How to Plan Your First Pickleball Holiday

Step 1: Pick a format (the most important decision)

The format you pick shapes the entire trip. There are three core options.

• Retreat: hosted, fixed-date, structured. The trip is built for you. Best for solo travellers, beginners and players who want improvement structure. See our Retreats Guide.
• Resort: flexible dates, self-directed schedule, mixed amenities. Best for couples, mixed-interest groups and travellers who want a real holiday with pickleball as part of it. See our Resorts Guide.
• Rental: private property, exclusive court, group-focused. Best for groups of four-plus who want full control. See our Rentals Guide.

Step 2: Pick a destination

Once you've picked the format, the destination shortlist narrows. Some destinations are stronger for some formats.

• Retreats: Naples, Tulum, Bali, Scottsdale all have deep operator scenes.
• Resorts: Scottsdale, Cancún, Naples, Palm Springs, Dubai lead.
• Rentals: Florida (Naples especially), Riviera Maya, Scottsdale, Costa Rica.

The full Best Pickleball Destinations Guide covers all twelve top options ranked across criteria.

Step 3: Pick the right time of year

Most pickleball destinations are seasonal. Get the timing wrong and you'll either overpay or face weather issues.

Step 4: Set a budget

Budget per person varies by format and destination. Realistic ranges for first-time travellers:

• Weekend retreat (3 nights): $500 to $1,200 per person all-in
• Week-long retreat: $1,800 to $3,500 per person all-in
• Resort week (mid-tier, including meals): $1,500 to $3,000 per person
• Rental week (split across 6 people): $700 to $1,200 per person

Add flights, paddle, travel insurance and tips. International destinations save money on the retreat but cost more in flights.

Step 5: Book early

Book 2 to 4 months ahead for popular destinations and dates. Premium retreats with named coaches can sell out within weeks of opening registration. Peak winter weeks in Florida, Mexico and Arizona book out 4 to 6 months ahead.

Step 6: Pack right

• Your own paddle (always)
• Court shoes (proper ones, not running shoes)
• Multiple sets of synthetic playing kit
• Sun protection: hat, sunscreen, UV shirt
• Travel insurance
• A backup grip and a few extra balls
• Paddle case for protected travel

For full packing detail, see our complete packing checklist.

What to expect on the trip itself

First-time pickleball travellers consistently report two surprises. First: how much faster the social side moves than expected. Within 24 hours of arriving at a retreat, you have a friend group; by day three you're swapping numbers. Second: how tired your body is by mid-week. The compound load of multiple hours of daily play is real, regardless of fitness level.

Build in a rest day mid-week if your trip is longer than 4 days. Hydrate aggressively. Stretch in the morning. The trip is more enjoyable when you arrive at day five with energy still left.

Frequently asked questions

How do I plan my first pickleball holiday?

Pick a format (retreat, resort or rental), then a destination that suits that format, then dates 2 to 4 months out. Set a per-person budget, then handle flights and packing. The format is the biggest decision because it shapes how much of the trip is built for you versus organised yourself.

How much does a first pickleball holiday cost?

Realistic per-person ranges are $500 to $1,200 for a weekend retreat, $1,800 to $3,500 for a week-long retreat, $1,500 to $3,000 for a resort week with meals, and $700 to $1,200 for a rental week split across 6 people. Add flights, insurance and tips on top.

Should I book a retreat or a resort for my first trip?

Retreats suit solo travellers and improvement-focused trips. Resorts suit couples, mixed groups and trips where pickleball is part of a bigger holiday. Choose based on whether you want structure (retreat) or flexibility (resort).

How far in advance should I book?

Book 2 to 4 months ahead for popular destinations and dates. Premium retreats with named coaches can sell out within weeks of opening registration. Peak winter weeks in Florida, Mexico and Arizona book out 4 to 6 months ahead.

What level do I need to be to go on a pickleball holiday?

Any level. Many retreats are explicitly beginner-friendly and group players by skill. Beginners often improve fastest on these trips because of the concentrated practice and accessible coaching.

Do I need to bring my own paddle?

Yes. Most properties offer loaner paddles but quality varies. Playing on a paddle that matches your home setup means coaching feedback transfers when you return. Always bring your own.

Related guides

Continue exploring the complete pickleball travel library.

• Pickleball Holidays: The hub guide. Retreats, resorts and rentals compared.
• Pickleball Retreats Guide: All retreat formats explained.
• Coaching Holidays: Coach-led trips for skill development.
• Resorts with Courts: Hotels with on-site courts.
• Vacation Rentals with Courts: Private villas with their own court.
• Best Destinations: Top 12 places to travel.