How to Use Points and Budget Apps to Book the 17 Best Places to Travel in 2026

Make 2026 the year you stop hoarding points and actually go — without breaking the bank

Trip planning feels like a second job: juggling award availability, tracking sales, and saving money across multiple accounts. If you’re fed up with fragmented planning and want a single, repeatable system to book one of The Points Guy’s 17 best places to travel in 2026, this guide is your playbook. I’ll show you how to combine modern budgeting apps (including a discounted Monarch Money annual plan), fare alerts, and a step-by-step points strategy so you can save smarter and book faster in 2026.

Why this matters in 2026: trends that change the rules

Late 2025 and early 2026 accelerated several trends that directly affect how you should save and redeem points:

• Wider rollout of dynamic award pricing — more redemptions are priced like cash, so availability matters even more.
• More airline route growth — carriers restored many long-haul routes and added seasonal services, creating fresh award opportunities.
• Personal finance apps are maturing — tools like Monarch Money now let you build dedicated sinking funds, auto-categorize travel spending and sync non-bank transactions (Amazon, Target) via browser extensions.
• Bank and transfer promos continue — late‑2025 saw transfer bonuses and targeted offers that reward flexible points strategies.
• Higher ancillary fees and dynamic baggage pricing mean you must factor cash costs into your travel budget, not just the ticket price.

How this guide is structured

First, I’ll outline a repeatable six-step process that combines a budgeting app workflow with a points-first booking strategy. Then I’ll map that process to representative destinations from The Points Guy’s 2026 picks (real examples you can follow). Finally, you’ll get advanced tactics and an actionable 90-day timeline you can copy.

Six-step travel finance & points strategy (the system)

1. Decide the trip and target bucket — pick one of TPG’s 17 picks or a destination category: short-haul city break, long‑haul Europe/Asia, tropical island, or remote-adventure.
2. Estimate total trip cost — flight (cash + taxes), award taxes, hotel, internal transport, activities, and a buffer for ancillary fees.
3. Set up a dedicated travel goal in a budgeting app — create a sinking fund and automated transfers; use Monarch Money (sale code NEWYEAR2026) to centralize accounts and track progress.
4. Hunt award availability & fare alerts — use Google Flights, Skyscanner, and point tools (Point.me, AwardWallet) to find award space and set fare alerts for cash fares you can mirror with points.
5. Choose the redemption window — either book now with a combination of cash + points or hold using free/courtesy holds if available; plan a transfer timeline if you rely on bank points.
6. Lock the booking, then use the budget app to pay or reimburse — move reserved cash out of day-to-day accounts into your travel sinking fund; track spending and adjust categories in Monarch.

Step 1 — Decide the trip and target bucket

Start with the destination category rather than an exact itinerary. That helps you choose the right points currency and the quickest way to secure seats. Examples:

• Short-haul US or Mexico: focus on regionally strong airlines and domestic award programs.
• Europe or long-haul: prioritize transferable points (Chase, Amex, Capital One) and alliance partners.
• Tropical islands: consider mixed cash/night strategies — fly award, pay for an off-grid hotel with cash.

Step 2 — Estimate total trip cost (quick budgeting template)

Use a conservative 10–20% buffer for 2026 due to variable fees. A simple baseline:

• Flight: cash taxes $50–$250 (long haul higher) or equivalent points
• Hotel: $80–$350 per night depending on destination
• Daily expenses: $60–$250/day
• Transport + activities: $100–$500
• Buffer: 10% of total

Step 3 — Build the travel sinking fund in Monarch Money

Monarch Money is an excellent choice in 2026 because of its flexible goal tools, transaction syncing and web extension that auto-categorizes purchases. Right now Monarch often runs a promotional rate — new users can get 50% off the annual plan using code NEWYEAR2026 (final cost about $50/year during the sale).

How to set up:

1. Create a dedicated “Travel: [Destination]” goal with a target amount and a target date.
2. Link all relevant accounts — checking, credit cards, savings, and even brokerage accounts for opportunistic cashbacks or rewards.
3. Use automatic transfers from checking to savings each payday — treat the transfer like a recurring bill.
4. Enable the Monarch web extension to capture retail transactions (useful for tracking refundable hotel deposits and activity purchases).
5. Choose a budgeting style (flexible vs category budgeting) and pin the travel category to your dashboard so progress is always visible.

Step 4 — Hunt award space and set fare alerts

Tools and playbook:

• Google Flights — quick cash price checks and calendar view. Use ‘track price’ for notifications.
• Skyscanner & Momondo — great for flexible date searches and alternative airports.
• Point search tools — use AwardWallet, Point.me or airline sites to check award availability across partners.
• Set multiple alerts — one for cash fares, one for award availability (if your tools allow it), and one for specific seat classes.

Pro tip: when dynamic award pricing is in play, mirror the cash fare you see. If the cash price dips, the award 'price' is often more favorable or becomes available at lower mileage bands.

Step 5 — Time transfers and holds

When you find availability, you have two timing levers: bank transfers and reservation holds.

• Transfer timing — do not transfer flexible bank points (Chase Ultimate Rewards, Amex Membership Rewards, Capital One Miles) until you’re ready to book unless there’s a transfer bonus. Transfers are usually irreversible and immediate in many programs.
• Holds & phone bookings — many airlines and hotels allow free holds for a limited time. Use holds to lock a cash price while you finish transfers or move money into your travel sinking fund.
• Hybrid book — sometimes the optimal strategy is to book a refundable cash ticket with a credit card that offers trip delay/cancellation protections and then cancel once award space appears and you can redeposit points.

Step 6 — Lock, track and reimburse

After booking:

• Record the transaction in Monarch’s goal and tag it to the trip.
• Set reminders for cancellation windows and potential re-deposits (award ticket change fees have become more common in 2026).
• Use the budgeting app to reconcile actuals vs planned; adjust future contributions if necessary.

Applying the system: real-world examples from The Points Guy’s 2026 picks

Below are representative destinations that mirror categories in TPG’s 17 picks. For each I give the fastest points route, a cash+points fallback, and a Monarch Money savings plan example.

1) Lisbon (Europe city break)

• Points route: Transferable points to Avianca LifeMiles or Iberia Avios for direct flights via partner airlines (look for off-peak Avios awards).
• Fallback: Watch cash fares on Google Flights — price dips often correlate with increased award availability.
• Savings plan: $1,200 trip in 6 months = $200/month auto-transfer into Monarch. Set a dedicated category for dining and tram passes.

2) Kyoto (long-haul Asia)

• Points route: Transfer Chase/Amex to ANA or partner carriers for front-cabin sweet spots; watch for seasonal business award space.
• Fallback: Consider a one-way award + one-way cheap cash fare trick to secure dates.
• Savings plan: $2,500 trip in 9 months = $278/month. Use Monarch to track JR Pass or regional rail passes in the spending plan.

3) Reykjavik / Iceland (outdoor / adventure)

• Points route: Short-haul flights often have low-cash prices; use points for hotels or upgrade with miles.
• Fallback: Book cheap economy and use points to reserve a rental car or pricey excursions.
• Savings plan: $1,600 trip in 6 months = $267/month. Factor rental car insurance and fuel into Monarch budgets.

4) Oaxaca or Mexico cultural trip

• Points route: Domestic award space via partner airlines or cheap cash fares; keep an eye on holiday surcharges.
• Fallback: Use flexible reward points to fly into Mexico City and take a short regional flight with points or low-cost carrier cash.
• Savings plan: $900 trip in 3 months = $300/month. Monarch’s extension helps track artisan purchases for customs and spending caps.

5) Cape Town (long-haul + seasonal)

• Points route: Transfer points to Star Alliance or use dynamic awards on carriers serving South Africa; book early for summer season.
• Fallback: Set fare alerts across multiple departure airports — routing via Europe can create price drops.
• Savings plan: $3,400 trip in 12 months = $283/month. Use Monarch to model currency exchange fees and local safety net.

Advanced tactics (2026-ready)

Use hybrid cash+points bookings to neutralize dynamic pricing

When award prices spike, a smart hybrid is to book a cash ticket with a changeable fare class and then watch for award space — once it appears, cancel or change. That reduces risk of missing out entirely and lets you capitalize on later award windows.

Exploit bank transfer bonuses and targeted offers

Late 2025 continued to see banks offer targeted transfer bonuses to partner airlines. Keep an eye on bank inboxes and monetary portals — a 20–30% transfer bonus can turn a marginal award into a steal. Monarch can centralize your card benefits and fee schedules so you know which card to use when booking.

Stack offers: promos + coupon codes + app cashbacks

Layer retail and travel promos: browser extension coupon fetchers, store-specific credits, and cash-back portals. Document each stacked saving in Monarch so you actually apply them and track final out-of-pocket.

Short-term liquidity: micro-savings and side-hustle buckets

Use Monarch’s tagging to allocate oddball refunds, gift-card credits or marketplace sales to your travel goal. Micro contributions (e.g., $40 per ‘side gig’ sale) compound quickly and reduce pressure on primary paychecks.

Monitor award availability systematically

1. Create a spreadsheet or use an alert tool that checks partner inventory daily.
2. Set a 48–72 hour window for decisive action — if an award space opens that matches your budget and dates, transfer the points immediately unless a transfer bonus is running.
3. Use browser-based saved searches for exact flight numbers to capture sudden availability after schedule changes.

90-day action plan you can copy

Days 1–7: pick destination + open Monarch

• Choose one of TPG’s 17 picks (or a category) and estimate costs.
• Sign up for Monarch Money and apply code NEWYEAR2026 for the discounted annual plan if available.
• Create a travel goal and enable automatic transfers.

Days 8–30: research awards + set alerts

• Search award space, set Google Flights price trackers, and create Skyscanner alerts.
• Map out the best transfer partners for your primary points currencies.

Days 31–60: build balance + monitor

• Top up your sinking fund weekly and track progress in Monarch.
• Watch for transfer bonuses and reprice opportunities.

Days 61–90: commit or hedge

• If award seats exist, transfer and book. If not, secure refundable cash fares or holds while continuing to monitor awards.
• Record the booking in Monarch and set calendar reminders for refunds, re-deposits, and pre-trip purchases.

Common pitfalls and how to avoid them

• Transferring too early: avoid irreversible transfers without a confirmed seat.
• Underestimating fees: factor in baggage, seat selection and local taxes in Monarch so your goal is realistic.
• Over-optimizing for points: sometimes a cheap cash fare + points for hotels creates the best total value — compare total cash vs total points value.
• Fragmented tracking: centralize all receipts and confirmations in Monarch so refunds, credits and adjustments don’t slip through the cracks.

“Make 2026 the year you stop hoarding points for ‘someday’ and book that trip.” — The Points Guy (paraphrased)

Key takeaways

• Use a dedicated travel goal: Monarch Money’s sinking funds and auto-transfers turn vague intentions into booked trips.
• Hunt award space early: dynamic pricing means availability is your biggest lever.
• Time transfers smartly: don’t send bank points until you have a confirmed booking window unless there’s a transfer bonus.
• Stack discounts: small savings add up — promo codes, cashbacks and targeted bank offers reduce real costs.
• Plan, then act: use the 90-day plan above to transform a saved goal into a ticket on your calendar.

Final checklist before you book

• Have your award availability confirmed or a refundable cash hold in place.
• Know how long it will take for bank transfers (some partners are instant; others take days).
• Confirm Monarch shows the trip as fully funded (including a realistic buffer).
• Ensure you have travel protections (card trip delay/cancel benefits) and any required entry documents.

Call to action

Ready to book one of The Points Guy’s 17 best places to travel in 2026? Start by creating a travel goal in Monarch Money and apply code NEWYEAR2026 to save on your first year. Then set up Google Flights and award alerts for your chosen destination — follow the six-step system above and check back in 90 days. If you want a tailored plan for one of TPG’s picks, tell me your top destination and budget and I’ll map a personalized points + savings timeline you can act on today.

Related Reading

• Green Stays: Sustainable Features to Look for in Villas, Prefab Hotels and Mountain Lodges
• Energy-Savvy Winter Comfort: Are Hot-Water Bottles a Better Deal Than Turning Up the Thermostat?
• How Italy’s Probe Into Activision Blizzard Could Change Microtransaction Design Forever
• Will Class Actions Be the Next Wave? How Mass Account Breaches Could Lead to Group Litigation
• How to Keep Tropical Aquariums Cosy in Winter: Insulation Tricks Inspired by Hot-Water Bottles