Travel Advisor

Jimmy Cunningham

Expertise

  • Solo Travel,
  • Couples Travel,
  • US Cities,
  • Caribbean,
  • Luxury Travel,
  • Fitness Travel
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Jimmy Cunningham Travel Agent wearing red sports jersey

About

Fitness fanatic and travel enthusiast. My full-time job as a Senior Sales Engineer in Boston, MA allows me tons of travel to our HQ in Germany and many more great places.

Home airports

BOS.

My travel style

I thrive in travel middle-grounds. I typically will combine elements of rugged, nomadic type travel that is full of adventure with more leisurely opportunities to relax in luxury. This can be through a combination of the stays I book or the excursions and adventures I set off on.

Favorite hotels

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Costa Blu Beach Resort, Trademark Collection by Wyndham

A colorful and laidbaid tropical-design adults-only retreat with stunning views of the Caribbean and surrounded by natural beauty of Belize.

Margaritaville Hotel Nashville

A casual and fun escape from Downtown Nashville with a brightly-colored, coastal-inspired interior and laidback attitude for fun-lovers.

The Westin Kierland Resort & Spa

This family-friendly hotel in the quiet Sonoran Desert of Scottsdale, AZ has an aquarium, award-winning golf course and spa on-site.

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Recently returned from:

  • Beer tasting at brauhaus’ in Munich.

  • Swimming with sharks at the two biggest barrier reefs on Earth – Australia and Belize.

  • Chanting songs at a Chelsea game in London.

  • Watching the championship game at the famous MSG arena in NYC.

Dreaming of:

  • Safari in Africa.

  • Hiking in Machu Picchu.

  • Croatia and the Greek islands.

  • Driving across New Zealand.

One thing I can't travel without...

Airpods.

Two truths, one lie:

  1. I've been to all 50 states.

  2. I was a professional athlete.

  3. I've swam with sharks at the two biggest barrier reefs in the world.

Jimmy's guides

Jimmy Cunningham Travel Agent wearing red sports jersey

Travel Advisor

Jimmy Cunningham

Get in touch with Jimmy

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

You can normally expect a response from Jimmy within a business day or so. You'll also be subscribed to our travel newsletter (you can unsubscribe at any time).