How to Convince Your Boss That a Company Cruise Is a Good Idea

Organizing a company cruise might seem like an ambitious ask. With tight budgets, busy schedules, and varying personal preferences to consider, convincing your boss can feel like an uphill battle. However, when presented with the right information and benefits, a company cruise can transform from an ambitious idea to the ultimate team-building experience.
Both of us (Marcella and Josh Kuchar) have enjoyed being on company cruises. We’re sure your adventure will be filled with just as many great stories as ours have been. This is why we created a guide to assist you in convincing your boss a company cruise is a great idea.
Why a Company Cruise Is Worth It
Before attempting to convince your boss, it’s helpful to understand why a company cruise is such an excellent idea. Here are three standout benefits of organizing one for your company.
1. It’s a Unique and Memorable Experience
A company cruise offers far more than the traditional office holiday party or weekend retreat. It offers the chance for co-workers to goof around with one another and connect outside of work. For some co-workers it’s also a way to enjoy a relaxing weekend and converse with co-workers over dinner. Believe us when we say it’s a setting that fosters memories your team will fondly recall for years.

To this day, my co-workers and I share memories from our cruise that took place over 2 years ago.
2. A Tax Write-Off Opportunity / Affordability
If your boss tends to worry about cost justification, point out that company events, including cruises, often qualify as tax-deductible expenses. Show how the cruise can be a financially smart choice alongside being an enjoyable outing. This win-win solution allows the company to plan something special while keeping the budget balanced.
Cruises are very affordable for companies! It typically only takes 8 rooms to unlock group rates (talk with one of our advisors for details on group rates and qualifications by brand).
3. A Chance to Engage Families
A company cruise can shift the focus from corporate to community. Many cruise packages are family-friendly, offering activities for kids and partners. This inclusion reinforces a wholesome culture that values employees’ loved ones, improving overall satisfaction and reinforcing loyalty.
Steps to Convince Your Boss
Now that you understand the benefits, it’s time to map out how to approach your boss. Their personality and priorities are key factors to account for, so tailor your strategy to suit their characteristics.
Step 1: Do Your Research
Before presenting the idea, gather all the relevant information. Research cruise options, pricing, travel dates, and packages. Many cruises offer discounts for group bookings, so include comparative pricing for 20, 50, and even 100 participants to show flexibility. Additionally, prepare data around employee engagement trends and how collaborative events improve morale, retention, and productivity rates.
Sounds like a lot of work? No problem, ask one of our advisors to help!

Step 2: Build a Persuasive Case
Structure your approach based on your boss’s personality traits. For example:
- If they’re data-driven: Share statistics and measurable benefits, such as “team-building activities contribute to a 22% increase in employee productivity.”
- If they’re frugal: Highlight cost reasons, like group pricing deals, and remind them of the tax-deductible opportunity.
- If they’re team-oriented: Focus on how the cruise fosters stronger collaboration, encourages creativity, and helps align teams around shared goals.
- If they’re open-minded: Stress the innovative nature of the idea, showing that it’s a modern and creative way to engage employees.
- If they’re family-focused: Discuss how the cruise doubles as a family-friendly event to honor both employees and their loved ones.
Step 3: Propose Ideas for Engagement
Introduce concepts for activities or mini-events during the cruise like team-building workshops, award ceremonies, or brainstorming sessions designed to align with the company’s goals. This shows how the cruise can be more than a “fun getaway” but also an enriching corporate experience. Also, emphasis that the team could schedule to have dinner at the same time every night, fostering comrodary.
Step 4: Prepare a Budget Estimate
When approaching your boss, clarity around costs is non-negotiable. Provide a detailed breakdown of expenses, including potential savings based on group discounts. Present how a larger turnout lowers the per-person cost, and explain why it’s a cost-effective alternative to traditional event venues. (Our advisors can assist you with this)
Step 5: Provide Logistics Options
Outline location options, cruise durations (e.g., 3-day vs. 7-day itineraries), and nearby port access to show how simple and convenient the planning process can be. For a busy boss, being prepared with logistics makes the proposal easier to approve.
Step 6: Anticipate Objections
Be prepared for questions or pushback. For example:
- Concern about costs? Reiterate tax write-offs and group discounts.
- Concern about timing? Focus on how cruises can be scheduled during quieter business periods.
- Concern about organizing? Offer to take ownership of coordinating the event or bring in a travel planner to manage the details.
- Concern for a lack in interest? Offer to run a company survey and gauge interest

Email Templates That Work
To make your case even stronger, use these email templates to pitch the idea effectively. As always, adjust the templates to fit your voice and writing style.
1. Subject: Team Cruise For Our Next Event?
Hi [Boss’s Name],
I hope this email finds you well! I’d like to propose an idea for our next team-building event—a company cruise. It’s a unique, cost-effective option that combines team bonding, and professional development..
I’m happy to coordinate the efforts with a local travel advisor. This way it minimizes your need to be involved and the advisor can ensure I don’t spend too much company time planning.
Would you be open to exploring this further? I’d be happy to compile additional details and share potential options.
Best regards,
[Your Name]
2. Subject: Holiday Cruise This Year?
Hi [Boss’s Name],
For the last few years we’ve gone the traditional route when it comes to our company holiday party. Have we considered doing a cruise?
I’m happy to coordinate the efforts with a local travel advisor. This way it minimizes your need to be involved and the advisor can ensure I don’t spend too much company time planning.
I know this will be super popular around the office, but i’m wiling to run a survey and see how many people would prefer a holiday cruise.
Thanks for considering,
[Your Name]
Talking Points to Use
When sharing your idea with your boss—whether in person, over email, or in a meeting—use these concise talking points to address key benefits and common objections:
- “We can enhance team collaboration and engagement with a unique and memorable experience.”
- “Group bookings significantly lower costs, making this not only fun but financially smart.”
- “Our employees will feel valued, especially with inclusive family-friendly activities.”
- “This is an innovative, modern strategy to keep morale high and retain top talent.”
- “It’s a tax-deductible event, balancing costs with benefits for the business.”
- “It’s easier to plan a holiday cruise than it is to plan a holiday party”
Common Objections and How to Address Them
Planning a corporate retreat or group travel can come with its fair share of concerns and objections. Below are some of the most common challenges organizations may face, along with professional responses to help overcome them:
- Objection: “It’s too expensive for our budget.”
Counter: Highlight the availability of group travel discounts and cost-sharing opportunities. Bring up that if the cruise prevents one person from leaving, it will be a positive ROI.
- Objection: “Our team is already too busy and can’t spare the time.”
Counter: Showcase the long-term productivity benefits of taking time off for team-building activities. Link to research articles or studies demonstrating the ROI of corporate retreats, such as higher employee engagement and improved collaboration. Time management tools and pre-planned schedules can also help minimize disruption to daily operations.
- Objection: “Not everyone will want to participate.”
Counter: Provide ideas for inclusive activities that cater to team members with varying interests and preferences. Engaging everyone in the planning process or offering optional attendance for certain events can make participation more appealing without imposing.
- Objection: “It’s too complicated to organize.”
Counter: Propose working with a travel advisor who specializes in coordinating company cruises. Their expertise can help find you the best deals, coordinate any pre and post travel accommodation needs. They can also assist travelers with upgrading their packages if desired, without it affecting the company’s budget.
- Objection: “The location may not suit everyone.”
Counter: Share survey tools to collect team preferences on destination and activities ahead of time. This approach ensures the location aligns with the majority’s preferences, fostering excitement and ownership over the event.
Proactively addressing these concerns can not only reduce hesitation but also build confidence in the value of corporate retreats. Transparency, strategic planning, and the right resources can turn objections into opportunities, setting the stage for a successful and well-received event.
Make the Cruise Happen
Securing approval for a company cruise doesn’t have to be daunting. By highlighting the unique benefits, presenting clear facts and numbers, and aligning the idea with your boss’s priorities, you’ll be better equipped to make a compelling case. Invest time in research, preparation, and communication, and your idea may soon set sail—literally.
Once you have the green light, talk with one of our advisors! We’ll make planning the cruise so easy, you’re boss will want to book another for next year.

The post How to Convince Your Boss That a Company Cruise Is a Good Idea appeared first on Best Adventure Spots Travel Advisors.
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