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!
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Reviews (21)
Heather L.
travel to Amalfi Coast
8 days ago
This was our first trip working with Maddie and we would do it 100x over again. Maddie’s communication was extremely timely and detailed… she answered any question we had and didn’t hesitate to alter our itinerary every time we changed our minds. We had a small issue with a tour in Rome and Maddie was on top of it and able to get us rescheduled for the next day. Our itinerary was detailed without being overwhelming. Maddie’s expertise as a travel advisor but also her own shared experiences with traveling made our trip stress-free. Thanks again for everything Maddie! We are already talking about our next trip!
Riley G.
travel to Sicily
11 days ago
Working with Madeleine was so easy! She was quick and prompt with her responses if we had any questions or concerns. It was nice having a planner for this trip so we could truly relax and enjoy everything. She made all the difference in this trip and going forward we’re confident/feel more comfortable using travel planners for our trips. If you need a planner, don’t hesitate to use Maddie.
Bailey L.
travel to Porto
about 1 month ago
Maddie was a joy to work with. She was responsive, kind, and handled last-minute changes with ease. Everything felt seamless from start to finish. We’ll definitely be booking our next trip through her.
Katherine F.
travel to Portugal
about 1 month ago
Quick and clear communication and easy to book everything!
Daniel D.
travel to Cancún
about 2 months ago
Maddie was absolutely exceptional when it came to planning our honeymoon. Her recommendations were spot-on, and her communication made the entire process seamless and stress-free—exactly what we needed while juggling wedding planning.
She handled every detail with care, from booking our stay and securing an incredible room to arranging airport transportation and recommending the best things to do and places to eat. Her responsiveness, both before and during our trip, gave us so much peace of mind.
We couldn’t have asked for a better experience and will absolutely be booking with Maddie again in the future.
Heather L.
travel to Amalfi Coast
8 days ago
This was our first trip working with Maddie and we would do it 100x over again. Maddie’s communication was extremely timely and detailed… she answered any question we had and didn’t hesitate to alter our itinerary every time we changed our minds. We had a small issue with a tour in Rome and Maddie was on top of it and able to get us rescheduled for the next day. Our itinerary was detailed without being overwhelming. Maddie’s expertise as a travel advisor but also her own shared experiences with traveling made our trip stress-free. Thanks again for everything Maddie! We are already talking about our next trip!
Riley G.
travel to Sicily
11 days ago
Working with Madeleine was so easy! She was quick and prompt with her responses if we had any questions or concerns. It was nice having a planner for this trip so we could truly relax and enjoy everything. She made all the difference in this trip and going forward we’re confident/feel more comfortable using travel planners for our trips. If you need a planner, don’t hesitate to use Maddie.
Bailey L.
travel to Porto
about 1 month ago
Maddie was a joy to work with. She was responsive, kind, and handled last-minute changes with ease. Everything felt seamless from start to finish. We’ll definitely be booking our next trip through her.
Katherine F.
travel to Portugal
about 1 month ago
Quick and clear communication and easy to book everything!
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
