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Chicago Sightseeing & Sailing Getaway **2 SPOTS LEFT**

July 23 - July 29

Set sail with us and embark on a maritime adventure that combines the thrill of sailing with breathtaking views of Chicago’s iconic skyline. It’s not just a retreat; it’s a salute to your service, a voyage of appreciation, and a celebration of the indomitable spirit that defines our military community.

Our focus with any gathering is to test our personal limits in regards to healthy risk-taking. By redefining what we consider “risky,” we can discover new heights and break glass ceilings that we thought were impenetrable. Be it extreme sports or deeper human connections, risk ultimately varies to each of us and lies on a spectrum. Our goal is to create a transformative trip filled with moments of awe-inducing adventure, cultural connections, personal development and celebration.

Service Level: Standard – Comfortable accommodations at the beautiful Freehand Chicago Hotel, sharing three, 4-bed private suites. 

Trip Overview

Day 1: Tuesday, July 23, 2024

Welcome to Chicago! Take time to check-in to the hostel and enjoy the various amenities before our group dinner! This is just the start of a life-changing journey in one of the most beautiful cities in the country. 

Meals included: Dinner

Day 2: Wednesday, July 24, 2024

Indulge in a private breakfast, followed by a guided group discussion and activity aimed at equipping you with tools to enhance your well-being and strengthen connections with others. Our next stop is Montrose Harbor for an immersive classroom session with No Salt Sailing, delving into the fundamentals and introductory basics of sailing in preparation for the adventures that await on Lake Michigan.

Please note that we’ll be using public transportation for the 45-minute commute to and from the harbor. Your tickets for all three days at the harbor are included, offering a delightful and cost-effective way to experience local travel.

As the day unfolds, we’ll conclude with a mesmerizing 90-minute sunset kayaking tour, paddling through the soft golden twilight glow amidst Chicago’s renowned architecture. Experience the city’s beauty at its peak, savoring the Historic Chicago Tour as the sun sets. Fewer boats on the river in the evenings help make this one of the most serene and relaxing excursions, suitable for all ages and ability levels.

Meals included: Breakfast | Snack

Day 3: Thursday, July 25, 2024

Get ready to hoist the sails, master the basics, and set course for an adventure-filled exploration of the open waters. The first day of sailing instruction promises not only valuable learning but also the thrill of embracing a new skill set as we prepare to navigate the beautiful expanse of Lake Michigan in the days ahead.

Later on we’ll experience a colorful side of Chicago history with a Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Meals included: Breakfast | Lunch + Snack

Day 4: Friday, July 26, 2024

Building upon the skills acquired throughout the program, this final session at Montrose Harbor is designed to fine-tune your sailing expertise and instill a deep sense of confidence on the open waters of Lake Michigan. The last day promises to be a memorable finale, setting the stage for you to confidently navigate the vast expanse of Lake Michigan with newfound skills and a profound connection to the open sea.

Later on, we’ll gather with fellow participants, instructors, and newfound friends to relive the highlights of our sailing adventure. As we savor some delicious eats, share stories, and bask in the warmth of camaraderie, this barbecue becomes more than a meal—it’s a celebration of achievements, memories made, and the bonds forged during our time on the open water.

Meals included: Breakfast | Lunch | Dinner

Day 5: Saturday, July 27, 2024

Whether you’re captivated by the modern skyline or drawn to the echoes of the past, walking the streets of Chicago is a way to discover the multifaceted charm that makes this city a truly exceptional destination. Our walking tour will also take us to significant military sites, each holding a piece of Chicago’s patriotic legacy. From the iconic Soldier Field, a testament to the city’s deep connection with its armed forces, to the Chicago Veterans’ Memorial Plaza, where the sacrifices of servicemen and women are commemorated, every stop is a moment of reflection and honor.

A visit to the Windy City wouldn’t be complete without diving into the food scene! In an exciting three hours, you’ll feast on Chicago culinary legends such as deep-dish pizza, Italian Beef, a Chicago-style hot dog, and a delectable dessert!

This is just the start to an evening out on the town. From the trendy bars and rooftop lounges in River North to the soulful jazz clubs in the historic South Loop, Chicago’s nightlife offers something for every taste.

Meals included: Breakfast | Lunch | Dinner

Day 6: Sunday, July 28, 2024

Before bidding farewell to the enchanting city of Chicago, we’ll provide you with a curated list of tours and attractions to explore at your leisure. Whether you opt for solo exploration or a laid-back day of self-care, this free day is the perfect opportunity to reflect on the incredible experiences of the past week and create your own memorable moments in the vibrant tapestry of Chicago.

As a final touch, join us for a guided discussion and activity, creating a space to share experiences, insights, and perhaps a few laughs, as we prepare to pack our bags. It’s a moment to reflect on the incredible journey we’ve shared, ensuring that your time in Chicago is not only filled with exploration but also enriched by connections and memories that will linger long after you’ve left the Windy City.

Meals included: Breakfast 

Day 7: Monday, July 29, 2024

This isn’t a goodbye, just a see you later! If your plans include extended time in the area, feel free to contact us for suggestions or ideas on where to next continue your trip!

Meals included: N/A

WHO CAN ATTEND

There are 7x spots available for U.S. service members and veterans only. No guests or pets allowed. If you have a service animal, please contact us directly to discuss.

COST – Now $1,500 thanks to our official sponsor, Official Military Skate

$250 DEPOSIT REQUIRED & PAYMENT PLANS AVAILABLE, CONTACT US

WHAT’S NOT INCLUDED

  • Transportation to and from Chicago.
  • Transportation to Freehand Chicago Hotel.
  • Departing transportation to Chicago O’Hare International Airport.
  • Travel insurance. We are an operating travel agency and can help provide a quote so you are insured and covered for any issues that may arise during this retreat
  • Souvenirs
  • Any additional or optional activities not outlined in the schedule.

FAQS

  • Why is this group trip special? We provide a unique community experience for travelers to try new, positive activities amongst supportive brothers and sisters of the U.S. military. Our retreats offer an unparalleled opportunity for affordable and enriching experiences that contribute to mental, emotional, and physical well-being. While ample free time allows for personal relaxation, rest assured that you’re always in close proximity to friendly companions who share a common bond.
  • Who can attend? Active duty, reservists, national guard members and veterans of the U.S. Armed Forces of any branch, era or discharge.
  • Who is this trip ideal for? This trip is tailored for service members and veterans seeking an exceptional sailing experience facilitated by an accredited military non-profit. Whether you’re looking to enhance your sailing skills or deepen your connection with the vibrant city of Chicago, this adventure offers a unique blend of camaraderie, discovery, and personal development.
  • Can I drive? If you currently reside in or around Chicago, you are welcome to commute and join our group locally! We just ask that you attend the entirety of the retreat. 
  • What activities are optional? Meditation practices and yoga classes are not mandatory, but are included at discount. There are numerous benefits to military personal in regards to meditation and yoga, so it is highly encouraged to participate. Any other additional tourist activities are optional at an additional cost.

Sign Up & Pay for Chicago Sailing & Sightseeing

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We have group chats for each trip that you will need to join. We will only text or call if we are unable to reach you through email for event attendance.
Month, Day, Year
Events and trips are for U.S. military only, no guests unless specified in the event description.

Details

Start:
July 23
End:
July 29
Event Category:

Organizer

LiboRisk

Venue

Chicago
Chicago, IL United States

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