Cape Cod and The Islands Travel Agent Expert

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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
Reviews
My Places
Travel Stories & Media

Areas of expertise

Destinations:

Cape Cod, Marthas Vineyard, Nantucket, Massachusetts, Boston

Interests:

Beach Vacations, Vacation Rentals, Golf, Sailing & Boating, Fishing & Hunting

About Me

Beautiful Cape Cod & The Islands
Beautiful Cape Cod & The Islands

**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!

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.
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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.
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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.
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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.
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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.
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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

Cape Cod, Nantucket and Martha’s Vineyard
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    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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    Bachelorette Party at Chatham Bars Inn

    Summer on Cape Cod

    One of my absolute favorite experiences on the Cape was during the summer of 2020. I booked my dear friend's bachelorette party at The Chatham Bars Inn. We had three rooms and could not have been happier with the beautiful accommodations. We took the resorts tour boat out to the sandbar which was a great time seeing the seals. I set up a beautif...
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