Private Pickleball Trips

We design the perfect blend of sport and relaxation for family, friends, and pickleball groups.

Enjoy Pickleball, a Gorgeous Setting, and Our Meticulous Planning

Indulge in the ultimate pickleball getaway with our private trips created for your group only. Take your loved ones, friends, or pickleball squad to the breathtaking Caribbean and experience a fusion of sports and travel like never before. With our bespoke itineraries tailored to your every whim, you get complete control of your vacation with no stress of planning.

We take care of everything from court reservations to room bookings so that you can sit back and enjoy a stress-free all-inclusive trip with all the VIP perks. Our team is committed to making your dream pickleball trip a reality – so what are you waiting for? Plan your exclusive pickleball retreat today!

Stress-free pickleball trip planning with our no-cost concierge travel agent service

Luxury all-inclusive Caribbean resorts or cruise ships

Complementary room for the trip leader or resort credit for the entire group

Daily and nightly resort activities that let you relax and experience the vacation of a lifetime!

Planning a Group Pickleball Trip with Pickleball in Paradise is EASY!


We find you the perfect destination to fit your group size and budget.


We work with the resort to get you the best group rate with usage of court space and other additional spaces needed


We build your groups a landing page where your group can see their room/package options and where they will submit their deposit (if everyone is paying separately)


We offer travelers travel insurance and collect their flight information


We build your group itinerary on our Travel App including everyone’s flights and transfers


We are here for questions and changes along the way and have you prepared with everything you need


We connect you with the resort so you have a contact person on site (unless one of our travel professionals is traveling with you.)

What’s Included in Your Private Pickleball Trip

All-Inclusive Experience

With our all-inclusive packages, everything is included except airfare.  All pickleball, all meals, all drinks, water sports, land sports, nightly entertainment,  transfers to and from the airport, all taxes, everything!

Pickleball Your Way

We can book a pickleball pro for your trip or you can have use of the facility solely for your group for your own round-robin tournament. You will have a perfect private pickleball trip just for your group!

Private Events

A private trip means private events only for your group! We will help you book a private beach dinner, a cocktail party, or any excursions at the all-inclusive resort so that you can have the ultimate private vacation experience!

Special Touches

We can personalize your trip with welcome gifts, custom shirts, beach bags, and exciting excursions. Share your wishlist and we’ll make it happen! Private banquet rooms are also available for meetings or celebrations.

Upcoming Private Pickleball Trips

Private Pickleball Trip Destinations

Experience an unforgettable trip to Paradise planned exclusively for your group. Our partnership with the top all-inclusive resorts in the Caribbean ensures that you’ll have access to fun in the sun, relaxation by the beach, and exceptional dining and entertainment options. We can also help you book a private pickleball trip on a cruise ship. Let us bring your dream pickleball vacation to life!



Turks and Caicos

Cruises (Caribbean, Alaska, Mediterranean)

Sandals All-Inclusive Resort in the Bahamas
Beaches Resort Turks and Caicos

Private Pickleball Trips FAQ

How much extra does it cost to create a private pickleball group?

Nothing, we add zero fees unless you would like to add in money for tee shirts, awards, or a group excursion.  The cost you see online is higher than the cost you will pay as we will get you a group rate and possibly complimentary rooms.

How will I give information about the trip to my group?

You will have a private website created for your group with all of the information they need to know.  You just have to send the invitation to your group event and we handle the rest! 

Will we have a pickleball instructor on the group trip?

This is up to you, we can add in money to send a pro with you or you can just have use of the facility solely for your group for your own round robin tournament.  

Are there perks for creating a private group?

YES- depending on the time of year, you will receive a 6th or 12th complimentary room.  This means for every 6 rooms you have, you receive the value of that 6th room (based on the lowest room rate booked) or for every 12 rooms you have, you receive the value of that 12th room (based on the lowest room rate booked).  You can use these free rooms as

* Free rooms for guests or to bring a pro
* Money for airfare for guests
* Upgrades, excursions, prize money/awards
* Money to keep or donate to your pickleball group
* Money towards a DJ, band, or entertainment at your event

Can we have a private party at the resort or on the cruise ship?

Yes, depending on the number of guests.  For our all-inclusive resorts, you will need a minimum of 10 rooms to have a private cocktail party and private beach dinner.  For a cruise, you will need 25 rooms, but we have some great ideas to work around that big 25 number!

What if we need to cancel?

We certainly hope you don’t, but if you do, you will be refunded 100% of your deposit up until 90 days before your trip.  We do add on a fee for the time we spend building your website.  If you decide to reschedule your event, the fee will be waived as we can change your private website with the new dates. 

What if there is a hurricane?

We always recommend travel insurance and offer different policies that are affordable and reputable.  We do all of the work for you to find you the best option. 

What is included in the cost of the event for my guests?

With our all-inclusive packages, everything is included except airfare.  All pickleball, all meals, all drinks, water sports, land sports, nightly entertainment,  transfers to and from the airport, all taxes, everything!

Get a Quote for Your Private Pickleball Trip

Private Event Questionnaire
Your preferred method of communication
The purpose of your trip

Your Trip Details

Do you have a location in mind for your event?
Do you know the exact dates or are your dates flexible?
Will you be paying for everyone attending or do you need pricing and availability listed in your event for payment from others?