Gulfside 2026-2027 Season Guidelines Rules and Expectations

What’s New at Gulfside Baseball Academy?

We’re excited to share some key updates to our team structure, pricing, and player development model—designed to give your athlete the best baseball experience possible.


Age Groups & Team Structure

  • Training Program Only: Focus on development with training, scrimmages, and a few games.

  • 10U – 14UTravel Teams:

    • $575 Annual Membership

    • $820 Per Season (Spring & Fall)

Seasonal Schedule:

  • Spring: January – May

  • Fall: August – December


Team Philosophy

We’re moving away from large player pools and event-based rosters. Instead, each team will consist of 10-12 dedicated players. If enough athletes register, we will form multiple teams based on skill level—ensuring competition, chemistry, and development for all.

  • Consistent Rosters: Players will remain with the same group to build camaraderie and chemistry.

  • Flexibility: Athletes may move between teams based on performance and growth, but we aim to keep transitions minimal.


Pricing Model

We’ve introduced a Gulfside Annual Membership and streamlined our seasonal fees:

  • Annual Membership – $575

    • Valid for 365 days from purchase

    • Includes access to practices, team training, and member-only discounts on:

      • Lessons

      • Camps

      • Gulfside apparel

  • Seasonal Fees – $820 per season

    • Can be split into payments

    • Covers field rentals, training equipment, coaching, and roster spot

Not Included:

  • Tournament entry fees

    • We aim to play around 4-8 tournaments per season, depending on what the players need, and we may play more or less.
    • This ensures you get what you pay for in a pay-per-tournament model
  • Uniforms (jerseys & pants good for both spring & fall)

    • Returning players keep hats and bags from previous seasons


What If My Son Doesn’t Make the Team?

We want this to be a positive experience for every family. Once team placements are announced:

  • You will have 7–10 days to accept or decline the offer.

  • If declined within this window, seasonal fees will be refunded in full.

  • After that period, our standard refund policy applies.

  • If he does not make a team, you will have the answers as to why. A complete evaluation with key points to work on are provided.

The Process

Step 1: Register

  • Secure your spot with the Gulfside Membership

  • Tryout registration is limited – first come, first served

Step 2: Tryouts

  • Held June 20th, 2026

  • Corkscrew Middle School

  • 9:00am-11:00am

Step 3: Evaluation

  • Families will receive a personal phone call

  • We’ll explain your athlete’s evaluation and team placement

Step 4: Team Registration

  • If selected, you’ll receive a link to sign up for your team


Fall Season Details

  • Start: August 10th

  • End: December 13th

  • Practice: 2–3 times per week (held locally around Naples, full practice schedule available February 1st)

  • Tournaments: ~1-2 per month


We’re committed to creating a competitive, developmental, and fun baseball environment for every athlete who joins Gulfside. Let’s make this our best yet