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GROUP TRAVEL PLANNING

Your group deserves a trip
they'll talk about forever

Group travel is one of my specialties. From pickleball retreats in the Caribbean to group cruises and girls' getaways, I handle every detail so your crew just shows up and has the time of their lives.

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Pickleball

ELITE AGENT - MAINSTREET TRAVEL

GROUP PLANNING CONSULTATION

RETREAT PLANNING

Upcoming group trips

Join one of my organized trips - or let me plan a custom one for your group

Pickleball Retreat - Jamaica

March 29 - April 4, 2027        Sandals South Cost

Following the success of our St. Lucia retreat, we're heading to Sandals South Coast in Jamaica for round two. Pristine beaches, state-of-the-art courts, gourmet dining, and a community of fellow pickleball lovers — all in one incredible package.

    World-class pickleball courts with breathtaking views

    Skill-building sessions and group play

    All-inclusive luxury: dining, drinks, and accommodations

    Water sports, snorkeling, and live entertainment

    Exclusive group discounts and added perks

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Jamaica

Sandals South Coast

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Alaska Cruise - Virgin Voyages

May 20 - 27, 2027        Seattle, Washington

We’re taking things to a whole new level… Alaska, but make it bold, elevated, and completely adults-only with Virgin Voyages.

This isn’t your typical cruise experience — think breathtaking glaciers, stunning coastal views, and that signature Virgin vibe that completely changes the game. If you haven’t sailed Virgin before, you truly don’t know what you’re missing.

    Adults-only experience — no kids, just pure vacation mode
    Exclusive group rates with 10% savings
    Complimentary onboard credit to use your way
    All dining included — elevated, world-class restaurants

    (no buffets here)
    Incredible entertainment, nightlife, and unique onboard experiences

 

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Alaska

Virgin Voyages

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Pickleball Retreat - Curaçao

October 22 - 28, 2027        Sandals Curaçao

The fun keeps going — our 3rd pickleball retreat is taking us to Curaçao. Crystal-clear waters, stunning island views, world-class courts, incredible dining, and a community of fellow pickleball lovers — all in one unforgettable experience.

    World-class pickleball courts with breathtaking views

    Skill-building sessions and group play

    All-inclusive luxury: dining, drinks, and accommodations

    Water sports, snorkeling, and live entertainment

    Exclusive group discounts and added perks

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Curaçao

Sandals Curaçao

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Why plan your group trip with me?

Group travel has a lot of moving parts — here's why having an expert matters

I negotiate group rates

Groups unlock perks that individuals can't get — room blocks, private receptions, complimentary upgrades, and pricing that gets better as more people join.

One person handles everything

No more group chats exploding with questions. I'm the single point of contact for bookings, payments, questions, and changes — for every person in your group.

I've done this before

My pickleball retreat in St. Lucia was a proven success. I know how to wrangle a group, manage logistics, and make sure everyone has an incredible time.

You get a better, more seamless experience

From the first conversation to the moment you get home, I’m guiding the process, anticipating issues before they happen, and making sure your group trip feels easy, organized, and actually enjoyable.

What kind of group trip can I plan?

If you can dream it, I can plan it

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Pickleball retreats

Sport + luxury + paradise.
My signature group experience.

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Group cruises

Cabin blocks, group excursions,
and private onboard events.

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Girl's getaways

All-inclusive resorts, spa days,
and pure relaxation.

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Family reunions

Bringing the whole family
together at a resort or on a cruise.

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Milestone celebrations

Birthdays, anniversaries,
retirements — let's celebrate big.

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Corporate retreats

Team-building travel your
colleagues will actually look forward to.

Ready to plan your group trip

Whether you want to join one of my upcoming retreats or plan something custom for your crew, let's start with a free conversation about what you have in mind.

Courtney's Crazy Amazing Adventures

Family vacation planning specialist.

Disney   Universal   All-inclusive   Cruises   Group Travel

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