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
My Travel Specialties
Reviews
Certificates & Awards
My Places
Travel Stories & Media
Client Testimonials

Areas of expertise

Destinations:

Dominican Republic, Jamaica, Costa Rica, Italy, Sicily

Interests:

Adult Only, All Inclusive, European Culture, Groups, Honeymoons

Suppliers:

Beaches Resorts by Sandals, Classic Vacations, Delta Vacations, Globus, MSC Cruises

About Me

Josephine DiMaggio — Italy & Europe Travel Special

Some people visit Europe. I help you experience it. I'm Josephine DiMaggio, founder of DiMaggio Travels, Inc. and a travel advisor with a deep, lifelong love for Italy and Europe. From the cobblestone streets of Rome to the sun-drenched terraces of the Amalfi Coast, I've spent years exploring every corner of the continent and I bring that firsthand knowledge to every itinerary I design. Since founding DiMaggio Travels in 2010, what began as a passion has grown into one of the area's leading travel agencies. My team and I specialize in crafting seamless, deeply personal European getaways for every kind of traveler, whether you're planning a romantic honeymoon in Tuscany, a family adventure through Sicily, or a group journey across the Mediterranean. For me, travel has always been about more than reaching a destination. It's the meals, the connections, and the stories that last long after you're home.
Additional Languages
Italian,
Spanish

My Travel Specialties

Travel Agent Specializing in Sicily, Italy

Travel Agent Specializing in Sicily, Italy
Sicilia nel Sangue: Why Sicily Runs Through My Veins Ah, Sicily. The very name flows like waves caressing its sun-warmed shores, conjuring visions of golden vistas, fragrant citrus groves, and a history as rich and layered as its finest olive oil. "Sicilia nel sangu...Read More ▶

Why Hire Me to Design your Vacation?

Why Hire Me to Design your Vacation?
Hiring me, Josephine DiMaggio of DiMaggio Travels, means you've got a partner who listens not just to what you say, but also to what your heart whispers. I'm not about off-the-rack travel plans; I'm all about the bespoke suits of travel, the kind that fit you like a glove. Imagine wanderin...Read More ▶

Your Personal Travel Agent

Your Personal Travel Agent
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 lon...Read More ▶

Travel Agent Specializing in Costa RIca

Travel Agent Specializing in Costa RIca
Everyone should be experiencing the "Pura Vida" once in their lifetime! My endeavor to Costa Rica felt like stepping into a living, breathing masterpiece. Everywhere I looked was a vivid splash of green, a canvas where life thrived in every corner. From the sprawling rainf...Read More ▶

Travel Agent Specializing in Mexico

Travel Agent Specializing in Mexico
I am your one stop shop for travel in Mexico!  Our agency has visited Mexico numerous times and I fall in love with it over and over. As someone who embraces the joy of travel, I could not be more excited to tell you why I believe everyone should experience the allure of Mexico. It's not j...Read More ▶

Travel Agent Specializing in Punta Cana

Travel Agent Specializing in Punta Cana
I'm your personal travel aficionado, and I must confess, my heart belongs to the unparalleled shores of Punta Cana. The allure of this tropical paradise isn't merely the sun-kissed beaches or the whisper of the palm fronds in the ocean breeze, it's the spirit of escape that it breathes into your ...Read More ▶

Let's Travel to Italy your Way!

Let's Travel to Italy your Way!
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 ...Read More ▶

Travel Agent Specializing in Italian Ancestry

Travel Agent Specializing in Italian Ancestry
Trace Your Roots: Italian Ancestry Travel Your family's story didn't begin here. Let's go find where it did. As a travel advisor specializing in Italian heritage journeys, I create deeply personal experiences for travelers who want more than sightseeing — they want ...Read More ▶

Travel Agent Specializing in Jamaica

Travel Agent Specializing in Jamaica
I'm your travel ambassador to all things exquisitely beautiful. But let me tell you, there's one particular gem that's captured my heart like no other—Jamaica, the land of wood and water, rhythm and sway, igniting my spirit with its fiery sunsets and cool mountain mists. This love affair, ...Read More ▶

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.
AMA Academy
AMA Academy
AmaWaterways Specialist
AmaWaterways Specialist
Celebrity Learning Certification
Celebrity Learning Certification
Regent Seven Seas Luxury Cruise Expert
Regent Seven Seas Luxury Cruise Expert
Royal Caribbean University - Bachelor of Adventure
Royal Caribbean University - Bachelor of Adventure
Royal Caribbean University - Master of Adventure
Royal Caribbean University - Master of Adventure
Seabourn Academy Graduate
Seabourn Academy Graduate
TRACKS (Rocky Mountaineer Specialist)
TRACKS (Rocky Mountaineer Specialist)
Windstar Star Specialist
Windstar Star Specialist
Italy Specialist
DESTINATION WEDDING UNIVERSITY EXPERT
DWHSA
CLIA CERTIFICATION
Sicily Specialist
Honeymoon Specialist
IADWP
IATA CERTIFICATION
DESTINATION WEDDING UNIVERSITY
ASTA

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

25th Anniversary trip to California
View Album

    My Travel Stories

    A day exploring the Egadi Islands

    A Day Experiencing the Egadi Islands in Sicily

    Oh, where do I even start? Our day started on a boat ride to Favignana, the heartbeat of the Egadi Islands, kissed by a breezy Mediterranean embrace. I took a seat at an outdoor café adorned with the charm of Sicily and treated myself to a delectable pastry, a cannolo, and a robust espresso to awaken my senses to the day ahead. With an ea...
    Read more

    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