About Cruise Holidays of Oakville

We opened our doors in downtown Oakville as Cruise Holidays Oakville in September of 1996 and have been successfully helping our clients plan memorable cruise and land vacations since. Founded in 1984, Cruise Holidays is North America’s oldest and largest cruise-specialty retail franchise with locations throughout the United States and Canada. As our names suggests, we specialize in cruise travel, providing unparalleled expertise in matching clients with the cruise ships and destinations that are right for them.

Although Cruise Holidays of Oakville focuses specifically on cruise travel, our service doesn’t stop there. Cruise Holidays of Oakville can also provide travelers with pre- and post-cruise travel arrangements and options like hotel packages, shore excursions and tours – all at competitive prices.

Cruise Holidays of Oakville and My Luxury Cruises are members of Cruise Lines International Association and The Travel Industry Council of Ontario and all of our cruise specialists are TICO Certified.

Awards & Accolades

President’s Circle 2010, 2011, 2013, 2014, 2015, 2016, 2017, 2018
Certified Luxury Cruise Specialists
Top Producer, Cruise Holidays Canada – Oceania Cruises
Top Producer, Avalon Waterways

Meet Our Cruise Specialists

Lola Vassilliadis MCC

Lola Vassiliadis, MCC
Owner/Manager

Aside from being a mother and grandmother to three I have been blessed with a career that has afforded me hours of joy and wonderful memories.

I entered the world of cruise travel in December of 1992 after graduating with honours from the Mississauga School of Travel and Tourism. For the next five years I was with The Cruise Professionals. After leaving The Cruise Professionals an opportunity presented itself that turned out to be one of the best decisions I have made during my working career. And that was to join the Cruise Holidays family.

We opened our doors in downtown Oakville in September of 1996 and proudly hung our Cruise Holidays sign. I started with myself and one employee and we have steadily grown over the years to a team of seventeen.

Contact Lola
905-337-2228
MY REVIEWS

Travel Specialties:

  • Cruises
  • River Cruises
  • Luxury Cruises
  • World Cruises
  • Small Ship Cruising
  • Long Voyages
  • All Inclusive Resorts
  • Disney Vacations
  • Luxury Travel

Destination | Supplier Expertise:

  • Australia / New Zealand
  • Middle East
  • Caribbean
  • Alaska
  • Iceland
  • Celebrity Cruises
  • Royal Caribbean International
  • Regent Seven Seas
  • Seabourn
  • AmaWaterways
  • Viking Cruises
Contact Lola
905-337-2228
MY REVIEWS
Rosemary Bartello

Rosemary Bartello
Cruise Specialist

Travel has always been a love of mine. From the time I graduated from university and spent six weeks in Europe I knew that I wanted to be a travel agent or a flight attendant. However I took a detour for a number of years and worked in our family business before starting on my “travel” career in 1997.

I’ve been told that I’m a natural at helping my clients plan their cruise and land vacations. My excitement coupled with extensive knowledge of various cruise lines and ships, as well as a multitude of worldwide destinations keep my clients coming back time and again. I am privileged to say that I have been helping many of my clients for more than twenty years.

Contact Rosemary
905-337-1540
MY REVIEWS

Travel Specialties:

  • Women’s Travel
  • Golf
  • Cruises
  • River cruises
  • Luxury Cruises
  • World Cruises
  • Italy
  • Alaska
  • Caribbean
  • Mediterranean
  • Europe
  • Canada

Destination | Supplier Expertise:

  • Oceania
  • Regent Seven Seas
  • Uniworld
  • Avalon Waterways
  • Royal Caribbean
  • Paul Gauguin
  • Crystal Cruises
  • Seabourn
  • Princess
  • Celebrity
  • Holland America
Contact Rosemary
905-337-1540
MY REVIEWS
Anne Marie Hanlon

Anne Marie Hanlon
Cruise Specialist

You can’t be everything to everyone! But you can be the best at what you do! These are statements I take to heart and do my best to live up to. That is why I chose to specialize in cruise vacations. Being able to focus on cruising allows me to give my clients superior service with years of knowledge on all things cruising – both ocean and river cruising.

Needless to say I love travelling and cruising in particular. And I enjoy being able to create the type of memorable experiences that I have had, for my clients. No request is too large or detail too small. Whether you need help in booking just a cruise or a cruise and customized land/air arrangements – I’m your girl.

I have seven years of experience helping clients with their cruise vacations – family cruises, honeymoon cruises, winter getaways and cruises to new and exciting destinations on your bucket list. Let’s talk and plan the perfect cruise for your next vacation.

Contact Anne Marie
905-337-2228
MY REVIEWS

Travel Specialties:

  • Long Voyages
  • World Cruises
  • Luxury Cruises
  • Small Ship Cruising
  • Cruises
  • River Cruises

Destination | Supplier Expertise:

  • Alaska
  • Bermuda
  • Caribbean
  • Europe
  • Scandinavia
  • USA
  • Oceania
  • Regent Seven Seas
  • Avalon Waterways
  • Azamara Club Cruises
  • Celebrity Cruise Lines
  • Riviera Maya/ Cancun Travel Specialist
  • Viking River Cruises
Contact Anne Marie
905-337-2228
MY REVIEWS
Karen Plante

Karen Plante
Cruise Specialist

My cruise travels and tours have taken me to many places near and far giving me fresh insights in to destinations for your vacation. From being transported back to medieval times in the south of France, to savoring the views from the top of Gibraltar or wandered past castles along the beautiful rivers of the Rhine Valley, I can help create your dream vacation.

In my younger years, I loved doing everything on my own, taking self-guided tours and discovering local restaurants without a guide. Now I’ve come to realize there is also great peace of mind to be found in planning ahead and having someone ready to transfer me from place to place, a highly recommended tour or guide to show me around and then a waiting comfy bed on the ship to return to each night.

Having experienced both sides of travel, I am able to help create a trip that suits your personality. No matter which cruise line you’re considering I have probably traveled on it and received additional certifications to know exactly which one will have the port calls, dining, atmosphere and entertainment that best suit you.

Contact Karen
905-734-8521
MY REVIEWS

Travel Specialties:

  • Family Vacations
  • Groups
  • Cruises
  • River cruises
  • Luxury Cruises
  • World Cruises

Destination | Supplier Expertise:

  • Caribbean
  • Mexico
  • Europe
  • Mediterranean
  • British isles
  • Costa Rica
  • Uniworld
  • Amawaterways
  • Princess Cruises
  • Paul Gauguin Cruises
  • Celebrity Cruises
  • Norwegian Cruises
  • Fairmont Hotels
  • Starwood Hotels & Resorts;
  • Sandals
  • Club Med
  • Bermuda Specialist
Contact Karen
905-734-8521
MY REVIEWS
Jenny Richardson

Jenny Richardson
Africa Specialist

I have been in the travel business for over 20 years and have intimate knowledge of all areas of Southern and Eastern Africa having lived in the area and travelled extensively within South Africa, Namibia, Botswana, Uganda, Kenya and Tanzania. I have also spent some time travelling around Australia and can give you insights into ‘must sees’ on both continents.

My tours include experiences out of the normal busy tourist areas and into the heart of the African and Australian bush with a high level of comfort and security for my clients. I personally work with you to ensure that you get the trip you are dreaming of. Nothing cookie cutter! Whatever you can think up or have on your wish list can be done.

Contact Jenny
705-794-7632
MY REVIEWS

Travel Specialties:

  • Cruises
  • Safaris
  • Animals & Wildlife
  • Escorted Tours
  • Adventure Travel

Destination | Supplier Expertise:

  • Australia
  • Africa
  • South Africa
  • Botswana
  • Tanzania
  • Great Barrier Reef
Contact Jenny
705-794-7632
MY REVIEWS
Lola Vassilliadis MCC

Carol and Barry Tarling
Leisure Travel Specialists

Cruising is their first is our love, having sailed on a number of cruise lines to the Mediterranean, South America, Alaska, the Fjords of Norway, Panama Canal, Eastern, Western, & Southern Caribbean.

We also have developed a significant Religious Tour Business. We have escorted their forth group to Israel As well as groups to Greece and Turkey following in the Steps of Saint Paul.

Escorted Groups are a speciality for us. Our most recent wedding group was to the fabulous Riu property in Cabos San Lucas, Mexico. In 2011, we had the privilege of escorting a Horticultural Group to Alaska, visiting the gorgeous Gardens of Alaska and Victoria.

We have also worked with fundraising groups – most notably the Shriners and Royal Victoria Hospital as well as organizing and participating in four ballroom cruises. In 2013 we escorted a small group to Zimbabwe, specifically Victoria Falls, Botswana Chobe National Park Africa and experienced the most amazing events, riding elephants, and the highlight walking with lions a true bucket list adventure.

We are passionate about customer service and it is our desire to exceed your valued customer expectations!

Contact Barry & Carol
705-321-0496
MY REVIEWS

Travel Specialties:

  • Cruises
  • Group Cruises
  • Escorted Groups
  • Fundraising Groups
  • Faith Travel
  • All Inclusive Resorts

Destination | Supplier Expertise:

  • Alaska
  • Middle East
  • Caribbean
  • Africa
  • Celebrity Cruises
  • Royal Caribbean International
  • Cunard
Contact Barry & Carol
705-321-0496
MY REVIEWS