About

Welcome to Boundless by Alaina, where your travel dreams get the personal attention they deserve. Our agency emerged from founder Alaina Gallagher’s realization that life's most meaningful adventures shouldn't come from a cookie-cutter template.

After years of mapping out her own journeys and helping friends craft their perfect getaways, Alaina finally turned her passion for personalized travel into something more. Drawing from countless stamps in her passport and an intimate understanding of what makes each traveler unique, she created Boundless to be more than just another travel agency – it's your personal gateway to adventures that feel distinctly yours. Here, we believe that the best trips aren't just about where you go, but how that destination aligns with your individual style, interests, and dreams.

Colorful buildings and a clock tower by Lake Como, surrounded by green hills.

FAQs

General Travel

  • Yes, I can provide quotes for comprehensive travel insurance plans tailored to your specific trip. While insurance is optional, I strongly recommend it to protect your investment. Today's travel insurance can cover trip cancellation/interruption, medical emergencies abroad, evacuation, lost luggage, and even "cancel for any reason" options. I'll help explain the coverage options so you can make an informed decision based on your comfort level and trip details.

  • Booking timelines vary by destination and season:

    • For peak travel periods (summer, holidays) or popular destinations: 6-12 months in advance

    • For cruises: 8-12 months for best cabin selection and early booking discounts

    • For standard vacations during regular season: 3-6 months ahead

    • For international travel: At least 4-6 months for better flight options

    • For last-minute domestic travel: 2-4 weeks is often still workable

    Earlier planning generally provides better availability, more options, and sometimes better pricing, but I can also help with last-minute arrangements when needed.

Travel Services

  • Working with me offers several advantages:

    • Time savings: I handle all research, comparisons, and booking details

    • Industry expertise: Access to promotions and perks not available to the public

    • Personalized service: Recommendations tailored to your preferences, not algorithm-based

    • One-stop convenience: One contact for all your travel needs instead of multiple websites

    • Travel advocacy: If something goes wrong, I work to resolve issues on your behalf

    • No hidden costs: Transparent pricing with no surprise fees

    • Emergency support: Assistance available during your travels if unexpected situations arise

  • My booking process is straightforward:

    1. Initial consultation to understand your travel needs and preferences (via phone, email, or video call)

    2. Research and preparation of personalized recommendations

    3. Review of options and refinement based on your feedback

    4. Booking confirmation once you approve the itinerary

    5. Receipt of all necessary documents and itinerary details

    6. Pre-departure check-in to answer any last-minute questions

    7. Follow-up after your return to ensure everything met your expectations

  • I don't charge planning fees for most trips. My compensation comes from commissions paid by hotels, tour operators, and other travel providers. This means you get professional planning services at no additional cost beyond the actual travel expenses. For highly complex itineraries or specialty research that requires extensive time, I may discuss a modest planning fee upfront, but this is rare and always clearly communicated before any work begins.

  • Absolutely! I regularly assist clients with:

    • Dietary restrictions and food allergies

    • Accessibility requirements

    • Room location preferences

    • Celebration arrangements (birthdays, anniversaries)

    • Children's needs (connecting rooms, cribs, etc.)

    • Medical accommodations

    • Cultural or religious considerations

    Please share any special needs, and I'll ensure they're communicated to all relevant providers.

  • I offer a full spectrum of travel services tailored to your needs. This includes:

    • Simple hotel-only bookings

    • Flight arrangements and airline ticket purchases

    • Rental car reservations

    • Cruise bookings

    • Complete vacation packages

    • Custom itinerary development with activities and excursions

    • Group travel coordination

    • Honeymoon and special occasion planning

    • End-to-end travel planning with all details handled

    You can choose exactly how much or how little assistance you need.

  • I work with clients traveling to destinations worldwide and don't limit myself to specific regions or travel styles. I have resources and connections to help with everything from beach vacations and city breaks to adventure travel and luxury experiences. This flexibility allows me to be your single point of contact for all your travel needs, regardless of where you want to go or what type of experience you're seeking.

  • I provide my clients with direct contact information and am available to help resolve issues while you're traveling. Whether it's a flight cancellation, hotel problem, or other unexpected situation, I'll work with travel providers on your behalf to find solutions. Having a dedicated travel agent means you don't have to spend your valuable vacation time on hold with customer service lines or navigating complex rebooking processes.

Ready to start planning your next trip?

Let’s get connected

boundlessbyalaina@gmail.com
Based in: Chicago | Traveling: Worldwide