What are some of the best tools to help plan a vacation itinerary?

Question

Your destination is set, your flight is booked - now what? Looking for some smart tools/resources to help plan what to do, where to eat and where to stay. Google searching, scouring traditional travel sites, and reading reviews on Trip Advisor, etc. are tedious and unhelpful (IMO). Are there any truly great resources that utilize algorithms, VR/AR, custom recommendations, etc? Google Trips is a start, but there's so much room to grow. Is anyone truly disrupting the s**t out of travel prep?

Sarah A. Downey · Accepted Answer

Hopper is amazing--you can look up flights and immediately see how expensive they are to book over the next 6 months. It gives you quick visual feedback on when to buy, and you can get push notifications when flights you're watching are about to get more expensive.

Ryan Hoover · Answer

Journy is awesome.  Me and my girlfriend used it in Lisbon last year.  They pair you with a real life human (crazy, huh?) that plans your trip, hour-by-hour.  They'll select the restaurants, sites, and other activities based on your requests.

As someone that hates to plan trips, it's super useful and only $15/day.

Kris Knowles · Answer

If you have a Gmail account, Google Trips is a great way to aggregate your confirmations from your Gmail account and create itineraries. It also provides travel guide information, such as things to know, places to see, and is integrated with places you have ⭐️  saved in Google Maps.

Marcus Vlahovic · Answer

Cheap, cheap, cheap - (really) the cheapest flights. This + my next suggestion = travel godmode.

Marcus Vlahovic · Answer

In combination with SkyScanner (or without) Rome2Rio is crazy good for planning out your vaca travel on the cheap. Example - to get to TNW 2017 you could use SkyScanner to fly to Slovenia for half the price of Amsterdam (from the US) and then use rome2rio for trains + buses, all mapped out for you, on the cheap.

Austin · Answer

Thanks for the suggestion, Kris. I really like Google Trips too. I'm using it as the base of our itinerary. I think Trips will evolve into something amazing, but the lack of a synched desktop version frustrated me a bit. Also, their "Day Plans" is promising, but you cannot easily add a stop along the way unless it's an existing POI (or unless you star it in Maps first, then jump back into Trips). Unless I'm wrong :)