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Best pickleball vacations - top 6 compared

picture of Brandon Mackie
Brandon Mackie

Published on: Jul 1, 2024

Pickleheads co-founders Brandon Mackie, Max Ade, and Ian Langworth with other pickleball players

Ever thought about going on a getaway that includes lots of time on the courts? On a pickleball tour, you get to play the game you love, improve your skills, and meet fellow pickleheads all while seeing a new part of the world.

Below you'll find my list of the best pickleball vacations with a diverse range of choices to suit your interests. Whether you're interested in a cruise, want to travel through Europe, or have a pickleball staycation in the US, there's something here for you.

Best pickleball vacations at a glance

Best overall

Pickleball Getaways logo

1. Pickleball Getaways

Pickleball Getaways was founded by pro players Ben Johns and Dekel Bar. These pickleball-heavy trips are immensely popular and feature guest pro clinics.

Read my deep dive

Best budget

Dink Destinations logo

2. Dink Destinations

Dink Destinations is run by experienced travel planners who just happen to be big pickleball players. They've created fun-filled group trips at great prices.

Best cruises

Pickleball At Sea Group Cruise logo

3. Pickleball At Sea Group Cruise

Play pickleball at sea and ashore on 5-day and 8-day cruises through the Caribbean. These trips are really well priced for such rewarding experiences.

Best in Europe

Evyssa Vacations logo

4. Evyssa Vacations

Evyssa Vacations boasts a diverse range of European trips. Cruise down the Danube River in Central Europe or play pickleball in places like Greece and Iceland.

Best in the Caribbean

Pickleball In Paradise logo

5. Pickleball In Paradise Caribbean Resorts

Pickleball in Paradise honors its name, providing players with all-inclusive pickleball vacations in luxury Caribbean resorts.

Best custom

Shoreline Destinations logo

6. Shoreline Destinations

Shoreline Destinations brings their expertise to personalized vacations to the pickleball world. They'll work with you to create your dream getaway.

The best pickleball vacations in 2024

With pickleball still booming in popularity, more and more vacation companies are now offering pickleball-focused trips. Pickleball Getaways, one of the longest-running pickleball trip specialists, saw off the competition this year. Read on for my full list.

Best overall

1. Pickleball Getaways

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Frequent getaways to beautiful locations for training days with pro coaches.

Book if:

  • You want to improve your game:

    these getaways have a strong focus on training, with daily clinics from top coaches to help you work on your game.

  • You want to learn from the pros:

    guest pros help out on these tours, so you'll have a chance to be coached by the likes of Collin Johns.

  • You want an international trip in a beautiful location:

    the Mayan Riviera, Antigua, and Costa Rica are all lined up this year.

Pass if:

  • You're looking for a pickleball cruise:

    Pickleball Getaways doesn't offer cruises, so check out Pickleball At Sea on this list.

  • You'd prefer a US trip:

    Dink Destinations has great affordable pickleball trips in the United States.

  • You want a customized trip:

    Shoreline Destinations allows you to personalize your vacation for the type of getaway you want.

Pickleball Getaways

Pickleball Getaways

Countries Regions Offered

Europe, Caribbean (including Mexico), South America

Domestic Or International

International

Vacations Per Year

Around 10

Average Pricing

$3,300

Average Duration

7-10 days

If you want to know my #1 recommendation for pickleball vacations, Pickleball Getaways is it. They're one of the longest-running dedicated pickleball vacation companies, set up by none other than the GOAT Ben Johns and top-ranking pro Dekel Bar.
Their trips take you to some of the best vacation spots on the planet, with well-planned itineraries including sightseeing excursions and daily pickleball clinics. These focus on helping you improve your game.
Aside from the destinations themselves, one of the biggest draws is the guest pros. In the past, participants have been lucky enough to be coached by players like Collin Johns as they train in the sunny Caribbean or Mediterranean.

Destinations

According to Pickleball Getaways, their fan-favorite destination is the Mayan Riviera near Cancun. They organize multiple trips a year to this beautiful strip of Mexico's Caribbean coast.
This year, they will also be going to Antigua and Costa Rica. Past trips have included Ecuador, the Dominican Republic, Portugal, Spain, Croatia, and Slovenia.

Pricing

The cost of a 7-day trip is around $3,300 for single occupancy, paid in two installments. There are discounted rates for groups and guests (you can bring a friend or partner who won't be playing pickleball). For example, on their Costa Rica trip this October, triple occupancy costs $7,995, which works out at $2,665 per person.
Prices vary depending on the vacation, though usually not by much. So, be sure to look through their upcoming trips to see individual pricing.

Reviews

People who've gone on these tours have praised the planning, the destinations, and the high level of instruction and accessibility of the pro coaches, who even go on excursions with the group. Many reviewers said they would book another trip.

Read more reviews of Pickleball Getaways

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My verdict
If you want to learn from expert coaches, all while soaking up the sights in some of the prettiest places on Earth, this is my recommendation to you. Founded in 2019 by Ben Johns and Dekel Bar, Pickleball Getaways is a well-run institution at this stage.

Today’s best deal

Pickleball Getaways logo
Best budget

2. Dink Destinations

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Well-priced, fun, and instructive group trips in the US for pickleball players.

Book if:

  • You're on a budget:

    some of these trips are half the price of others on this list.

  • You want to stay local:

    if a staycation is your thing, Dink Destinations has you covered with trips across the US.

  • You want to learn from a pro coach:

    you'll hit the courts with a pro instructor who'll help you hone your skills.

Pass if:

  • You're looking for an international trip:

    all the other companies in my top 6 offer tours outside the US.

  • You want to go on a pickleball cruise:

    check out the Pickleball At Sea Group Cruises on my list.

  • You want a personalized vacation:

    Shoreline Destinations offers a tailored pickleball experience with your own dedicated travel agent.

Countries Regions Offered

Midwest & Florida (at the time of writing)

Domestic Or International

Domestic

Vacations Per Year

2

Average Pricing

$1,499

Average Duration

4 days

Dink Destinations is my recommendation to anyone looking for an affordable group trip that won't break the bank. You'll get to know 20 or more fellow pickleheads while training with top pros like James Ignatowich.
When not on the courts, you'll take part in planned excursions like museum trips, city tours, and sunset cruises. The organizers know the top local dining-out spots too, so expect some great culinary experiences and happy hours—all included in the price.

Destinations

The next trips lined up for Dink Destinations are Grand Rapids, Michigan and St. Augustine Beach, Florida. Whichever trip you book, you'll be coached on private courts.

Pricing

With prices starting at $1,499, these vacations offer a big saving compared to most other pickleball getaways. As with all of the tours on this list, the cost varies depending on the trip itself and your requirements. If you want more information about pricing, contact Dink Destinations.

Reviews

With some of their upcoming trips already sold out, it's fair to say Dink Destinations is a hit with traveling pickleball players. People like the quality of pickleball training, getting to practice with pros and pickleball ball machines.
Some players commented on the communal aspect of the trips and the range of levels. The skill rating levels go from beginners and up, with everyone making improvements in their game.
These vacations are also praised for being really well run by the organizers. They always include plenty of excursions and all-inclusive restaurant trips.
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My verdict
If you want to meet other pickleball players and drill with top coaches without breaking the bank, Dink Destinations is my top choice for you. These trips are run by some friendly pickleball enthusiasts who know how to plan trips for large groups that encourage camaraderie.

Today’s best deal

Best cruise

3. Pickleball At Sea Group Cruise

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Well-priced Caribbean cruises with a strong pickleball focus.

Book if:

  • You want to play pickleball while you cruise:

    daily play onboard in your own private group training room and also onshore, with instruction from a certified pro.

  • You want to do plenty of sightseeing:

    these cruises are ideal for those who want to blend practice time with travel.

  • You want affordable options:

    these cruises are surprisingly affordable, starting at around $1,500 for a solo traveler.

Pass if:

  • You want to go to Europe:

    check out Evyssa Vacations, with trips planned to places like Greece and Central Europe.

  • You want to stay at a Caribbean resort:

    Pickleball in Paradise partners with some of the best resorts in the Caribbean.

  • You can't easily travel to Texas or Florida:

    these cruises embark from Galveston, TX and Fort Lauderdale, FL, so make sure you can get there.

Pickleball At Sea Group Cruise

Pickleball At Sea Group Cruise

Countries Regions Offered

Caribbean (including Central America)

Domestic Or International

International

Vacations Per Year

5+

Average Pricing

$1,500-2,500

Average Duration

5-8 days

Pickleball At Sea is my top choice for anyone wanting to sail on a Royal Caribbean cruise ship while playing pickleball every day. You'll play both on a private onboard court and ashore, with a certified pro as your coach.
You'll also get plenty of opportunities to socialize with your tour companions on daily excursions and meet-ups.
There's plenty more to keep you occupied off the courts too. Amenities include surf simulators, zip lining, rock climbing, Vitality Spa, movie theaters, and dozens of bars and restaurants.

Destinations

The 5-day cruises head to the Bahamas, while the 8-day cruises stop in Roatan, Honduras, and Costa Maya and Cozumel in Mexico. Both offer an exclusive local pickleball experience ashore.
The 5-day cruises leave from Fort Lauderdale, Florida and the 8-day trips embark from Galveston, Texas. So, you'll need to make your own way there first.

Pricing

I was surprised at the affordability of these cruises. The 5-day trips start at $1,436 and the 8-day ones start at $2,534 per person. You can also bring along a friend or partner who doesn't play pickleball. Plus, there are discounts for groups of more than five.
The pricing includes all of your pickleball activities as well as onboard meals and access to swimming pools, fitness centers, and more.

Reviews

Pickleball has become really popular on Royal Caribbean ships and many reviewers love the opportunity to play while on a relaxing cruise. I've heard that the ship's motion and occasional wind can make it a different playing experience, but a lot of people either don't notice it or get used to it.
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My verdict
Pickleball At Sea is my top recommendation if you want to work on your pickleball game while soaking in the sun and enjoying the cruise experience. These trips are specially catered to pickleheads. They offer pro instruction, private onboard courts, onshore playing in Caribbean resorts, and the whole range of experiences that only a cruise ship can bring. All at affordable prices too.

Today’s best deal

Best in Europe

4. Evyssa Vacations

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River cruises, Greek Islands, and more European adventures.

Book if:

  • You want to go on a river cruise in Europe:

    the 8-day cruise down the Danube River takes you through four Central European countries.

  • You want to soak up the sun in Greece:

    see ancient sites in Athens and experience the Greek Islands while hitting local pickleball courts.

  • You'd like to go on an Icelandic adventure:

    the "Pickleball Vikings" tour immerses you in a truly unique landscape.

Pass if:

  • You don't want to travel far:

    check out Dink Destinations for pickleball trips in the US.

  • You want to visit the Caribbean:

    lots of the other companies provide Caribbean tours, with the best resorts provided by Pickleball in Paradise.

  • You want a cheaper cruise:

    the Caribbean cruises offered by Pickleball At Sea are more affordable.

Countries Regions Offered

Central Europe, Greece, Iceland

Domestic Or International

International

Vacations Per Year

4

Average Pricing

$4,783-6,850

Average Duration

8 days

Evyssa Vacations offers the best European pickleball tours because they cover multiple countries and pack their trips with the most exciting excursions. Pickleheads of all skill levels with get to play on some of Europe's top courts, all while visiting ancient capitals, islands, and other stunning regions.
Evyssa are relatively new to pickleball but they have a ton of experience organizing tours all over the world since 2009. They've hired a dedicated, certified American pickleball instructor to lead their pickleball trips.

Destinations

The 8-day river cruise travels through four countries: Germany, Austria, Slovakia, and Hungary. They then offer excursions to Passau, Regensburg, Vienna, Bratislava, Budapest, and the Lake Balaton region.
The Greek "Spartan Adventure" takes you to Athens, Santorini, and Crete. Meanwhile, the "Viking" tour in Iceland is based in the capital Reykjavik from which you'll explore the Golden Circle and go on wildlife tours.

Pricing

Pricing for the river cruise start at $4,783 per person. The Greek trip starts at $5,850 while the Iceland trip starts at $6,850 per person.

Reviews

So far, Evyssa Vacations has only completed the Danube cruise, but I see it as a good sign that their upcoming Greek tour is already sold out. Evyssa comes with a solid reputation for luxury vacations, and are known for organizing every element of their trips.
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My verdict
Evyssa Vacations is my top pick if you're after a pickleball vacation in Europe. They might be new to the pickleball scene, but they know what they're doing. Their pickleball instructors focus not just on pickleball but also on giving you a European trip to remember. They'll take you to the best sites rather than try to go cheap. While this comes with a premium price, it's worth it if you want the pickleball adventure of a lifetime.

Today’s best deal

Best in the Caribbean

5. Pickleball In Paradise Caribbean Resorts

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Relax on white-sand beaches in between games of pickleball.

Book if:

  • You're looking for a luxury pickleball vacation:

    Pickleball in Paradise partners with some of the top luxury resorts in the Caribbean.

  • You want a wide range of location choices:

    you can choose from five Caribbean countries, including Jamaica and the Bahamas.

  • You want to train with pros and coaches:

    you'll be coached by certified pros and instructors to help you enhance your game while vacationing in paradise.

Pass if:

  • You'd prefer to cruise around the Caribbean:

    check out Pickleball At Sea for the best pickleball cruises in the Caribbean.

  • You're not interested in a Caribbean trip:

    Evyssa Vacations has great European trips, while Dink Destinations offers vacations in the US.

  • You want a tour run by top pros:

    my top choice, Pickleball Getaways, was founded by world #1 Ben Johns.

Countries Regions Offered

Caribbean (including Mexico)

Domestic Or International

International

Vacations Per Year

Around 15

Average Pricing

$1,499-3,449

Average Duration

6 days

Pickleball In Paradise is my top recommendation if you're after a pickleball vacation in the Caribbean. They're one of the top travel sites for pickleheads because of their wealth of options, from cruises to tournament trips.
For their Caribbean vacations, they've partnered with a wide range of luxury resorts including Sandals, Iberostar, and Beaches to give you lots of choice. They also have one of the largest number of trips to the Caribbean per year. Plus, on each trip, you'll be mentored by pickleball pros and coaches.

Destinations

They offer a range of Caribbean destinations, so you'll have plenty to choose from. Options include the Bahamas, Curacao, Jamaica, Mexico's Playa del Carmen, Turks and Caicos. Whichever you pick, you'll stay at an all-inclusive resort with swimming pools and access to beautiful beaches.

Pricing

Prices vary depending on the location and whether you book private or join a group trip. It ranges from about $1,499 to $3,449, but you can find one that suits you on the Pickleball In Paradise trips page. You can then submit a deposit or get more information.

Reviews

The choice of resorts is a big draw, with multiple reviewers commenting on the local beauty. People also recommend Pickleball In Paradise for the communal experience of their group trips, and appreciate the chance to improve their game with pros and coaches.
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My verdict
Pickleball In Paradise is my #1 for the Caribbean because they offer multiple trips a year to a wide range of luxury destinations. Each trip is well-planned to give you a good balance of playtime with dedicated coaches and relaxation. There's plenty on offer and it's one of the cheaper options on my list, so you're getting good value for money.

Today’s best deal

Best custom

6. Shoreline Destinations

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A seamless customized experience—tell Shoreline what you want and they'll do the work for you.

Book if:

  • You want a pickleball vacation tailored to your needs:

    Shoreline Destinations gives you a dedicated travel agent who'll plan your trip with you.

  • You want to play pickleball in beautiful locations:

    you'll get to visit some of the most idyllic, sun-soaked locations on Earth.

  • You want to join a group trip:

    meet fellow pickleheads on a group vacation to the brand-new AVA Resort in Cancun, which has five pickleball courts.

Pass if:

  • You'd prefer a pre-planned trip:

    if you don't want to work with a travel agent, try my best overall vacation, Pickleball Getaways.

  • You're looking for a budget getaway:

    Dink Destinations is my favorite affordable pickleball vacation company.

  • You want a European trip:

    check out Evyssa Vacations for pickleball tours in Greece, Iceland, and Central Europe.

Countries Regions Offered

Caribbean and Mexico

Domestic Or International

International

Vacations Per Year

Rolling

Average Pricing

Custom pricing

Average Duration

Flexible

Shoreline Destinations is my top pick for anyone wanting a personalized pickleball vacation. With years of experience planning weddings in Mexico and the Caribbean, this travel agency is now bringing their expertise to pickleball trips.
They've even partnered with top resorts in some of the most picturesque places on the planet.

Destinations

The main destinations for Shoreline's pickleball vacations are in Mexico and the Caribbean, and they have a ton of places to choose from.
For the Mexico trips, you'll find resorts all over the Caribbean coast—including in Cancun and on the Mayan Riviera—as well as the Riviera Nayarit on the Pacific Coast.
For the Caribbean, they partner with Sandals Resorts to give you a huge choice of options in Jamaica, Anguilla, Antigua, Bahamas, St Lucia, and Turks and Caicos.

Pricing

Prices vary widely because everything is catered to your plans. They cater to everything from solo trips and group trips to cruises, so I'd recommend checking them out if you want that flexibility. You can request a quote from Shoreline Destinations to get started.

Reviews

Shoreline Destinations is well known for their wedding vacations in Mexico and the Caribbean. They have excellent reviews, with people recommending them for the ease, professionalism, and attentiveness they take when customizing your trips.
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My verdict
Shoreline Destinations is my recommendation to anyone who'd benefit from a dedicated agent who will plan the perfect pickleball trip for them. They work around your needs and desires, so you get a trip that suits you personally. It's exciting to see such a respected travel company tailoring trips specifically for pickleheads.

Today’s best deal

Other great pickleball vacations

In case you didn't find what you're looking for above, I've included even more great pickleball vacations, with trips to destinations across Mexico, Europe, and beyond. I'll keep adding to this list, so check back in if you're still searching for the right vacation for you.

Spain

7. Pickleball Tours Spain

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Pickleball Tours Spain specialize in 9-day trips to Spain, making them a great option if you're looking to visit that part of the world specifically. These tours are extremely popular and run regularly, with ten trips scheduled in 2024. Not only will you play pickleball with your tour companions and instructor, but you'll also get to play with locals.
When not on the courts, you'll experience guided tours to UNESCO sites, vineyards, and much more in places like Malaga, Madrid, and Barcelona. There are optional add-on Southern Spain tours for extra traveling (and more pickleball). Prices start at $3,650.

Today’s best deal

Mexico

8. Tres Palapas Baja

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Tres Palapas Baja is a great option for pickleball enthusiasts at any level who want a self-catered getaway. You'll stay in a traditional Mexican lodging on a dedicated pickleball resort with ten onsite courts—right at the foot of the idyllic Baja California Peninsula on Mexico's west coast.
You'll get to participate in weekly clinics, Pro-Series camps run by professional players, private lessons, and monthly tournaments all on your doorstep. In between games, you can unwind at the courtside bar or head to the nearby beaches. Pricing starts at $289 per person per night.

Today’s best deal

France

9. Pickleball de France

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Pickleball de France is for anyone who likes the idea of playing pickleball on the French Riviera. On this 5-day tour, you'll join a small group (capped at 16) to train boot-camp style with Nike's Director of Pickleball Camps, Andy Rubenstein. This is designed for players between 3.0 and 3.5 levels.
The team's dedicated local travel director pulls out all the stops with chauffeured Mercedes transportation, private beach lounging, and meals at exclusive restaurants. You'll be staying in Old Town Nice and exploring the Riviera on guided tours.
Prices begin at $4,390 per person, and you can bring along a non-pickleballer for a reduced price.

Today’s best deal

Italy

10. Pickleball Italy Trips

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Whether you're a casual player or more advanced, Pickleball Italy Trips is worth checking out if you like the idea of a vacation in Italy. They offer casual open play trips where you'll join fellow travelers and Italian players, as well as more intensive trips led by pro coaches. They also have luxury retreats coming soon.
These tours are run by Italians whose local knowledge and connections elevate the whole experience. You'll get to know the best eateries, sites, and cultural spots in whichever part of Italy you choose.
Tours take place in Sicily, Rome, Puglia, Basilicata, Piedmont, and Lombardy. Open play vacations start at $2,150 per person while pro coach tours start at $2,950. For any guests not playing pickleball, there's a $200 discount.

Today’s best deal

Multiple locations

11. Pickleball Trips

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Pickleball Trips is unique because they offer vacations to countries not covered by anyone else on my list, including Belize, Japan, Thailand, and New Zealand. They're also one of the few to offer both domestic and international trips. So, if you want some more exotic choices, they're worth checking out.
Their tours are open to all skill levels, capped at 16 people for a nice small-group feel, and run by certified American pickleball instructors. For pickleball getaways in the US, check out their upcoming tours in Montana and Arizona.
Pricing varies but is generally between $3,400 and $4,400 per person. You can bring along a partner or friend who isn't playing pickleball too.

Today’s best deal

How to choose the best pickleball vacation

It's important when embarking on a big trip that you don't end up disappointed. You want to get the most out of your pickleball vacation and have a memorable experience, so avoid rushing into the decision. Here are some tips:

  • Check out each company's website and familiarize yourself with their tour itineraries so you can choose the one that appeals most to you.
  • Reach out to the company with any questions. This will tell you how responsive they are and whether they're able to meet your needs.
  • Read as many reviews as you can from people who've gone on the tours before you.
  • Make sure the vacation accommodates your skill level. Most are open to all players but some cater to specific levels.

Bottom line

Whatever type of trip you're imagining, I hope you've found one that excites you in my list of the best pickleball vacations. My top choice is Pickleball Getaways.

They have a lot of experience, their trips are super-immersive, their locations are amazing, and they're run by some of the best players in pickleball history. It won't suit everyone, though, so I've tried to give you plenty of choice.

Here's a recap of my favorite vacations for pickleball players:

  1. Pickleball Getaways - Best overall
  2. Dink Destinations - Best budget
  3. Pickleball in Paradise Cruises - Best cruises
  4. Evyssa Vacations - Best in Europe
  5. Pickleball in Paradise Caribbean Resorts - Best in the Caribbean
  6. Shoreline Destinations - Best custom

FAQs

About the author
Brandon Mackie
Brandon is an avid writer and co-founder of Pickleheads™. Once a competitive tennis player, Brandon can now be found these days honing his dinks on pickleball courts near Phoenix, Arizona.
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