of the cave was also fantastic. I kept thinking what an interesting brainstorming it must have been for whoever decided to add an amphitheater and a concert to a cave exploration. The boat ride was shorter than I thought, but it was fun to say we did it.

Mallorca is famous for Majorica Pearls. The story Ester told us was that two brothers, both fishermen, were working when one found an oyster with a pearl in it, which he gave to his wife. She told her sister-in-law, who then also wanted a pearl of her own. Her husband couldn't find an oyster, so he used crushed scales and shells that he blew into a glass pearl (slightly bigger than the real pearl his brother found). And now glass pearls are famous, and there is a store right by the caves.

We got drinks and snacks at Benja's before gathering our stuff and heading to the airport.

Thursday, May 28

Another breakfast at Brunchit before starting our day. Our first stop was writing out wishes at Calle de los Deseos. Then we went on the hunt for artwork vending machines, one of which was at Kon Kafé - Specialty Coffee and Cookies.

We made our way to the meeting spot for Madrid: Small-Group Royal Palace Guided Tour (Up to 8). The Madrid Royal Palace is gigantic; 3,418 rooms gigantic. We only got to see a handful of them, but the ones we did see were beautiful. I loved how each room had its own tapestry pattern and colors. Manuel led us through the palace and shared many fun facts.

Afterward, we walked through the Almudena Cathedral before finding something to eat at Cervecería La Plaza.

On our first night in Madrid, we walked past Restaurante Bestial by Rosi la Loca, and knew we had to try it before leaving, so we finally did. A themed restaurant is always fun, and this one was no exception—an under-the-sea experience from the decor, to the drink cups, to the bathrooms.

I ended the night with a KALA Greek Frozen Yogurt.

Friday, May 29

Davis was our tour guide for the Madrid: Segovia and Toledo Tour, Alcazar, and Cathedral. In each city, Davis led us on an overview tour, and then we had a bit of free time to explore. We saw cathedrals, aqueducts, and gorgeous city skylines.

In Segovia, we ate lunch at Cañas y Tapas, and back in Madrid, we had a nightcap at La Merecida.

Saturday, May 30

Our last full day was an early one as we made our way to the train station to go to Seville. Once there, we got some breakfast at Alfonsito.

Laura was our guide all day on the Alcazar and Cathedral of Seville Tour with Skip the Line Tickets. We thought this would be a 4-hour tour; it was closer to 6, and it was hot, but the Alcazar and Cathedral are gorgeous. We did get about an hour and a half break in between for lunch. Laura was knowledgeable and patient with the number of people she had to keep track of.

We had time for a quick drink at Universal People Bar de Tapas before going to Seville: Casa de la Memoria Flamenco Show. The Flamenco show was amazing, there were three dancers and a three-piece band. It was my first time seeing a Flamenco show, and it was definitely the place to see it.

Overall, Madrid was a fantastic city to visit. You could probably cover the major highlights in four or five days, but taking time for day trips to other cities was definitely worth it.

Italy | November 22 - December 1, 2024

I’d been planning this trip for a while. I presented the idea on my laptop in the middle of a Longhorn Steakhouse during my dad’s birthday dinner in September 2023. Initially, it was 13 days, and we would stay in 4 different cities. After considering some logistics, I narrowed it to 10 days, with two different accommodations and two day-trip excursions.

This was not my first time in Italy, which made deciding what to see a little easier. However, it still took a long time to figure out the best way to see as much as possible. Thankfully, a lot of people love Italy and have recommendations that I was able to sift through.

Friday, November 22

Today was easy; most of us worked at least half a day and then went to the airport for our red-eye flight to Rome. 

Saturday, November 23

The cheapest way to travel was to book a round-trip flight in and out of Rome. However, we wanted to start our vacation in Florence, so we also booked a one-way flight from Rome to Florence. We spent a few hours in FCO waiting for our next flight, and it was a long few hours, but eventually, we ended up in Florence. There were seven people in our group, and when we got our luggage, we got in a taxi that fit all of us, which was very convenient.

During our stay in Florence, we stayed at the Rivalta Florence Hotel. They were great from the very beginning. When I emailed them to let them know we had a large group, they helped me book the correct number of rooms. Although it was colder during our stay, the hotel has a great outdoor seating area and rooftop terrace. It’s located right on the Arno River, and all the sights are within a twenty-minute walk. We ended most nights at the hotel bar before retiring to our rooms.

After checking into the hotel, we had dinner reservations at Buca Mario. Our waiter, Aldo, was excellent—he had a song for everything we said. The food was delicious. My dad and brother got a Florentine steak, which was the biggest cut of steak I’ve ever seen. On our way out, the hostess gave my mom and aunts’ aprons and my sister and me a tote bag.

Sunday, November 24

Fun fact: Today was the Florence Marathon. I found out about this through the hotel about a week or so before our trip. Coming from Boston, I was a little panicked about what this could mean, but it didn’t disrupt our day very much.

We didn’t have anything booked for today but knew we wanted to see the Duomo and Accademia Gallery, so we started walking that way. For breakfast, we ate at Caffe Gilli, which was delicious, before making our way to the Cathedral of Santa Maria del Fiore. You can climb the Duomo if you want, but there are many stairs, so our group decided not to and just took pictures from the outside instead.

Outside the Accademia Gallery are different lines based on which ticket you buy. There was also a QR code to purchase the tickets, which resulted in us accidentally buying tickets for the Uffizi Gallery. Thirty feet away from us was a ticket office we went to and wished we noticed in the first place. The Accademia Galley is home to the Statue of David, but my favorite part is the half-finished works leading up to David. I find it so impressive that Michaelangelo took a rectangular prism of marble and was able to make intricate sculptures.

We walked through the Piazza Della Signoria while deciding what to do next. We were tired and a little hungry but didn’t want to return to the hotel, so we had “A Sit & A Snack” at Cacio & Pepe to regroup.

My sister’s most anticipated museum was the Gucci Garden, so we walked through that next before using our accidentally bought Uffizi Gallery tickets. Gucci Garden is a quick museum, but it’s very fun. One room has mirrors on all of the walls, so the bags look like they go on forever. 

Nobody cared that the time on our Uffizi tickets was incorrect. This Gallery is ginormous. Every room seems to lead to three more rooms, and the building is horseshoe-shaped, which I overlooked from the outside. A person could probably spend an entire week deciphering all of the bible depictions.

We ended the day testing our luck at the Fontana del Porcellino, pre-dinner drinks at Cavallino, and dinner at Mama Eat.

Monday, November 25

Since we had done so much on Sunday, we had nothing planned for Monday morning, so we decided to walk across the Ponte Vecchio to the Piazzale Michelangelo. For anyone who hasn’t been, it’s uphill and upstairs—lots of hills and lots of stairs. However, the view is worth it. 

Our A Sit & A Snack for the day was at Ditta Artiganale. Then we crossed the river and looked around Scuola del Cuoio. I wish I were more of a pocketbook person because the bags were beautiful. Around the corner was the Christmas Market in Piazza di Santa Croce, which was a fun surprise.

For dinner, we participated in the Fresh Pasta and Gelato Authentic Cooking Class. We made two types of pasta and enjoyed wine and gelato. The cooking class was a lot of fun, and the food was delicious.

Afterward, we walked around the Gucci Store, the Palazzo Strozzi, which showcases “Drift Art,” and back over the Ponte Vecchio before calling it a night.

Tuesday, November 26

We made our way to Venice! We got up early and walked to the train station. The woman at the desk was very helpful in getting us our tickets.

Once in Venice, we walked to the Libreria Acqua Alta, which, for some reason, I thought was a bookstore on a gondola. However, it’s a whole store.

After a quick coffee at Illy, we did the Murano, Burano, and Torcello Half-Day Sightseeing Tour. We saw a demonstration at the Gino Mazzuccato Glass Factory in Murano. Then we went to Torcello and took a picture on the Ponte del Diavolo before walking to Basilica di Santa Maria Assunta. My brother, sister, dad, and I climbed the bell tower. After seeing the colorful houses on Burano, we grabbed a snack at Fritto Misto. Our tour boat dropped us off right by the train station, so we grabbed a drink at Olimpia before getting on the train.

That night, we had dinner at Oliviero in Florence.

Wednesday, November 27

I purposefully booked an afternoon bus from Florence to Rome in case we had any last-minute sights. We wanted to see nothing new, so we enjoyed one last day in Florence.

We started the day with breakfast at Riviore, which has a delicious hot chocolate. Then, we returned to Scuola del Cuoio and the Christmas Market in Piazza di Santa Croce. Before getting to the bus station, we had some bellinis at Battipalla and gelato at Vivoli. 

Once we arrived at our Airbnb in Rome, we had dinner down the street at Le Tavernelle. Our waiter, Bill, played the song "More Than a Feeling" when he learned we were from Boston. That’s one of my dad’s favorite songs, so he was thrilled.

Thursday, November 28

My dentist told me about a great private tour company called My Best Tour. We booked them for a day and a half of tours. Although their website was a bit tricky to navigate, once we started an email chain, it was easy to book everything.

The first one we did was a 4-hour private Golf cart tour around Rome. Our driver was Chiara, and she brought us to Heart Park, Spanish Steps, Santa Maria Minerva, Pantheon, Trevi Fountain, and Santa Maria Maggiore. She gave us some facts at every location so we could get out and walk around.

After a quick lunch at Pizza Della Madonna, we started a second tour with Pino as our guide. This was a three-hour walking tour of the Colosseum and Roman Forum. We also talked a lot about Palatine Hill. Pino was very knowledgeable.

A Sit & A Snack was on the San Clemente terrace's rooftop. Dinner was at La taverna dei monte. My sister and I got gelato at Glauco, and then we walked back up to Santa Maria Maggiore. We thought the Christmas tree would be lit up, but it wasn’t.

Friday, November 29

We ate breakfast at Caffe del Commari before meeting Pino again for a walking tour of the Vatican Museums, Sistine Chapel, & St. Peter’s Basilica. The Sistine Chapel is a must-see, but I also really liked all of the tapestries in the museums. 

We grabbed lunch at Ristorante Giovanni before checking out Sant’Ignazio of Loyola Church. It’s one of the churches with a mirror to see the ceiling and film it as a TikTok trend. The line was really long, though, so I didn’t wait. I watched some people go through it.

After going back to the Airbnb to relax for a little bit, we walked back to the Trevi Fountain and Spanish Steps. Italy is planning for their Jubilee, so the fountain has scaffolding for cleaning, but they’ve added a bridge that allows you to get closer to the statues than you would normally.

We ate dinner at Ristorante Alla Rampa, located by the Spanish Steps. The waiter hated us in the most comical way. He judged everything we ordered and made faces.

Saturday, November 30

Our last day in Italy was spent on the Citywonders tour: a day trip to Pompeii, the Amalfi Coast, and Positano from Rome.

The most extended stop was a private tour of Pompeii. I've been before and know the history from Latin class, but it’s astounding to see the plaster casts of people trying to outrun their fate from Mount Vesuvius. 

Before arriving in Positano, we walked through the Limoncello Dicapri Factory. By the time we reached the Amalfi Coast, we didn’t have much time to explore, but we took photos by the Tyrrhenian Sea and sat in the church of Santa Maria Assunta.

Sunday, December 1

We woke up and headed to the airport to go home. It was an easy travel day because the direct flight was seven hours long. However, anything more than five hours is very long for me.

Check out my entire itinerary on the Out of Office app!

Scottish Highlands | October 12-15, 2024

As many of you know, Scotland is one of my favorite places. A few months ago, I looked at flights and noticed I could visit Inverness and the Isle of Skye for a reasonable price. So, I booked a ticket and invited some friends. One said yes, and off we went.

An unexpected stop in London

After a red-eye flight to Heathrow Airport, we promptly missed our connection due to delays taking off in Boston and a short layover. We got onto the flight to Inverness that night, left our luggage at the airport, and took the Heathrow Express into the city.

I have a photo of myself sitting in front of the lion statues in Trafalgar Square, and I was thinking of recreating it until I saw the signs forbidding people from climbing Nelson's Column. Instead, we walked down to Buckingham Palace. From there, we walked down to see Big Ben and the Palace of Westminster. Since it was Saturday, it was packed with people, so we didn't hang out for too long. Instead, we decided to walk along the River Thames before we got too hungry and had to make a stop at Pret-A-Manger. 

It was too early to head back to the airport, so we took the train to Notting Hill and looked at the colorful homes. We looked at some of the Saturday Market stalls that were open in the streets and then walked a giant circle around the area before the rain became too much, and we chose to take the bus back to Paddington Station to the Heathrow Express. 

Inverness

We eventually made it to Inverness, where we promptly dropped our suitcases off and made our way to the Hootananny Pub. A childhood friend of mine, who now lives in Germany, decided to come to Scotland as well, so we caught up with her. Even though we thought we'd only be good for one drink, we stayed out until almost 2 a.m.

Sunday

The two of us met up with my friend from Germany and her friend for breakfast at Charlie's Cafe before deciding what to do for the day. We had planned to take a bus up to Dunrobin Castle but quickly realized that some countries and cities relax on Sundays. The bus wasn't running when we needed it, and a taxi would have been too expensive, so we started walking around Inverness instead.

We walked down to Dolphin Spirit, but there were only two spaces left on the boat, so we headed to Uilebheist Distillery & Brewery for a drink instead. Afterward, we walked down to the Ness Islands before returning to the city center.

We had lunch at the Highlander (I had a delicious steak and ale pie) before the two girls caught a bus to Glasgow, where they would return home to Germany. 

The rest of the day consisted of shopping in any open souvenir shop, getting dinner at Blackfriars, returning to the Highlander for some live music, and then one last drink at Ash before heading to bed.

Monday

Today, we took the Rabbie's Skye & Eilean Donan Castle tour. This was a big reason I chose to stay in Inverness, and it did not disappoint. Our tour guide's name was Dave, and he was very knowledgeable about the area and its history. 

We stopped for photos at Loch Ness and Loch Cluanie before our first big stop at the Eilean Donan Castle. At the castle, you can pay to go over the bridge to walk the grounds or enter the castle. After grabbing some hot drinks, we only had time to walk the grounds, but we were fine with that choice. The original castle was destroyed in the 18th century as punishment for its use in the Jacobite Rebellions. Lt Colonel John Macrae-Gilstrap purchased and rebuilt it in the 20th century.

After driving over the Skye Bridge, we stopped for lunch in Portree. The two of us ate at Cuchullin, where I tried mussels for the first time. I ate a few but mainly stuck with the salmon and scallops. I also tried and enjoyed Cullen Skink, a traditional Scottish smoked haddock chowder. 

Our next stops were Kilt Rock, a view of the Old Man of Storr, and Quiraing, which offered some beautiful views. Our last stop was in Kyleakin, where we grabbed a drink at Saucy Mary's before the bus took us back to Inverness.

My only complaint was that we didn't get to pet any Highland cows. We saw some from the bus, but Dave wasn't able to find a good place to stop. 

I would have also done the Fairy Pools walk if we had toured the Isle of Skye alone. This tour didn't take us anywhere near them, which was fine, but they would have been a fun experience.

Tuesday

After checking out of our hotel but leaving our bags, we walked over to the Victorian Market for a hot drink at Milk Bar before taxiing to the Culloden Battlefield.

Dave gave us a summary of the battle during our Rabbie tour, but walking through the museum and reading about everything that happened was very informative. We saw clan grave markers and walked around the battlefield. 

There were Highland cows here, but they refused to come to the fence to be petted. I asked two cabbies if they knew anywhere nearby to pet some Highland cows, but we were out of luck on this trip.

We headed straight to Leakey's Bookshop, the largest second-hand bookshop in Scotland. Neither of us bought anything, but it was a really cool bookshop to look around in. 

We ended our trip with afternoon tea at Best Western Inverness Palace Hotel & Spa. It was delicious, but if I were to go back and had more time, I'd go a little outside of Inverness to Bunchrew House or Quila Cridhe. The Mustard Seed is a nice restaurant, and we couldn't get a table Sunday night for dinner, so we decided to have a goodbye wine to end the trip.

The Inverness Castle is closed for renovations, but we would have done that Sunday or Tuesday.

Where We Stayed

When booking our trip, we were between two hotels and decided to treat ourselves and go with the slightly more expensive Royal Highland Hotel. It was a great choice. This hotel has so much history, and it's absolutely gorgeous. We heard someone say the stairs were designed by the same architect who did them on the Titanic, and we believed it. They look very similar. 

Included with our booking was a complimentary drink and a 2-course meal ticket at the connecting restaurant Ash. When we returned from the Rabbie's tour, we got an appetizer to split, an entree each, and a dessert to split. 

It's also in the perfect location. Right next to the ScotRail, a block from the bus stops, and across the street from the Victorian Market.

Overall

It was a great trip. We could have used one more day since we ended up in London on Saturday, and a lot of stuff was closed on Sunday, but we saw everything we could in Inverness. The weather was a little chilly but not as rainy as I expected. Seeing a part of Scotland that I hadn't visited before was fun.

Salem, MA | November 10-12

A friend of mine organized a long weekend in Salem, MA, for her birthday. We rented a house and spent time exploring the downtown. We shopped, tracked down the filming locations from Hocus Pocus, and ate some great food. We were back at the house playing Who Would Rather and Jackbox Games when we weren't exploring.

What We Did:

You can't go to Salem without doing a few Halloween-related activities. We went to two different museums, both of which were quick to walk through and located right in the downtown area.

Count Orlok's Nightmare Gallery | $15

Count Orlok's Nightmare Gallery is a horror film museum in Salem, Massachusetts, that opened in September 2007. The collection is owned by James Lurgio and includes life-sized sculptures of several horror movie monsters, movie props, and life masks of various horror actors and directors.

Horror movies aren't my thing AT ALL, so I wasn't able to identify all of the characters, but I knew a decent amount. I kind of surprised myself, if I'm being honest. Some were terrifying; all were very cool.  

Halloween Museum of Salem | $10

The Halloween Museum is Salem’s premier Halloween-themed experience, with exhibits in 10 different rooms. The Histrionic Academy LLC operates the Museum. 

The museum is decorated with neon paint that leads you from room to room. It's filled with Halloween relics like old McDonald's toys and Barbies. As well as decorated house exteriors. 

What We Ate:

The Cheese Shop of Salem
Roseadela's shop and cafe
Engine House Pizza
Turner's Seafood
The Derby