Amy Cummings

Ask me about

City Travel

Couples Travel

NYC

USA

Europe

Peru

My Story

NYC-based trip planner who treats every vacation like it’s her dissertation.

My Travel Style

Rooted in the Midwest and now living in NYC, I bring a unique perspective to travel planning. I started with budget-friendly adventures but have since leaned into boutique and luxury travel. Whether it’s uncovering hidden gems, planning food-focused itineraries, or blending style with practicality, I craft experiences that feel curated, elevated and unforgettable.

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My reviews (5)

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Margaret T.

travel to Dubrovnik

6 months ago

This was again a knock out selection on the hotel from Amy. It was perfectly walkable, so convenient to all the activities and sights, while being secluded enough to be quiet and peaceful retreat.

M

Margaret T.

travel to Split

6 months ago

M

Margaret T.

travel to Zagreb

6 months ago

Amy did a fabulous job of finding a convenient hotel for my trip, and she focused on my priority -- close to sights and walkability.

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Elinor M.

travel to San Antonio

6 months ago

Amy was an incredible! She took the time to help me find the best dates and room options, and went above and beyond answering all my questions. Traveling with kids is no small task, but Amy made it easy. She took care of us every step of the way and checked in before, during, and after the trip. You can tell she truly cares—we felt so supported!

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Caroline B.

travel to Washington, DC

9 months ago

Amy was very communicative and understanding when I needed to make last-minute changes to my itinerary. She communicated with the hotel on my behalf and managed to extend my trip and keep me in the same room without requiring me to do anything. I really appreciated her attention to detail and communication :)

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Margaret T.

travel to Dubrovnik

6 months ago

This was again a knock out selection on the hotel from Amy. It was perfectly walkable, so convenient to all the activities and sights, while being secluded enough to be quiet and peaceful retreat.

M

Margaret T.

travel to Split

6 months ago

M

Margaret T.

travel to Zagreb

6 months ago

Amy did a fabulous job of finding a convenient hotel for my trip, and she focused on my priority -- close to sights and walkability.

E

Elinor M.

travel to San Antonio

6 months ago

Amy was an incredible! She took the time to help me find the best dates and room options, and went above and beyond answering all my questions. Traveling with kids is no small task, but Amy made it easy. She took care of us every step of the way and checked in before, during, and after the trip. You can tell she truly cares—we felt so supported!