Where to Go in 2026: A Points-and-Miles Playbook for The Top 17 Destinations

Stop hoarding — start booking: a 2026 award-travel playbook for The Points Guy’s top picks

If fragmented advice and confusing award charts keep you from booking that once-in-a-lifetime trip, you’re not alone. In 2026 the biggest challenge isn’t earning points — it’s converting them into predictable, low-fee award itineraries before dynamic pricing and route growth change the math. Below is a practical, destination-by-destination playbook that turns The Points Guy’s 2026 inspiration into bookable award strategies: the best frequent-flyer programs to target, routing hacks and seasonal timing to maximize value.

How to use this playbook (read first — then pick a city)

Quick approach: 1) Identify the program(s) that consistently release saver awards to your destination; 2) Search partner and alliance inventories; 3) Hold or transfer points only when award space appears; 4) Use open-jaw/one-way routing to reduce price and add experiences; 5) Time travel for shoulder-season award availability.

2026 trends that shape award strategy: dynamic award pricing dominates many carriers, but valuable fixed-price options still exist via legacy partner awards, regional carriers and niche programs. In late 2025 and early 2026 we saw continued route expansion (more U.S.–Europe and U.S.–Middle East nonstops) and airlines refining loyalty rules — that means more opportunities but shorter windows for saver space. Refurbished phones and simple mobile hubs are a practical way to run airline apps and alerts without tying up your main device. Transferable points (Chase, Amex, Citi, Capital One) remain your most flexible currency.

Core tools and rules-of-thumb (actionable)

• Search like a pro: Use Google Flights to identify routings and times, then search award inventory on airline sites and partner portals (e.g., Aeroplan, Alaska, Avianca LifeMiles, Flying Blue). For automated monitoring and community-contributed signals, consider community-powered flight alerts as part of your toolkit.
• Hold before you move points: don’t transfer transferable points until you find award space — transfers are often irreversible and immediate.
• One-way + open-jaw: book one-way awards (mix programs) and use open-jaws to add city hops without extra miles — pairing an international award with local experiences like local pop-up markets can make the extra city stop feel seamless and curated.
• Protect against dynamic pricing: target partner-program fixed charts (e.g., Avianca Lifemiles, Asia Miles, ANA) when possible; if dynamic, be ready to transfer at moment of booking. For destination logistics and on-property fulfillment tips (helpful when booking boutique stays), see our on-property micro-fulfilment playbook.
• Set alerts: use ExpertFlyer, Award Nexus or airline alerts — and augment them with community flight-alert tools — for premium cabin availability and last-minute saver releases.

The 17-destination award playbook (quick, actionable plans)

Below are 17 destinations inspired by The Points Guy’s 2026 roundup and a concise award plan for each: best programs, routing tips and ideal timing. Apply the same playbook to similar nearby cities.

1. Lisbon, Portugal — Best for Avios and Flying Blue flexibility

Best programs: British Airways/Iberia Avios, Flying Blue (Air France–KLM), United MileagePlus for Star Alliance options.

Routing tips: Look for Iberia and British Airways nonstop availability from major U.S. gateways. Iberia often releases cheaper Iberia+Avios seats for midweek departures. If Avios shows high taxes, check Flying Blue promos and transfer partners (Amex, Chase, Capital One) for mixed-carrier itineraries.

Seasonal timing: Shoulder seasons — March–May and September–October — have lower award demand and often better premium-cabin availability. Book 4–6 months ahead for better business class saver seats.

2. Kyoto / Tokyo, Japan — Use ANA and Asia Miles for premium cabins

Best programs: ANA Mileage Club (roundtrip saver value), Cathay Pacific Asia Miles (one-ways, flexible partner calendars), United MileagePlus for partner options.

Routing tips: Use one-way awards with partners to mix carriers (e.g., depart via United/ANA and return on a different carrier). If you target ANA’s roundtrip chart, search nonstop outbound and inbound from U.S. hubs and be ready to book the roundtrip when both legs show saver space.

Seasonal timing: Late March (cherry blossom) is peak and expensive for awards; aim for autumn (Oct–Nov) for the best award availability. For peak windows, look 8–12 months out for business-class saver seats.

3. Reykjavík / Iceland — Capitalize on low-cost partnerships and positioning flights

Best programs: Avios (Aer Lingus, British Airways), Icelandair stopover-friendly fares, and United for Star Alliance connections via Europe.

Routing tips: Position to major East Coast gateway flights and connect via Aer Lingus or BA to get competitive Avios pricing. Icelandair’s stopovers make open-jaw itineraries simple; combine with low-cost intra-Europe awards.

Seasonal timing: Shoulder seasons (April–May and Sep–Oct) give aurora/chilly landscapes without peak pricing. If chasing Northern Lights, book Nov–Mar but expect premium demand.

4. Cape Town, South Africa — Use Star Alliance and oneworld partners

Best programs: United MileagePlus (Star Alliance partners), Avianca LifeMiles, Qatar Privilege Club for Qsuites access via Doha.

Routing tips: Look for availability via European or Middle Eastern hubs (Doha, Addis Ababa, Istanbul). Consider positioning to larger hubs for better business-class availability and check LifeMiles for occasional good-value sales on partner awards.

Seasonal timing: South Africa’s summer (Dec–Feb) is peak; aim for shoulder seasons (Mar–May, Sep–Nov) to get low award demand and pleasant weather.

5. Oaxaca, Mexico — Short-haul wins: use domestic partners and bank transfers

Best programs: Avianca LifeMiles (Copa/Interjet partners regionally), American AAdvantage for oneworld options, Alaska Mileage Plan when itineraries include Alaska partners.

Routing tips: Look for positioning flights to Mexico City and then pay a separate short-haul award or use low-cost carrier segments. In 2026 more U.S.-Mexico nonstops opened in 2025, increasing availability.

Seasonal timing: Oaxaca’s high season is winter (Dec–Feb). Book shoulder months (Nov, Mar–Apr) for lower award demand and local festivals with manageable crowds.

6. Cartagena, Colombia — Use Avianca LifeMiles and United Star Alliance routes

Best programs: Avianca LifeMiles (excellent for intra-Latin America), United MileagePlus for Star Alliance networks.

Routing tips: Search LifeMiles for direct Avianca award space; it often shows good value and low surcharges. One-way awards make combining partners simple: fly into Bogota or Medellín and connect to Cartagena on a short partner flight.

Seasonal timing: Dry season (Dec–Mar) is peak — aim for shoulder months around Nov or Apr to book awards at lower mileage levels.

7. Auckland / New Zealand — Long-haul business value via Asia gateways

Best programs: Air New Zealand Airpoints (limited transfer partners), United MileagePlus and Avianca LifeMiles for partner awards, Virgin Atlantic/Delta partnerships for transpacific access.

Routing tips: Consider routing via Asia (Tokyo, Singapore) to combine two premium legs with better award availability. LifeMiles and Virgin Atlantic sometimes show competitive partner availability to Auckland.

Seasonal timing: Southern Hemisphere summer (Dec–Feb) is busy. Spring (Sep–Nov) and autumn (Mar–May) give better award availability and lower hotel rates.

8. Petra / Jordan — Mix airlines via Middle Eastern hubs

Best programs: Qatar Privilege Club (Qsuite access), Emirates Skywards, Flying Blue (Air France/KLM via Paris/Amsterdam) for combined Europe access.

Routing tips: Use Doha or Dubai as connectors and then position to Amman on regional carriers. Qatar’s Qsuites availability frequently appears on partner searches — book quickly and transfer points accordingly. If you’re timing a night arrival, consider local innovations in urban mobility and autonomous night taxis as a potential last-mile option in some cities.

Seasonal timing: Peak spring (Mar–May) and autumn (Sep–Nov). For cooler weather and fewer crowds, aim for Oct–Nov.

9. Barcelona / Spain — Leverage Avios and Flying Blue promos

Best programs: Avios for short transfers inside Europe and Iberia/BA transatlantic awards; Flying Blue for promo awards and occasional discounts.

Routing tips: Use Avios intra-Europe redemptions to hop between Spanish cities and mix with an Iberia inbound. Flying Blue monthly promo awards often include Barcelona on discounted mileage, especially off-peak.

Seasonal timing: Shoulder seasons (Apr–Jun, Sep–Oct) are ideal. Summer brings heavy demand and high award costs.

10. Buenos Aires, Argentina — South America premium cabins via carrier partners

Best programs: Aerolineas Argentinas (if available), Avianca LifeMiles and United MileagePlus for Star Alliance partner routing via São Paulo/Bogotá.

Routing tips: Look for award space from U.S. east coast gateways; long-haul transatlantic or transcontinental routing can open better premium availability. LifeMiles often provides steady award inventory on long-haul partners.

Seasonal timing: Argentine summer (Dec–Feb) is peak. Late spring (Nov) and autumn (Mar–May) have lower award demand and pleasant weather. If you’re planning boutique stays, consult an operational playbook for boutique hotels to coordinate awards with hotel availability and direct-book perks.

11. Banff / Canadian Rockies — Use Aeroplan and Avios for intra-North America hops

Best programs: Air Canada Aeroplan (excellent routing rules), British Airways Avios for short domestic legs, Alaska Mileage Plan for West Coast connections.

Routing tips: Use Aeroplan’s varied partner network and flexible routing rules to combine North American partners and avoid fuel surcharges. Combine with a short Avios redemption for nearby regional flights.

Seasonal timing: Summer is peak for hiking; winter is ski season. Shoulder months (Jun, Sep) give fewer crowds and better award availability. Pack smart and consider smart luggage tech for concierge-friendly arrivals.

12. Amalfi Coast / Italy — Combine open-jaw Italy entry/exit

Best programs: Flying Blue, Avios, United MileagePlus for Star Alliance routing into Rome or Naples.

Routing tips: Book an open-jaw arriving in Rome and departing from Naples or vice versa. Use Avios for short regional hops or low-cost carrier segments. Flying Blue often has promos into Italian airports.

Seasonal timing: May–June and Sep–Oct avoid July–Aug crowds while delivering warm weather and easier award availability.

13. Maui / Hawai‘i — Domestic award sweet spots and positioning

Best programs: Alaska Mileage Plan (excellent for intra-Pacific), HawaiianMiles, United MileagePlus for cross-country connections.

Routing tips: Use Alaska for West Coast carriers’ availability and consider positioning flights from major West Coast hubs. HawaiianMiles can be profitable for nonstop flights from the West Coast if awards are released in advance.

Seasonal timing: Winter is popular (Dec–Feb); plan shoulder months (Apr–May, Sep–Oct) for lower award demand and pleasant weather.

14. Dubai — Book via Middle East alliances and premium-products

Best programs: Emirates Skywards (direct access to Emirates flights), Qatar Privilege Club (via Doha), and partner programs that access one of the gulf carriers.

Routing tips: If Emirates shows high dynamic pricing, search partner programs (e.g., Alaska, Qantas) for better-value awards on the same flights. Consider night-time arrival to maximize first-day exploring.

Seasonal timing: Best weather Oct–Apr; avoid summer (Jun–Aug) when demand is lower but daytime temperatures high.

15. Alaska (Denali & coastal cruises) — Mix positioning flights and cruise award credit

Best programs: Alaska Mileage Plan, American AAdvantage (for oneworld partners), and Chase transfers to Alaska partners.

Routing tips: Use Anchorage as your hub; combine an Alaska award with a later regional hop. For cruises, verify which frequent-flyer programs allow crediting full segments to build toward elite perks.

Seasonal timing: Alaska operates primarily May–Sep for most cruise and park activities. Book award travel early (8–10 months) for summer premium cabin seats.

16. Mexico City — Capitalize on dense network and short-haul partners

Best programs: Avianca LifeMiles, United MileagePlus, American AAdvantage for one-way mix-and-match options.

Routing tips: Mexico City is well-served — look for direct transborder award seats and short domestic partner legs. LifeMiles’ robust Latin-America coverage makes it a top pick for low-fee redemptions.

Seasonal timing: Year-round travel with peak in winter. Shoulder months (Mar–May, Sep–Nov) are comfortable and award-friendly.

17. Galápagos Islands — Plan for strict carrier and park rules

Best programs: Avianca LifeMiles and American AAdvantage (partners for connecting flights), and local carriers that fly to Galápagos (often paid segments).

Routing tips: Award routes typically end in Quito or Guayaquil — you’ll have to pay a short domestic flight into the islands. Book these internal flights early; they sell out and sometimes have limited award availability. Consider combining an award long-haul to Quito with a separately purchased domestic leg to maintain flexibility.

Seasonal timing: June–September is drier and popular; shoulder months (Apr–May, Oct–Nov) reduce crowding while keeping wildlife viewing strong.

Advanced booking plays and sample flows (how to actually book)

1. Find space: Use Google Flights to identify exact carrier and flight times you want. Then check the airline’s award search tool and partner programs to confirm inventory.
2. Lock a one-way: If you see one leg, consider booking the one-way with a program that charges less for that leg; mix and match to avoid high roundtrip dynamic pricing.
3. Hold while you transfer: some airlines allow holds (or pay a small fee to hold). If not, make sure you have the points in your transferable account or split the booking into a refundable paid leg as a placeholder.
4. Transfer and confirm: transfer points only once award space is confirmed. For Chase/Amex/Citi/Capital One transfers, note transfer times (some are instant; others take hours).
5. Protect your booking: consider trip protection or credit card travel insurance for high-value redemptions; some cards offer trip delay/cancellation cover that can protect award bookings.

Pro tip: When airlines use dynamic pricing, the fastest route to a good deal is often a partner with a fixed chart. Keep a shortlist of “go-to” partner programs (Avianca LifeMiles, Air Canada Aeroplan, Alaska Mileage Plan, British Airways Avios, ANA) and monitor them regularly. For stay logistics and in-destination operations, check smart-luggage and boutique-hotel playbooks like smart luggage tech and the operational playbook for boutique hotels.

Actionable checklist before you hit Book

• Search award space on the operating carrier and at least two partner programs.
• Confirm taxes/fees — high fuel-surcharges on some carriers (e.g., certain transatlantic redemptions) may make a cash fare + points credit card perk better.
• Check transfer partner speed and minimums for your points currency.
• Set alerts for last-minute saver releases (they often appear within 2–3 weeks of departure) — use community flight alerts alongside airline notifications.
• Consider refundable paid tickets as a backstop if you must lock accommodation or tours; and plan on-the-ground experiences like local markets and micro-experiences to make an open-jaw extra-city visit feel curated.

Final takeaways — what to remember in 2026

In 2026 award travel is still beatable with a disciplined approach: be flexible on dates and routing, prioritize programs that reliably release partner inventory, and use transferable points as your leverage. Recent route growth and dynamic pricing mean the edge goes to travelers who combine quick searches, timely transfers and creative routings (open-jaw and one-way mixes). For destination tools and trip planning, don’t forget to pack practical travel tech and guides like the Termini Atlas Lite travel toolkit and smart-luggage recommendations.

Next steps (call to action)

Ready to convert points into one of these 17 trips? Start by picking a destination from this playbook, then use the checklist above to run a 15–30 minute award search. If you want a personalized routing for your exact home airport and current points balances, sign up for our award-search newsletter or request a custom itinerary — we’ll send a step-by-step plan with the programs to target and the optimal transfer timing.

Book smarter in 2026: stop overthinking — with the right program and timing, your points will take you farther than ever.

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