San Luis Obispo Venture Fitness Retreats

2:00 PM — Coastal Hike A scenic coastal hike along Avila Ridge, with sweeping views over the Pacific and the Central Coast hills. Moderate terrain gets the legs moving and the mind clear — a perfect way to shake off travel and settle into the retreat's pace before the days of training and adventure ahead.

Yoga and a beach workout on the grassy bluffs overlooking Shell Beach. Ocean views, fresh coastal air, and open space to stretch, breathe, and move — energizing the body after the hike and setting the tone for the retreat ahead.

Morning- Airport transfers and check-in at Hotel Cerro Possible 1-on-1 assessment for early arrivals. Free pickup from wherever you land in San Luis Obispo. We'll take you straight to your accommodation for the week. Check in to Hotel Cerro, your boutique home base for the week in the heart of downtown San Luis Obispo. Enjoy the rooftop bar and pool, a relaxation terrace, and optional Spa Cerro treatments. Every guest gets a 1-on-1 movement assessment with a coach — early arrivals may fit theirs in here before activities begin.

7:30 AM – Optional morning yoga with Alex: Gentle movement and breathwork on Hotel Cerro's rooftop, overlooking the city as you ease into the day before training begins.

Kayak session through Shell Beach Caves: Paddle along the dramatic coastline of Shell Beach and through its sea caves and rock formations — a scenic, low-impact way to experience the Central Coast from the water. Guided by local kayak instructors, no experience necessary.

Sessions follow Tom's core programming principles — a strong community feel, with quality movement and proper tension prioritized over chasing specific positions. Training balances heavy structure work, technique and mobility, and high-intensity workouts. We follow a fundamental program throughout the retreat but adapt it to your goals and preferences based on your pre-retreat call and assessment findings.

Throughout retreat, everyone will get a 1 on 1 assessment. A private movement assessment with a certified coach to identify imbalances and personalize your training approach for the rest of the retreat.

7:30 AM – Optional morning yoga: Another rooftop session at Hotel Cerro to start the day — gentle movement and breathwork with sweeping views over the city before the group's next adventure.

Headstrong Fit, continuing the retreat's functional strength and conditioning programming

E-Bike tour in Morro Bay: We team up with Cal Coast Adventures for a fun, scenic guided electric bike tour through Morro Bay. Led by a knowledgeable local guide, you'll ride comfortable e-bikes along the coast, exploring iconic landmarks including Morro Rock, Estero Bay, Morro Strand Beach, and the state park. Enjoy breathtaking coastal views, rolling hills, and peaceful bays while learning about the area's natural beauty and history. The tour is flexible and tailored to the group's pace and interests — whether you want to dive into local stories and ecology or simply cruise, take photos, and soak in the scenery.

Afternoon – Recovery time, pool, and 1-on-1 assessments: Downtime to recover and relax by the pool, along with any remaining individual movement assessments with your coach.

Free evening to explore SLO: An open night to explore downtown San Luis Obispo at your own pace — great restaurants, bars, and local spots all within walking distance of the hotel.

Morning run or bike ride to the coast: An easy-paced run or bike ride down to the coastline to start the day moving, with ocean views the whole way

Surfside sauna session: A morning recovery session at the oceanside sauna in Avila Beach. Enjoy the heat of the sauna with the option to dip in and out of the ocean as much as you like. This contrast therapy (sauna + cold ocean plunges) is incredibly effective for muscle recovery, reducing inflammation, and resetting your nervous system. It's one of the most refreshing and popular experiences on the retreat — combining heat, cold water, and beautiful ocean views.

Free time at the beach: Open time to relax, swim, or explore the shoreline at your own pace.

Wine tasting: We head into the scenic hills of San Luis Obispo for a private wine tasting at Filipponi Ranch — a beautiful, secluded family-owned winery in the heart of Central Coast wine country. Set on a stunning property with a relaxed event space and plenty of lawn, the ranch is perfect for our group. You'll enjoy excellent local wines while playing lawn games like bocce ball and horseshoes, with some friendly competition guaranteed. It's the perfect way to unwind, connect with the group, and experience the laid-back charm of California wine country.

Farmers Market: SLO's famous Thursday night Farmers Market on Higuera Street — five blocks, 120+ vendors, live music, and the longest-running night market in the country.

Optional morning yoga: Gentle movement and breathwork on Hotel Cerro's rooftop, overlooking the city before the day begins.

Surf or Hike: We partner with Cal Coast Adventures to deliver a classic California surfing experience on the Central Coast. For beginners, you'll start with a thorough safety briefing, an overview of surf conditions, and basic techniques, followed by over an hour in the ocean with your instructor providing real-time coaching. For more experienced surfers, you're welcome to join instructors to refine your skills, or surf on your own — boards and wetsuits are provided for all guests either way. For those who'd rather skip the waves, join a guided hike through Montaña de Oro State Park instead, followed by lunch with the group.

A coached strength and conditioning session following Tom's core programming principles, balancing structure, technique, and high-intensity work.

Free time, pool, and hotel: Downtime to relax at Hotel Cerro's rooftop pool or recharge before the evening.

Evening – Sunset picnic dinner at TV Tower Hill: On your final evening, we head into the hills for a catered dinner overlooking all of San Luis Obispo — the coastline, the valley, the whole trip laid out below you as the sun goes down. This might genuinely be the most breathtaking part of the entire retreat. Whenever Tom or Alex bring family and friends up here, it's almost always the moment they remember most.

One big last workout at Headstrong Fit with the whole community — a final push together to close out the retreat after breakfast, before departures.