Last Minute Travel Deals

Escapevelocity

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I'm retiring in one month and wife doesn't work. We're both 55 yo.

One of the ideas I have long dreamed about is the freedom and leverage that being unencumbered by work will provide in terms of last minute travel deals. I always get these airline deals in my email with crazy low fares but they usually require travel within 30-60 days.

I'd like to hear from you if you have regularly taken advantage of these type of deals and your favorite ideas or creative approach for maximizing the value of flexibility when it comes to your cost to travel. I'm thinking we should shift our mindset to not planning any significant paid travel more than 2 months in advance and just jumping on last minute deals to save 50-75% on typical costs.
 
I plan to, but so far haven't done much "real travel." I am looking forward to a road trip this spring with a somewhat loose itinerary. I may look into travel social groups at some point as I prefer to travel with someone (but not crazy about group itineraries). I am jumping on flights to visit my family more now that I'm free... occasionally can fly RT for ~$100.
 
I had the same thoughts when first retired, but rarely found any great deals ?

Still if folks know of some, please post :)

Thinking hard, I did find an Alaska cruise this past summer, 1 week and cost was ~$500 pp for an extra large balcony room, Airfare was extra. It was great and we enjoyed it.
 
Pre covid , post retirement, we did a fair amount of last minute travel. Usually 2 months on international travel in the fall, and again in the winter.

Last minute for us can mean a month in advance down to the next day. Airline, hotel, cruise, AI. We use all sorts of vendor and third party sites, Many non NA sites since we typically travel in Southern Europe in the fall and SE Asia/Australia or Central America/Mexico in the winter.

Two reasons for last minutes. Pricing opportunities plus we may not like a place as much as we thought. Last pre covid trip we booked 3 days in Huatulco and expected to spend a week or more. We wanted to move on so we went up the coast to Puerto Escondido. Booked two nights. Stayed for 7. Same in Acapulco and a few other places. Picked up 2 last minute AI stays prior to that in Playa and after that in PV....booked both last minutes through a UK web site.

On a prior trip we were sitting in our hotel in Saigon after four days thinking about where to go next. Saw a $27 flight to Da Lat on Jetstar so we we flew there the next morning.

We have taken advantage of numerous last minute 7 day AI's (than included air) to Mexico, DR, and Cuba. The closest being three days out.

Since retiring the only cruises we buy are inside the final payment window. Anywhere from a few days out to five or six weeks out from sailing. We establish a buy price. When our price hits we buy. If not, we walk and do something else.
 
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One of the ideas I have long dreamed about is the freedom and leverage that being unencumbered by work will provide in terms of last minute travel deals. I always get these airline deals in my email with crazy low fares but they usually require travel within 30-60 days.

As a frequent traveler myself, a few things:

- Once you start looking, you'll find better deals than those dropped into your email box (by combining airlines + flying low cost airlines). For example, to get to many places in Europe you can fly to AMS or CDG roundtrip from USA and then change to some local EU airline.

skyscanner.com, google flights are good start for those. Avoid "watch airfares" websites which all seem to be garbage.

- Saving on flight only makes sense for short trips; for 4+ weeks stay in many locations you'd be looking for accommodation deals, not flight deals.
 
We've done last minute cruises-usually 2-3 weeks out. We are driving distance to four ports so it's no problem. My "target" price is about 100/day for a balcony including port fees/taxes. So about 1500 all in for a week for 2.

I was following a certain cruise in April of last year as a relative was already booked on it (December cruise). Nobody knew if it was even going to happen. It was hovering around 2500-3000 for several months. Then I stopped looking.

Omicron took off and the prices dropped. Started looking again mid-November.
Booked two weeks out from the cruise date for 1400, balcony for two.

Also Princess has "drop and go" for last minute ones. Did a 10-day NY to Quebec for about 800 pp all in.

That's how we do our cruises.
 
We are on the list for Princess.

Celebrity and RCI have, or used to have, Tuesday specials. The one proviso is that you need to understand what an average price is and what a good price is.

We usually follow pricing for 2 or 3 ships on the same date/same itinerary. When our price hits we buy. Sometimes it doesn't so we always have a Plan B because we are invariably in the midst of a land trip.
 
We used to live in Atlanta, and Delta Airlines would often throw out incredible deals out of Atlanta on flights with a 1 week notice. You could go out on Friday and come back on Mondays.

We often would take advantage of those incredible deals.

If we had the chance today, we'd take a last minute deal. That's how I prefer to travel anyway--on the cheap. And we don't like to plan too far ahead on vacations.
 
I love having the flexibility of using the low-fare calendar on Southwest which lets me see the cheapest days to travel. This last summer I flew to Hawaii to visit a friend (in on Tuesday - out on the second Friday) for $198 roundtrip, all fees and taxes included! (A side benefit was that the planes were quite empty, which was great for COVID distancing.)

Last minute travel sounds good, but it's not always practical and you can sometimes save as much, and lock in your plans, by booking earlier rather than later - on flights and on cruises. Cruises will usually offer early-booking discounts, shipboard credits and other perks just after announcing the itinerary.

On Southwest, since I fly them often, when rates are low I will buy a ticket way in advance [using their calendar] to lock in the low fare and use it as a 'save the date' assuming everything works out. For example, I bought tickets to visit Puerto Rico during Christmas six months in advance when cheap seats were available and rates were really low. I knew I wanted to go, but wasn't sure if my schedule (or COVID) would pan out. Fortunately I ended up taking the trip; but if something had come up, or I decided not to go, I could have cancelled [up to the day of the flight] and applied the entire fare to another Southwest flight without penalty.
 
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During the pandemic, we've been using relatively last minute deals on airfare (mostly via DW's premium Scotts cheap flights membership), as well as taking advantage of cheaper lodgings via airBnB and other sites.

Prior to pandemic, we tended to plan well in advance because our desired trips tended to book fast. Given the ever-changing entrance requirements for countries (and in 2020, for Alaska), we've quit doing this for now.

(Still have a 3 week Antarctica/etcetera cruise that we booked in 2018. Hopefully, we'll finally get to do that this year!)
 
I think it sounds great in theory and obviously works for many, but I guess we’ve been too committed to particular destinations and times to travel so we end up booking in advance. We may pay more, but at least we go where we want and stay where we want. We’ve only cut one trip short in the past because we didn’t like the destination we chose.
 
I think that whether or not you take advantage of last minutes depends on your travel habits. Where you like to travel, for how long, etc.

In my business life my frequent travels were very well planned. As was vacation travel.

Since retiring we have changed that regimen to much longer, more frequent, and very spontaneous travel. With carry on only.

We may pick up a last minute AI from our home that includes air. Hit the buy key and a few days later we are on a plane to Mexico, DR, or Cuba. All we need to do is pack...all other arrangements included.

Our typical twice yearly pre covid trips might simply start with Sept/Oct air reservations into Athens and a flight home from London. Winter may look like a flight to Bangkok and a flight home from Sydney to HNL. Then we worry about getting the rest of the way home. Everything in between is typically very 'open' with the exception of a few days before/after each flight. We know generally where we want to go but the length of time in each location or the order in which we travel may vary greatly from our original expectations and thoughts.

This type of travel is not for everyone. We started off retirement with seven months of travel like this. We had an African safari booked in November and a condo in Costa Rica booked for a month in January. We had plan, but it was invariably subject to change.

After doing this, and enjoying it so much, we changed to this mode of travel because it suits us. The emphasis is how and where we travel. Picking up last minute offers was ana pleasant afterthought and experience.
 
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