Ashley Desmond, Travel Agent in Boston, MA

Ashley Desmond

Boston, MA Travel Agent
Super Agent

Ashley Desmond

Boston, MA · 24 Years of Experience

Davisville Travel, an independent agent with Travel Leaders Davis, CA
5.0
(26)
100% Recommended
I went on a solo trip to Sanibel. I was referred to Ashley to help with my flight from CA and with hotel selections. I selected... Read More >
About
My Travel Specialties
Reviews
Certificates & Awards
My Places
Travel Stories & Media

Areas of expertise

Destinations:

Bermuda, Puerto Rico, England, Greece, Iceland

Interests:

Adventure, All Inclusive, Archaeology, Beach Vacations, Family Vacations

About Me

Luxury Global Travel Agent Specialist

Let’s get traveling! I am your dedicated travel agent, ready to help you plan the adventure of a lifetime. Whether it’s booking flights, securing hotels, curating restaurant recommendations, or organizing unforgettable excursions, I’m here to ensure your travel experience is nothing short of extraordinary. With extensive travels under my belt, including studying abroad in London and trips to the enchanting landscapes of Ireland, and the sun-kissed shores of the Caribbean. I have a wealth of knowledge and passion for exploration. Whether you’re dreaming of a romantic getaway, planning a bachelor or bachelorette party, organizing a destination wedding, touring through the cultural wonders of Europe, or embarking on a breathtaking hike in the White Mountains, I take great pride in providing personalized care for each client. My mission is to not only meet but exceed your expectations, turning your travel dreams into cherished memories. Let’s embark on your next journey together!

My Travel Specialties

Boston Travel Agent Specialist

Boston Travel Agent Specialist
Hello! I’m your dedicated Boston travel agent specialist, and I’m thrilled to help you discover the charm and excitement of this incredible city! With a degree from Bentley University and 14 years of living in vibrant Back Bay, I’ve immersed myself in all that Boston has to offer. Whether you’re ...Read More ▶

Florida Travel Agent Advisor

Florida Travel Agent Advisor
Welcome to Florida! I'm your dedicated travel agent, here to turn your dream vacation into a reality. With a passion for creating unforgettable experiences, I specialize in making magical moments with Mickey and Minnie that both kids and adults will cherish for a lifetime. Whether you’re yearning...Read More ▶

Ireland Travel Agent Expert

Ireland Travel Agent Expert
Fáilte Go HÉirinn! Welcome to Ireland!**Meet Your Travel Expert:** Are you ready to embark on an unforgettable journey to the enchanting land of Ireland? I’m here to craft your perfect Irish experience, making memories that will last a lifetime. From the awe-inspiring Trinity Library and vibrant ...Read More ▶

Bermuda Travel Agent Professional

Bermuda Travel Agent Professional
Welcome to Bermuda, where pink sands and turquoise waters await you! I’m your dedicated Bermuda travel agent specialist, here to craft the vacation of your dreams on this enchanting island. Whether you're wanting a romantic getaway lounging by the pool at the luxurious Hamilton Princess, or seeki...Read More ▶

WORLD CUP SOCCER 2026 Travel Agent Expert

WORLD CUP SOCCER 2026 Travel Agent Expert
THE WORLD CUP 2026 IS COMING TO FOXBORO STADIUM IN MASSACHUSETTS!! I can assist you with everything from booking your flights, TO FINDING A HOTEL THAT ACTUALLY IS NOT ALREADY SOLD OUT! Plus transportation and other suggestions to do while here visiting in Massachusetts. I have lived in Boston sin...Read More ▶

Iceland Travel Agent Professional

Iceland Travel Agent Professional
Hello and welcome! I'm thrilled to introduce myself as your dedicated Iceland travel agent, here to guide you through the wonders of this incredible country. If adventure calls your name, you're in for a treat! Iceland is a paradise for nature lovers and thrill-seekers alike, boasting stunning vo...Read More ▶

Ireland Everywhere from Dublin to Galway

Ireland Everywhere from Dublin to Galway
Hello! I’m Ashley Desmond, and I’m thrilled to help you create unforgettable memories on your journey to Ireland. With a passion for travel and an in-depth knowledge of this stunning country, I specialize in curating personalized itineraries that encompass everything from the vibrant streets of D...Read More ▶

Ring Of Kerry And Skellig Michael Await You!

Ring Of Kerry And Skellig Michael Await You!
I am your dedicated travel expert specializing in the breathtaking landscapes and rich history of Ireland. With a passion for uncovering hidden gems, I believes that no visit to the Emerald Isle is complete without experiencing the iconic Ring of Kerry and Skellig Michael. The Ring Of Kerry invit...Read More ▶

Greece Travel Agent Specialist

Greece Travel Agent Specialist
Welcome! I am your dedicated Greece travel agent specialist, passionate about crafting unforgettable experiences in this stunning country. With my expertise, I can assist you with every detail of your trip—from booking flights and arranging scenic tours to securing the perfect hotel or resort acc...Read More ▶

Across The Pond! England! Travel Agent Expert

Across The Pond! England! Travel Agent Expert
Welcome to England! I am your dedicated travel expert ready to make your visit truly exceptional. My journey began at Bentley University, where I studied abroad and fell head over heels for this remarkable country. With a passion for travel and a deep appreciation for England's rich history and v...Read More ▶

Puerto Rico Travel Agent Expert

Puerto Rico Travel Agent Expert
Meet Your Puerto Rico Travel Specialist!** Welcome to the enchanting paradise of Puerto Rico! I'm your dedicated travel agent, here to craft an unforgettable experience that will leave you with cherished memories for years to come. Whether you're dreaming of a romantic couples getaway, planning a...Read More ▶

Bahamas Travel Agent Specialist

Bahamas Travel Agent Specialist
Meet Your Bahamas Travel Specialist! Welcome to The Bahamas, where paradise awaits! I am your dedicated travel agent specializing in the beauty and allure of this tropical haven. Whether you're dreaming of a romantic couples getaway, an unforgettable bachelor or bachelorette trip, a picturesque d...Read More ▶

Greek Islands Travel Agent Expert

Greek Islands Travel Agent Expert
Welcome to Greece! I’m your dedicated travel agent specialist, here to help you create unforgettable memories in this breathtaking country. Whether you're dreaming of a romantic getaway, planning a destination wedding, embarking on a honeymoon while exploring the stunning blue hues of the Greek i...Read More ▶

Weddings and Honeymoons Travel Agent Expert

Weddings and Honeymoons Travel Agent Expert
Congratulations on your upcoming wedding! I’m thrilled to be your dedicated travel agent, here to make your dream honeymoon a reality. With a passion for creating unforgettable experiences, I specialize in ensuring seamless travel for you and your guests while presenting an array of fabulous acco...Read More ▶

Cape Cod and The Islands Travel Agent Expert

Cape Cod and The Islands Travel Agent Expert
**Meet Your Cape Cod & Islands Travel Expert!**Hello and welcome! I'm thrilled to be your go-to travel expert for Cape Cod, Martha's Vineyard and Nantucket. With a passion for all things coastal, I specialize in crafting unforgettable experiences that make your trip to these stunning destinations...Read More ▶

Dublin Travel Agent Specialist

Dublin Travel Agent Specialist
Fáilte Go HÉirinn! Welcome to Dublin Ireland! Meet your dedicated Dublin travel expert! With a passion for this vibrant city and its rich history, I’m here to ensure your time in Dublin is filled with unforgettable experiences. Whether you want to explore stunning Trinity College and marve...Read More ▶

REVIEWS

Rating: 5.0
26 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
Search reviews:

Showing 26 reviews

Sanibel and Fort Myers
Reviewed By Sanibel - New Jersey | Traveled to Sanibel Island | Florida | USA
I went on a solo trip to Sanibel. I was referred to Ashley to help with my flight from CA and with hotel selections. I selected the Sundial Resort from her list of hotels and could not have been more pleased.
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Fort Lauderdale
Reviewed By FLTRIP - Texas | Traveled to Fort Lauderdale | Florida | USA
Ashley helped my husband and I book our flights and a great room at the W Hotel! She was very responsive and a bottle of bubbles and chocolate in our room when we arrived!
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Iceland Trip!
Reviewed By Icelandfan - Indiana | Traveled to Iceland | Europe
It was our first trip to Iceland, other than staying in the airport for a connecting flight. Ashley mapped out our itinerary to a T. She booked us on a waterfall viewing tour and helicopter viewing of volcanos. We highly recommend her if you are considering a trip to Iceland!
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Time Away With My Girlfriend In Grand Cayman
Reviewed By GFAN - LA | Traveled to Grand Cayman | Cayman Islands | Caribbean
Ashley was fantastic in planning my vacation away with my girlfriend, now wife. She recommended The Westin Grand Cayman Seven Mile Resort, took care of our stay package which included the best spa experience! We had a bottle of Veuve Clicquot and strawberries in our room on arrival. We recommend her and look forward to working with her again soon.
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
St Thomas!
Reviewed By stthomas - AZ | Traveled to Caribbean
If you are looking to have a destination wedding, connect with Ashley. Ashley helped my husband and I plan our wedding in St Thomas. She took care of every detail and worked very well with our wedding planner. Our wedding was at the Marriott. Thanks to the "A" team, our friends, family had a wonderful time!
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO

Certifications & Awards

ASTA is the leading global advocate for travel agents, the travel industry and the traveling public.It is the world's largest association of travel professionals.Our members include travel agents and the companies whose products they sell such as tours, cruises, hotels, car rentals, etc.Expand your world. Go with the pros.

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.

My Photo Albums and Videos

Iceland
View Album

    My Travel Stories

    CBI

    Cape Cod: Chatham Bars Inn

    I have been staying at the Chatham Bars Inn known as CBI for years. CBI is perfect for you if you are looking for luxury, relaxation, family friendly, great menus, gorgeous pool, tennis courts, white sandy beach with daily boat rides to and from the sandbar. Last summer my friends and I stayed in late August, which I must say, between July 1st a...
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    The Bahamas!

    Ladies All-Inclusive Vacation- In The Bahamas

    I recently had the pleasure of booking an absolutely wonderful vacation on very short notice for two lovely ladies! Even though we are in the busy season, DOES NOT MEAN vacation dreams can not be made. My clients contacted me asking to be on the beach and loving life in the Bahamas...in TWO WEEKS! They are celebrating the 40th anniversary...
    Read more

    Boston!

    Boston At Its Best

    Welcome to Boston! I’m thrilled to be your guide through our vibrant historical city, where history meets charm, diversity, character, enthusiasm for sports, shopping and a huge variety of fantastic places to dine. Having gone to college here and having lived here since 2001, I have a passion for all things Boston. I’m dedicated to making your v...
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    Athens

    Amazing Athens

    Hello! I'm thrilled to have the opportunity to help you embark on an unforgettable journey to one of the world's most historical and mythological destinations. With a passion for travel and a deep appreciation for rich histories, I specialize in curating personalized experiences that encompass everything from arranging your flights to securing u...
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    The Blue Lagoon on an 80 degree day!

    Iceland

    The best and luckiest time I experienced in Iceland was in late July 2021. My friends and I went to the Blue Lagoon, as we had done many time before. The difference this time was that it was the first 80 degree sunny day in YEARS! There was a bit of a wait to wash off and get into the pool for obvious reasons. It was the most beautiful experienc...
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