Pickleball Vacations

All-inclusive Pickleball Vacations to the Caribbean at 5 Star Resorts

Pickleball in Paradise

Join our facebook group- https://www.facebook.com/groups/501515061364282

Do You Love Pickleball and Vacationing? 

Then you found the right place.

IF YOU DON’T SEE A DATE THAT FITS YOUR NEEDS OR WANTS BELOW, EMAIL – PICKLEBALL@STRAIGHTAWAYTRAVEL.COM TO BE ADDED TO OUR DISTRIBUTION LIST AND WE WILL BE UPDATED ON OUR TRIPS AND PROS ATTENDING.

Barb Strait, founder of Straight Away Travel has been a professional in travel for 11 years and has paired up with some of the best pickleball instructors around. This ultimate pickleball vacation includes instruction from some of the nation’s top pickleball players at the Caribbean’s best all-inclusive resorts. Pickleball in Paradise is a vacation adventure of a lifetime! Whether you are a beginner or a 4.5 player, your vacation will not only be relaxing and fun but also improve your game while playing lots of pickleball with current and new friends! We have 4 group dates for 2022 in Sandals South Coast Jamaica and are building group space at other locations as well.

Our groups are open to any level as we split the groups up for part of the session by skill level. We also work with pickleball clubs to build custom pickleball in paradise adventures exclusively for your group or club.

View the Highlights of a Pickleball and Paradise Trip

What’s Included in Your Pickleball Vacation Trip

Pickleball instruction and plenty of court time with a national pro

5 star global gourmet dining and top shelf drinks (ALL food and drinks are included)

Snorkeling adventures (scuba training optional)

5-star resort accommodations (upgraded concierge and butler suites are available) 

Private beach dinner with all participants

Welcome cocktail reception for all participants

Watersports (hobie cat sailing, waterskiing, paddleboarding, kayaking and more)

Optional yoga and fitness classes available

Best pickleball courts in the Caribbean. Play as much or as little as you want

Interested in a private pickleball trip instead? We can customize a trip for your family, friends, and pickleball group!

Always a Five-Star Experience

My wife Lynn and I had so much fun at Pickleball in Paradise last year that we are headed to Jamaica again this year! The pickleball and players were fun and we never went thirsty or hungry. Our private snorkel boat trip to Peter Tosh Reef was a highlight as was our group dinner on the beach. Lynn and I usually don’t do all inclusive because we enjoy cooking and look for deals. It was nice to travel light and to have all our food prepared and drinks made for us. We also could use the paddle boards and kayaks when we wanted.

Thanks for putting this together Barb,

~Pat and Lynn Patterson

Straight Away Travel made going to Sandals even more VIP than it already is. Our agent arranged to have our favorite wine and appetizer brought to our room as soon as we got there. She informed us off all the must visit restaurants and even made sure that we had lobster on the beach one day for lunch. As a free service, there is no question, we will always use her for our trips and have recommenced many others to her. Thank you!

Barb did an absolutely amazing job coordinating our Pickleball in Paradise vacation last year. It was everything we had hoped. She had tons of activities for us but no pressure to do anything. It was fantastic. The pickleball was great and we had lots of fun playing with the pro for sure.

~Carla Chavez

My husband & I are going back to Jamaica for our 2nd Pickleball in Paradise trip in September. Barb Strait takes care of everything! She makes vacationing so easy. We were able to relax knowing everything was taken care of. There are plenty of Pickleball drills & games. Plus, there was still time for all the other resort fun; swimming, snorkeling & eating fantastic chef inspired food. I highly recommend this experience to beginner players to the 5.0 player; there’s room for everyone

~Christina Scott

This was a fantastic experience. We enjoyed learning how to improve our pickleball game from Kyle Yates who was so fun and engaging. We made new friends and the resort was absolutely beautiful. Highly recommend.

~Natalie Macdonald

Upcoming Pickleball Trips

Trips are currently planned at the gorgeous Sandals’ resort in South Coast, Jamaica, Sandals Royal Bahamian Spa Resort and Offshore Island, and Beaches’ Turk and Caicos .  Dates and pros for each group are listed in the event calendar below.

Turks Pickleball Throwdown: A pickleball Tournament in Turks & Caicos

Turks Pickleball Throwdown: A pickleball Tournament in Turks & Caicos

$2100

Pickleball in Paradise presents the “Throw Down in Turks & Caicos" , a round robin, skill level Pickleball tournament.  Skill levels 3.0, 3.5, 4.0+.  Limited to 60 players by skill level 3.0, 3.5 & 4.0+.  Each bracket will be capped at 20 players, split into pods.   In the event that one bracket is not ... Read more

Find out more »
20 September 2023
Pickleball In Paradise in Turks and Caicos with Pros- Chris Powers, Sally Nowak, & Jenn Markling!

Pickleball In Paradise in Turks and Caicos with Pros- Chris Powers, Sally Nowak, & Jenn Markling!

$1970

Improve your game while enjoying Paradise... Play pickleball each morning with four-time National Gold Medal Champion, Chris Powers and master coaches, Sally Nowak and Jenn Markling, learning technique and proper form, and ultimately discovering what you truly need to work on! Individualized instruction at the Caribbean's finest resort, Beaches Turks and Caicos! Play with new ... Read more

Find out more »
29 September 2023
Island Jams in Jamaica- Pickleball Tournament in South Coast, Jamaica

Island Jams in Jamaica- Pickleball Tournament in South Coast, Jamaica

$2037.

Pickleball in Paradise presents "Island Jams in Jamaica", a round robin, skill level Pickleball tournament.  Skill levels 3.0, 3.5, 4.0+.  Limited to 60 players by skill level 3.0, 3.5 & 4.0+.  Each bracket will be capped at 20 players, split into pods.   In the event that one bracket is not full and another bracket ... Read more

Find out more »
05 October 2023
PRIVATE PICKLEBALL Event: Ignite Pickleball! Invitation only

PRIVATE PICKLEBALL Event: Ignite Pickleball! Invitation only

$1999

Join Us for a Pickleball Vacation at a 5 Star Resort with friends! Let's vacation on the white sandy beach of Jamaica! This is a private event carefully planned for Ignite Pickleball. You will arrive in Montego Bay, Jamaica on October 18th and be transported to Sandals, South Coast, Jamaica. From there, you will meet ... Read more

Find out more »
18 October 2023
Pickleball In Paradise with Kyle Yates and Jonny Pickleball in TUrks and Caicos!

Pickleball In Paradise with Kyle Yates and Jonny Pickleball in TUrks and Caicos!

$2100

Improve your game while enjoying Paradise... with Kyle Yates and Jonny Pickleball. Play pickleball each morning with four-time #1 World Champion Kyle Yates and master coach, Jonny Pickleball, learning technique and proper form, and ultimately discovering what you truly need to work on! Individualized instruction at the Caribbean's finest resort, Beaches Turks and Caicos! Play ... Read more

Find out more »
21 October 2023
Halloween Pickleball in Paradise, Sandals South Coast, Jamaica with Scott Golden

Halloween Pickleball in Paradise, Sandals South Coast, Jamaica with Scott Golden

$2800

Pickleball Pro- Scott Golden and TBA Come improve your pickleball game while enjoying paradise. Straight Away Travel's Pickleball in Paradise Vacations is creating a festive adventure in South Coast, Jamaica. Instead of trick or treat, it will be Dink and Eat with some new players from the US and Canada. You will be spending a ... Read more

Find out more »
28 October 2023
November Pickleball in Paradise: Sandals Royal Bahamian Spa Resort and Offshore Island, Nassua , Bahamas

November Pickleball in Paradise: Sandals Royal Bahamian Spa Resort and Offshore Island, Nassua , Bahamas

$1900

Pickleball Pros- Bob and Elizabeth Higginbottom Come improve your pickleball game while enjoying paradise. Straight Away Travel's Pickleball in Paradise Vacations has created the ultimate pickleball adventure in the Bahamas. As the weather starts to cool in the US, you will be enjoying the Caribbean sunshine! On this trip, you will vacation at the recently ... Read more

Find out more »
02 November 2023
Battle In The Bahamas: Sandals Royal Bahamian Spa Resort and Offshore Island, Nassua , Bahamas

Battle In The Bahamas: Sandals Royal Bahamian Spa Resort and Offshore Island, Nassua , Bahamas

$1900

Pickleball Tournament Coordinators - Bob and Elizabeth Higginbottom Come level up your pickleball game while enjoying paradise. Pickleball in Paradise presents “Battle in the Bahamas”, a round robin, skill level Pickleball tournament.  Skill levels 3.0, 3.5, 4.0+.  Limited to 24 players by skill level 3.0, 3.5 & 4.0+.  Each bracket will be capped at 8 ... Read more

Find out more »
06 November 2023
Pickleball in Paradise: Sandals Royal Bahamian Spa Resort and Offshore Island, Nassua , Bahamas

Pickleball in Paradise: Sandals Royal Bahamian Spa Resort and Offshore Island, Nassua , Bahamas

$1900

Pickleball Pros- Leesa and John Walker Come level up your pickleball game while enjoying paradise. Straight Away Travel's Pickleball in Paradise Vacations has created the ultimate pickleball adventure in the Bahamas. As the weather starts to cool in the US, you will be enjoying the Caribbean sunshine! On this trip, you will vacation at the ... Read more

Find out more »
10 November 2023
We Be Jammin In Jamaica, Sandals South Coast, Jamaica

We Be Jammin In Jamaica, Sandals South Coast, Jamaica

$2800.

Private Pickleball Trip- Invitation Only Come level up your pickleball game while enjoying paradise. Straight Away Travel's Pickleball in Paradise Vacations is creating a festive adventure in South Coast, Jamaica. You will be spending 7 nights with players from across the U.S. and Canada at Sandals South Coast, a luxury resort with 12 pickleball courts. ... Read more

Find out more »
12 November 2023
pickleball project, Sandals South Coast, Jamaica

pickleball project, Sandals South Coast, Jamaica

$1900.

Private Pickleball Trip- Invitation Only Come level up your pickleball game while enjoying paradise. Pickleball Project is traveling to Sandals, South Coast, Jamaica to play Pickleball in Paradise. We will be spending 5 nights with players invited by Pickleball Project. Each morning, we will play round robin tournaments and open play. The courts are lined ... Read more

Find out more »
14 November 2023
Pickleball In Paradise at Beaches Turks and Caicos

Pickleball In Paradise at Beaches Turks and Caicos

$2950

With Pickleball Pros- Marhelen Atkins and Bob Higginbottom Improve your game while enjoying Paradise... on one of the world's most beautiful beaches, Grace Bay in Turks and Caicos Play pickleball each morning with national Pickleball Pros learning technique and proper form, and ultimately discovering what you truly need to work on! Straight Away Travel's inaugural ... Read more

Find out more »
09 December 2023
December Pickleball in Paradise, Sandals South Coast, Jamaica

December Pickleball in Paradise, Sandals South Coast, Jamaica

$2080.00

Pickleball Pros- Wes Gabrielsen and Andy Gensch Come level up your pickleball game while enjoying paradise. Straight Away Travel's Pickleball in Paradise Vacations is creating a festive adventure in South Coast, Jamaica. You will be spending 5 nights with players from across the U.S. and Canada at Sandals South Coast, a luxury resort with 12 ... Read more

Find out more »
12 December 2023

Frequently Asked Questions

Pickleball is the fastest growing sport in the USA.  It is the fastest growing sport not only because it is so much fun to play and keeps you active, but people of all athletic abilities and ages can play.  Pickleball is a racket/paddle sport that was created by combining elements of several other racket sports. Most people describe pickleball as a combination of ping pong and tennis.  

Everything is included except airfare.  

  • Transportation from the airport to the resort,
  • A “welcome” to the resort from a staff member who will take care of your luggage, hand you a cooling spa towel for your neck, and check you in, 
  • 5 star resort accommodations,
  • A private cocktail reception with the pickleball pros and players,
  • Pickleball clinics every morning and the option to play in the evenings as you have access to 12 courts for the duration of your stay,
  • All food and beverages (you will not have to pay for any additional food or drinks the entire stay!),
  • All water-sports (snorkeling, kayaks, waterskiing, windsurfing, sailboats, tubing, paddle boards, glass bottom boats, wakeboarding, kneeboarding),
  • A private beach dinner with the pickeball pros and players,
  • Transportation back to the airport. 

You will never need your wallet.

Yes, in addition to the water-sports, there are also lots of land sports included – ping pong, shuffleboard, lawn chess, croquet, basketball, beach volleyball, tennis, board games, bocce ball.

Our 2022 groups will all be going to the gorgeous Sandals South Coast in Jamaica.  

No, that is the only additional cost to the trip.  

No, we include that with your Pickleball in Paradise package

Not this one, sorry, we must be 18 to be at the resort. Enjoy your adult time away from the kids.

Each trip has either a national pickleball pro or a certified pickleball instructor. You are sure to leave with new skills and be a better player.  

Yes, we welcome all levels of players and you will be paired and instructed based on your level of play.  

You can travel alone but you will have to pay for a double occupancy room so it is better to bring a friend even if they don’t play.  We have many players that bring a spouse or a friend that doesn’t play as they can relax on the beach, use the water-sports, or sleep in while you are on the courts.  

Yes, bring them for sure! We have many players that bring a spouse or a friend that doesn’t play as they can relax on the beach, use the water-sports, or sleep in while you are on the courts.  

Join our newsletter and receive the latest promotions and best tips to save $$ on your vacation!

Newsletter Signup