Travel Advisor

Jon Herlihy

He/Him

Expertise

London,
New England,
Italy,
Japan,
Luxury Travel,
Arts & Culture

Based in

Bay Area & Boston

Travel Advisor

Jon Herlihy

Profile details

About

If travel planning were an olympic sport, I’d be going for gold. For 15+ years I obsessed over the details as a Marketing Director in Tech, and now I’m taking my passion for travel full-time.

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Travel style

Once I have a destination in mind, I map out the top sites and activities, best hotels, and of course, restaurants. I choose hotels based on central location, value (price & perks) and unique experiences they offer. My ultimate city travel day: free breakfast at the hotel — then off to explore museums, cafes, and...the unexpected. Meet up with old friends for dinner or a show, and top it off with a nightcap in the lobby bar. Ultimate beach vacation? Watching the waves with a coconut drink in one hand and a mystery book in another.

Contact me if you have an upcoming trip and want to explore how to travel like a pro.

Jon 's travel guides & trip reports

View of the flowers and the sea at Wequassett Resort.

Guide

Planning a Destination Wedding on Cape Cod

Cape Cod is a summertime hot spot for locals and tourists alike, but it’s also a booming wedding destination for couples from all over the world. Known for its historic cottages and picturesque...

A white sailboat with the sail number 520 on open water.

Guide

Summer in Boston

Boston is one of the most dynamic and exciting cities to visit in summer. Steeped in history and culture, Boston is walkable and tourist friendly. From world-class museums and sports teams to sunset...

A big ferry wheel near a water body during day time.

Guide

Complete Three Day London Itinerary

No matter how many times you’ve been to London, there is always something new to see, do or experience. The city is steeped in rich cultural history, but is also paired with a modernity and ease of...

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Favorite hotels

Corinthia London

Unrivaled luxury London hotel with elegant style, complimentary English breakfast and panoramic penthouses.

Fora Perks

★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Castello di Casole

La dolce vita brought to life on 4,200 acres of fairytale Tuscan countryside.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Bernardus Lodge & Spa, Carmel Valley

A true Wine Country escape in Carmel, with oversized suites and standalone villas, plus a lauded farm-to-table restaurant.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade whenever possible.

The Upper House

Chic hotel in a high-rise building with modern suites and city views.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Jon 's travel photos

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Jon 's reviews

Jon was fantastic to work with. Willing to hear my suggestions and together with his ideas we had a wonderful trip. No problems with hotel or tickets. I definitely will reach out to Jon again.

Kathy F.
Booked travel to Las Vegas
December 2024

Herlihy is a pro. We enjoyed working with him.

Robert K.
Booked travel to Italy
November 2024

Love the personalization of the recommendation and the lovely welcome gift. Jon reached to let me know that the hotel was expecting me and checked in to see how my stay was. Great service!

Alpa V.
Booked travel to San Francisco
September 2024

Working with Jon was so easy and helpful. He sent us an itinerary ahead of time. Followed up several times to make sure we were all set. By booking with Jon we were also upgraded to the one bedroom suite which was such a special treat. Jon is communicative, always available to answer questions, and had great recommendations. I look forward to booking my next trip with Jon!

Jennifer S.
Booked travel to California
May 2024

Get in touch with Jon

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

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