Retreat Itinerary
Below is the planned schedule for the Land Squad Inner Circle Retreat. Each day blends business discussions, networking, wellness activities, and curated experiences designed to help guests connect, recharge, and grow.
Day One Itinerary
Thursday, Oct 8th, 2026
Arrival & Welcome Experience
Please schedule flights to arrive at Orlando International Airport (MCO) before 1:00 PM EST on arrival day.
Arrival At Orlando International Airport (MCO)
Transportation will depart the airport at scheduled pickup times and bring guests directly to the retreat location.
1:00 PM – 5:30 PM
Guest Arrival, Check-In & Estate Orientation
Guests will check into their rooms, unpack, and become familiar with the estate and its amenities. During this time, attendees are welcome to relax, explore the property, enjoy the pool and outdoor areas, or connect with other guests as everyone settles into the retreat environment.
6:00 PM – 8:30 PM
Welcome Dinner Experience
Enjoy a Bridgerton-themed dinner inspired by the elegance of the year 1814. Guests are invited to step into the charm of Regency-era society and arrive in their finest attire for an evening of refined ambiance, delightful conversation, and a beautifully curated dining experience.
Theme: Bridgerton-Inspired Formal Dinner
Dress Code: Regency Era / Bridgerton-Inspired Elegant Attire
9:00 PM – 10:30 PM
Inner Circle Game Night
Following dinner, members can participate in a game-night designed to encourage conversation, connection, and relationship building among attendees.
Day Two Itinerary
Friday, Oct 9th, 2026
Wellness & Branding Day
7:30 AM – 8:30 AM
Group Hot Mat Pilates
Start the morning with an energizing group workout led by Instructor Sam. This hot mat pilates session will combine movement, core strength, and an upbeat trap music playlist to wake up the body and set a positive tone for the day ahead.
8:30 AM – 9:15 AM
Breakfast
Guests will gather for breakfast and light conversation before beginning the day’s scheduled activities.
10:30 AM – 3:00 PM
Branding Workshop & Content Creation Experience
This extended session focuses on personal brand development and capturing professional content. Guests will rotate through multiple stations, including personal brand positioning, professional photography opportunities, short-form video creation, and social media content planning. The goal is for attendees to leave with high-quality media and new ideas for strengthening their professional presence.
3:00 PM – 6:00 PM
Relaxation & Spa Time
Guests will have time to unwind and enjoy the estate amenities, including the pool, sauna, spa areas, and outdoor lounges. Massage and wellness services will be available during this period for those looking to relax and recharge.
7:00 PM – 9:00 PM
Dinner Experience | 50 Shades of Brown
Enjoy a 50 Shades of Brown themed dinner inspired by rich tones, warm ambiance, and Asian-inspired cuisine. Guests are invited to dress in elegant shades of brown and enjoy a sushi and Nobu-style dining experience in a stylish evening setting.
Theme: 50 Shades Of Brown
Dress Code: Shades Of Brown
9:30 PM – 11:00 PM
Paint & Sip + Karaoke Experience
The evening continues with a relaxed creative activity featuring painting, music, and karaoke. Guests can unwind, have fun, and continue connecting with fellow attendees in a laid-back environment.
Day Three Itinerary
Saturday, Oct 10th, 2026
Mastermind & Networking Day
8:00 AM – 9:00 AM
Breakfast
Guests will gather for breakfast and morning conversation before the day’s mastermind sessions begin.
9:00 AM – 10:30 AM
Hot Seat Mastermind Session
During this session, attendees will have the opportunity to present current business challenges, opportunities, or deals they are working on. The group will collaborate by sharing insights, strategies, and ideas to help move each business forward.
10:30 AM – 12:00 PM
Industry Panel Discussion
Developers, hedge fund managers, and homebuilders will join a moderated panel discussion to share insight into current real estate trends, development opportunities, and how they evaluate deals in today’s market. Guests will also have the opportunity to ask questions and engage directly with the panel.
12:00 PM – 2:00 PM
Lunch
Guests will enjoy a Haitian/Southern-inspired meal together while continuing conversations and networking.
1:30 PM – 9:00 PM
Pool Party & Networking Experience
The afternoon transitions into a relaxed networking environment where guests can enjoy the estate’s amenities, including massages, facials, the 115-foot saltwater pool, spa areas, outdoor lounges, and entertainment spaces.
6:00 PM – 9:00 PM
BBQ Dinner
Enjoy a casual BBQ-style dinner served buffet style while the pool party and networking continue into the evening. Guests can relax, socialize, and enjoy the atmosphere of the estate as the day winds down.
Day Four Itinerary
Sunday, Oct 11th, 2026
Charity Golf Tournament & Farewell Celebration
8:15 AM – 9:15 AM
Morning Group Workout
Begin the final day with a refreshing group workout to energize the body before the day’s activities.
9:30 AM – 10:30 AM
Breakfast
Guests will gather for breakfast and morning conversation before preparing for the afternoon golf event.
12:00 PM – 1:00 PM
Golf Tournament Guest Arrival & Networking
Additional guests and golfers will arrive for the charity golf event. Light appetizers and drinks will be served as guests check in, network, and prepare for the tournament.
1:00 PM – 4:00 PM
Charity Golf Tournament
Participants will compete in the charity golf tournament while enjoying a relaxed afternoon of networking with fellow entrepreneurs, sponsors, and retreat guests.
4:00 PM – 6:00 PM
Awards Ceremony & Sponsor Recognition
Following the tournament, guests will gather for the awards ceremony, where tournament winners will be recognized. Sponsors will also be acknowledged, and giveaways will take place.
7:00 PM – 9:00 PM
Latin-Inspired Farewell Dinner
The retreat concludes with a vibrant Latin-inspired farewell dinner where guests will celebrate the relationships, conversations, and experiences shared throughout the four-day retreat.
