Indonesia
24 years of experience

Ashley Desmond

Boston, MA Travel Agent

(26 reviews)
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!

Specializations

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 i...

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...

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 ench...

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 c...

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...

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...

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 f...

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 unco...

Greece Travel Agent Specialist

Welcome! I am your dedicated Greece travel agent specialist, passionate about crafting unforgettable experiences in this stunning...

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 Univ...

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, her...

Bahamas Travel Agent Specialist

Meet Your Bahamas Travel Specialist! Welcome to The Bahamas, where paradise awaits! I am your dedicated travel agent specializing...

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...

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 real...

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, Ma...

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 i...

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 a corporate business trip or a fun filled and exciting vacation, "Quacking" on a Duck Boat Tour, walking the historical Underground Railroad Trail or visiting renowned gems like the Museum of Fine Arts and the Museum of Science, I’m here to ensure your experience is seamless and memorable. Get ready to cheer on the Red Sox at Fenway Park, skate at the Frog Pond in the Commons, and soak in breathtaking views from the Prudential Building’s 360 Observation Deck. From the picturesque gaslight streets of Beacon Hill to the foodie delights of the South End, I’ll guide you to the best local restaurants, shopping on Newbury Street, and even an unforgettable whale watch in the summer. Boston is a treasure trove of experiences, and I can’t wait to help you create memories that will last a lifetime! Let’s embark on this exciting journey together!

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 for a relaxing beach getaway on the stunning shores of Sanibel Island, teeing off at the renowned Hammock Beach Golf & Spa, exploring the wild beauty of the Everglades, or seeking thrills at Busch Gardens, I’ve got you covered. From indulging in the vibrant art and culture of South Beach to savoring exquisite dining at the Fontainebleau in Miami. I meticulously handle every detail from start to finish. Let me help you discover all that the beautiful Sunshine State has to offer, ensuring your Florida adventure is nothing short of spectacular!

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 Temple Bar in Dublin to the exhilarating falconry at Ashford Castle, I will guide you through the best the Emerald Isle has to offer. Tee off at the breathtaking Old Head Golf Links in Kinsale, explore the medieval charm of the Dunguaire Castle in Galway, and stand in awe at the Cliffs of Moher and the scenic Aran Islands in Doolin. We’ll venture into Northern Ireland to marvel at the Giant's Causeway, boat to the breathtaking heights of Skellig Michael in Portmagee by The Ring Of Kerry and much more! I take care of all the details—your flights, transportation, accommodations, and visits to historical sites—ensuring you experience the best local pubs and hidden gems along the way. Let’s raise a glass to your Irish adventure—Sláinte!

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 a round of golf at the exclusive Ocean's Club, I’ll ensure every moment is unforgettable. Dive into the rich culture and history at Fort St. Catherine in Hamilton. Head down to the Royal Naval Dockyard where the America's Cup was held in 2017. All combined that make Bermuda so special. Let’s work together to create lasting memories in this breathtaking paradise—your perfect Bermuda escape and Dark and Stormy are just a consultation away!

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 since 2001. I would love to help you out with your World Cup Plans, time is seriously of the essence so get in touch with me!

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 volcanoes, breathtaking waterfalls, magnificent glaciers, and the iconic Blue Lagoon. As you explore, you'll also savor the delicious local cuisine, primarily featuring fresh seafood that captures the essence of Iceland's coastal culture. With my insider knowledge of downtown Reykjavik’s vibrant scene, including its renowned museums and cultural hot spots, I'm committed to crafting an unforgettable journey tailored just for you. Let’s join forces and create an extraordinary experience that will leave you with lasting memories!

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 Dublin to the breathtaking landscapes of the Cliffs of Moher and the enchanting Aran Islands. Whether you want to explore the historic charm of Kilkenny, savor the culinary delights of Kinsale, or take in the majestic views along the Ring of Kerry, I’m here to ensure every detail is seamlessly planned. Together, we’ll find the perfect accommodations, from cozy bed and breakfasts to luxurious hotels, and of course, discover where to enjoy the best pint of Guinness! Let’s collaborate to make your trip to Ireland as efficient and exciting as possible. I can’t wait to help you start this incredible adventure! ??

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 invites you to embark on a thrilling journey along the winding roads, stunning valleys and panoramic views whisper tales of ancient giants sculpting the landscape.

Next, take the guided tour leaving from Portmagee to Skellig Michael and Little Skellig, where you'll be captivated by the natural beauty and the playful puffins that call these islands home. As you ascend the ancient steps of Skellig Michael you witness where the Gaelic Christian monks founded their monastery in the 6th century. Surviving Viking invasions that led to their only cow being taken.

With my expert knowledge and personalized service as your travel agent, prepare to immerse yourself in Ireland's incredible history and breathtaking sites and views. Lets work together to create unforgettable memories on your next adventure to Ireland!

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 accommodations and recommending top dining spots. Whether you're dreaming of a romantic getaway on the sun-kissed shores of Santorini, an enriching family adventure steeped in ancient history, or a magical destination wedding or honeymoon, I am here to listen to your desires and tailor a journey that meets your unique vision. Let’s embark on this exciting journey together and start planning the trip of a lifetime to Greece!

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 vibrant culture, I'm here to ensure that every moment of your stay is unforgettable. Whether you're eager to explore iconic landmarks like the Tower of London, Kensington Palace, Windsor Castle, or the breathtaking Cliffs of Dover, or if you want to indulge in the luxury of shopping at Harrods, I’ve got you covered. I pride myself on providing the best recommendations for sightseeing tours, excursions, and delicious dining experiences at local restaurants and pubs. Want to capture a moment at the legendary Abbey Road? Let’s take the tube together and snap a photo at the iconic crosswalk made famous by The Beatles. And for the football enthusiasts, I can arrange tickets to see your favorite teams in action, whether it's Liverpool, Manchester United, Manchester City, Chelsea, or Arsenal. Let’s work together to plan your perfect getaway across the pond. I can’t wait to help you create memories that will last a lifetime!

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 an epic bachelor or bachelorette party, tying the knot with a stunning destination wedding, celebrating your honeymoon, or seeking quality time with friends and family, I'm here to listen to your needs and desires. With my expertise, I’ll provide personalized recommendations and assist you in scheduling flights, choosing resort accommodations, arranging thrilling excursions, booking captivating tours through the rain forest, and making dining reservations at the finest local spots. Immerse yourself in the vibrant culture, savor the rich flavors of authentic Puerto Rican cuisine, discover breathtaking beaches, and dive deep into the island's fascinating history. Let’s collaborate to transform your vacation into a fantastic experience you'll treasure forever!

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 destination wedding, a blissful honeymoon, or a fun-filled escape with friends and family, I’m here to turn your vision into reality. I take the time to listen to your unique wants and needs, providing personalized selections and recommendations tailored just for you. From booking air travel and arranging ground transportation to securing resort accommodations, exciting excursions, and fine dining experiences, I handle all the details so you can focus on enjoying your getaway. Picture yourself lounging on stunning sandy beaches by day and indulging in luxurious evenings or trying your luck at the blackjack table. Let’s work together to craft the perfect Bahamas vacation, where memories will last a lifetime!

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 islands, or organizing a fun-filled trip with friends and family to immerse yourself in Greece's rich ancient history, I’m here to ensure your experience is nothing short of perfect. I take the time to listen to your needs and provide tailored recommendations, covering everything from flights and ground transportation to selecting the best resorts, hotels, excursions, tours, and restaurants. Let’s collaborate to craft the ideal Greek adventure that suits your vision!

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 accommodation options. When it comes to your honeymoon, I believe every detail matters. From booking the most romantic all-inclusive resorts in the Caribbean to arranging enchanting excursions in Europe or indulging in the breathtaking vineyards of California, I’m committed to making your journey easy and enjoyable. My goal is to go above and beyond for you, curating not just trips, but lasting memories that you will cherish forever. Let’s work together to transform your ideas into an incredible adventure that reflects the love you share. Your magical time awaits—let's make it unforgettable!

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 truly exceptional. Whether you're dreaming of sunny days on the beautiful beaches such as Chatham's Lighthouse or Nauset Beach, enjoying the world's best lobster roll at the Raw Bar in Mashpee, or savoring the breathtaking sunsets while dining at Galley Beach in Nantucket, I'm here to make sure every moment of your journey exceeds your expectations. Whether looking for a family vacation, golf adventure, fishing trip or a romantic getaway, I am here to help with recommendations for every aspect of your travel. Let me guide you through the hidden gems and local favorites that will make your adventure most memorable. Together, we’ll create the perfect itinerary that captures the essence of the Cape and the Islands!

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 marvel at the ancient Book of Kells, visit the magnificent St. Patrick's Cathedral, or enjoy a tour of the iconic Guinness Storehouse, I've got you covered. From Dublin Castle to the serene beauty of the National Botanical Gardens and the lively atmosphere of Temple Bar, I’ll help you discover the best that Dublin has to offer. I take care of all the details—travel arrangements, transportation, accommodations, and event tickets—so you can focus on making memories. Let’s start planning your fantastic adventure in Dublin today!

Destination Specialties

Athens

Europe

Cancun

Mexico

Corfu

Europe

Cork

Europe

Dublin

Europe

Fort Lauderdale

USA

Grand Cayman

Caribbean

Hamilton

Caribbean

London

Europe

Mykonos

Europe

Nassau

Caribbean

Ponce

Caribbean

Reykjavik

Europe

San Juan

Caribbean

Waterford

Europe

Boston

USA

Fort Myers

USA

Grand Bahama Island

Caribbean

Kerry County

Europe

Limerick

Europe

Miami

USA

Nantucket

USA

Orlando

USA

Thessaloniki

Europe

Vieques Island

Caribbean

USA

Bahamas

Caribbean

Puerto Rico

Caribbean

Iceland

Europe

England

Europe

Ireland

Europe

France

Europe

Italy

Europe

Greece

Europe

Florida

USA

Bermuda

Caribbean

Santorini

Europe

Paradise Island

Caribbean

Akureyri

Europe

Galway

Europe

Blarney

Europe

Clare

Europe

Doolin

Europe

Delphi

Europe

St. George

Caribbean

Glastonbury

Europe

Stonehenge

Europe

Southampton

Caribbean

Woburn

USA

County Cork

Europe

County Clare

Europe

Windsor

Europe

Cambridge

USA

Carolina

Caribbean

Crete

Europe

Massachusetts

USA

Marthas Vineyard

USA

Newport

USA

Cape Cod

USA

Lesbos

Europe

Vik

Europe

Great Exuma

Caribbean

Ring of Kerry

Europe

Naxos

Europe

Seydisfjordur

Europe

Royal Naval Dockyard

Caribbean

Certifications & Awards

Reviews

(26 reviews)

BOSTON-CAPE COD-NANTUCKET-MARTHA’S VINEYARD

Reviewed By Kentuckytonantucketfan1 - Kentucky | Traveled to Nantucket | Massachusetts | USA

Ashley was the BEST! She flew my husband and I into Boston, then flew us down to Nantucket, we did shark diving!!! Ashley set us up at the best hotel, The White Elephant. Everything was flawless. We recommend working with Ashley ??

Athens Trip!

Reviewed By athens2023 - Portland, ME | Traveled to Greece | Europe

i took my parents to Athens and sought Ashley to be our agent. She was incredibly response and helpful mapping out our historical tour through Athens and Olympia

Bermuda

Reviewed By midoceangolf - New York | Traveled to Bermuda | Caribbean

Ashley helped my wife and I get a tee time at the Mid Ocean Club. It was a beautiful day. The lunch and beach were not to be missed.

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.

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!

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!

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.

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!

Best Trip To London!

Reviewed By british2 - CA | Traveled to London | England | Europe

We were recommended by friends of ours who recently worked with Ashley, she helped us have an absolutely wonderful trip to London. Couples getaway! She found us a great hotel in Kensington and helped us book a historical walking tour.

Ireland!

Reviewed By ireland24 - Natick, MA | Traveled to Ireland | Europe

I was recommended to work with Ashley to help me with my solo vacation to Ireland. Ashley was a wealth of information and helped make my time in Ireland so special. She recommended a plan that started in Dublin and scheduled private tours in Dublin, Belfast and Galway. I met a bunch of new people and very much enjoyed my time. Ashley was detailed and incredibly responsive. I recommend working with her if you need a travel agent.

ASHLEY DESMOND RESPONDED

"Awesome, thank you and I am so glad you had a blast!"

Ready to plan
your next getaway?

Share your vision—we’ll take care of the rest.

Plan a Trip

Explore the world’s most
inspiring places

Explore the world’s most inspiring places

Expertly crafted itineraries, tailored around you.

See Destinations