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Make Memories with a Custom Trip

Do you have a bucket list destination?  Are you celebrating a big milestone? Or, maybe you want to see you favorite band in a very special location like clients who saw U2 in Ireland?  We can help you curate that special, one of a kind trip, whether that's yoga on the beach of Costa Rica or exploring the Colosseum in Italy. These are the trips we will customize to be the vacation you're dreaming of.

When planning a custom trip, the details matter most. We want to make your dreams reality.  We do this by getting to know you and using our expertise and resources to curate your unique experience. 

Your trip can be a land-based, a independent or guided tour, a specialty cruise like  transatlantic or river, or a custom combination based on you! You may already know we're experts with cruise vacations and all-inclusive packages and Cruisin' with the Drennans are also experts in creating one-of-a-kind getaways.

Creating Your Customized Trip

When creating a customized itinerary, we start with the most influential components of your trip. We know that things like the guest(s) you are traveling with, desired bucket-list activities, and important celebrations, can play a huge role in your plans. Some of these components we consider might include...

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Travel Ideas





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Special Occasions

There are a million reasons to travel, and Cruisin' with the Drennans is here to support them all! You bring the dreams and the celebrations and we'll do the rest. Here are some of the most popular reasons our clients plan custom trips.


Birthdays & Anniversaries

Craft a celebration in paradise your loved one(s) will remember forever. With special touches like day-of wakeup calls, celebratory champagne waiting for you upon arrival, and arranged specialty dining, your celebration can be treated with the special attention to detail it deserves. Bring along friends and family or keep the celebration private with your special someone. Consider customizing your trip in paradise with privately-held events, spa days, or premium spirits to celebrate in a luxurious way. It's your day to celebrate; have your trip your way.

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Destination Ideas

After we learn the why as well as the hopes and dreams behind your trip, we get to dive into our destination options. Each destination offers a variety package options, as well as individual customizations. A few examples are...

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Costa Rica

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Machu Pichu


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Package Options

  • Flights

  • Transfers

  • Car rental

  • Hotel/resort stay

  • Cruise accommodations 

  • Accommodations  

  • Tours, tickets, and parks

Ways to Customize 

  • Flight Upgrades

  • Private Transfers

  • Private tours 

  • Destination Excursions  

  • Celebrations

  • Spa Packages

  • Private events

The true benefit of having Cruisin with the Drennans as your preferred agency is having seasoned travel experts to advocate for you. We assist you from the time you start thinking about your next trip until you arrive home as a happy traveler. Our services include...

  • Advice and guidance on booking the best travel package for you

  • A direct point of contact to ask travel related questions 

  • Cross referencing vacation options between travel partners to find the best rates and values

  • Managing reservations and trip details 

  • Communicating important travel information and updates 

  • Standby service while you travel in case of emergencies 

Vacation Partners

Book Your Next Trip with Us

What's on your bucket list? Are you celebrating a special birthday, anniversary or event? Do you want to do the next family reunion someplace unique?  Schedule a quick call with us to start the conversation.  The possibilities are endless and we can help you find the right destination for you!

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