Travel

Researching

Some people tell me they never travel because they get lost doing the research. Hopefully this site gives you a head-start, but here are some other tips.

Choosing A Destination

Start with the end in mind. If you want a beach vacation, don’t start researching Ireland. What do you desire in your next trip? Nature, luxury getaway, girls trip, romance, downtime? Decide this first then keep that goal in mind when you start to wander.

Don’t forget to consider time of year. Yes, it’s easy to pick the Caribbean when it’s winter in New England, but realize that it does get cold in Bermuda and Hawaii has a very rainy season – so even though these places evoke tropical breezes, it depends when you go. Take a quick minute to research the climate or “travel season” of your potential destination.

PRO TIP: Don’t be afraid to travel to a destination just because it is “off” season. That usually means less than perfect weather, but it also means less crowds and cheaper prices. Researching will also help you decide how far in advance you need to plan. While most trips don’t require much, if you want to attend the Running of the Bulls in Spain or a trip to the Galapagos, you may need to plan this more than a year in advance to have the best experience.

Google is ready to serve you. If you have no idea where to go, try Googling “best girl’s getaway weekend in March” or something like that. Read articles from travel sites and magazines like Travel & Leisure, Lonely Planet or National Geographic. Sometimes I’ll add these brands directly to my Google search because they are reputable and reliable for good info.

You can also just go to Google maps, and start with where you are. Zoom way in. Now drag the map around, zooming in and out to see what’s around you that you might have overlooked.

Need inspiration? Click through my destination pages above. I also have a Journal of Possibilities page where I’m building outlines of future destinations I plan to travel to.

Travel Time

How much time do you have? You can’t go to Europe for a long weekend. Start by figuring out your window.

I like to group travel into 3 buckets: long weekend, week long and 2+ weeks. If you only have a long weekend, you can consider destinations in driving distance or places that are accessible by direct flight from your local airport.

For someone that lives in New York, you can go nearly anywhere in the world direct. If you live in a city that doesn’t have a lot of direct flights, recognize that this will take precioius hours out of a vacation day.

If you’ll be flying, figure at least 2 hours from the time your flight is scheduled to land before you will have your bags, arrive at your home base and have a minute to freshen up. Add an hour for international destinations to allow for customs. If you try to go too far, your long-weekend just turned into only a few hours of actual destination time.

Budget

This is the hardest part for me. But it is a good idea to have a general budget in mind. If you plan to fly to your destination, it’s a good idea to price out flights before you get too far. That also gives you schedules which helps you carve out how much actual time you will have in your destination.

Maybe the bulk of your budget can be allocated for accommodations because you’re going to be hiking or attending free festivals. But if you are headed to Disney, a big piece of your budget will be park tickets and food. You can pick modest accommodations because you’ll be too exhausted to care where your head hits the pillow.

Home Base

Once I’ve narrowed down one or two possible destinations, I usually start looking at accommodations. How much time will you spend in your home base? I’m always tempted to go luxury and tend to pick places that end up being so much more than I needed.

The purpose of travel is to explore and immerse, so all you really need is a safe, clean place to keep your suitcase, shower and sleep.

EXCEPTION: There are exceptions to this general rule. First, there is beauty in booking a luxury hotel for a long weekend with the intention of staying in your room, ordering room service and having spa treatments. Another exception is a ski, beach or boat vacations where you might want a full kitchen, especially in remote destinations where restaurants and nightlife are limited.

Where To Start Your Research

Let’s assume you’ve got a destination in mind now. My first stop is TripAdvisor. I go to the location, click on “hotels” and sort by highest rated. Then I scroll to “reviews”. TripAdvisor has implemented an AI review summary which I find helpful. Also look at the “tips” section above reviews for valuable pointers.

If you are booking last minute, TripAdvisor has a booking tool built in so you can plug in your dates and not waste time looking at properties that are booked. Use the sort features – you can sort by best value, traveler rated, distance to a city center, etc.

PRO TIP: On the left side there are several filters you can apply. One of my favorite secrets is to click “specialty lodging” under “Property Types”. I’ve found some hidden gems by using this filter. It will sometimes include private rentals, Air B&B type properties or more mom-n-pop places. This tool helped me avoid almost booking a room in Europe that did not have a private bathroom!

Using TripAdvisor

• When researching a specific hotel, click “reviews”. Then sort by time of year, or solo travel, or families. Note the bars that quickly show the overall rating that previous travelers have given, from Excellent to Terrible.
• Ignore reviews that rant about bad experiences. They are usually one-off situations.
• Look at the real traveler photos. Hotel websites always make the property look better than it is, so viewing real traveler photos ensures you don’t have too high of an expectation
• Another hidden tool on TripAdvisor under the Review section is “Room Tips”. This can be very helpful. You thought you wanted a room with a view until you read that it came with significant city street noise. Now when you book, you can save money by not reserving that view.

Start Booking

The great thing about booking most things is that you can cancel. Plane tickets may not always be refundable, but there nearly always changeable. Rental car reservations don’t require a credit card and there is no cancellation penalty.

That means there is no reason not to go ahead and secure a reservation for a room, a tour, a rental car or a restaurant in advance. It might help you feel like you’re making progress to get one thing crossed of the list. Not to mention that it is very frustrating if you do all your research, pick the ideal hotel and then find out two weeks later when you are ready to book everything that it is full.

I often use sites like TripAdvisor and Expedia to quickly research prices and availability for hotels. But I ALWAYS go directly to the hotel website to actually book. The only exception to this is when you are going to use credit card points to pay in which case you must book through your credit card site.

PRO TIP: Do your homework before booking through your credit card. I have found that the credit card booking engines typically spit out a price SIGNIFICANTLY HIGHER than the hotel will have if you book directly. I’ve found sometimes it makes more sense to charge the room and use points for rental cars and flights which tend to not have markup.

It is extremely rare for the price to be higher when you book directly vs. using a booking site. Yes, I realize that Travelocity will never sponsor my website if I tell you not to use them, but in my experience you always do better booking with the property directly.

Why? If you use a mass-booking site and then have issues with reservations or rates, you’ve got to deal with 1-800-whomever. The hotel can’t help you. Have a special request? Or want to negotiate for an upgrade when you check in? The hotel can’t adjust your rate if you book through a booking site. So while they would have upgraded you to the penthouse suite for an extra $50 a night, you are out of luck because your rate is already locked in through the booking agency.

PRO TIP: Ask for upgrades! If you don’t ask, you won’t receive. Also specify things like “prefer a room farther from elevator” or “prefer higher floors” in your reservation. You’ll usually get it.

Credit Card Points

This is a treasure that I learned to take advantage of years ago, and I’m still stunned at how many people don’t. The key here is to do your research on credit cards. I used to think it was bad to have three or four cards but I got over that.

You can get great insights on the latest credit card point deals through The Points Guy. I am a loyal subscriber to this site. They are full of great tips and information, even for the road warrior pro traveler.

CREDIT CARD PRO TIP: Updated Feb 2025

I recently did extensive research on this because after many years of loyalty to the Chase Sapphire Reserve card, I realized Chase had made changes to their points earning system and their transfer partners that seriously eroded the value of that card.

Do you own homework, but my current card lineup as of February 2025 is:

• Citi Aadvantage Master Card – I had a heart attack last year when I realized I could no longer transfer points from credit cards to American Airlines. I live in Dallas which is a major American hub and I committed to one airline for the sake of earning status years ago so this was a huge shock. I had an American Airlines card through Barclay but rarely used it because Chase had better miles/dollar. I figured out if I switched to American’s card through CitiBank, I get better mile accumulation and perks (like I get Admiral’s Club access automatically just for having the card). You get 4x miles for dollars spent on flights (it was only 1 mile with Barclay). I also just figured out that Aadvantage Shopping is a site where I can buy all sorts of items and get bonus points for them. Who knew? You just look up a store or item and it tells you if you can earn extra miles per dollar versus just charging to your Aadvantage card where your only getting 1 mile/dollar. Example: I just searched for my favorite shampoo. It was available on several sites, but Dermstore was offering 8x points per dollar. No brainer! I just clicked and it takes me to the Dermstore site where I can shop to my heart’s content on beauty products and earn way more points than if I had just purchased directly on Amazon. I pay my apartment rent on this card (small fee required) and though I only get 1 mile/dollar, it’s a consistent way to build miles throughout the year. I do a lot of my Amazon spending on this card for the same reason.
• Capital One Venture X – This has become a go-to card for a lot of purchases simply because at this time it is the only card offering 2x points on all purchases. Chase Sapphire Reserve used to give 3x points for all purchases but somewhere along the way they dropped it to 1 mile per dollar. Capital One can’t transfer to American, but they have other airline and hotel transfer partners or you can use their booking engine to pay with points. This card gives you a $300 travel credit annually that automatically credits the first $300 you charge for a travel-related expense. I get Hertz President’s Club status with this card. Perhaps the most valuable perk is CELL PHONE PROTECTION FOR FREE. You also get 10,000 bonus miles every year on your anniversary. Annual fee is $395 but since you get a $300 travel credit, it’s technically only $95 per year (which more than pays for the other benefits – especially if you need the cell phone protection).
• Chase Sapphire Reserve – I keep this card specifically for dining out. I get 3x points for eating out plus 10x points on Lyft (so make sure to set this up as your default payment in Lyft). I also get the $300 travel credit annually with this card. The annual fee is now $550 so after the $300 travel credit, your looking at $250 per year which is mostly offset by the extra points you earn if you eat out fairly regularly and charge your Lyft rides to them. Chase now has airport lounges like Amex (Capital One Venture X is also building lounges) and you get access to that. Limited value in my opinion but nice to have.
• American Express Platinum – Ah, the shiny AMEX platinum card. I’ve been a member since 1999 but have determined this card is no longer worth the hefty annual fee of $695. They used to have a $200 per year travel credit, but I noticed last year that it only applies to checked luggage fees (I never check luggage and if I did my fees are covered by my American status) or onboard purchases like internet or drinks (also all covered by my status). There are some other interesting perks with Platinum like a twice per year $50 credit at Saks Fifth Avenue (got some new wineglasses this year). I get Hilton Gold and Marriott Bonvoy Gold status which is a nice-to-have-but-not-life changing benefit. This card offers the cell phone protection benefit, but I get that with Venture X so no longer need AMEX for it. I get a $20/month automatic credit for certain digital entertainment platforms (it’s covering my Hulu monthly fee). It also has a benefit that is enough to cover both my NY Times online and Wallstreet Journal online subscription. They offer a $200 annual hotel credit but you have to book the hotel through their booking engine and it must be a 2-night minimum. I usually figure this out but due to how jacked up their hotel prices are, it’s harder than you’d think to use this. Finally, I get a $15/month automatic credit to Uber/Uber Eats ($20/month in December) so remember to set your default payment in Uber to AMEX if you have this card. Bottom line on AMEX – the cost isn’t worth it anymore. I’ve kept it for the last few years because of the AMEX airport lounge access, but I rarely get a chance to use that and I now have Admiral’s Club access which is essentially the same thing (and Chase club and Capital One club). Last year I went to cancel the card and they offered me several benefits to stay. I think I had to charge $3000 on the card in 90 days and it gave me a $300 statement credit. That, combined with the $200 hotel credit plus the credits toward entertainment, news and Uber basically nullified the annual fee. But who cares about that unless you get the benefit of earning usable points? AMEX has no real value above 1 mile/dollar unless you book your travel through their excessively overpriced engine. I’m officially canceling this year no matter what they offer me