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Playbook

We’re glad you’re here.


We appreciate you
all for your constant and ongoing support, as we attempt the grow the most helpful travel tips & tricks brand in the world. 🙂 

This Playbook is only for our VIP email list… it’s hidden from public view and only accessible from this link, so be sure to bookmark or save this link to access it in the future! 

We will be making updates regularly as we discover new information. 

Our goal for this Playbook is to share all of that information with you in a condensed and singular place. We’ve put a LOT of information in here already, but we’ve tried to keep it as short as possible! 

We sincerely hope you enjoy and find value in this resource.  Please share the playbook sign-up page with your friends and family if you do!

Until then, we’ll see y’all in another video soon!

   – Austin & Courtney

Flight Tips & Tricks

With this tool, you can search an entire continent (or even put “anywhere”) and find flights + prices from your departure airport of choice to various cities around the world.

You don’t even have to put specific dates if you want to keep it as open-ended as possible! 

Filters, Track Prices, Date Grid, & Price Graph

These incredibly useful charts and graphs are all accessible from the main Google Flights search page.

Each tool provides a unique insight into helping you plan the perfect time to plan and book your upcoming trips and flights! 

One of our favorite Google Flights hacks is the “Track Prices” feature.

After you have entered a detailed search, including the necessary filters, you can toggle on “Track prices” and you will receive an email every time the price goes up or down. It’s amazing… AND it’s free.

We track every upcoming flight that we plan on booking within the next year.

Southwest Companion Pass

Speaking of Southwest Airlines …

One of the greatest travel perks of all time is the Southwest Companion Pass. This is a Buy-One-Get-One FREE perk that you can share with a companion of choice.

Courtney and Austin have had this for the past couple of years and it has saved them thousands of dollars on flights.

We outline EXACTLY how to earn the companion pass in our blog:
How To Earn The Southwest Companion Pass

book "backwards" - aka, be flexible.

This is how most people book a trip:

  • Choose where they want to go 
  • Decide the dates they want to go there 
  • Then, they look up flights and book the flights that fit both the exact location AND dates that they previously decided.

Booking “backward” can save you hundreds, if not thousands of dollars on your flights!

Instead of:
Exact Date + Exact Location = Overpaying…

Try this instead:

Pick a general timeframe that you would like to travel, then use tools like Google Flights and Going to find a deal to a location you are interested in!

You decide on a General Time Frame + Crazy Good Deal, then the Location Based on the Deal!

How to find these deals?

Our favorite flight website is called Going … which is an awesome resource that tracks and analyzes flights from the US to cities all around the world and emails you when a flight price drops significantly! Then you can book that deal directly with the airline.

They just find the deals for you, and then you book as normal!

Our 2 best deals with Going …

  • Nonstop ATL-St Thomas USVI Feb 2022 $132 per person roundtrip on Delta

  • Nonstop JFK-Paris March 2024 $230 per person roundtrip on American.

resources

Mobile Passport Control App
 When returning to the US from an international trip, you may see an MPC line in customs that is WAY shorter than the main line!

The app is free and super easy to use. Everyone should have this app downloaded on their phones before returning to the US!

TSA PreCheck
it’s only $78 for 5 years and has saved us more hours than we can count.

Keep shoes on and laptops in bags. Here are the details and how to apply. The application is super simple, and you need a quick in-person interview that is even offered at some Staples locations!

Global Entry 
This is like the Mobile Passport Control on steroids. When returning to the US from a foreign country, you’ll breeze past customs. $100 for 5 years.

Oh, and guess what? It includes TSA Precheck!!

We highly recommend Global Entry for anyone who travels 2+ times per year out of the United States.

The application process is a little tougher than TSA precheck, but we’ve found the easiest way is Enrollment Upon Arrival.

Basically, you get preapproved online and when you arrive home in the US on your next international trip you can visit the EUA offices in the customs building and knock out your interview in around 15 min!

(This is what Courtney did. We had a tight layover to catch and she still made it in time!)

Clear 
Clear lets you skip the TSA line and go to the front. We recommend Clear for anyone who flies more than 10 times per year.

The cost is $189, but you can add up to 3 family members for $70/ea.

If you have TSA Precheck AND Clear, then you get to skip the TSA Precheck line – which is awesome. We love having both, and rarely wait more than ~5 min in security at small airports and ~10 min at larger airports.

Pro Tip:
Read our next section to see which Travel Credit Cards include TSA Precheck, Global Entry, and CLEAR … For Free 🙂

All Things Points & Miles

points/miles/ rewards program organizer

We created a Points, Miles & Rewards Organizer for y’all in Google Sheets!

It’s super easy to use. If you click the Cell to the left of Column A and above Row 1 it will select all Cells. Click Command C or right click then Copy the sheet. Create a new Google Sheet or Excel and paste our template inside!

Fill out your points and enjoy having everything all organized in one place. Don’t forget to update every now and then!

If you frequent any of these popular companies, make sure you register for a free rewards account with them!

These cruise lines, hotels, casinos, etc. ALL have great membership programs that you should be signed up with. We always recommend booking directly, or through a trusted travel agent.

This way, you will earn status with these brands and if something goes wrong, you will be able to deal directly with the company (instead of a third party).

Our Fave Everyday Credit Cards

These are our TOP 3 Favorite every day Credit Cards for getting a TON of points…

(AKA, points that you can transfer to your preferred airline partners and redeem for amazing deals like $10,000 business class & first class flights!)

We recommend having at least 2 in your arsenal!

  1. Chase Sapphire Preferred® Card (Find Best Travel Cards HERE)
    • 3x Ultimate Rewards points on restaurants, select streaming services, and online groceries (excluding Target, Walmart, and wholesale clubs). *Note this also excludes in-store grocery purchases.
    • 2x Ultimate Rewards points on all travel purchases outside of the Chase Travel℠
    • $50 Annual Chase Travel Hotel Credit
    • Free DashPass (when card used through DoorDash)
    • Primary rental car insurance when you pay with the card
    • Trip cancellation/interruption insurance (terms apply)
  2. American Express® Gold Card (rates & fees) –
    • 4x points at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1x.
    • 4x points at U.S. Supermarkets, on up to $25,000 per calendar year in purchases, then 1x.
    • Up to $120 Restaurant Dining Credit – When you dine at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. (Enrollment required)
    • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and each month automatically get $10 in Uber Cash for Uber Eats orders or Uber rides in the U.S., totaling up to $120 per year. Effective 11/8/2024, an Amex Card must be selected as the payment method for your Uber or Uber Eats transaction to redeem the Amex Uber Cash benefit.
    • $100 Resy Credit: get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. (That’s up to $50 in statement credits semi-annually. Enrollment required.)
    • $84 Dunkin’ Credit: With the $84 Dunkin’ Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin’ locations.
  3. Capital One Venture Rewards Credit Card – 
    • 2x miles on every purchase
    • Up to $120 credit for Global Entry or TSA PreCheck Value

Our Fave Credit Card for travel perks

This is our Favorite Credit Cards For Travel PERKS.

This isn’t typically a better spending card than the 3 listed above to maximize points, but it has amazing perks and sign-up bonuses that make it worth adding as an additional card in your wallet.

  1. The Platinum Card® from American Express (rates & fees)  – 
      • 1x points on all purchases
      • Priority Pass + Centurion Lounge access. (Enrollment Required)
      • $199 CLEAR® Plus Credit – Breeze through security with CLEAR® Plus at 100+ airports nationwide and get up to $199 back per year on your membership (subject to auto-renewal) when you use your Platinum Card®. (Enrollment Required)

      • Up to $120 application fee credit for Global Entry or TSA PreCheck*

      • Up to $200 in Uber credits annually (Enrollment Required)
      • Up to $200 in airline fee statement credits per year after you select a qualifying airline and incidental fees are charged by the airline to your Platinum Card®. (Enrollment Required)
      • Up to $200 in hotel credits (enrollment required). Up to $200 back in statement credits each year on prepaid Fine Hotels + Resorts® or The Hotel Collection booked with Amex  Express Travel when you pay with your Platinum Card®. (Enrollment Required) The Hotel Collection requires a minimum two-night stay
      • Up to $240 in digital entertainment credits issued in up to $20 in statement credits for select streaming services each month when you pay for eligible purchases with the Platinum Card® (Enrollment Required)
      • Gold status with Marriott and Hilton (Enrollment Required)

      *Receive either a $120 statement credit every 4 years for a Global Entry application fee or a statement credit up to $85 every 4.5 years for a TSA PreCheck® (through a TSA official enrollment provider) application fee, when charged to your Platinum Card®. Card Members approved for Global Entry will also receive access to TSA PreCheck at no additional cost

    • The Centurion Lounge is one of our favorite airport lounges which includes gourmet food and top shelf beverages. You also get access to Delta Lounges when flying the same day on Delta.
    • This card is loaded with perks, but after you earn the signup bonus it’s better to just keep it for the perks and spend money on cards that earn more points!
For more information and additional card options, check out our blog discussing all of our favorite credit cards here!

so You've got a bunch of points... now what?

What do you do once you’ve accumulated all of these points?

There are so many ways to redeem points once you’ve earned them, but we always recommend transferring credit card points in order to maximize your value.

Amex, Capital One and Chase all have great travel portals, but using points in a portal can normally only get you $.01 to $.0125 per point, while transferring points can get you $.02-$.10+ if done correctly!

Point.Me is an amazing website that makes transferring points for the highest value possible … very, very easy!

Here’s a quick video we made explaining how it works: 

This website helped walk us through the steps to transfer Amex points to Emirates and redeem them for two business class seats from Newark to Athens, Greece in May of 2023.

It was one of the best flight experiences we’ve ever had! We only paid $100 each in taxes for a flight that can cost well over $4,000!

With code MAXWELLSTRAVEL, new users will get their first monthly subscription for just $5!

For a more in-depth explanation of gaining credit card points and how to use them, check out our blog post HERE!

Points Path

FREE TOOL: Award Search for Google Flights!

If you’re ever wondering when’s the best time to use your frequent flyer miles, this is the tool you’ve been waiting for!

Points Path is the first award flight search engine that provides both the cash price AND the points price of every flight in a Google Flights search.

Using Points Path is easy! Just install the extension on your browser, then search for your trip on Google Flights as you normally would.

In addition to getting Google’s regular cash-only results, Points Path will add the current points or miles price to each flight (when available) and also let you know which is the better deal!

When you’re ready to book a flight, click through to the normal Google Flights booking page, where you’ll find the option to book with your points directly with the airline (via Points Path) right next to all the usual cash options.

Points Path is an all-in-one solution that ensures you’re always getting the best deal for your travel, no matter how you pay.

Transfer Bonuses

… And if you want even more bang for your buck, look no further!

Transfer bonuses are a powerful way to maximize the value of your credit card points when booking travel. These promotions, often offered by credit card issuers like American Express, allow you to transfer points to specific airline or hotel loyalty programs with a bonus percentage.

For example, in December, American Express offered a 40% transfer bonus to Flying Blue, the loyalty program for Air France and KLM. This means for every 1,000 Amex Membership Rewards points transferred, you’d receive 1,400 Flying Blue miles—essentially stretching your points further.

By timing your transfers during these promotions, you can significantly reduce the number of points needed for flights, hotels, or other travel rewards. Keep an eye on your credit card issuer’s transfer partner promotions to ensure you’re getting the most out of your hard-earned points.

Cruising: Insider's Edition

Notes From The Maxwells:

Cruising is one of our absolute favorite ways to explore new places!

Though cruising can be a very polarizing method of travel (you either love it or you hate it), we believe that many of those who have had a bad experience with cruising may not have experienced its full potential. We’re here to provide you with all of our tips and tricks to make you fall in love with cruising!

First of all, to make sure you’re starting off your cruise the right way, you need to make sure you’re getting the best price.

Before we book with our trusted travel advisor, we make sure to log onto cruise.com to help us easily compare prices! From this site, you can filter by destinations, ports, cruise lines, ships, dates, and lengths, and then easily compare pricing. 

After we slim down our choices, our travel advisor will help us get the best price possible, along with any additional perks!

How to choose a cruise line

Choosing the perfect cruise line depends on your travel style, preferences, and budget.

Cruise lines are categorized into mainline, premium, entry-luxury, ultra-luxury, expedition, and river cruises, each offering unique experiences. Mainline cruises cater to families and budget travelers with activities for all ages, while premium lines elevate the experience with enhanced dining, service, and amenities.

Entry-luxury and ultra-luxury lines focus on exclusivity, fine dining, and personalized service, often appealing to seasoned travelers seeking indulgence. Expedition cruises bring adventure and nature to the forefront with destinations like the Galápagos or Antarctica, and river cruises offer an intimate way to explore Europe, Asia, and beyond.

To dive deeper, check out our blog, where we break down each category and explain which lines fit your travel personality. It’s a helpful guide to ensure your next voyage perfectly matches your dream experience!

Etiquette

This is a key component of your overall experience. 

Though you may feel that these things are common sense, we feel that it is important to include them due to their importance — 

  • Chair Courtesy – a simple fact of life: cruises can’t possibly include a pool deck lounge chair for each and every guest, so plain & simple – don’t be a chair hog! If you’re using a lounge chair, great, and if not, take your towel off and let someone else use it!
  • Dressing & Attire – Though cruise ships have become much more casual over the years, we feel that it is still very important to look your best for certain occasions!

    As much as you want to wear your swim trunks and Crocs to dinner, a more appropriate outfit for the dining rooms will gain you respect from the staff and most likely, better service!

  • Respect – the most basic, but most important piece of etiquette! Every staff member, from cabin stewards to wait staff to captains, should be treated with the utmost respect and kindness. Respect and kindness are reciprocated, and you will receive top-notch service from your cruise staff as long as they feel respected!


In conclusion: Be Aware, Be Kind, and Be Respectful!

The Ultimate Cruising Checklist

Use these tips to navigate your next cruise and find out why we love cruising so much! 
  1. PRE-BOOK EVERYTHING – 100% of the time, spa packages, dining packages, drink packages, etc. will be much cheaper if you pre-book them as opposed to booking once you board the ship!
  2. Upgrade your dining experience – one thing we will always preach is “you get what you pay for.” Typically, complimentary restaurants onboard cruise ships (unless you sail with a luxury cruise line) are going to be fine – but do you really want your vacation food to just be fine?! In our opinion, specialty dining restaurants are more than worth the upcharge – with improved service, increased food quality, and a much more luxurious atmosphere for dining – we think you’ll agree!
  3. Book a convenient cabin – when initially booking your cabin, you will have the option to choose where you would like to reside for your sailing. Make sure to do some research on your ship beforehand and locate the places you will frequently visit. Whether that is the buffet, the main pool, the adults only pool, or your favorite bar, choose a cabin that makes sense for YOU! We typically try to book a high-floor mid-ship cabin.
  4. Bid on a higher category cabin – unless a ship is completely booked, you should receive an email from your cruise line regarding “upgrading” your cabin.Though most will shrug this off as an attempt for the cruise line to make more money, it is actually a way for you to stay in a nicer room for a decreased price! For example, we have previously booked an interior cabin, then a few weeks prior to our sailing, we received the upgrade email, asking us to “bid” on a balcony cabin. Depending on our desire for that balcony, we could bid anywhere from a specified “minimum price” to a “maximum price.” Typically the week before the sailing, we would be notified if our bid was accepted or denied based on the amount of other passengers who bid on the available balcony cabins. Such a simple way to upgrade your experience!
  5. Specify your drinks – if you purchase the unlimited drink package, there will be a certain category of drinks included in your package depending on the cruise line. More often than not, top-shelf liquor is actually included, so make sure you’re ordering it! Instead of ordering a “margarita,” order a “margarita with patron (or other preferred tequila)”! Instead of just ordering a “strawberry daiquiri,” order a “strawberry daiquiri with the best rum included in my package”! By purchasing the drink package, you have already paid for these top-shelf liquors, so make sure you’re ordering them!
  6. Book port excursions outside of the cruise line – this one can be a touchy subject, but in our experience, we have ALWAYS had a better quality excursion when booking outside of the cruise line! Typically, a cruise line excursion is going to pack as many people as possible in order to make the most money – however, when booking independently, this is not the case. For example, we once went on an independently booked excursion on a catamaran with 10 people total – the cruise line excursion on the same size catamaran booked 40 people. But how do you find reliable excursions that are 1. Safe and 2. Will make sure to get you back to the boat in time?!

    Insert Viator – our favorite excursion booking website! On Viator, excursions are reviewed and rated by actual people who completed each excursion – by booking highly rated excursions, you can trust that you’re going to have an amazing experience!

  7. Go where the people are NOT – A frequent complaint we hear about cruising is that the ships are too crowded, but that is certainly not the case! These ships were built with the crowds in mind – the problem is, everyone does the SAME thing!Next time you’re on a cruise, try to break yourself out of the mold. When everyone heads to the buffet for lunch, try a sit-down lunch in the main dining room. When everyone herds to get off of the ship in each port, grab a coffee and watch the chaos – then disembark 30 minutes later! This is one of the simplest, yet most effective tips we can give to make your cruise experience feel more luxurious!
  8. Show up prepared – limit your travel stress tenfold by preparing for your trip appropriately! 
    • Step 1: Check into your cruise online – this will give you the ability to choose your preferred boarding time & complete any paperwork beforehand
    • Step 2: Download the app – cruise line apps can be SO helpful! From giving you the layout of your ship to listing the daily activities to explaining your itinerary, the cruise apps are a wealth of information
    • Step 3: Print your boarding documents – make your life easier and print everything you need ahead of time! Confirmation document, luggage tags, etc.
    • Step 4: Pack in advance using our CRUISE PACKING LIST – and thank us later. 🙂

Finding Reliable Excursions

Whether you’re on a cruise or remaining in one place for a trip, excursions play such a big role in your ability to explore a new location and provide extra fun!

We often get asked how we find our excursions and how we know they are going to be safe and reliable – it’s actually a lot simpler than it seems!

We have two favorite websites that we use to book each and every excursion – www.viator.com and www.tripadvisor.com

Each of these websites are fueled by reviews! This means that you are able to see explanations of real experiences and a breakdown of why (or why not) each excursion is worth your time and money. You can either go into each of these websites with an idea of what you want to do and search from there, or you can simply filter through the hundreds of different excursions available until you find the right fit!

Either way, you want to make sure you are thoroughly reading reviews and choosing the top rated excursions – this way, you can go into your excursion confident that you fill have a great time!

Here are a few of our current favorites: 

Apotheoseas BVI Boat Charter – British Virgin Islands

Sting Ray City Catamaran – Cayman Islands

Jolly Pirates Snorkel, Sail, & Swim Cruise – Aruba

Serendipity Charters Luxury Cruise – Costa Rica

Cliff-Jumping UTV Tour – Aruba

Capri & Blue Grotto Boat Charter – Sorrento, Italy

Midnight Sun Boat Charter – US Virgin Islands

Shareholder free credits

Get onboard credit on your next cruise! 

If you are a shareholder of over 100 stocks on Norwegian Cruise Line, Royal Caribbean Group, or Carnival Corp., you can submit a shareholder form and request $100 onboard credit on your next cruise. 

It’s a pretty cool feature that we just recently took advantage of on our last cruise – Check it out! 

NCL Shareholder OBC Benefit

Royal Caribbean Shareholder OBC Benefit

Carnival Shareholder OBC Benefit

Book Cruises with POINTS

Virgin Red just made cruising history by letting you book ANY Virgin Voyages cruise with points – one of the first major cruise lines to go all-in on points bookings! What You Need to Know Virgin Red members can now use their points to book select Virgin Voyages cruises – a game-changer in the industry! Current options include:
  • 4-night Caribbean “Fire and Sunset Soirées” cruise from 305,000 points
  • 5-night “Dominican Daze” from 380,000 points
  • European adventures starting from 515,000 points
Important to note: these rates are per CABIN (not per person), and currently only Sea Terrace cabins are available for points bookings. These adults-only luxury cruises include gourmet dining, entertainment, Wi-Fi, and gratuities in your points booking!
How to Get Virgin Points Don’t worry if you don’t have Virgin points yet – they’re some of the easiest points to accumulate:
  1. Transfer from credit card partners – Virgin Red has partnerships with all major credit card programs, including:
    • American Express Membership Rewards
    • Chase Ultimate Rewards
    • Capital One Miles
    • Citi ThankYou Points
    • Bilt Rewards
  2. The new Virgin Red Rewards Mastercard – Earn 40,000 bonus points after spending $3,000 in the first 90 days, plus earn 100 points per night when sailing with Virgin Voyages!
  3. Link Virgin Atlantic Flying Club – If you have Virgin Atlantic Flying Club points, you can link your accounts and transfer points seamlessly between them at a 1:1 ratio.
Maximizing Value Watch for transfer bonus promotions between Virgin Red and popular rewards programs like Chase Ultimate Rewards and American Express Membership Rewards – these bonus offers happen frequently throughout the year! When these bonuses are active, you can stretch your existing points even further when transferring them to Virgin Red. For example, if there’s a 30% transfer bonus, transferring 100,000 credit card points would give you 130,000 Virgin Red points – getting you significantly closer to that dream cruise.
The Booking Process
  1. Sign up for Virgin Red (it’s free)
  2. Browse available cruises on the Virgin Red redemption page
  3. Select your preferred cruise and cabin
  4. Transfer your points if needed
  5. Complete your booking through Virgin Red’s platform
Is It Worth It? Based on typical cash prices, these point redemptions can provide decent value, especially for Sea Terrace cabins on popular routes. Let’s break down the value:
  • A 4-night Caribbean cruise in a Sea Terrace can typically cost $1,800-$2,400 for two people
  • At 305,000 points, you’re getting roughly 0.6-0.8 cents per point in value
While this is not nearly as high as some premium flight redemptions, it’s an okay value for an all-inclusive vacation where nearly everything is covered once you’re onboard!
Our Take If you have credit card points or Virgin Red points available, this gives you an opportunity to experience a premium adults-only cruise where nearly everything is included. Once onboard, you won’t be nickel-and-dimed since your food, drinks, entertainment, Wi-Fi, and gratuities are all covered! For cruise enthusiasts who also collect points and miles, this represents an exciting new frontier in travel redemptions. It’s especially valuable for those who might not have quite enough points for premium international flights but still want a luxury travel experience. Quick Tips
  • Compare the points cost against current cash prices before booking
  • Consider any current transfer bonuses to maximize your points
  • Remember these are per-cabin rates, not per-person
  • Book as early as possible for the best selection of sailing dates
  • The Virgin Red Rewards Mastercard can help you earn points faster for future sailings

The Art of Cabin Upgrades

Let’s be honest – who doesn’t dream of opening their cruise cabin door to find a spacious suite or balcony room when they only paid for an interior cabin? While the days of completely free upgrades are largely behind us, there are still several proven strategies to score better accommodations without breaking the bank. The Reality of Cruise Upgrades First, let’s set realistic expectations. Truly free upgrades are rare in today’s cruising world. What’s more common are:
  • Discounted upsells: Paying a reduced rate to move to a better cabin
  • Same-category upgrades: Moving to a better location or higher deck within your booked category
  • Bidding opportunities: Offering money for a chance at a better room
With that understanding, here are strategies that actually work:
1. Take Advantage of Bidding Programs Many major cruise lines now offer upgrade bidding programs:
  • Royal Caribbean: RoyalUp
  • Norwegian: Upgrade Advantage Program
  • Celebrity: MoveUp
  • MSC: Plus Grade
How it works: You’ll receive an email invitation (usually 2-4 weeks before sailing) to bid on available upgrades. You select how much you’re willing to pay per person for various cabin categories, and the cruise line accepts or rejects your bid a few days before departure. If your bid is accepted, your card will automatically be charged the bid amount and you will be relocated into your new cabin prior to embarkation. If your bid is declined, no harm no foul – you will not be charged any additional money. Pro tip: Bid slightly above the minimum amount to differentiate yourself from other bidders. For example, if the minimum bid is $75 per person, offer $95 to increase your chances.

2. Look for Special Upgrade Offers
Cruise lines regularly send promotional upgrade offers to already-booked passengers, especially if a sailing isn’t selling well.

What to watch for: Keep an eye on your email for offers 2-6 months before sailing. These upgrades aren’t free but typically cost much less than the difference between the categories at the time of booking.

Pro Tip: Compare the upgrade offer price against current fares before accepting. Sometimes, prices drop across all categories, making the “special” upgrade less special.

3. Sail During Off-Peak Times Ships are less likely to sail full during shoulder seasons, which increases your upgrade chances. Consider:
  • Caribbean: September through early November (hurricane season)
  • Alaska: May and September (cooler weather)
  • Europe: November through April (excluding holidays)
  • Mexico: Early January and May (when school is in session)
4. Leverage Loyalty Status Cruise lines reward repeat customers. Higher-tier loyalty members get priority for both free and paid upgrades. Pro Tip: If you enjoy cruising, stick with one or two cruise lines to build status faster rather than spreading your sailings across many companies.
5. Book Through a Well-Connected Travel Agent Travel agents with strong cruise line relationships sometimes have access to special upgrade offers not available to the general public. Bonus: Agencies occasionally purchase blocks of cabins and may upgrade their clients if premium cabins go unsold. When to Say No to an Upgrade Sometimes, it’s better to decline an upgrade offer:
  1. If location matters more than size: An upgrade might move you from a perfectly located mid-ship lower deck room to a larger but rockier cabin at the front or back of a high deck.
  2. If you’ve booked connecting rooms: Upgrade offers typically apply to single cabins, not groups of connecting rooms.
  3. If you need a specialized cabin: Accessible cabins, family suites, or spa rooms with special amenities might be more valuable than a standard upgrade.
Our Experience One of our most notable cabin upgrade experiences was on Norwegian Cruise Line, where we bid around $500/pp to upgrade from a regular balcony room to The Haven! This was well worth it, since The Haven suites are a ship-within-a-ship concept with access to several private areas and typically go for a few thousand dollars extra.  The Bottom Line The key to successful cruise cabin upgrades is being strategic, flexible, and proactive. While free upgrades aren’t guaranteed, using these tactics can significantly increase your chances of enjoying a better cabin without paying full price.

Miscellaneous (but awesome) things we couldn't fit above

Getting Free Help

Sometimes, planning a trip can feel like an unattainable goal because of how much effort it takes. From finding the right vacation destination to searching through hundreds of resorts or cruises, planning a trip takes time AND energy! 

What if we told you that there is a way for you to sit back and relax while someone else does the work for you? >>> Travel Agents! 

Most have heard of travel agents, but the role of a travel agent is often misunderstood. While many believe that travel agents cost a fee to the user, that is typically not the case! More often than not, travel agents are completely free to use, and instead receive payment through resorts and cruise lines. A travel agent has already done the research, so you don’t have to! They are extremely knowledgeable in their field and can provide you with the help you may need to plan the perfect trip.

On top of planning your trip, a travel agent may also be able to provide you with extra discounts or perks that a non-travel agent would not have access to. From onboard cruise credit to bar tabs or special dinners, travel agents can work with resorts and cruise lines to add that “something extra” to make your trip one to remember!

Interested in using a travel agent to book your next trip?

You’re in luck! 

At The Maxwells Travel, we have a fully licensed and certified travel advisor for Oasis Travel on staff and ready to work with you. Fill out the form at the link below with your trip request details and Nicole Maxwell will be in touch to help you out! 

(Nicole just happens to be Austin’s mom, so you know you’ll be in great hands!)

Spotify Playlist

It’s a scientific fact that listening to music is associated with direct effects on your overall mood and stress levels, and we are strong believers in enhancing every experience with music!

That’s why we have created the official Maxwells Travel Vacation Vibes playlist – available on spotify! Currently, our playlist includes over 19 hours of music aimed at getting you in your vacation zone – find it here.

Our Travel Must-Haves

Travel Like The Maxwells

Curious about some of the incredible trips we’ve been on?

Whether you’re just looking for some travel inspiration or a loose itinerary to follow, we’ve got plenty of both waiting for you on our blog

Check out a few of our notable trip highlights: 

Ultimate Guide: Puerto Vallarta

10 Days Aboard Explora Journeys (Southern Caribbean) 

7-Day Cruise in the Mediterranean

If you’d prefer to see the sights for yourself, we also have in-depth explorations and fun-filled experiences documented on our YouTube Channel

Pack Like a Pro

Packing efficiently is an essential skill for any traveler, whether you’re embarking on a weekend getaway or a month-long adventure.

By being strategic about what and how you pack, you can minimize stress, maximize space, and ensure you have all your essentials without overpacking. Thoughtful preparation allows you to focus on the joy of the journey rather than worrying about lugging around an overstuffed suitcase.

Here are some of our favorite packing tips:

  1. Start by choosing versatile clothing pieces, sticking to a color palette to maximize outfit options. 

  2. Use packing cubes to stay organized, and roll your clothing pieces to save space.

  3. Prioritize multi-purpose items, like a scarf that doubles as a blanket or shoes suitable for multiple occasions. 

  4. Don’t forget to create a packing checklist to ensure you don’t leave any essentials behind. 

With smart packing techniques, you can travel lighter while still having everything you need. For a full breakdown of tips and tricks, check out our blog, Efficient Packing 101.

AI Travel Planning Tools we love

Planning your next trip is now a whole lot easier!

AI-powered travel assistants have come a long way, and 2025 has seen impressive advancements that can truly transform how you organize and book your travels. Let’s explore the best AI travel planning tools to help make your next adventure hassle-free.

Why Use AI Travel Planners? Travel planning can be time-consuming and overwhelming – researching destinations, comparing prices, creating itineraries, and booking everything from flights to activities. AI travel tools streamline this process by:
  • Creating personalized itineraries based on your preferences
  • Optimizing your daily schedule to minimize wasted time
  • Suggesting hidden gems you might otherwise miss
  • Helping you find the best deals across multiple platforms
Top AI Travel Planning Tools for 2025

1. Wonderplan

Wonderplan functions like having a personal travel agent in your pocket. This free AI trip planner excels at crafting bespoke itineraries tailored to your interests and budget. You can easily reorder, add, or remove locations on your itinerary, and even download your plans as a PDF for offline access. Best for: First-time travelers who want comprehensive, easy-to-follow itineraries without spending hours on research.

2. Trip Planner AI

This tool uses advanced algorithms to optimize your travel routes, ensuring you make the most of your time. Trip Planner AI stands out for its ability to integrate social media insights – you can share travel content you like, and it will create a custom itinerary based on those inspirations. Best for: Efficient travelers who want to maximize their experiences while minimizing transit time.

3. Mindtrip

Mindtrip shines with its group planning features. You can start a group chat, share ideas, and ask the AI for recommendations that balance everyone’s preferences – perfect for planning trips with friends or family. It also lets you start planning from a photo, screenshot, or PDF you find inspiring.

Best for: Group trips and travelers who get inspiration from social media and visual content.

4. Layla

Layla creates custom itineraries in seconds for everything from city escapes to epic road trips. It offers personalized destination ideas alongside visual content from creators whose style matches your preferences, helping you visualize your trip before booking.

Best for: Visual planners who want inspiration alongside practical planning tools.

5. Expedia Trip Matching

This innovative tool from Expedia allows you to build an itinerary based on Instagram Reels you love, then book directly through Expedia. It’s a perfect marriage between social media inspiration and practical booking capabilities.

Best for: Social media enthusiasts who discover travel destinations through platforms like Instagram.

How To Get The Most From AI Travel Tools
  1. Be specific about your preferences – The more details you provide about your travel style, interests, and constraints, the better your AI-generated itinerary will be.
  2. Use them for inspiration, but verify details – While AI tools are getting better at providing accurate information, always double-check opening hours, prices, and availability.
  3. Combine multiple tools for best results – Use one for itinerary creation, another for finding deals, and perhaps a third for local recommendations.
  4. Don’t forget the human touch – AI can’t replace local knowledge. Consider supplementing your AI itinerary with advice from locals, specialized travel forums, and your travel agent.
  5. Save and export your plans – Most tools allow you to download or share your itineraries. Keep offline copies of your plans in case you lose internet access.
Our Experience We recently tested several AI planning tools for our Japan trip and found them incredibly useful for discovering off-the-beaten-path restaurants and optimizing our island-hopping schedule. The time saved on research allowed us to focus on enjoying our trip rather than stressing about logistics! The Future of AI in Travel The lines between traditional booking sites, AI assistants, and social media are blurring. By 2026, we expect to see fully agentic AI travel planners that can not only suggest itineraries but also negotiate deals between travelers and travel suppliers for you automatically. 
That's All, Folks!

You made it to the end… Congrats!
Thank you for reading and we sincerely hope this Playbook was helpful resource.

Don’t forget to bookmark this Playbook and follow us on Facebook, Instagram, Youtube, TikTok, and LinkedIn for more Travel Tips & Tricks!

   – Austin & Courtney

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Editorial Note

Content is not provided or commissioned by credit card issuers. Opinions expressed here are author’s alone, not those of the credit card issuers, and have not been reviewed, approved or otherwise endorsed by the credit card issuers.

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