Stop Searching...

If possible, get travel advisor recommendations from friends & family who have traveled where and how you would like to go.  Or, try these:

Zicasso  -- For high(er)-end trips

4 & 5 Star custom travel packages for journeys designed just for you.

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Mindtrip -- Let AI do the heavy lifting

“Start Anywhere” builds trips from a single photo and lets friends co-plan in one feed.​​

There are some great technological helpers for all aspects of travel planning.  Here are some of our favorites (click here for more).

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TripIt -- Keeps your information in an itinerary

Website and phone app 

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Viator -- Provides great excursions & day tours

Can book everything from cooking classes to airport transfers, to sightseeing tours, OR use it for ideas!

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Mindtrip -- AI helps pull your trip together for you

Check the details, though!

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Google maps & Google translate

Enables you to get around, find your way, and communicate when you're away from home.​​​​​​​

Internet searches for travel can be infuriating.  But AI requests, if prompted well, can be a pleasure and save you all sorts of time and money. 

Here are some of our most successful prompts to use with Chat GPT, Claude, or whatever AI platform you prefer.  Just remember these two things:

1. The more details you give it about what you want, the closer to ideal your results will be;

2. You can use one output as the basis for the next prompt, adding/ specifying what was missing.

3. ALWAYS DOUBLE CHECK THE OUTPUT as AI has been known to make up results.​​

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Planning a trip yourself is a sure-fire way to ensure you travel where you want, when you want, and how you want.  But it does require some work.  But don't worry, we break down all the steps (many of which you can outsource), here.

Flights:

While airfare prices fluctuate constantly, these guidelines can help you book smarter:

• Domestic flights: Book 1–3 months in advance

• International flights: Book 3–6+ months in advance

• Holiday flights: Book as early as possible

• Non-holiday flights: Monitor prices and book during dips

Click here for a more thorough discussion of flight booking strategies

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Hotels:

Booking hotels strategically can lead to better prices, better rooms, and a smoother travel experience.

• Domestic hotels: Book 2–4 weeks ahead

• International hotels: Book 1–3 months ahead

• Holiday travel: Book as early as possible

• Non-holiday travel: Book closer and watch for deals

• Resorts: Book early

• Non-resorts: Be flexible and monitor prices

Click here for a more thorough discussion of hotel booking strategies.

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Restaurants:

If you have a restaurant you know you want to dine at, make your reservation as soon as possible. 

• If reservations are not open/ available yet, find out how far in advance they open up and add a calendar event to remind you to do so. 

• If you have a trusted travel advisor/ concierge, ask them to secure the reservation for you.​​

Tours are a great option for folks who don't want to figure out the details necessary to see and do what they want.  People can take an escorted tour as their trip, or people can take excursions/ day trip tours.

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Viator -- For excursions/ day-tours. 

Pay attention to the ratings and reviews before booking!

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Tauck & Abercrombie & Kent -- Luxury escorted tour providers

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G Adventures -- Small group, more adventure-focus, pretty budget-friendly.

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Insight  & Collette -- More affordable escorted tour providers

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Adventures By Disney & Road Scholar -- Escorted tours for the family & for Seniors

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National Geographic Expeditons -- Expeditionary tours and immersive trips

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Backroads -- For active tours ​​​​​​​

There are cruises to meet virtually all your needs, and you can read about them here.  But, for a list of lines we regularly recommend to folks, here you go.

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Silversea -- Luxe cruise operator with all fees included.

Think: daily excursions as well as butlers, stocked mini-fridge, and unlimited caviar

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Explora -- New cruise line (and ships), unstuffy, and on-board luxury

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Royal Caribbean -- Large ships with solid offerings for everyone, at a more accessible price point.

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Lindblad -- The cruising arm of National Geographic

Offering expeditionary travel to all sorts of exotic locales.

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Disney -- For the young and young-at-heart Mickey lovers.

The name says it all and people LOVE these cruises!

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Tauck & Viking -- Riverboat cruises (Viking also offers solid ocean cruises as well).​​

There are so many ways and interests to consider when deciding what type of trip to take.  Click here for a full-write-up of them and how to make a decision.  Or, here are just a few top-of-mind  recommendations...

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Disney -- offers both escorted land tours and cruises

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Backroads or VBT (for Biking specifically) -- staying active on vacation

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VolunteerWorld or Habitat for Humanity -- service trips

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Natural Habitat or Wilderness Travel -- getting out in nature trips​​

Sometimes you know where you want to go, but then aren't sure about what you need to see or do when you're there.  Afterall, it would be a shame to miss an important site which you may later regret because you simply didn't know about it (or didn't plan far enough in advance to make it work).

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We have a lot to say about this (here) but in a nutshell we recommend:

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• Asking trusted friends & family

who have been there for what they liked best and what they were unimpressed with

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• Checking escorted tour company itineraries

to see what they include

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• Checking Viator

to see what tours and excursions are most popular

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• Asking AI for advice

giving the prompt as much information about what you like and don't like as possible

The world is a big place, with much to explore.  If you aren't sure where you want to go, we have some ideas to give you direction.

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Here's something to get you started.

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And here's information with considerations by general geographic area, along with some inspiration.

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Or, you can always ask Chat GPT or another AI platform and be sure to give it as many parameters as you can.  If you are unsure about how to use AI for travel, read this.

If you're looking for premium seats when you travel, Fly Basis is the website we use.  It has found better fares than booking through other business and first class websites as well as booking directly through the airlines on a couple of occasions, and that's why it's my go-to.   In terms of service, if you have a unique request, they WILL get back to you, but it might be the next day -- so be patient.  For economy flights, we've not found a consistent website that offers reliable low fares.

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