Travel Advisor

Charlotte Flynn

She/Her

Expertise

Food & Wine,
Boutique Travel,
New England,
Italy,
Portugal

Based in

Boston & Rhode Island

Travel Advisor

Charlotte Flynn

Profile details

About

New England-based travel expert passionate about discovering unique boutique hotels and one-of-a-kind stays, both locally and abroad, to create unforgettable travel experiences.

Travel style

I specialize in curating travel experiences that go beyond the typical tourist path, focusing on smaller hotels that offer a more unique stay. I also love discovering the best local restaurants and off-the-beaten-path excursions to help connect with the true character of the destination.

Charlotte's travel guides & trip reports

Guide

3 Days in Comporta: Portugal's Beachside Hidden Gem

Comporta is a hidden gem on Portugal’s coast, just 1.5 hours south of Lisbon, offering a perfect blend of natural beauty and laid-back charm. With its beautiful beaches and tranquil rice fields, it's ...

Guide

Discover Montepulciano: A Guide to Wine Tasting, Relaxation and Delicious Dining

As a lover of food and wine, Montepulciano is one of my favorite places I've traveled to. Its town is picturesque, the restaurants offer fantastic local cuisine and the wineries are some of the best...

VIEW ALL

Favorite hotels

Lupaia

Ideally located between the towns of Montepulciano and Pienza, Lupaia is one of Tuscany's most magical countryside estates.

Fora Perks

★
Food / beverage or spa credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

The Woodstock Inn & Resort

Quaint and charming resort nestled in the heart of Woodstock, Vermont, offering a perfect blend of classic New England charm and modern comforts.

Fora Perks

★
$100 resort / hotel credit.
★
Welcome amenity.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Quinta da Comporta

Nestled in the serene landscape of Comporta, Portugal, this tranquil retreat harmonizes luxury with nature, featuring eco-conscious design, a stunning infinity pool and a spa inspired by local traditions.

DUKES London (temporarily closed)

Upmarket property in London's Mayfair neighborhood with posh rooms and suites.

Fora Perks

★
$50-100 hotel / spa credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Ocean House

World-class charming guesthouse offering true New England style and hospitality on Rhode Island's beachfront.

Fora Perks

★
$100 hotel / resort credit.
★
VIP welcome amenity.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Charlotte's reviews

Working with Charlotte made planning our travel a breeze! She listened to all of our wants and budget restrictions for the trip and curated thoughtful recommendations. She answered all of our questions in a timely manner and worked with the hotel to ensure our stay was comfortable and unique to us. When we arrived to the hotel we were greeted with flowers and a personal note from Charlotte, and those thoughtful touches really show how much she cares about her clients. I would recommend working with Charlotte to anyone who is planning an upcoming trip!

Mary H.
Booked travel to California
March 2025

Charlotte was extremely easy to work with and provided us a lot of great hotel options along with great restaurant ideal. Highly recommend using her!

Andrew C.
Booked travel to Mexico City
March 2025

Charlotte Flynn curated by Charlotte Flynn

Get in touch with Charlotte

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Charlotte within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).

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