7 NIGHTS   May 16 th-May 23 th, 2026

What to Expect on Your Pickleball Cruise with Old School Pickleball Club

Our pickleball cruises are designed for players who want more than just a vacation. This is a travel experience built around connection, quality play, improvement, and fun.

1. Meet New Friends Who Love Pickleball

You will be surrounded by people who share your passion for the game. Many players find long-term tournament partners on our trips. Some even meet their “pickleball soulmate.” You never know when the right partner — on or off the court — will step into your life.

2. Travel with a Group That Understands You

Sometimes you travel with family, but you are the only one who truly wants to play pickleball. Maybe your spouse prefers the spa while you want court time. That’s exactly why this group exists.

With us, you are not alone. You will always have players ready to drill, compete, and enjoy the game while still enjoying the full cruise experience.

3. Play on Indoor Courts at Select Islands

When possible, we coordinate indoor court bookings at select islands we visit. If there is enough interest, we organize structured play sessions and even friendly games with local players. This adds an international dimension to your pickleball experience.

4. A Strong, Fun Group Atmosphere

Cruising is always better with a great group. We dine together, explore together, play together, and create lasting memories. The energy of traveling with motivated, active players makes the entire trip more dynamic.

5. Video Analysis & Performance Review (Optional – Extra Service $100)

If you want to elevate your game, I offer professional video recording of your play. You will receive:

• Technical breakdown of strokes

• Positioning and footwork analysis

• Tactical decision-making review

• Written improvement recommendations

This is an optional premium service and available by request. It is a powerful tool for serious improvement.

6. Beginner Coaching Support (Optional – $50 per Lesson, Per Person)

For beginners, I provide structured guidance during open play:

• Proper grip and paddle control

• Court positioning and movement

• Rules and scoring

• Real-time corrections during live games

After instruction, you will step into real games while I observe and provide immediate feedback.

Lesson fee: $50 per person, per lesson
Group pricing may vary depending on the number of participants.
Venmo payment required.
Private message me for details and scheduling.

Call out Travel agent Yulia Gavva

941-234-2817 for assistance or 

contact me directly for more information

808-325-5517