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Josephine DiMaggio, Travel Agent in Islip Terrace, NY

Josephine DiMaggio

Islip Terrace, NY Travel Agent
Super Agent

Josephine DiMaggio

Islip Terrace, NY · 25+ Years of Experience

DiMaggio Travels, an independent agent with KHM Travel Group, a Travel Leaders Network Affiliate Agency
5.0
(24)
100% Recommended
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... Read More >
About
Reviews
Certificates & Awards
My Places
Travel Stories & Media
Client Testimonials

Areas of expertise

Destinations:

Sicily, Italy, Sorrento, Tuscany, Venice

Interests:

Honeymoons, Heritage, Couples & Romance, European Culture, Family Vacations

Suppliers:

MSC Cruises, Auto Europe, Belmond, Classic Vacations, CIE Tours

About Me

At DiMaggio Travels, we believe every journey to Italy should be as unforgettable and one-of-a-kind as you are. Whether your heart longs for Florence’s timeless romance, Rome’s buzzing energy, Venice’s magical canals, or Palermo’s sun-soaked charm, we’ll design your Italian adventure to fit your style, pace, and passions.

? Why Italy, Why Now? Italy isn’t just a destination — it’s a living masterpiece. Imagine breathtaking art and history at every corner, cuisine that delights every sense, and people whose warmth makes you feel instantly at home.Picture yourself wandering cobblestone streets, sipping espresso in a lively piazza, or savoring handmade pasta while overlooking rolling Tuscan hills. Italy isn’t just a trip — it’s a love affair for your senses.

?? Your Style, Your Story Whether it’s:Adults-only escapes made for romance and relaxation family adventures filled with fun and discovery cultural immersions exploring Renaissance treasures beach side bliss on the Amalfi Coast or Sicilian Castle stays where history meets luxury European rail journeys that are scenic, seamless, and oh-so Italian Honeymoons designed with the perfect touch of romance we make it yours.

?? Imagine This: A perfectly poured glass of Chianti in a Tuscan vineyard. Sunset glowing over Rome’s Colosseum after a day of exploring art and history. Or the vibrant markets of Palermo, alive with fragrant lemons and fresh seafood. Whatever speaks to your soul, we bring Italy’s magic to life — no cookie-cutter tours, only experiences crafted for you.

?? Why Choose DiMaggio Travels? Because we don’t just plan trips — we curate your story. With over a decade of expertise and a lifelong passion for Italy, Josephine DiMaggio ensures every detail is seamless, every moment authentic, and every memory unforgettable.

?? Ready to say “Ciao!” to your dream Italy trip? Let DiMaggio Travels take you there. Because when it comes to Italy, why settle for ordinary when extraordinary awaits?

Additional Languages
Italian,
Spanish

REVIEWS

Rating: 5.0
24 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 24 reviews

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 28 people found this review helpful. Was this review helpful to you?YES|NO
Amazing Travel Agent
Reviewed By Tom - Pennsylvania | Traveled to Italy ~ Europe
Josephine did an extraordinary trip for our family. Her personal touch and keeping in touch making sure everything was going ok was over and beyond.
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
TOP NOTCH TRAVEL AGENT
Reviewed By DENISE - NEW YORK | Traveled to Italy ~ Europe
"DiMaggio Travels: Unforgettable journeys, impeccable service, and personalized adventures galore!"
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.
Italy Specialist
Sicily Specialist
Honeymoon Specialist

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

ITALY
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    Client Testimonials

    California Trip 25 year anniversary
    Josephine planned such a wonderful Vacation for us.. we started in Sonoma and visited the McEvoy ranch, hot air balloon ride over the vineyards… ate in some wonderful restaurants like LaSalette.. the. While in Sonoma we headed down to Tomales bay and viewed Hog Island oyster farm.. Next we visited Monterey and the aquarium.. We loved Carmel by the Sea. It was so quaint.. We finished up with a in San Francisco with a bike ride over the Golden Gate bridge to Sausalito. Thanks again Josephine we had so much fun.
    Anthony and Jen G
    Best Group Trip to Italy
    What a wonderful trip. Coordinated so well and we saw so much. No glitches for us but if you have one they will fix. No worries. Ireland was great and so was DiMaggio Travels. We will be sure to use them again.
    Holly G.
    Positive: Professionalism, Quality, Responsiveness
    Josephine has booked two very special vacations for my family. One was for my husband and our children to tour Italy. She was so patient and listened to exactly what we wanted to see and do. She nailed every location and hotel and tour that we wanted perfectly. The second trip was my son and daughter-in-law’s honeymoon. Due to Covid, their original honeymoon was canceled a month before they were set to go. She scrambled to get another honeymoon in place and the day we were going to book/pay, again it was canceled! She pulled through and found somewhere they could go with no issues and everything was amazing for them! She listens to exactly what you want to get out of your trip and to your budget! Thank you so much, Josephine!!!
    Theresa L
    What an amazing, seamless experience.
    Josephine is the best. A++++ service. Had to worry about nothing. She set up the trip itinerary, the flight, all that I wanted and everything was seamless at my destination in Hawaii. Cannot wait to plan my next trip including excursions with her again. She was attentive to all my needs. Reached out to her while away, was speaking with her within seconds after I texted. I was treated like a VIP. She was available if I ever needed her. If anyone is looking for an honest, passionate at what she does, who finds you the best for you and your family for your next vacation, look no further. DiMaggio Travels should be your only stop. Josephine, thank you so must for an amazing trip, itinerary, and seamless vacation. You are the best. A+++++++ Travel Agent!!!!
    Nicholas S.
    BESbswy