Best Pickleball Vacations - Top 6 Compared | Pickleheads (2024)

1. Pickleball Getaways

2. Dink Destinations

3. Pickleball At Sea Group Cruise

4. Evyssa Vacations

5. Pickleball In Paradise Caribbean Resorts

6. Shoreline Destinations

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

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

My verdict

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

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.

My verdict

Well-priced Caribbean cruises with a strong pickleball focus.

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.

My verdict

River cruises, Greek Islands, and more European adventures.

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.

My verdict

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

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.

My verdict

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

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.

My verdict

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.

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.

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.

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.

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.