points & miles2026 traveldeals

Ultimate 2026 Bucket List: How to Use Points and Deals to See the 17 Best Places to Travel

bbookers

2026-02-01

12 min read

Turn The Points Guy’s 17 best places into a step-by-step 2026 rewards plan—timing, best points, and budget hacks to get you on the move.

Beat scattered search results and hidden fees: a step-by-step 2026 plan to use points and deals to visit the 17 best places

You know the pain: toggling between airline sites, credit card portals and hotel pages, losing a seat while you confirm a redemption, and paying surprise taxes and fees at checkout. In 2026 the good news is that points and miles remain the fastest way to make big trips affordable—if you use them with a plan. Based on The Points Guy's "Where to go in 2026" picks, this guide turns that inspiration list into a pragmatic, destination-by-destination rewards strategy with timing, budget hacks and step-by-step booking moves you can use today.

Quick strategy summary — use this checklist before you book

Prioritize transferable currencies (Chase Ultimate Rewards, Amex Membership Rewards, Capital One Miles, Citi ThankYou) for flexibility across airlines and hotels.
Match the destination to the alliance (Star Alliance, OneWorld, SkyTeam) and choose a primary transfer partner with reliable award space.
Book one-ways and open-jaws to combine award availability and build multi-city routes at lower total cost.
Watch award windows: off-peak inventory, promo awards and last-minute saver seats each have different release patterns.
Stack deals: card welcome offers + transfer bonuses + airline promotions + hotel member rates = biggest savings.

2026 trends that change the rules

Before we dive in, a few marketplace realities shaping reward travel in 2026:

Dynamic award pricing is now the norm—expect more variability in required miles and plan for ranges, not fixed charts.
Airlines continue to release both predictable saver seats (several months out) and last-minute blocks—set alerts and be ready to act.
Bank programs are increasingly issuing targeted & time-limited transfer bonuses (late 2025 and early 2026 saw multiple promotions); these can flip a marginal redemption into a bargain.
Flexible change/cancel policies remain common; book sooner when inventory is thin and adjust if better deals appear later.

How to use this guide

Below you'll find the 17 destinations and, for each, a concise, actionable plan: the best reward-currency to use, ideal timing to search & book, one or two budget hacks, and a sample itinerary approach. Treat this as your one-stop checklist to move from "someday" to a ticket.

The 17 places — reward strategies, timing and budget hacks

1. Lisbon — Europe's warm welcome and cheap intra-Europe hops

Best points: Chase UR > transfer to Flying Blue or Iberia Plus; Capital One to Air France/KLM or TAP (when available).
Timing: Book transatlantic award seats 6–10 months ahead for the best saver availability; watch Flying Blue promos (monthly).
Budget hack: Use Iberia off-peak awards or split your trip—award to Madrid + cheap train to Lisbon for big savings.
Itinerary idea: Night in Madrid (or Porto), 3–4 nights in Lisbon; use Avios for regional flights or trains.

2. Kyoto — seasonal windows and intra-Japan value

Best points: Amex MR > transfer to ANA or JAL partners; Citi/Capital One to Japan Airlines on OneWorld.
Timing: Cherry blossom and fall foliage windows are competitive—lock flights 9–12 months out if traveling peak season.
Budget hack: Use one-way awards to Tokyo + Shinkansen discounts (book local rail passes early) or overnight regional flights.

3. Reykjavik / Iceland — capital of last-minute deals and adventure add-ons

Best points: Transferable points to Aer Lingus (Avios) or use SkyTeam partners for routing via Europe.
Timing: Shoulder seasons (spring, early fall) yield lower taxes/fees and cheaper car rentals.
Budget hack: Search for cheap one-way fares into Europe + Avios to Iceland, or use positioning flights with low-cost European carriers.

4. Cape Town — long-haul comfort via smart partner routing

Best points: Chase/Amex transfers into South African partners or to Star Alliance carriers (e.g., Lufthansa, Swiss via mixed routings).
Timing: Book 5–9 months ahead; winter months (June–August) are high season in South Africa—plan earlier.
Budget hack: Combine business-class transatlantic redemptions with discounted cash internal flights; open-jaw between Cape Town and Johannesburg saves backtracking time.

5. Buenos Aires — luxury for less with off-peak awards

Best points: OneWorld partners (British Airways Avios, Iberia) and Star Alliance via Aerolineas or partner routings; transferable points give flexibility.
Timing: Southern hemisphere summer (Dec–Feb) is popular; target shoulder months (Mar–May, Sep–Nov) for easier award availability.
Budget hack: Use off-peak award pricing and consider cheap intra-Argentina cash flights for regional hops.

6. Medellín — city-with-nature and repeatable low-cost flights from the U.S.

Best points: Amex/Chase transfers to Avianca LifeMiles (Star Alliance) or Avianca's own promos; Southwest and JetBlue are often good cash-options from U.S. hubs.
Timing: Year-round; pick shoulder months for lower hotel rates.
Budget hack: Combine budget cash flights from nearby U.S. airports with a cheap award return to maximize seat availability.

7. Oaxaca — Mexico's cultural gem with hotel bargains

Best points: Transferable points to airlines that fly Mexico or regional low-cost carriers; hotel programs like Marriott Bonvoy often have reasonable standard-category hotels nearby.
Timing: Day-of-the-dead (Nov) is book-ahead—otherwise shoulder months are ideal.
Budget hack: Use fewer miles for shorter regional flights and transfer hotel points during targeted bonuses.

8. Vancouver — North American city + gateway to nature

Best points: West Coast U.S. flyers should leverage Alaska Airlines miles or Amex/Chase transfers to Air Canada via Star Alliance for cross-border redemptions.
Timing: Summer is busy; shoulder spring/fall has lower hotel rates and good award availability.
Budget hack: Use short-hop Avios redemptions for coastal flights; book hotels with free cancellation and monitor lower prices.

9. Amalfi Coast (Italy) — combine low-cost European flights with hotel points

Best points: Transfer UR/Amex to Flying Blue or Avios for intra-Europe legs; use Marriott/Hyatt for boutique coastal lodgings.
Timing: Late spring and early fall for fewer crowds and more award availability.
Budget hack: Fly into Naples or Rome on an award, then use regional trains/ferries—avoid high-season surcharges on coastal resorts.

10. Nairobi & Masai Mara — safaris via smart positioning

Best points: Star Alliance options (via Nairobi hub) or OneWorld routings; transferable points turned into business-class awards are value-packed for long flights.
Timing: Booking peak wildlife season requires earlier searches; shoulder months can still yield good sightings and better award pricing.
Budget hack: Book multi-night safari packages during hotel program sales or use points for cheaper city hotels while paying cash for safari camps that include meals/transport.

11. Patagonia — long-haul planning and regional routing

Best points: Star Alliance or OneWorld partners into Buenos Aires or Santiago; then book regional flights with low-cost carriers or domestic award inventory.
Timing: Southern hemisphere spring (Oct–Dec) is ideal for weather and quieter trails.
Budget hack: Use award flights to gateway cities and purchase regional flights in cash when award space is limited—often cheaper than premium award surcharges.

12. Santorini — classic islands with seasonal award swings

Best points: Avios for short intra-Europe hops; transfer points to Flying Blue or Aegean Miles+Bonus for better award availability to Greece.
Timing: Early summer is busy; aim for late spring or September for lower fees and easier award seats.
Budget hack: Book mainland Greece hotels on points and take a cheap ferry—save points for flights where they give the most value.

13. Barcelona — city breaks and sweet spots on short European awards

Best points: Transferable points to Iberia or Avios for short-haul redemptions; Amex/Chase to Flying Blue if routing via Paris/Amsterdam works better.
Timing: Book 4–8 months ahead for premium cabins; off-peak months are October–April (excluding holidays).
Budget hack: Use low-tax flights into nearby airports and train in; Avios short-haul pricing often beats cash.

14. Tokyo (If separate from Kyoto) — leverage award sweet spots for premium cabins

Best points: Transfer to JAL/ANA via Amex, Capital One or Citi; consider Alaska Airlines miles for OneWorld partner redemptions into Japan.
Timing: Peak cherry blossom season demands 9–12 months lead time for business class awards.
Budget hack: Mix economy inbound with business-class return for best value; many travelers find the upwards value is on long-haul return legs.

15. Seoul — cheap intra-Asia hops and premium cabin value

Best points: Transferable currencies to Korean Air or Asiana (when available) or OneWorld partners via JAL.
Timing: Spring and fall are excellent; award inventory often releases earlier for weekday travel.
Budget hack: Use loyalty program sales for hotels and combine with award flights booked during transfer bonuses.

16. Alaska — domestic adventure with regionally useful points

Best points: Alaska Airlines Mileage Plan, American AAdvantage and transferable points for domestic carriers; consider intra-state air passes for remote routes.
Timing: Summer is peak; book well ahead for award seats and cruises/charters.
Budget hack: Use stopovers where programs allow (Alaska Mileage Plan historically allows stopovers on award tickets) to string together a multi-leg trip for little extra cost.

17. Hawaiian Islands — domestic awards that feel like an international getaway

Best points: Alaska, HawaiianMiles, Chase transfers to Hawaiian partner airlines and domestic carriers.
Timing: Holiday weeks sell out; off-peak shoulder months offer lower award rates and hotel deals.
Budget hack: Book early for inter-island awards (Avios and HawaiianMiles often have the best short-haul pricing); use vacation rental discounts for longer stays.

Step-by-step booking process you can replicate for any of the 17 places

Pick your primary currency. If you own transferable points, start there. If you have a large balance in an airline program, check partner award charts first.
Search award space broadly. Use Google Flights to identify routings and dates, then search airline award portals for seat availability. Monitoring and alerts—set alerts for target dates.
Consider one-ways and open-jaws. Book outbound and return separately. Open-jaws let you fly into Lisbon and out of Rome, covering more ground with no backtrack.
Stack a points-transfer bonus. Wait for a bank transfer bonus if your window allows—many 2025–2026 promotions offered 20–40% extra value when converting to certain partners.
Lock in hotels with free cancellation. Use points or a flexible rate now and reprice later if a better deal appears.
Use stopovers smartly. If the program allows (some carriers still permit free stopovers), add a city to your journey without extra award cost.
Pay attention to fees. Taxes and carrier-imposed surcharges can change the total. Move to a different partner or route to reduce those if needed.

Advanced tactics that produce outsized savings

Transfer timing: Never transfer points until you are ready to book—transfers are often irreversible.
Use award repositioning: Book a cheap cash one-way to a hub with better award availability, then use miles for the long-haul segment.
Leverage card perks: Companion passes, free checked bags, and statement credits reduce cash burn—include them in your cost calculation.
Mix cash+points: When award inventory is poor, using a hybrid pay-with-points or part-cash can keep your travel flexible and affordable.

"In 2026, the traveler who wins is the one who thinks in currency buckets—transferable points for flexibility, airline miles for targeted sweet spots, and hotel points for value nights." — Practical advice from experienced bookers

Real example: Turning a 100k points balance into a two-city European trip (case study)

Scenario: You have 100k transferable points (Chase UR or Amex MR) and want Lisbon + Amalfi Coast for 9 nights in May 2026.

Search flights: Use Google Flights to find dates with low cash fares and note routing hubs (Madrid vs. Lisbon direct).
Check awards: Search Flying Blue and Iberia award space for transatlantic one-ways. If Flying Blue shows a promo reward, you can often land a transatlantic economy or premium economy for much less.
Build the trip: Book a one-way award to Madrid and cheap train to Lisbon (or an Avios award to Lisbon), use points for 2–3 nights in Lisbon via Marriott/Hyatt partners (off-peak standard rooms), then take a cheap regional flight to Naples and use points or moderate cash to reach the Amalfi Coast.
Result: With 100k transferable points plus minimal cash, you can secure long-haul transport and several hotel nights—this approach stretches points by avoiding high cut-rate premium cabins and by cash-paying for short regional legs where awards are expensive.

Monitoring and alerts — the tools to use

In 2026, automation matters. Use fare and award alerts so you don't refresh pages all day. Essential habits:

Create Google Flights alerts for cash fares to identify when award redemptions become attractive.
Sign up for airline award alerts—some sites and communities track sweet-spot award availability and publicize them.
Follow targeted transfer bonus announcements from card issuers and newsletters (many promos are short-lived).

Final checklist before you click "book"

Do I have > the required points after any transfer? (Remember transfer bonuses.)
Have I compared partner award pricing vs. direct program pricing?
Are taxes/fees acceptable or is there a lower-surcharge routing?
Have I reserved any necessary ground transfers (ferries, trains, safari pickup) separately if they aren’t covered by the award?

Actionable takeaways

Don’t hoard points forever: Use them on trips that matter—points often lose relative value because programs change and dynamic pricing increases.
Focus on one transferable currency: If you have balances across banks, designate one primary transferable currency for 2026 trips to simplify transfers and capture bonuses.
Time your bookings: For most long-haul 2026 travel, 5–10 months ahead is your sweet spot; for high-season events or limited inventory, move earlier.
Stack every deal: Welcome bonus + transfer bonus + promo awards + hotel loyalty sale = maximum value.

Why this matters in 2026

Travel demand remains robust and award seats are more variable than ever. That makes planning smarter, not harder, the edge that gets you a business-class seat or a perfect hotel for a fraction of the cash price. The 17 destinations above are high-value targets in 2026 because they combine great experiences with realistic award and cash deal pathways—if you know where to look and how to act.

Ready to build your own 2026 bucket-list trip?

Start with a single decision: pick the destination and the month. Then use the 7-step process in this guide—search broadly, keep transfers until booking, and stack promos. If you want personalized help turning your points into an itinerary from the The Points Guy-inspired 17, compare award-friendly routes and current transfer bonuses on bookers.site and sign up for our weekly alerts.

Book smart, use points with intent, and make 2026 the year you actually go.

bookers

Contributor

Senior editor and content strategist. Writing about technology, design, and the future of digital media. Follow along for deep dives into the industry's moving parts.