Molly Chester
Based in New England
English
Molly Chester
Ask me about
My Story
Give me a far-flung locale with a little luxury and a hint of adventure and I'm there.
Travel Style
Seizing every opportunity to see the world! I’m fortunate to have made a lot of headway on my personal travel bucket list (forever evolving), and I am as passionate about planning a trip as I am about going on it. I have long shared my personal and aspirational itineraries with friends, colleagues, and clients with much success, and I love being a part of expanding peoples’ horizons and experiences and helping enrich their lives through travel. I can’t wait to learn what makes you want to travel, and hear how you want to spend your time away. I can make sure you have the best time, wherever you may be going! www.mchestertravel.com for more about me!
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Reviews (25)
Brittany J.
29 days ago
Molly is the best! We are very well traveled and used to book on our own but now only use Molly!
Brian C.
about 2 months ago
I want to take this opportunity to not only THANK Molly for making our Dad-daughter trip to Italy the most memorable experience it could possibly have been, but also for being one of the kindest, most considerate people I have ever had the pleasure of working with. Molly helped plan and create one of the most fabulous trips I have ever taken. If that was all she did it would have been more than enough. But it was not. Molly was ALWAYS there for us when unexpected changes seemed to be called for. Sometimes while away, as things unfold, plans need updating — and Molly was right there to make it happen. We never felt like we were alone. Molly was always there to be reached by a simple text to help with something, like a better guided tour or a new restaurant reservation, right there on the fly. I can’t explain the sense of confidence and relief my daughter and I felt just knowing that we had Molly standing by when we needed her. I could go on and on (like I sometimes did in our conversations), but I’ll just conclude by saying that once you work with Molly Chester for a planned travel experience, you’ll know that you have a travel expert for life — just as I now do. I can’t thank you enough Molly for what you helped create for my daughter and me. We will be forever grateful.
Pamela H.
5 months ago
Molly from M Chester travel was so easy to work with and her attention to detail helped ease my mind when planning a trip for my elderly mom to California and Ireland. She was so accommodating and agreed to meet us with very little notice in Scarborough Maine to plan out the itinerary. The attention to detail that she showed with all the different locations and different hotels was amazing. Planning a trip for a senior can be stressful, but Molly was thoughtful and able to make very insightful recommendations. She was patient and had insight into our mobility preferences. Her responsiveness made us feel well cared for and safe before and during our travels. I would highly recommend M Chester travel for your next trip whether it’s local or far away.
Kristi W.
5 months ago
Molly helped us plan the perfect trip to Japan; it was truly magical and life-changing. Our flight and seating were just what we needed to get there in style and to feel ready to explore. The amount of days at each stop worked well, and the hotels she helped us select were ideal. The tour she recommended in Kyoto introduced us to the major shrines and temples, and our ski and onsen stay was stellar. Molly’s guidance is invaluable!
Heather O.
6 months ago
Molly was incredible. I'd absolutely use her services again. She had great suggestions from the start, and was very patient while we had to pause planning due to a schedule change on our end. She was incredibly responsive every time I emailed her and I just can't say enough about how much I enjoyed working with her!
Brittany J.
29 days ago
Molly is the best! We are very well traveled and used to book on our own but now only use Molly!
Brian C.
about 2 months ago
I want to take this opportunity to not only THANK Molly for making our Dad-daughter trip to Italy the most memorable experience it could possibly have been, but also for being one of the kindest, most considerate people I have ever had the pleasure of working with. Molly helped plan and create one of the most fabulous trips I have ever taken. If that was all she did it would have been more than enough. But it was not. Molly was ALWAYS there for us when unexpected changes seemed to be called for. Sometimes while away, as things unfold, plans need updating — and Molly was right there to make it happen. We never felt like we were alone. Molly was always there to be reached by a simple text to help with something, like a better guided tour or a new restaurant reservation, right there on the fly. I can’t explain the sense of confidence and relief my daughter and I felt just knowing that we had Molly standing by when we needed her. I could go on and on (like I sometimes did in our conversations), but I’ll just conclude by saying that once you work with Molly Chester for a planned travel experience, you’ll know that you have a travel expert for life — just as I now do. I can’t thank you enough Molly for what you helped create for my daughter and me. We will be forever grateful.
Pamela H.
5 months ago
Molly from M Chester travel was so easy to work with and her attention to detail helped ease my mind when planning a trip for my elderly mom to California and Ireland. She was so accommodating and agreed to meet us with very little notice in Scarborough Maine to plan out the itinerary. The attention to detail that she showed with all the different locations and different hotels was amazing. Planning a trip for a senior can be stressful, but Molly was thoughtful and able to make very insightful recommendations. She was patient and had insight into our mobility preferences. Her responsiveness made us feel well cared for and safe before and during our travels. I would highly recommend M Chester travel for your next trip whether it’s local or far away.
Kristi W.
5 months ago
Molly helped us plan the perfect trip to Japan; it was truly magical and life-changing. Our flight and seating were just what we needed to get there in style and to feel ready to explore. The amount of days at each stop worked well, and the hotels she helped us select were ideal. The tour she recommended in Kyoto introduced us to the major shrines and temples, and our ski and onsen stay was stellar. Molly’s guidance is invaluable!
Travel ideas (4)
Briland: Barefoot Luxury, Pink Sands & a Standing Return Ticket to Harbour Island, Bahamas
I’ll be honest: Harbour Island is a place I almost don’t want to share. I’ve visited more times than I can justify given my ever-growing bucket list, but I’m already planning my next return. There are no high-rises, no sprawling resorts, no chain restaurants. Instead, there are miles of powder-soft pink sand, impossibly clear water, pastel-painted clapboard houses, and conch shells piled outside every door. Harbour Island is called “the Nantucket of the Caribbean,” and it really does feel like the Nantucket of my childhood. The luxury here is barefoot and unpretentious, and the locals are some of the most genuine and welcoming people I have ever had the pleasure of meeting. I keep going back, and I think you might too.
Briland: Barefoot Luxury, Pink Sands & a Standing Return Ticket to Harbour Island, Bahamas
I’ll be honest: Harbour Island is a place I almost don’t want to share. I’ve visited more times than I can justify given my ever-growing bucket list, but I’m already planning my next return. There are no high-rises, no sprawling resorts, no chain restaurants. Instead, there are miles of powder-soft pink sand, impossibly clear water, pastel-painted clapboard houses, and conch shells piled outside every door. Harbour Island is called “the Nantucket of the Caribbean,” and it really does feel like the Nantucket of my childhood. The luxury here is barefoot and unpretentious, and the locals are some of the most genuine and welcoming people I have ever had the pleasure of meeting. I keep going back, and I think you might too.
Velázquez & A Magnificent Courtyard: A Stay at Palacio de los Duques in Madrid
Madrid has some truly gorgeous hotels, but this one really stole my heart. Palacio de los Duques feels like a hidden garden tucked just behind the Royal Palace—it's elegant and peaceful, yet only a short stroll from the city’s most iconic sights. The building is historic and grand, and the atmosphere is elegant but unpretentious. I loved starting my day with coffee in the courtyard or heading up to the rooftop for a quiet swim before the city woke up. In the evenings, the same amazing courtyard turns buzzy and moodily beautiful, with a lively but low-key local crowd enjoying cocktails, music, and the twinkling lights overhead. It’s everything I love in a city stay: beautiful design, thoughtful service, and pops of personality and charm, all centered around one of the most inviting outdoor spaces I’ve seen in any city hotel.
Velázquez & A Magnificent Courtyard: A Stay at Palacio de los Duques in Madrid
Madrid has some truly gorgeous hotels, but this one really stole my heart. Palacio de los Duques feels like a hidden garden tucked just behind the Royal Palace—it's elegant and peaceful, yet only a short stroll from the city’s most iconic sights. The building is historic and grand, and the atmosphere is elegant but unpretentious. I loved starting my day with coffee in the courtyard or heading up to the rooftop for a quiet swim before the city woke up. In the evenings, the same amazing courtyard turns buzzy and moodily beautiful, with a lively but low-key local crowd enjoying cocktails, music, and the twinkling lights overhead. It’s everything I love in a city stay: beautiful design, thoughtful service, and pops of personality and charm, all centered around one of the most inviting outdoor spaces I’ve seen in any city hotel.
Iceland in 5 Nights: Waterfalls, Glacier Lagoon, The Golden Circle & Some Serious Relaxation
Iceland is one of my favorite places to revisit and recommend, partly because it’s so easy to get to from the US East Coast and partly because you can fit an incredible amount into a short trip. The landscapes are surreal, it feels like you are truly somewhere ELSE, and the drives between destinations are almost as memorable as the destinations themselves. This itinerary is one I’ve done in full and in pieces over the years, and it works just as well condensed into two nights as it does stretched into a full week.
Iceland in 5 Nights: Waterfalls, Glacier Lagoon, The Golden Circle & Some Serious Relaxation
Iceland is one of my favorite places to revisit and recommend, partly because it’s so easy to get to from the US East Coast and partly because you can fit an incredible amount into a short trip. The landscapes are surreal, it feels like you are truly somewhere ELSE, and the drives between destinations are almost as memorable as the destinations themselves. This itinerary is one I’ve done in full and in pieces over the years, and it works just as well condensed into two nights as it does stretched into a full week.
Cape Town: A City for Any Type of Traveler
Cape Town is the rare destination that is truly perfect for all types of travelers. Whether you're looking for adventure, luxury, food, family experiences, an incredible bang-for-your-budget or some combination of all, Cape Town checks all the boxes. The natural beauty, year-round fabulous weather and accessibility of so many bucket-list experiences make Cape Town one of my favorite places to visit and recommend.
Cape Town: A City for Any Type of Traveler
Cape Town is the rare destination that is truly perfect for all types of travelers. Whether you're looking for adventure, luxury, food, family experiences, an incredible bang-for-your-budget or some combination of all, Cape Town checks all the boxes. The natural beauty, year-round fabulous weather and accessibility of so many bucket-list experiences make Cape Town one of my favorite places to visit and recommend.
Briland: Barefoot Luxury, Pink Sands & a Standing Return Ticket to Harbour Island, Bahamas
I’ll be honest: Harbour Island is a place I almost don’t want to share. I’ve visited more times than I can justify given my ever-growing bucket list, but I’m already planning my next return. There are no high-rises, no sprawling resorts, no chain restaurants. Instead, there are miles of powder-soft pink sand, impossibly clear water, pastel-painted clapboard houses, and conch shells piled outside every door. Harbour Island is called “the Nantucket of the Caribbean,” and it really does feel like the Nantucket of my childhood. The luxury here is barefoot and unpretentious, and the locals are some of the most genuine and welcoming people I have ever had the pleasure of meeting. I keep going back, and I think you might too.
Briland: Barefoot Luxury, Pink Sands & a Standing Return Ticket to Harbour Island, Bahamas
I’ll be honest: Harbour Island is a place I almost don’t want to share. I’ve visited more times than I can justify given my ever-growing bucket list, but I’m already planning my next return. There are no high-rises, no sprawling resorts, no chain restaurants. Instead, there are miles of powder-soft pink sand, impossibly clear water, pastel-painted clapboard houses, and conch shells piled outside every door. Harbour Island is called “the Nantucket of the Caribbean,” and it really does feel like the Nantucket of my childhood. The luxury here is barefoot and unpretentious, and the locals are some of the most genuine and welcoming people I have ever had the pleasure of meeting. I keep going back, and I think you might too.
Velázquez & A Magnificent Courtyard: A Stay at Palacio de los Duques in Madrid
Madrid has some truly gorgeous hotels, but this one really stole my heart. Palacio de los Duques feels like a hidden garden tucked just behind the Royal Palace—it's elegant and peaceful, yet only a short stroll from the city’s most iconic sights. The building is historic and grand, and the atmosphere is elegant but unpretentious. I loved starting my day with coffee in the courtyard or heading up to the rooftop for a quiet swim before the city woke up. In the evenings, the same amazing courtyard turns buzzy and moodily beautiful, with a lively but low-key local crowd enjoying cocktails, music, and the twinkling lights overhead. It’s everything I love in a city stay: beautiful design, thoughtful service, and pops of personality and charm, all centered around one of the most inviting outdoor spaces I’ve seen in any city hotel.
Velázquez & A Magnificent Courtyard: A Stay at Palacio de los Duques in Madrid
Madrid has some truly gorgeous hotels, but this one really stole my heart. Palacio de los Duques feels like a hidden garden tucked just behind the Royal Palace—it's elegant and peaceful, yet only a short stroll from the city’s most iconic sights. The building is historic and grand, and the atmosphere is elegant but unpretentious. I loved starting my day with coffee in the courtyard or heading up to the rooftop for a quiet swim before the city woke up. In the evenings, the same amazing courtyard turns buzzy and moodily beautiful, with a lively but low-key local crowd enjoying cocktails, music, and the twinkling lights overhead. It’s everything I love in a city stay: beautiful design, thoughtful service, and pops of personality and charm, all centered around one of the most inviting outdoor spaces I’ve seen in any city hotel.
Iceland in 5 Nights: Waterfalls, Glacier Lagoon, The Golden Circle & Some Serious Relaxation
Iceland is one of my favorite places to revisit and recommend, partly because it’s so easy to get to from the US East Coast and partly because you can fit an incredible amount into a short trip. The landscapes are surreal, it feels like you are truly somewhere ELSE, and the drives between destinations are almost as memorable as the destinations themselves. This itinerary is one I’ve done in full and in pieces over the years, and it works just as well condensed into two nights as it does stretched into a full week.
Iceland in 5 Nights: Waterfalls, Glacier Lagoon, The Golden Circle & Some Serious Relaxation
Iceland is one of my favorite places to revisit and recommend, partly because it’s so easy to get to from the US East Coast and partly because you can fit an incredible amount into a short trip. The landscapes are surreal, it feels like you are truly somewhere ELSE, and the drives between destinations are almost as memorable as the destinations themselves. This itinerary is one I’ve done in full and in pieces over the years, and it works just as well condensed into two nights as it does stretched into a full week.
Travel photos
