Do you charge a fee?
I do not! There is no planning fee to work with me in almost all cases

What are you getting out of this if you’re not charging me a fee?
Hotels and travel partners build commission into their pricing. When you book through me, I’m compensated by the supplier, and you do not pay anything extra. You get curated options, booking support, and help before and during travel, and often get the added benefit of perks only available by booking through a connected travel professional!

Can I work with you if I want to book everything on my own?
In the vast majority of cases, I’m able to offer complimentary full planning support when I’m also handling the hotel bookings. If you’d like itinerary design only without booking, for example if you’d like to book with credit card points, I do offer that as a separate planning service. Send me an email to talk specifics! molly@mchestertravel.com

Who are you, and why are you the right choice to help me plan my travel?
I'm Molly, and I am a professional travel advisor, experienced trip planner, and longtime middle school science teacher. Years in the classroom have made me calm under pressure, highly organized, and comfortable managing lots of moving parts - skills I bring to every itinerary I help orchestrate. I’ve traveled across five continents and built strong industry relationships that unlock exclusive perks, VIP upgrades, and insider pricing. From a city break in sprawling Tokyo to a Thailand beach escape to complex, multi-stop adventures, I offer thoughtful research, personal care, and expert support every step of the way. Learn more about me here.

What exactly do you do as a travel advisor?
I offer custom travel planning that includes curated hotels, thoughtfully designed itineraries, and seamless logistics. If you’re off on a luxury honeymoon, a family vacation, or a last-minute weekend escape, I’ll help you shape and book a trip that fits your travel style, goals, and budget.

Why should I book through you instead of doing it myself online?
I have access to exclusive perks (like free room upgrades, early check-in/late check-out, $100 credits left and right), often better pricing, and I work with trusted local partners that aren’t accessible to the general public. I also take care of the research, timing, and details, so your trip flows naturally and includes thoughtful extras that are often missed with DIY planning.

Do I still have control over my trip?
Of course! You’ll always have the final say. I’ll offer options and advice, and then help you book the pieces that make sense for you. You set the tone, and I’ll make sure everything fits together smoothly.

Can you help if I don’t know where I want to go yet?
Absolutely, that’s my favorite! Many clients come to me with just a season, budget, or general vibe in mind. I’ll help you narrow down the best destinations based on travel style, timing, and what kind of experience you're looking for. Whether it's a South-American city-hop, a Seychelles beach week, or something completely different, I’ll guide you toward a plan that makes sense.

What kinds of trips do you plan?
I specialize in travel to Europe and the Caribbean, with a particular focus on cruising, but I love planning all types of travel. From multi-country itineraries and safari adventures to group trips or something completely unique, I’ll help you find the right destination and design an experience that works for you.

Do you only work with people in Maine & Rhode Island?
Not at all! I may be based in Scarborough, ME and Little Compton, RI but I work with travelers all across the U.S. and beyond. No matter if you're down the street or across the country, we can plan your trip virtually from start to finish.

What happens if something goes wrong while I’m traveling?
If your plans change or a hiccup pops up while you're away, I’m on call to help. I work closely with you and all providers across your stay, and can get things sorted quickly so you can keep enjoying your trip.

How can I share feedback about accessibility on this site?
I want this website to be welcoming and usable for everyone! If you run into any difficulty using the site, or have suggestions for how I can improve accessibility, please let me know. You can reach me directly here or through the contact form. I truly value your input and will do my best to make adjustments quickly!