
Meet Your Host
Hello, I’m Michelle — your dedicated travel host and full-service travel specialist. I lead two unique travel brands designed to help you see the world your way: On The Fly Vacations and Whiskey, Wine & Dine Tours.
On The Fly Vacations
With On The Fly Vacations, I specialize in hosted group travel, cruises, and Alaska adventures. My approach goes beyond planning — I personally host select trips, so you can travel with confidence, community, and ease. After a brief consultation, I’ll recommend the cruise line, itinerary, or group journey that best matches your style.
Alaska is one of my most requested destinations, and for good reason — it’s a bucket-list adventure. Whether you want a sea-only sailing, a land tour, or a combined land-and-sea experience, I’ll design a package that lets you see the best of Alaska, stress-free.
Whiskey, Wine & Dine Tours
For travelers who love food and culture, Whiskey, Wine & Dine Tours is a delicious way to explore the world. From vineyard tastings to guided food tours, I create itineraries where every day is a chance to savor something new. Already have your trip planned? I can add culinary experiences that fit right into your schedule, giving your vacation a flavorful twist.
Why Work With Me
When you book through me, you’re not just planning a trip — you’re joining a thoughtfully curated experience designed around connection, culture, and unforgettable memories. I handle the details so you can focus on the joy of travel.
As a CLIA Accredited Cruise Counselor (ACC) and a Certified Travel Associate (CTA) with The Travel Institute, I combine professional training with real-world hosting experience to give you both peace of mind and a one-of-a-kind journey.
📩 Contact me today and let’s start planning your next adventure.

Ready to start planning?
516-473-6940
Frequently Asked Questions
1. Do I have to know anyone else on the trip?
Not at all! Many of our travelers come solo and leave with lifelong friends. These hosted group trips are designed to build community while giving you the comfort of traveling with a dedicated host (that’s me).
2. Can I book a trip if I’m traveling alone?
Absolutely. You can book a private single room/cabin or choose a double occupancy option if you’re coming with a friend, family member, or partner. Either way, you’ll be part of the group experience.
3. What’s included in the price?
Each trip page clearly lists what’s included (accommodations, select meals, guided tours, transfers, etc.) and what’s not (such as personal expenses, some meals, or airfare, if applicable). I make it transparent so there are no surprises.
4. How do payments work?
Every trip offers a low deposit to secure your spot, along with flexible payment plan options. Final balance deadlines are listed on each trip page. Payment reminders are sent automatically to help you stay on track.
5. What if I need to cancel?
Life happens. Each trip has its own cancellation policy, which is listed on the booking page. Deposits are non-refundable, but you may be able to apply them toward a future trip depending on the timing of your cancellation.
6. Is it safe to travel on these trips?
Yes. All trips are hosted, vetted, and use licensed guides, reputable accommodations, and trusted transportation partners. I travel with the group to ensure everything runs smoothly.
7. Can I bring a friend, spouse, or family member?
Of course! Many travelers bring a plus-one or even a group. Just select the double occupancy option when booking, and you’ll be placed in the same room/cabin.
8. What makes your trips different from booking on my own?
When you book with me, you’re not just buying a package — you’re joining a curated, stress-free group experience. I handle the logistics, incorporate cultural touches you won’t find on your own, and personally host the trip, ensuring you’re supported from start to finish.