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Josephine DiMaggio

Josephine DiMaggio

Islip Terrace, NY Travel Agent

Josephine DiMaggio

Islip Terrace, NY Travel Agent
DiMaggio Travels, an independent agent with KHM Travel Group, a Travel Leaders Network Affiliate Agency
12 reviews
100% Recommended
23 Years of Experience

Destination Wedding and Group Travel Specialist


I have a driven passion for travel.  My love is to organize vacations for families, honeymooners, destination weddings. I want to send people to all inclusive resorts around the world and to cater to the hungry for the adventurous experience.

I believe each trip should be as special and unique as you are. It should be magical, rewarding, rejuvenating, and exciting, which is why I design each itinerary entirely around you.

I plan for your stay to be in the best accommodations, explore with top-notch guides, and enjoy genuine, personal experiences that you'll cherish forever.

When it comes to our guests, nothing is too much trouble. It's this attitude that drives me to create vacations that are extra special, and completely customized to you, because no two guests are the same.

Most clients come back to ask me to organize vacations to destinations, including Italy, Greece, Africa, Maldives, Seychelles, and South America. 

I love to travel and have traveled extensively to different countries including Europe, and the Caribbean. 

One benefit of my many years of experience is the connections I've made along the way. The network of in-country partners helps facilitate experiences that you would never find in the pages of a mass-produced guidebook.

If you're looking for one-of-a-kind experiences, be it on a cruise, land tour, or European getaway, my resources are the perfect place to start. 

Experience and commitment is why my customers return to me to help them plan their vacations year after year. I am committed to providing clients with peace of mind, quality service and lasting memories.  

Why hire  me as your travel agent?

1. Save yourself time dealing with every small detail associated with traveling at no additional cost to you.

2. Traveling to foreign countries can become a headache. Many people do not know that some countries, such as Brazil, require tourist visas.

3. Using me as your travel agent, I can  inform you the client where you can obtain passports, and provide you with the required documentation based on your destination.

4. Hiring me as your agent, will give you the ability to have a contact person or go to person to solve problems, deal with details, and handle any issues that may come up for you before, during and after your trip.

5. Last but not least hiring me as your travel agent is beneficial because we  have access to travel deals that aren't available to the public. Hotels, airlines and tours send us updated information. To drum up more business, airlines, and hotels will provide discount rates for me to pass on to my customers. 

Dest wed Consult


Travel  Consult



Independent Travel Advisor

Group Trip to Sicily

My passion and expertise will give you a vacation that you deserve.  I make sure that all components are taken cared of that you will have nothing to worry about.



DiMaggio Travels is the best around! Josie helped us plan our entire honeymoon and was so easy to work with. From start to finish her travel agency was there as soon as we landed in Greece and to every island we “hopped” to. They would meet us right away and were always on time. Never needed to worry about missing our boat our flight. We had a great vacation and would absolutely use them again!

Daniela, East Islip New York



Certificates & Awards

Travel Stories & Media

Client Reviews

Areas of expertise

Costa Rica
Destination Weddings
Bachelorette Parties & Girlfriend Getaways
European Culture
Family Vacations
Supplier Partners
Delta Vacations
Funjet Vacations
Disney Cruise Line

Certificates & 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 Photo Albums and Videos
Sicily 2024


    Rating: 5
    12 reviews
    100.00% Recommended
    She made planning easy!
    Reviewed By Highly Satisfied Customer - Kokomo, IN | Traveled to
    It was a delight working with Josephine in planning a surprise getaway for my husband 40th birthday. She helped me change current vacation plans as well as saved me an additional $500 by finding some great deals. I love it when planning for a vacation is easy and she ensured that it was the whole time. Thank you Josephine for your time and hard work. I know that my husband and I will have a great time this May. - Heather
    I would recommend this agent to my family and friends.
    35 of 61 people found this review helpful. Was this review helpful to you?YES|NO
    Best Travel Agent
    Reviewed By Kacey - Dix Hills, New York | Traveled to Dominican Republic ~ Caribbean
    Josephine goes out of her way up make sure that she fulfills your dream vacation. She takes her time to make sure she gets you what you want. Very professional courteous and friendly
    I would recommend this agent to my family and friends.
    12 of 20 people found this review helpful. Was this review helpful to you?YES|NO
    The best trip I ever had!
    Reviewed By Sadie - Huntington, NY | Traveled to Cancun ~ Quintana Roo ~ Mexico
    AMAZING WOMAN! AND GREAT TRAVEL AGENT! We had the time of our lives, and she knew everything. I do feel like I saved money going with her. Highly recommend commend!
    I would recommend this agent to my family and friends.
    15 of 27 people found this review helpful. Was this review helpful to you?YES|NO
    The most perfect trip to Italy!
    Reviewed By Savanna - Dix Hills, NY | Traveled to Italy ~ Europe
    Truly had the most perfect and seamless time! Josephine heard exactly what we wanted and did just that. She made it to easy and enjoyable. I look forward to hopefully planning another trip with her. My husband and I are truly grateful!
    I would recommend this agent to my family and friends.
    0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
    Honeymoon of our dreams
    Reviewed By JackieB - Oakdale New York | Traveled to Italy ~ Europe
    Working with Josephine was absolutely amazing. We told her a little bit of what we wanted to do and where we wanted to go and she executed it perfectly. She had us in each City for the PERFECT amount of time. The hotels she chose for us were out of this world, right in the middle of all the action in each city. Traveling to each city, she made it easy for us. When we got off each train there was always someone there picking us up and getting us to our destinations. Not only was our itinerary perfect but she laid it out by the minute! Making it so easy to know where to go and when. She was super responsive when we had any questions even with the time difference! In each city we went to, Josephine either gave us suggestions or booked different things for us. Our trip was once in a lifetime and we felt like we were living in a dream. I cant even put into words how amazing it was. Our future trips will definitely be booked with Josephine !!!
    I would recommend this agent to my family and friends.
    0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
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