Molly Chester
Based in New England
Speaks 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.
My 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 actually going on it. I have long shared my personal and aspirational itineraries with friends, colleagues, and clients to 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.hereswhatiwoulddo.com for more about me!
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My reviews (21)
Heather O.
9 days 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!
Nicole T.
4 months ago
Working with Molly was such an easy and enjoyable experience. I was booking last-minute, and she quickly pulled together a range of lovely options that were still within my budget. She also shared some of her own recommendations, which made planning my trip so much easier. Her efficiency, attention to detail, and warm approach made the whole process stress-free. She was truly great!
Elizabeth F.
7 months ago
Molly steered us right on this wonderful hotel.
Alex P.
7 months ago
Super helpful, wonderful recommendations. Molly was really excellent.
Jessica C.
8 months ago
Molly did an excellent job at working around all of the challenges that I threw at her. She was very flexible as I was changing dates, airlines, and length of stay. I would definitely use her again for planning a trip!
Heather O.
9 days 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!
Nicole T.
4 months ago
Working with Molly was such an easy and enjoyable experience. I was booking last-minute, and she quickly pulled together a range of lovely options that were still within my budget. She also shared some of her own recommendations, which made planning my trip so much easier. Her efficiency, attention to detail, and warm approach made the whole process stress-free. She was truly great!
Elizabeth F.
7 months ago
Molly steered us right on this wonderful hotel.
Alex P.
7 months ago
Super helpful, wonderful recommendations. Molly was really excellent.
My travel ideas (3)
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.
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.
My travel photos
