(33 Reviews)
100% Recommended

Jennifer Czerwinski

Oconomowoc, WI

Caribbean, All-Inclusive and Alaska Cruise Advisor

For 44 years I have built an extensive career in the dynamic world of travel planning. I have had the pleasure of curating memorable vacation experiences for countless clients, with a special focus on honeymoons and anniversaries. My intimate familiarity with destinations stems from my own travels—having journeyed through and stayed at various all-inclusive, adult-only resorts across the Caribbean and Mexico, including a majority of the Sandals and Secrets Resorts. Having walked down the aisle in Jamaica 28 years ago and experiencing multigenerational trips with my family fuels my passion for orchestrating dream getaways. In addition to tropical paradises, my expertise extends to the breath-taking tranquility of Alaska. Through both cruises and cruise tours, many of my clients have discovered the mesmerizing beauty of this glacier paradise, guided by my knowledge and experience. Connect with me at Travel Leaders and start your adventure today!

My Travel Specialties

Adult-Only All-Inclusive Resorts

Throughout my career I have stayed at and/or visited over 40 all-inclusive resorts. My favorites are adults-only brands such as Sandals, Breathless and Secrets. Two of my favorite properties are Secrets Akumal Riviera Maya in Mexico and Sandals Negril in Jamaica.

Secrets Akumal offers a memorable...
Read more from my Adult-Only All-Inclusive Resorts bio.

Sandals Negril 7-Mile Beach

Alaska Cruises

Across our company I’ve become the go-to travel advisor for Alaska Cruises. The cruise line I most often recommend is Princess Cruises because Princess has been doing Alaska for almost 50 years. For the land tours, they own the lodges guests stay in and the trains that take you to Denali. I am a Princess...
Read more from my Alaska Cruises bio.

Beautiful views all around

Tahiti and South Pacific

In 2012,  I was fortunate to go on a Paul Gauguin cruise in Tahiti. The Paul Gauguin is a unique small-ship experience known for the crew and their exceptional service. For example, after visiting one of the cocktail lounges the first night, every night after that the bartender remembered our drink...
Read more from my Tahiti and South Pacific bio.

My Favorite Bartenders, Francisco and Ernesto

Multi-Generational Groups

Whether you’re traveling with family, friends or a mixture of both I can help you have the best experience. I’ve created and expertly booked dozens of group trips for milestone celebrations, destination weddings and other occasions.

One memorable group was 22 people, going on a Cruise to Norway...
Read more from my Multi-Generational Groups bio.

The Caribbean is a great destination for groups

Caribbean, All-Inclusive and Alaska Cruise Advisor

For 44 years I have built an extensive career in the dynamic world of travel planning. I have had the pleasure of curating memorable vacation experiences for countless clients, with a special focus on honeymoons and anniversaries. My intimate familiarity with destinations stems from my own travels—having...
Read more from my Caribbean, All-Inclusive and Alaska Cruise Advisor bio.

Flowers from a Happy Client

My Travel Albums

Alaska Cruise
Our wonderful servers in the main dining room
Paul Gauguin Cruise in Tahiti
With the cruise director of the Paul Gaugin

Customer Testimonials

Excellent Service!

Jennifer is always very responsive and helpful when planning any trip. We have used Jennifer multiple times and often refer friends/family to her for their travel needs. She is very patient and responds quickly to any concerns and questions. Service is always given with a smile! Thanks, Jen!
Lisa J, Oconomowoc, WI

My Reviews

63 of 105 people found this review helpful
Very comfortable
Good experience working with Jennifer. Response was quick on all questions that I inquired about.
By  G  from  Watertown wi
Traveled to  Las Vegas ~ Nevada ~ USA
I would recommend this agent to my family and friends
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41 of 68 people found this review helpful
We loved the Secrets Resort!
Very informative
By  Karen  from  Oconomowoc, WI
Traveled to  Jamaica ~ Caribbean
I would recommend this agent to my family and friends
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42 of 71 people found this review helpful
Ideal location, beautiful resort!
Always has the answer!
By  WillyWallboard  from  Waukesha, WI
Traveled to  Costa Rica ~ Central America
I would recommend this agent to my family and friends
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37 of 62 people found this review helpful
Jennifer and Travel Leaders are Great!
I have worked with Jennifer for 3 Mexico vacations. She was so helpful the first time around we continued her service for our next two trips . We recruited another family to use her services as well. Jennifer is so easy to work with and very flexible. I may not be the best customer since I am so picky - but Jennifer worked with me and was so accommodating. I highly recommend her and Travel Leaders!
By  Holly  from  Oconomowoc, WI
Traveled to  Mexico
I would recommend this agent to my family and friends
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42 of 72 people found this review helpful
This was one of the best cruises we have done the
Jennifer has always bee a pleasure to work with when planing our trips & vacations. She is very knowledgeable & if she doesn't know an answer to a questions she will get that answer in a timely fashion.
By  Kati G.  from  Oconomowoc, WI
Traveled to  Caribbean Sea ~ At Sea ~ At Sea
I would recommend this agent to my family and friends
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Destination Expert:

  • Antigua & Barbuda
  • Jamaica
  • Alaska
  • Tahiti
  • Cancun
  • Bora Bora
  • Juneau
  • Dominican Republic
  • Moorea Island
  • Ketchikan
  • Mexico
  • Aruba
  • Papeete Tahiti
  • Skagway
  • St. Martin
  • French Polynesia
  • Riviera Maya
  • Hubbard Glacier

Travel Specialist:

  • Adult Only
  • Couples & Romance
  • Family Vacations
  • All Inclusive
  • Groups
  • Honeymoons
  • Luxury Cruises
  • Destination Weddings

Top Travel Partners:

  • Funjet Vacations
  • Inclusive Collection – World of Hyatt
  • Paul Gauguin
  • Princess Cruises®
  • Iberostar
  • Norwegian Cruise Line
  • Playa Resorts
  • Royal Caribbean
  • Holland America Line
  • Celebrity Cruises
  • Oceania Cruises
  • Riu Hotels

Certifications/Awards:

  • Certified Sandals Specialist
  • AMResorts Master Specialist
  • ALG Vacations Wavemaker
  • Oceania Cruises Specialist
  • Jamaica Travel Specialist

Industry Affiliations:

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