Adventure at a Glance
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Meet your hosts
Christina | Founder & CEO, Into An Adventure Travel
With a passion for travel, exploring new destinations, and creating memorable experiences, Christina brings her background in global travel, event management, hospitality, and travel planning to every adventure. As the founder of Into An Adventure Travel, she enjoys bringing people together through thoughtfully curated experiences that balance organization, exploration, and opportunities to create lasting memories. Christina will serve as your primary adventure host, helping coordinate the experience and ensuring travelers feel welcomed, comfortable, and supported throughout the journey.
Joining Christina on this adventure will be her husband, who brings the perfect balance to her personality and approach to travel. A true extrovert, he naturally brings fun, laughter, and connection to any group. He is also the person who always seems to have every gadget and gizmo packed and ready, just in case someone needs it! A natural protector with a caring heart, he brings a sense of comfort and reassurance to those around him. While Christina loves the excitement of planning and experiencing everything an adventure has to offer, he reminds everyone to slow down, soak in the moment, and enjoy the journey along the way. Together, they bring a wonderful balance of adventure, hospitality, fun, and genuine care for others.
Corey | Your NYC Adventure Expert
With decades of experience exploring New York City and leading group adventures through its neighborhoods, Corey brings extensive knowledge, personal connections, and a genuine love for the city. Having guided groups through NYC on multiple occasions and continuing to visit frequently to spend time with family and friends, Corey knows there is so much more to New York than its famous landmarks. He looks forward to sharing his favorite neighborhoods, local experiences, hidden gems, and stories that bring the city's history and culture to life.
Joining Corey will be his wife, who shares his extensive knowledge and love for New York City through years of personal experiences and connections with family and friends throughout the city. With her calm, loving personality and naturally caring spirit, she brings a comforting and welcoming presence to the group. She is the kind of person who makes everyone feel included, cared for, and right at home. A natural nurturer and caretaker, she brings kindness, patience, and genuine warmth to every experience, helping create the welcoming, family-like atmosphere that makes traveling together so special.
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Wednesday, July 21 - Monday, July 26, 2027
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New York City
Experience the heart of New York City through its iconic landmarks, historic neighborhoods, cultural destinations, museums, local food, and unmistakable energy. Explore favorites including the West Village, Chinatown, Times Square, Central Park, Little Island, the Meatpacking District, Chelsea Market, Ellis Island, the Statue of Liberty, and more, with a balance of guided experiences and independent exploration throughout the city.
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6 days - 5 nights (2 travel days)
The adventure includes 5 nights of accommodations in New York City and 4 full days of guided activities and experiences. Wednesday and Monday are designated travel days, with the guided adventure beginning Thursday morning and continuing through Sunday evening.
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12 travelers (6 pairs), including two host couples
Limited to just 12 travelers (6 pairs), including your hosts, this intimate adventure offers a balance of thoughtfully curated group experiences, local expertise, and opportunities to explore independently. With only four reservations available for purchase, each accommodating two adults sharing one private hotel room, our small group size allows us to experience the city together while still having the freedom to discover it in our own ways.
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There is something about New York City that captures your heart. Maybe it is the energy of the streets, the charm of its historic neighborhoods, the incredible food, the bright lights of Broadway, or the stories and traditions woven into every corner of the city. Maybe it is a quiet moment in Central Park, discovering a little neighborhood café, or sharing a late night adventure with someone special.
Whatever it is, New York has a way of making you fall in love with it, often in ways you never expected.
Fall in Love with NYC is an adults only guided adventure designed to help you experience the heart and soul of New York City. Rather than simply checking famous attractions off a list, we want you to discover the places, people, flavors, history, and unforgettable moments that make this city unlike anywhere else in the world.
This adventure is designed for couples, loosely defined. Whether you are traveling with your spouse, partner, best friend, or another favorite travel companion, the experience is about sharing the journey with someone you enjoy exploring the world with.
Limited to just 12 travelers (6 pairs), including your hosts, this intimate adventure offers a balance of thoughtfully curated group experiences, local expertise, and opportunities to explore independently. With only four reservations available for purchase, each accommodating two adults sharing one private hotel room, our small group size allows us to experience the city together while still having the freedom to discover it in our own ways.
Together, we will wander through the West Village, experience the culture and traditions of Chinatown, discover the charm of Little Italy and the energy of Times Square, explore Central Park, and take in the views and atmosphere of Little Island, Chelsea Market, and the Meatpacking District. We will experience the history of Ellis Island and the Statue of Liberty, enjoy authentic New York food, discover museums and cultural destinations, and take in the magic of Broadway.
Along the way, there will be time to slow down, explore unexpected places, enjoy great food, share plenty of laughs, and create memories with your travel companion and fellow adventurers.
And that is what Fall in Love with NYC is really about. It is not just seeing New York City. It is experiencing it. Feeling its energy. Learning its stories. Discovering its hidden gems. Connecting with the people and places that make it special. And finding those little moments that stay with you long after the adventure ends.
With NYC expertise, genuine Midwest hospitality, and a small group of fellow travelers, we invite you to experience the city in a way that feels personal, welcoming, and unforgettable.
Come discover what makes New York City so easy to fall in love with.
And we're off... into an adventure!
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This adults only guided adventure is designed for couples, loosely defined, who want to fall in love with the history, culture, food, neighborhoods, landmarks, and unforgettable energy of New York City while sharing the experience with a small group of fellow travelers. Whether you are traveling with your spouse, partner, best friend, or another favorite travel companion, this adventure is about experiencing the city together and creating lasting memories.
Whether this is your first visit to NYC or you have been many times before, the adventure offers a thoughtfully curated combination of iconic destinations, authentic local experiences, and opportunities to discover something new. With a balance of guided activities and independent exploration, you will have the freedom to experience New York City in your own way while enjoying the connections, laughter, and shared experiences that make small group travel so special.
This adventure is limited to 12 adults, including your hosts, with only four reservations available for purchase. Each reservation accommodates two adults sharing one private hotel room.
This trip is best suited for travelers who are comfortable with long days, significant walking, extended time in a busy city environment, public transportation, summer heat, and traveling together as a group throughout the city. Guests should also enjoy the social side of small group travel, including shared meals, group experiences, plenty of conversation, and connecting with other couples throughout the adventure.
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Trip Highlights:
Explore some of New York City’s most iconic neighborhoods, landmarks, and cultural destinations
Discover the West Village, Chinatown, Chelsea Market, Little Island, the Meatpacking District, and more
Visit the Statue of Liberty and Ellis Island
Experience Central Park and some of NYC’s most recognizable historic destinations
Enjoy a Broadway show
Experience unique and authentic New York food throughout the adventure
Explore NYC through personally guided neighborhood experiences and local favorites
Visit a world class New York City museum
Experience New York at Night: Pick Your Adventure, choosing the evening experience that best fits your interests
Enjoy thoughtfully selected group dining and social experiences
Take advantage of built in opportunities to explore independently as a couple
Experience New York City by foot, subway, ferry, and other local transportation
If weather permits, close out the adventure with charcuterie, wine, and Shakespeare in Harlem
Share four full days of exploring, eating, laughing, and experiencing NYC with a small group of couples
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Pace = Moderate to Active
New York City is best experienced on foot. This adventure will include full days exploring the city, significant walking, public transportation, time outdoors, guided tours, and extended periods in busy urban environments. While opportunities for independent exploration and downtime will be built into the itinerary, participants should expect an active city experience.
Participants should be comfortable with:
Walking approximately 5 to 8 miles on some days
Spending full days exploring New York City
Extended periods of standing during tours and sightseeing
Stairs and escalators
Using the NYC subway and other forms of public transportation
Navigating crowded sidewalks, attractions, subway stations, and public spaces
Summer temperatures, humidity, sun, smells, and changing weather conditions
Carrying personal belongings throughout the day
Traveling together as a small group throughout the city
Keeping pace with the group when traveling between scheduled activities
Dining, sightseeing, and socially connecting with other couples throughout the adventure
This adventure is designed to experience the energy of New York City, not simply observe it. Comfortable walking shoes, flexibility, and a willingness to embrace the pace of the city will be essential parts of the adventure.
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As Into An Adventure Travel continues to grow its Guided Adventures, Fall in Love with NYC marks another exciting first: our first domestic Guided Adventure.
For this adventure, I wanted to create something my husband and I could experience together and share with other adults who love to travel, explore, and make memories with someone special. New York City felt like the perfect place to do just that. It is filled with history, culture, incredible food, iconic experiences, and an energy unlike anywhere else. There is something about NYC that captures your heart, and I wanted to create an adventure that allows us to truly experience the city and discover what makes it so easy to fall in love with.
Joining me as a fellow host is Corey, one of our favorite people and someone who brings decades of experience exploring New York City and leading groups through its neighborhoods. Corey and his wife have spent years visiting the city, building connections, and discovering the places and experiences that make New York so special. Their knowledge and love of NYC, paired with genuine Midwest hospitality, gives us the opportunity to experience both its iconic destinations and some of the places we might not discover on our own.
This adventure brings together so many things I love about travel: experiencing places you have always wanted to see, discovering something unexpected, sharing incredible food, laughing together, making new connections, and still having the freedom to create experiences of your own. It is about slowing down enough to appreciate the little moments while embracing the excitement and energy of everything happening around you.
With just 12 adult travelers, including your hosts, and only four reservations available for purchase, this adventure is intentionally small, personal, and social. While we call it a couples adventure, our definition of couples is flexible. Whether you are traveling with your spouse, partner, best friend, or another favorite travel companion, the goal is the same: to share an unforgettable experience with someone you enjoy exploring the world with.
More than anything, I hope this adventure gives each traveler the opportunity to experience New York City in a way that feels personal and meaningful. To discover a favorite neighborhood, enjoy an unexpected moment, connect with new friends, and return home with memories and stories that will last long after the adventure ends.
And hopefully, somewhere along the way, you will discover a few reasons of your own to Fall in Love with NYC.
And we’re off... into an adventure!
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Personally guided adventure hosted by Christina Castillo, Founder and CEO of Into An Adventure Travel, and NYC expert Corey.
Five nights of comfortable accommodations in the heart of Manhattan
All organized group meals during the four core adventure days (one specialty beverage per person per meal)
Ground and public transportation throughout New York City as outlined in the itinerary
Admission to all scheduled group activities, tours, experiences, and attractions
Guided sightseeing and local experiences included in the itinerary
Personalized trip planning, coordination, and resources
Adventure Credit to use toward eligible expenses during designated independent exploration, if included in the final itinerary
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Airfare or other transportation to and from New York City
Ground transportation between the airport and accommodations on arrival and departure days
Travel insurance, strongly recommended
Optional activities and experiences during scheduled free time
Specialty beverages not included with organized meals (only one specialty beverage will be provided per person per meal)
Meals, snacks, desserts, or other food purchases outside of organized group meals
Souvenirs, shopping, and personal purchases
Personal expenses such as laundry, room service, and incidentals
Gratuities for local guides and other service providers
Any expenses not specifically outlined as included in the itinerary
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Adventure Investment: $5,400 per pair (2 adults)
$2,700 per person, based on double occupancy.
Each reservation includes two adult travelers sharing one private hotel room. Only four reservations are available for this exclusive small group adventure.
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Luggage Guidelines:
There are no specific luggage size or quantity restrictions for this adventure beyond any requirements established by your airline or other transportation provider.
Participants are responsible for their own luggage throughout the adventure, including transportation of luggage to and from New York City and between arrival or departure transportation and our accommodations.
Suggested Packing List:
Comfort is key when exploring New York City! Pack lightweight, versatile clothing that will keep you comfortable during long days of walking and exploring while also giving you a few options to dress up for dinners, Broadway, and evenings out. New York summers can be hot and humid, but indoor spaces can be heavily air conditioned and weather can change quickly. Comfortable walking shoes, light layers, and rain protection will help keep you ready for whatever the city brings.
Luggage that is comfortable and manageable for you
Personal item, backpack, tote bag, or daypack
Lightweight, comfortable summer clothing
A few dressier casual options for dinners, Broadway, and evenings out
Light sweater, cardigan, or jacket for air conditioned spaces
Lightweight rain jacket or compact umbrella
Comfortable walking shoes
Casual or dress shoes for evenings
Sleepwear
Undergarments and socks
Hat and sunglasses
Valid government issued photo ID
Credit or debit card and travel insurance information
Prescription and over the counter medications
Personal first aid supplies
Personal hygiene items and toiletries
Sunscreen and lip balm
Refillable water bottle
Phone, charging cables, and headphones
Portable battery pack
Camera, optional
Small crossbody bag, belt bag, or other secure day bag
Laundry bag
Snacks for travel and exploration days
Adventure Itinerary
Day 1 - And We're Off... Into An Adventure!
Wednesday, July 21, 2027
Your adventure begins the moment you arrive in the Big Apple! Settle into your Midtown Manhattan accommodations, take in the excitement of the city, and enjoy the evening at your own pace. Whether you venture out for your first slice of New York pizza, explore the neighborhood, or simply relax after your travels, tonight is yours to enjoy. Get ready for an unforgettable adventure as we prepare to fall in love with NYC together!
DAY 2 - Welcome to New York!
Thursday, July 22, 2027
We have arrived! Our first official day in NYC will begin with breakfast together, where you will meet your guides, get to know your fellow adventurers, and officially kick off Fall in Love with NYC.
To start our day, Tour Guide Corey will lead us through the West Village, sharing a neighborhood he knows and loves. We will wander its quaint streets, some still cobblestoned, lined with historic Federal style townhouses, designer boutiques, trendy restaurants, and neighborhood favorites. Along the way, Corey will introduce us to the Village’s rich history as a center for artists, musicians, theatre, and culture, including notable places such as the Stonewall Inn and the important role this neighborhood has played in New York City history.
After a quick New York lunch, we will continue exploring Greenwich Village and Washington Square Park before making our way toward the Hudson River. We will visit Little Island, a unique public park rising above the waterfront, before continuing into Chelsea to explore its famous market, shops, local vendors, and surrounding neighborhood.
The rest of the afternoon will give you some time to explore Chelsea and the Meatpacking District at your own pace. Shop, grab a drink or treat, explore the neighborhood, or simply find a spot to take in the energy of the city.
We will come back together that evening for our official Welcome Dinner at an authentic New York Italian restaurant. Over great food and conversation, we will get to know one another and celebrate the beginning of our adventure together.
DAY 3 - History and Cultural Immersion
Friday, July 23, 2027
Today we will immerse ourselves in the history, culture, and neighborhoods that have helped shape New York City.
Tour Guide Corey will start our day by leading us through Chinatown, sharing the history, culture, and stories of one of NYC’s most vibrant neighborhoods. Along the way, we will enjoy an authentic Chinatown lunch before making our way into Little Italy for a sweet treat from one of the neighborhood’s iconic Italian bakeries.
From there, we will make our way to Nolita, a charming neighborhood known for its picturesque streets, unique boutiques, designer shops, sidewalk cafés, and trendy local atmosphere. Enjoy some time to explore, shop, and experience the neighborhood before we step even further back into New York’s history.
Our afternoon continues with a Catacombs by Candlelight Tour at the Basilica of St. Patrick’s Old Cathedral, the original cathedral of the Archdiocese of New York. This unique experience will take us behind the scenes and into areas normally closed to the public, including the historic catacombs, walled cemeteries, and other spaces beneath the Basilica. Along the way, we will discover more than 200 years of New York history and the stories of prominent New Yorkers who found their final resting place here.
After a full day of exploring, we will head toward Times Square for a casual dinner with classic New York options. Grab a slice of pizza, a deli sandwich, salad, or something sweet before we make our way to the theatre.
Then it is time for one of the quintessential New York experiences as we enjoy a Broadway show together!
DAY 4 - A Day for Adventure
Saturday, July 24, 2027
Today we are diving into some of New York City’s most powerful history before experiencing the city in an entirely different way after dark.
After breakfast, we will head out to explore two of New York Harbor’s most iconic landmarks, the Statue of Liberty and Ellis Island. But our visit to Ellis Island will take us beyond the traditional experience. We will go behind the scenes on a guided Hard Hat Tour of the abandoned Ellis Island Hospital Complex, an area that was closed to the public for more than 60 years. This unique experience provides rare access to a part of the island most visitors never see and a fascinating look into its history.
Back in Lower Manhattan, we will enjoy a traditional menu of modern Irish comfort food and pub favorites at a destination inspired by the Irish immigrant history of 19th century New York. From there, we will explore Lower Manhattan on foot, including the 9/11 Memorial, Wall Street, the Financial District, and South Street Seaport.
New York at Night: Pick Your Adventure
Tonight, we will split into two smaller groups for two very different ways to experience New York after dark.
New York at Night with Corey
Join Corey for dinner and cocktails before heading out for a live burlesque performance and a memorable evening in New York City.
New York at Night with Christina
Join Christina for rooftop dining and cocktails before taking in panoramic sights of New York City from the ultimate observation deck, offering a complete perspective of the iconic skyline. From there, we will continue through Manhattan to catch live music and enjoy a final cocktail together.
Whichever adventure you choose, tonight is all about experiencing the energy, entertainment, and magic of New York City after dark.
DAY 5- City of Romance
Sunday, July 25, 2027
Today we will slow things down and enjoy a little romance in the heart of New York City.
After a leisurely breakfast, we will begin our day with a walk through Central Park, taking in one of the city’s most beautiful and iconic spaces together.
The afternoon is yours! Each couple will receive an Adventure Credit to create your own afternoon experience. Use your credit toward lunch and a museum of your choice, explore a little more of Central Park, or simply enjoy some time together in the city. With world renowned museums nearby, including The Met and the American Museum of Natural History, there will be plenty of ways to spend your afternoon.
Later, we will meet at Marcus Garvey Park in Harlem, where Corey and Stacy will have a picnic waiting for us. Enjoy sandwiches, salads, a charcuterie board, wine, and beverages as we relax together before the evening’s entertainment.
We will end our final night in New York with Uptown Shakespeare in the Park, presented by the critically acclaimed Classical Theatre of Harlem at the Richard Rodgers Amphitheater. This beloved summer tradition brings professional theatre outdoors for a memorable evening of Shakespeare under the stars.
Good food, great company, live theatre, and a summer evening in Harlem. It is the perfect way to spend our final night together in New York City.
Because Uptown Shakespeare in the Park is an outdoor experience, our evening plans will be dependent upon the 2027 performance schedule and weather conditions. If Mother Nature has other ideas, we will do our best to arrange a comparable entertainment experience for the group.
DAY 6- Until Next Time, New York
Monday, June 25, 2027
Enjoy one final breakfast together before it is time to pack our bags, check out, and say goodbye to New York City.
After an unforgettable few days of exploring, experiencing, eating, laughing, and making memories together, our Fall in Love with NYC adventure comes to an end. Departures are at your leisure, allowing you to make travel arrangements that work best for you.
We may be leaving New York, but hopefully we are taking home a little piece of the city, new friendships, and plenty of stories to tell.
Until next time, New York...
Before you book
Important Information
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Your investment includes five nights of carefully selected accommodations in the heart of Midtown Manhattan. Our accommodations have been selected for their cleanliness, modern comfort, welcoming hospitality, convenient location, and accessibility to the neighborhoods, attractions, and experiences we will be exploring throughout our adventure. Daily breakfast is included.
Located in Midtown East, just a short walk from Grand Central Terminal, our accommodations provide an excellent home base for experiencing New York City. Guests will enjoy modern, comfortable rooms and convenient access to dining, shopping, entertainment, and public transportation. This location offers a more relaxed Midtown atmosphere while keeping many of NYC's most iconic destinations within easy reach.
Accommodations are based on double occupancy, with one private guest room provided for each pair of travelers. Five nights of accommodations are included, beginning Wednesday, July 21, and continuing through Sunday, July 25, with departure on Monday, July 26, 2027. Daily breakfast for two guests per room is included throughout the stay.
After full days exploring the history, culture, neighborhoods, and unforgettable experiences of New York City, our goal is to provide a clean, comfortable, and conveniently located place to relax, recharge, and be ready for the next day's adventure.
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Reservations are confirmed upon receipt of the required deposit. Payments are due according to the published payment schedule. Because reservations, accommodations, and activities are secured well in advance, payment deadlines are firm. Travelers who reserve after an established payment deadline may be required to pay any missed installment(s) at the time of booking.
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Due to the nature of this small group guided adventure, accommodations, transportation, and activities are reserved and paid for well in advance. All payments are nonrefundable.
If a traveler is no longer able to participate, Into An Adventure Travel will make reasonable efforts to assist the traveler in finding a replacement participant to purchase their reservation at the original booking price, subject to availability and any supplier requirements.
If a replacement traveler is secured and all supplier reservations can be successfully transferred, Into An Adventure Travel will refund the original traveler any recoverable funds, less any nonrecoverable supplier charges, processing fees, or transfer costs.
If a replacement traveler cannot be secured, no refund will be issued.
Travel insurance that includes trip cancellation and interruption coverage is strongly recommended and should be purchased shortly after booking.
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While every effort will be made to operate this guided adventure as published, Into An Adventure Travel reserves the right to modify the itinerary, accommodations, transportation, activities, meal locations, or daily schedule when necessary due to circumstances beyond our control. These circumstances may include, but are not limited to, weather conditions, natural disasters, road closures, transportation delays or cancellations, supplier availability, government restrictions, safety concerns, mechanical issues, or other unforeseen events.
Any itinerary adjustments will be made with the safety, comfort, and overall experience of the group in mind. No refunds or compensation will be provided for changes resulting from circumstances beyond the reasonable control of Into An Adventure Travel.
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Travel involves inherent risks, including but not limited to accidents, illness, injury, property loss or damage, transportation delays, adverse weather, natural disasters, and the actions of third party suppliers.
By participating in this guided adventure, each traveler acknowledges and voluntarily assumes these risks.
Into An Adventure Travel serves as the organizer and host of this guided adventure and acts only as an intermediary between travelers and independent suppliers, including airlines, hotels, transportation providers, restaurants, tour operators, and attraction operators. Into An Adventure Travel is not responsible or liable for any injury, illness, death, accident, loss, damage, delay, inconvenience, or expense arising from the acts or omissions of these independent suppliers or from circumstances beyond its reasonable control.
Participants are responsible for exercising good judgment, following local laws, adhering to safety instructions provided by guides and operators, and maintaining appropriate personal health and fitness for the activities included in the itinerary.
Travel insurance that includes trip cancellation, interruption, medical expenses, emergency evacuation, and baggage protection is strongly recommended for all participants.
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Participants are responsible for ensuring they possess valid identification required for air travel and other activities included in the itinerary, arranging their own transportation to and from New York City, and purchasing any recommended travel insurance.
Participants are responsible for arriving at scheduled meeting locations on time, complying with instructions provided by local guides, transportation providers, and Into An Adventure Travel, and ensuring they are physically able to participate in the activities included in the itinerary.
Because this is an active city based adventure, participants should carefully review the trip pace and physical expectations prior to booking, including significant daily walking, extended periods of standing, stairs, public transportation, summer weather conditions, and extended time in busy urban environments.
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By submitting a reservation and paying the required deposit, the traveler acknowledges that they have read, understand, and agree to all Terms and Conditions established by Into An Adventure Travel. This includes, but is not limited to, the payment schedule, cancellation policy, itinerary change policy, assumption of risk, limitation of liability, participant responsibilities, and all other policies related to this guided adventure. Submission of a deposit constitutes acceptance of these Terms and Conditions and creates a binding agreement between the traveler and Into An Adventure Travel.
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At Into An Adventure Travel, we value your privacy and are committed to protecting the personal information you share with us. We collect information such as traveler names, contact details, travel preferences, dietary restrictions, allergies, emergency contacts, and reservation details to help us plan, coordinate, and provide personalized travel experiences.
Your information is used solely for business purposes, including processing reservations, communicating important travel details, and coordinating accommodations, transportation, dining, and activities. When necessary, we may share relevant information with trusted travel partners and service providers to ensure your adventure runs smoothly. We do not sell your personal information to third parties.
We take reasonable steps to protect your personal information and use third-party booking and payment platforms to process transactions. While we strive to maintain appropriate privacy and security practices, no electronic system can guarantee complete security. We retain information only as reasonably necessary for business operations and applicable legal requirements.
By booking with Into An Adventure Travel, you acknowledge that your information may be collected, used, and shared as outlined in this policy. If you have questions, would like to update your information, or wish to request its removal, please contact us through www.intoanadventuretravel.com. Certain information may need to be retained for legal or business purposes.
