Ashley Desmond

Boston, MA

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

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 planning...
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Florida’s Expert Travel Agent

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...
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The SunShine State

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 seeking...
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Pink Sands of Bermuda

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...
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Beautiful Cape Cod & The Islands

Dublin Travel Agent Specialist

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...
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Dublin Pub

Customer Testimonials

Cape Cod Bachelorette

I had my bachelorette party last summer 2024 on the Cape in Chatham. Ashley helped with reservations to stay at Chatham Bars Inn. There were five of us and we were able to have our rooms next to each other. Ashley recommended we have dinner at the Impudent Oyster and brunch and bloody marys at The Squire. We took a fish charter out, did not catch a tuna but we had a blast. Ashley was a huge help and I recommend her as your agent.
Tori from VT

Bachelorette Boston

My girlfriends booked my bachelorette party in Boston. There were four of us and I was the only one who never had been to Boston before. We connected with Ashley who lives in Boston which definitely helped make my Bachelorette weekend awesome. She recommended the Lenox Hotel in Back Bay because it is close to everywhere we wanted to go to. She made reservations at City Table at the Lenox for breakfast and dinner. My girlfriends and I felt special, is the word that comes to mind. Thank you Ashley for making my Bachelorette Party absolutely beautiful <3
Britney, CT

Bermuda trip

I took my parents to Bermuda to celebrate their 40th Wedding Anniversary. We connected with Ashley to plan the flights which were a challenge as we were coming from different states. She put us on flights where we arrived within one hour apart, which was very convenient. Ashley booked our stay at the Reefs Resort in Southampton. We had ocean front rooms and we very happy with the resort staff. The food also was a crowd pleaser. My parents and I highly recommend Ashley to help you with your vacation needs.
Brian C & Sara C, Chicago

Disney World Great Family Trip 2024

Our family and my brother's family took our families to Disney World this past summer and had a wonderful time. Ashley was so great, she took care of everything from flights, to our stay at Disney's Animal Kingdom. The kids loved the Animal Kingdom being able to interact with the animals. It was a great trip, smooth and we want to thank Ashley for making our trip as great as it was.
Mark & Sarah L, Hal & Lauri S.

Bermuda- America's Cup

Our family had the best experience working with Ashley for our America's Cup trip. Since everyone sails to some degree in the family, we sought to go to the Cup. Friends of ours worked with Ashley and highly recommended her. She booked the flights, stay at the Grotto Bay Resort and assisted securing tickets in the Goslings Rum viewing area. She was able to get a reduction on the ticket prices which freed up money for having actual Dark and Stormies. We had a great experiene and you will too! Cheers.
The Orr Family, MA

Boston

My wife and I were looking for a "stay-cation" and Ashley was fantastic in making our weekend. She recommended the Colonnade Hotel and took care of the booking. We stayed this past summer and loved loved the hotel roof deck pool and pool bar! We met a bunch of other couples staying the weekend doing a "stay-vacation" as well. For dinner Ashley recommended the Long Bar at the Raffles Hotel. She recured our reservation at the bar were we had a view of the city. Good job Ashley!
Andrew and Melissa

Best Time in Boston

My wife and I had a great experience working with Ashley to plan our family's trip to Boston this past fall. Ashley took care of getting our room situated at Lenox Hotel. She recommended the Lenox because it is a dog friendly hotel so our fur child Sammy could come along. She recommended the Duck Boat Tour and hepled getting us Red Sox tickets. We recommend working with Ashley Desmond.
The Jasiak Family

FL Beach getaway success!

Ashley planned and booked a long weekend away for my girlfriend and myself down to South Beach and Miami. Our time away was eays breezy. She booked our flights and recommended 1 Hotel South Beach and took care of the booking. I told her I was taking my girlfriend away, she had a bottle of champagne and chocolate strawberries waiting for us! Ashley recommended we go to Miami for dinner and drinks at the Fountainebleau. She was not wrong! She reserved us a great spot at the Bleau Bar. Thanks to Ashley's help we had a great well needed time away together!
Christopher T

Great Disney Vacation!

Ashley recently helped my family and I with our Disney Vacation! it was our sons first time to Disney World. She booked our flights and secured our stay at the Grand Floridian. Ashley had a few gifts for the boys waiting for us in our room, which we thought was a great nice extra. She had great knowledge of the parks and saved us a ton of time by recommending the Lightning Lane Passes. The boys liked Chef Mickey and they are picky! A big thank you to Ashley for making our vacation, no pun intended, "Magical!". Looking forward to working with Ashley again.
Danny & Erica M, CT

Destination Expert:

  • Bermuda
  • Ireland
  • Florida
  • Dublin
  • Boston
  • Cape Cod
  • Hamilton
  • Aran Islands
  • Miami
  • Marthas Vineyard
  • Southampton
  • Blarney
  • Belfast
  • Orlando
  • Nantucket
  • Massachusetts
  • Royal Naval Dockyard
  • Doolin
  • Ring of Kerry
  • Fort Lauderdale
  • St. George
  • Cork
  • Galway
  • Fort Myers
  • Newport

Travel Specialist:

  • Air Travel
  • Beach Vacations
  • Family Vacations
  • Golf
  • Historical Sites
  • Castles & Cathedrals
  • Culinary & Foodie
  • Honeymoons
  • Rail
  • Vacation Rentals
  • Couples & Romance
  • Groups
  • Sporting Events
  • Business Travel
  • Escorted Tours
  • Heritage
  • Sailing & Boating
  • Universal Parks & Resort Vacations
  • Bachelorette Parties & Girlfriend Getaways
  • Car Travel
  • Fishing & Hunting

Industry Affiliations:

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