Travel Advisor

Stephanie Cunningham

Expertise

Spain,
New England,
All-Inclusive Travel,
River Cruises,
Food & Wine

Based in

Boston, Massachusetts

Minimum booking Budget

$500/night

Travel Advisor

Stephanie Cunningham

Profile details

About

A native New Englander, lover of all things Spain and 20-year Meeting & Event Professional, I am passionate about providing personalized, collaborative expert travel solutions for both businesses and individuals. A lifelong learner, with a relentless curiosity for new places and a keen eye for detail — I remove the stress, time and overwhelm that comes with planning that perfect travel experience. While my forte is groups, corporate & MICE, I can also assist individuals looking for a hotel booking, excursions, tours, destination all-inclusives and anything in between!

Why work with me?

- One-on-one partnership

- Insider experience and tips

- Exclusive offers and perks

- Customized itineraries

As your personal Travel Advisor, I am dedicated to helping you create a lifelong tapestry of connections with people and places through travel!

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Travel style

I am the type of traveler that encompasses a measured amount of site seeing, relaxation and off-the-beaten-path activities.

Stephanie's travel guides & trip reports

Guide

Weekend in Chatham, Cape Cod

Cape Cod has been a reoccurring destination for many New Englanders over the decades and rightly so, it has all the components of a beach vacation that caters to all walks of life with plenty to do....

Trip Report

Property Spotlight: Hotel Aigua Blava - Costa Brava

In July 2023, I did a site inspection of the Hotel Aigua Blava located in Begur, one of the most beautiful coastal towns in Costa Brava. This property is situated in one of the many coves within the ...

Trip Report

5 Boutique Hotels in Boston

Welcome to Boston! Home of the lobster role, the World Champion Red Sox and Patriots and the best place to call home! A city steeped in history and vibrant culture, where every cobblestone street...

Trip Report

4 Martha's Vineyard Hotels

Martha’s Vineyard, one of the many gems of New England, is nestled off the coast of Massachusetts. “The Vineyard” is an idyllic island known for its pristine beaches, charming towns and rich history. ...

Guide

Discover Newport, Rhode Island

Welcome to Newport, Rhode Island! Where history, charm and coastal beauty converge to create an unforgettable destination. Only two hours from Boston, Newport is easy to get to and is nestled along...

Guide

Weekend Getaway Series: Lake Placid, NY

The Adirondacks hold a special place in my heart and visiting Lake Placid brought back a flood of wonderful memories. My grandparents owned a "camp" on Lake George, part of the broader Lakes Region,...

A picture of seven different colored ski helmets lined up on a wooden bench.

Guide

The Best Ski Resorts - East Coast

As a New Englander and snowboarder, I feel fortunate to have the opportunity to be within a few hours’ drive to some of the best snow-capped peaks and slopes in the world. The variation of each of...

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Favorite hotels

Mandarin Oriental, Barcelona

This grand hotel on the Passeig de Gràcia combines global luxury with authentic Catalan sophistication.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Chatham Bars Inn

A stunning resort situated along a private beach, with seasonal dining featuring ingredients from the onsite farm.

Fora Perks

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

Raffles Boston

Where historic legacy meets contemporary luxury, defining a new era of sophistication in the heart of Boston's vibrant Back Bay neighborhood.

Fora Perks

★
Hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Stephanie's travel photos

A bottom-up view of a stone building in Spain with detailing, tourists, green bushes and a blue sky in the background.

A sandy path, green wild grass and boats on the water at sunset.

Two beach chairs under a straw umbrella looking out to the blue water and waves rolling in.

A white house and lighthouse next to a fence, rocks, green grass and the blue sea in the background under a blue sky.

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Stephanie's reviews

Stephanie helped make our trip fabulous!

Tracy H.
Booked travel to The USA
April 2025

Diane & Chris C.
Booked travel to Cork
March 2025

Highly recommend Steph & Dixon! Our trip to Ireland was thoroughly and thoughtfully planned. Every detail from the airport and hotel transfers to the accommodations to the daily excursions, every detail was covered. We will be planning our next trip with Stephanie!

Diane & Chris C.
Booked travel to Ireland
March 2025

Stephanie was great. She was always on top of things, thorough and very good at communicating with us. We would highly recommend her!

Heather S.
Booked travel to Turks and Caicos
December 2024

Stephanie Cunningham curated by Stephanie Cunningham

Get in touch with Stephanie

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

You can normally expect a response from Stephanie 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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