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Josephine DiMaggio

Islip Terrace, New York Travel Agent

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Josephine DiMaggio

Islip Terrace, New York Travel Agent

DiMaggio Travels, an independent agent with KHM Travel Group, OH, a Travel Leaders Network Affiliate Agency

16 Reviews | 100% Recommended

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Travel Agent for Italy and Europe

I'm Josephine DiMaggio, your personal guide to the mesmerizing dance of destinations. My passion for being a travel agent stems from a deep-rooted love of discovery, the kind that you can only experience when you step into a new place. It's that indescribable feeling of excitement when your feet touch the cobblestone streets of Europe, that sense of peace as you sway with the rhythm of the Caribbean waves, and the vibrant spirit that dances through the air in Mexico. In 2010 I founded DiMaggio Travels, Inc. We are now one of the top Travel Agencies in the area and are waiting to work with you. I specialize in European, Caribbean and Mexico vacations. I am well versed in family vacations, honeymoons and group travel. For me, travel is not just about the destinations—it's about the memories we create, the people we meet, the food we savor, and the laughter we share. So, are you ready to embark on your next grand adventure? Here's to your next unforgettable journey!"

My Travel Specialties

Travel Agent Specializing in Sicily, Italy

Ah, Sicily – a name that rolls off the tongue like waves upon its shimmering shores, conjuring images of sun-drenched landscapes, aromatic citrus groves, and a history as rich and layered as its robust olive oils. "Sicilia nel sangue" (Sicily in the ... Read more from my Travel Agent Specializing in Sicily, Italy bio.

Travel Agent Specializing in Italian Heritage

Set sail with DiMaggio Travels on an enchanting journey into your ancestry, as we expertly craft a dual-faceted heritage exploration in Italy, with a special spotlight on the soulful island of Sicily. With our personalized approach, traverse the cobble stoned paths of your ... Read more from my Travel Agent Specializing in Italian Heritage bio.

Why Hire Me to Design your Vacation?

An afternoon in a vineyard in San Gimignano!

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, ... Read more from my Why Hire Me to Design your Vacation? bio.

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 ... Read more from my Travel Agent Specializing in Costa RIca bio.

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 ... Read more from my Travel Agent Specializing in Mexico bio.

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 ... Read more from my Travel Agent Specializing in Jamaica bio.

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, ... Read more from my Travel Agent Specializing in Punta Cana bio.

Your Personal Travel Agent

Hello! I'm your navigator through the fascinating world of travel. My life is a canvas painted with sunrise views from mountain tops, laughter echoing through historic streets, and the gentle touch of exotic sands. Being a travel agent is more than my ... Read more from my Your Personal Travel Agent bio.

CERTIFICATES & AWARDS

Avanti Certified Expert

Celebrity Learning Certification

AMA Academy

AmaWaterways Specialist

Regent Seven Seas Luxury Cruise Expert

Royal Caribbean University - Bachelor of Adventure

Royal Caribbean University - Master of Adventure

Seabourn Academy Graduate

TRACKS (Rocky Mountaineer Specialist)

Windstar Star Specialist

Globus Family of Brands University - Avalon Waterways Specialist

DESTINATION WEDDING UNIVERSITY EXPERT

DWHSA

CLIA CERTIFICATION

IADWP

IATA CERTIFICATION

DESTINATION WEDDING UNIVERSITY

ASTA

My Travel Stories

Mediterranean Cruise 2023

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Sicily 2023

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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 ... Read more from my A Day Experiencing the Egadi Islands in Sicily story.

My Reviews

Rating: 5 16 Reviews | 100% 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

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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

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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

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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

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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

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Amzing Honeymoon in Italy

Reviewed By Christina - Huntington, NY | Traveled to Italy ~ Europe

Josephine helped us plan our honeymoon to Italy. Not only was she knowledgeable of the destination, but very professional. She set everything up with the transfers, hotels and excursions. We had to do nothing except wake up and go to where our driver would be.

I would recommend this agent to my family and friends

16 of 31 people found this review helpful

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Impeccable Service

Reviewed By JD - Bohemia New York | Traveled to Negril ~ Jamaica ~ Caribbean

From the beginning to the end Josephine provided impeccable service. I knew that I wanted to book a sweet 16 trip for my daughter but I didn’t know exactly where to travel to. I explained to her what I wanted and she presented several quotes to different destinations. She knew everything about all these destinations. She knows her travel! I have used other travel agents before and they pale in comparison to DiMaggio Travel.

I would recommend this agent to my family and friends

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Exquisite planning and execution of our trip !

Reviewed By Maria C - Bethpage, NY | Traveled to Italy ~ Europe

I hired Josephine to plan my anniversary trip to Sorrento and to Taormina. Breathtaking! Josephine at DiMaggio Travels crafted our Italian romance with finesse. From spectacular views from our hotel, the private boat ride to Capri and Snorkeling to the sunset toasts in Taormina, every detail was tailored to perfection. Flawless reservations and insightful tips made our journey seamless. Unforgettable experiences wrapped in Italian luxury, thanks to Josephine's exquisite planning."

I would recommend this agent to my family and friends

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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

1 of 2 people found this review helpful

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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 1 people found this review helpful

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Mother and Daughter Trip

Reviewed By Annette - Suffolk County NY | Traveled to Italy ~ Europe

“I am so appreciative because this agency made my trip magical. My itinerary was so clear and easy to access in an app on my phone. It was effortless to move from city to city by train and by boat. I am so appreciative for the memories that will last a lifetime.”

I would recommend this agent to my family and friends

0 of 1 people found this review helpful

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Best cruise ever!

Reviewed By Ashley - Ft. Lauderdale, Florida | Traveled to Bahamas ~ Caribbean

Josephine was such a pleasure to work with. She was very knowledgeable and organized. She made my friends bachelorette cruise a very memorable experience. If there were ever any issues, Josephine was prompt in fixing it. We never had to worry about a thing. I highly recommend her!

I would recommend this agent to my family and friends

Josephine DiMaggio responded:
Thank you so much Ashley. I really appreciate it!

16 of 35 people found this review helpful

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Huge time saver!!

Reviewed By michelle - long island, ny | Traveled to

Josephine was great. We weren't sure where to go for a last minute getaway for 4 days once my parents took the kids for a long weekend. She helped us Plan a great cruise and took care of everything. Love that she dropped off a beach bag on my door with all the info. We booked another cruise with her less than a month from returning.

I would recommend this agent to my family and friends

31 of 66 people found this review helpful

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Amazing Family Getaway!

Reviewed By Jaymee - West Islip, NY | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean

We literally booked a trip three days prior to leaving and Josephine arranged everything!!!! With no time to research vacation spots, we put our trust in Josephine and she found us the perfect spot in Punta Cana to celebrate our daughters 16th birthday.

I would recommend this agent to my family and friends

Josephine DiMaggio responded:
It was my pleasure. Lets do it again soon!

12 of 30 people found this review helpful

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She made it so easy!!!

Reviewed By Krys - Sound beach, NY | Traveled to

I didn't have to do anything but give her my information and she found us the cheapest price and best bang for our buck! The price was great. The hotel she gave us was great it was everything we were looking for!

I would recommend this agent to my family and friends

24 of 56 people found this review helpful

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She made planning my trip so easy!!

Reviewed By Anna - New York | Traveled to

Josephine was extremely knowledgeable and helpful when we were planning our trip.. made going away a piece of cake..

I would recommend this agent to my family and friends

26 of 61 people found this review helpful

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My Travel Experience

Places I’ve personally traveled to or destinations I’ve booked for my clients.

Customer Testimonials

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.

Provided by 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!!!

Provided by 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!!!!

Provided by Nicholas S.