Travel Advisor

Advisor - Alaina Gregerson

Alaina Gregerson

She/Her

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Expertise

  • Europe,
  • Mexico,
  • Continental US,
  • Travel at All Budgets,
  • City Travel,
  • Couples Travel

Based in

The Second City — Chicago, Illinois

Profile details

About

Chicago-based advisor with too many tabs open planning trips, getting my heart set on adoptable dogs I don't have room for and keeping up with restaurant openings across the city.

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Travel style

Moving from budget adventures to more indulgent luxuries, I have loved exploring new cities and cultures. Finding the perfect balance between adventure, leisure and culture is my driving focus that has been tested from India to Europe to the Caribbean and beyond. We can find the perfect trip for your solo, couples' or group travel at any budget!

Alaina 's travel guides & trip reports

Drift Nashville: 3 Day Stay & Inspection curated by Alaina Gregerson
Trip Report

Drift Nashville: 3 Day Stay & Inspection

Drift Nashville opened in early 2024 after renovating a long-time eye-sore in Nashville along the interstate and close to Nissan Stadium. Those two things - close to the interstate and Nissan Stadium ...
A picture of a woman lying on a hammock near the beach.
Guide

Discovering Eleuthera: Your Ultimate Bahamas Escape

Eleuthera wasn't initially on my travel radar. However, upon discovering that a hotel I'd had my eye on was nestled on this charming island, we jumped on the chance to explore somewhere new for an...
The corner of a pagoda with red and orange foliage in the background during fall, one of the beautiful Japan seasons.
Guide

Seasonal Splendor: A Traveler's Guide to the Vibrant Japan Seasons

Introduced to a love of Japan by my brother many years ago, the unassuming archipelago in the western Pacific Ocean is full of cultural heritage, stunning landscapes and delectable cuisine. The Japan ...
A view from a Parisian rooftop with the city lit up below at night, the Eiffel Tower shining with lights in the distance.
Guide

7 Days Visiting Paris & Amsterdam

Paris and Amsterdam are two of the most visited cities in Europe annually. With an endless list of sites, monuments and neighborhoods to explore, it can be overwhelming to narrow it down for a 7-day...
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Favorite hotels

Alaina 's travel photos

A tall cactus in a desert with a pink and purple sunrise.
A beach as seen from a trail above with palm trees in the foreground and a rocky hill in the distance.
Boats along a river lined with trees
An upward angle of the Louvre on a sunny day with clouds
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Alaina 's reviews

Alaina made the entire experience worry-free. Her advice was spot on.

Overall we had a great time! I think leading up to the trip it would have been helpful for us to have a call or run through of the final itinerary before we left. More communication back and forth would have been great so we were left with less “is everything good to go?” leading up to the trip. Holland was easy to navigate and was really small so it was totally okay, but if we were traveling internationally I wouldn’t have felt as confident going into the trip. Overall though we had a great time and all the reservations and recommendations were great!

Working with Alaina was a great decision. She was able to provide great suggestions for planning out our trip like starting off with a hop on/hop off tour to get acclimated to the city and also advised to leave some open time in the itinerary to be able to explore at leisure without structured activities. Everything she ended up scheduling was a great time and she seemed to really know the cities. The trip would not have been the same without her assistance with itinerary planning!

Get in touch with Alaina

Reach out to customize and book your own experience. Or, just to chat about travel in general.

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Advisor - Alaina Gregerson

Travel Advisor

Alaina Gregerson