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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
Client Testimonials

Areas of expertise

Destinations:

Italy, Greece, Sicily, Spain, Amalfi

Interests:

Honeymoons, Family Vacations, European Culture, Food & Wine, Heritage

Suppliers:

Delta Vacations, Funjet Vacations, Globus, AmaWaterways, Disney Cruise Line

About Me

Sicily Stole My Heart!
Sicily Stole My Heart!

Some trips are planned. The best ones are felt.

I became a travel agent because I believe travel is one of life's most powerful teachers, it rewires the way you see the world, introduces you to people who leave lasting impressions, and drops you into moments so vivid they stay with you long after you're home. That belief shapes everything I do.

My job isn't just booking flights and hotels. It's learning what moves you and building a journey around it. With genuine passion for exploration and careful attention to every detail, I work with travelers who want more than a vacation, they want an experience worth remembering. Whether you're drawn to remote landscapes, cultural immersion, or pure relaxation, I make sure every piece is in place so you can be fully present when you get there.

No two travelers are the same, and no two itineraries I design are either. Your trip is built around you, your interests, your rhythm, your version of adventure.

Let's create something worth coming home and talking about.

Additional Languages
Italian,
Spanish

About Your Travel Advisor

At DiMaggio Travels, every journey I design starts with one thing - YOU!

With over a decade of experience as a travel advisor, I've built my practice on the belief that a great trip isn't just well-planned, it's deeply personal. I take the time to understand what you're looking for, what matters most, and what kind of memories you want to bring home. Then I handle every detail to make sure the experience lives up to that vision.

From destination selection to fully customized itineraries, nothing is left to chance. My clients don't just get a vacation; they get a journey thoughtfully crafted around their pace, their passions, and their idea of the perfect trip.

All you have to do is show up. I'll take care of everything else.

 

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.
Search reviews:

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.
DWHSA
CLIA CERTIFICATION
IATA CERTIFICATION
DESTINATION WEDDING UNIVERSITY

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.

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.
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