Madeleine Reeg
She/Her
Based in Boston!
English, Spanish, learning Italian
Trips starting at $400/night
Madeleine Reeg
Ask me about
My Story
A Boston-based travel lover who spends way too many hours a day researching hotels to add to my "Want to Go" list!
Travel Style
Seasoned traveler with a love of relaxation and adventure. If there’s an amazing beach or wine bar within a 20-mile radius, I will find it! I'm all about seeing the sights, enjoying, and exploring a new location, and leaving time to find amazing eats and delicious coffee or wine!
Stay connected
Reviews (31)
Alexander H.
travel to Portugal
6 days ago
Amazing communication and response times. It was such an easy process just clicking links on places we had setup to go as well as getting directions in a new city. Also Maddie was very fast with reaching out to places on our behalf with any problems.
Erin M.
travel to Anguilla
18 days ago
Maddie was so helpful throughout the whole process!! From the very first phone call, she gave so many amazing recommendations. She suggested we stay at Malliouhana, which was a perfect fit for our anniversary! She was timely and had great communication. She also booked our room and got us resort credit and free breakfast which was amazing. We will use her again!
Stephanie B.
travel to Rome
24 days ago
I am so grateful that I came across “Maddie’s Passport” TikTok reels. Her expertise saved me from making a huge mistake as far as my hotel location. She gave me pros and cons of a few options. After spending a few days in Rome, I realize that she was spot on with every single recommendation. She was always responsive and professional. FH55 Grand Palatino was the perfect hotel for my vacation.
Luke R.
travel to Rome
28 days ago
Madeleine was fantastic to work with, flexible, knowledgeable, and made us feel seen and special at every stop, which made our trip as special as it could be. We are thankful for her work in making our honeymoon a once-in-a-lifetime trip.
Alicia M.
travel to Curaçao
about 1 month ago
Madeleine was so easy to work with, she was very thorough and took such good care of us! She is very organized, I will definitely work with her in the future.
Alexander H.
travel to Portugal
6 days ago
Amazing communication and response times. It was such an easy process just clicking links on places we had setup to go as well as getting directions in a new city. Also Maddie was very fast with reaching out to places on our behalf with any problems.
Erin M.
travel to Anguilla
18 days ago
Maddie was so helpful throughout the whole process!! From the very first phone call, she gave so many amazing recommendations. She suggested we stay at Malliouhana, which was a perfect fit for our anniversary! She was timely and had great communication. She also booked our room and got us resort credit and free breakfast which was amazing. We will use her again!
Stephanie B.
travel to Rome
24 days ago
I am so grateful that I came across “Maddie’s Passport” TikTok reels. Her expertise saved me from making a huge mistake as far as my hotel location. She gave me pros and cons of a few options. After spending a few days in Rome, I realize that she was spot on with every single recommendation. She was always responsive and professional. FH55 Grand Palatino was the perfect hotel for my vacation.
Luke R.
travel to Rome
28 days ago
Madeleine was fantastic to work with, flexible, knowledgeable, and made us feel seen and special at every stop, which made our trip as special as it could be. We are thankful for her work in making our honeymoon a once-in-a-lifetime trip.
Travel ideas (3)
An Insider's Guide to Curaçao
Curaçao was the perfect warm weather getaway for total R&R for me this spring! An island perfect for beach lovers seeking a less crowded Caribbean experience.
An Insider's Guide to Curaçao
Curaçao was the perfect warm weather getaway for total R&R for me this spring! An island perfect for beach lovers seeking a less crowded Caribbean experience.
A Peek Into Portugal’s Best Treasure: Porto
Porto is often overlooked by its bigger sister to the south, Lisbon (Portugal’s capital), but after spending a week back to back in each city, I left yearning for Porto. And this is coming from someone who experienced torrential downpours five of the seven days they were there! Porto has a special, authentically Portuguese charm, incredibly friendly locals, and truly excellent dining outlets (plus, amazing wines).
A Peek Into Portugal’s Best Treasure: Porto
Porto is often overlooked by its bigger sister to the south, Lisbon (Portugal’s capital), but after spending a week back to back in each city, I left yearning for Porto. And this is coming from someone who experienced torrential downpours five of the seven days they were there! Porto has a special, authentically Portuguese charm, incredibly friendly locals, and truly excellent dining outlets (plus, amazing wines).
One Week in West Sicily for Foodies & Beach Lovers
Sicily is an island I’ve been fortunate enough to visit several times now, and each trip, I’ve taken my time through one section of the island. Sicily is a huge and beautiful island with so much to see and explore, and trying to do it all in a week is near impossible. For the beach lovers and foodies of the world (myself included!), the west of Sicily is a perfect destination for beautiful beaches and delicious eats, and a week gives you plenty of time to explore, but also to unwind and enjoy la dolce vita!
One Week in West Sicily for Foodies & Beach Lovers
Sicily is an island I’ve been fortunate enough to visit several times now, and each trip, I’ve taken my time through one section of the island. Sicily is a huge and beautiful island with so much to see and explore, and trying to do it all in a week is near impossible. For the beach lovers and foodies of the world (myself included!), the west of Sicily is a perfect destination for beautiful beaches and delicious eats, and a week gives you plenty of time to explore, but also to unwind and enjoy la dolce vita!
An Insider's Guide to Curaçao
Curaçao was the perfect warm weather getaway for total R&R for me this spring! An island perfect for beach lovers seeking a less crowded Caribbean experience.
An Insider's Guide to Curaçao
Curaçao was the perfect warm weather getaway for total R&R for me this spring! An island perfect for beach lovers seeking a less crowded Caribbean experience.
A Peek Into Portugal’s Best Treasure: Porto
Porto is often overlooked by its bigger sister to the south, Lisbon (Portugal’s capital), but after spending a week back to back in each city, I left yearning for Porto. And this is coming from someone who experienced torrential downpours five of the seven days they were there! Porto has a special, authentically Portuguese charm, incredibly friendly locals, and truly excellent dining outlets (plus, amazing wines).
A Peek Into Portugal’s Best Treasure: Porto
Porto is often overlooked by its bigger sister to the south, Lisbon (Portugal’s capital), but after spending a week back to back in each city, I left yearning for Porto. And this is coming from someone who experienced torrential downpours five of the seven days they were there! Porto has a special, authentically Portuguese charm, incredibly friendly locals, and truly excellent dining outlets (plus, amazing wines).
One Week in West Sicily for Foodies & Beach Lovers
Sicily is an island I’ve been fortunate enough to visit several times now, and each trip, I’ve taken my time through one section of the island. Sicily is a huge and beautiful island with so much to see and explore, and trying to do it all in a week is near impossible. For the beach lovers and foodies of the world (myself included!), the west of Sicily is a perfect destination for beautiful beaches and delicious eats, and a week gives you plenty of time to explore, but also to unwind and enjoy la dolce vita!
One Week in West Sicily for Foodies & Beach Lovers
Sicily is an island I’ve been fortunate enough to visit several times now, and each trip, I’ve taken my time through one section of the island. Sicily is a huge and beautiful island with so much to see and explore, and trying to do it all in a week is near impossible. For the beach lovers and foodies of the world (myself included!), the west of Sicily is a perfect destination for beautiful beaches and delicious eats, and a week gives you plenty of time to explore, but also to unwind and enjoy la dolce vita!
Travel photos
