17 Destinations to Book Now for 2026 — And How to Stretch Your Points

Book fast, pack light, and stop hoarding points: 17 Places to Go in 2026 — and how to stretch your miles for each

Short on planning time but heavy on points? You’re not alone. In 2026, travelers want high-value short trips that are easy to book, flexible, and memorable — without wasting months of research. Below you’ll find an action-first playbook: the 17 destinations The Points Guy highlighted for 2026, with a sharp points-and-miles strategy and a realistic 48-hour city-break itinerary for each. Use the included checklists and booking workflow to go from idea to paid award in under 90 minutes.

Quick primer: what’s different about award travel in 2026

Dynamic award pricing is the baseline — most major U.S. carriers moved fully to dynamic pricing by 2024–2025, and that continued into 2026. That means fixed award charts are increasingly the exception. Your advantage: flexibility on dates, airports and routing. If you can shift one travel day or accept a one-way/mixed-cabin itinerary, you can often cut the points cost by 25–60%.

Transferable points remain king. Chase Ultimate Rewards, American Express Membership Rewards and Capital One Miles continue to offer the best option mix in 2026 — frequent targeted transfer bonuses still pop up, especially around major regional travel slowdowns (late fall) and airline promotions.

New routes and regional carriers — post‑2025 route growth means more midweek award space to Europe and Asia. For short city breaks this opens cheap positioning flights and one-stop awards that use fewer points than direct flights.

How to use this guide

1. Scan the destination that fits your travel window.
2. Follow the points strategy under each city to search award inventory.
3. Use the 48‑hour itinerary to book experiences and know where to stay.
4. Apply the final booking workflow and packing checklist at the end of the article.

TPG’s 17 top picks for 2026 — paired with points strategies and short itineraries

1. Lisbon, Portugal

Why go in 2026: A surge in year‑round flights and cheaper off‑peak fares make Lisbon a top quick‑Europe pick.

Points strategy: Transfer Chase or Amex to Iberia/Avios for off‑peak short‑haul awards. Look for Iberia and TAP occasional transfer bonuses (5–25%). One-way economy from the U.S. to Lisbon often sits in the 25k–40k points range with dynamic pricing; business can be 60k–110k depending on demand. For hotels, leverage Marriott Bonvoy points for centrally located options in Baixa or Chiado (30k–50k/night) or use Marriott cash + points for savings.

48-hour itinerary (ideal for a Fri–Sun):

• Day 1 AM: Arrive early, check bags at a central hotel (Chiado). Coffee and pastel de nata in a local pastelaria (8–12:00).
• Day 1 PM: Tram 28 loop + Alfama walk to São Jorge Castle (13:00–17:00).
• Day 1 Night: Sunset at Miradouro de Santa Catarina, dinner in Bairro Alto (20:00).
• Day 2 AM: Day trip to Belém — Jerónimos and Pastéis (09:00–12:00).
• Day 2 PM: LX Factory market, riverfront stroll, airport transfer (13:00–18:00).

2. Kyoto, Japan

Why go in 2026: Post-Expo flight and hotel capacity has eased; spring and fall remain best but winter city breaks are quieter and cheaper.

Points strategy: Transfer Amex or Chase to ANA or JAL via partners; use Singapore KrisFlyer and Air Canada Aeroplan for better mixed-carrier availability on one‑way awards. Business-class awards from the U.S. to Tokyo often range 70k–120k one-way in 2026; positioning to Kansai (KIX) via a mid-size Asian carrier can reduce costs. For hotels, Hyatt and Marriott have great central properties; consider points + cash to offset high rates.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Arrive Kyoto Station, luggage to hotel, Fushimi Inari shrine early (07:30–11:00).
• Day 1 PM: Ninenzaka/Maruyama park, tea house visit (12:00–17:00).
• Day 1 Night: Dinner in Gion; look for an izakaya (19:00).
• Day 2 AM: Arashiyama bamboo grove + Tenryu-ji (08:00–12:00).
• Day 2 PM: Philosopher’s Path + Nishiki Market, late train to airport (13:00–18:00).

3. Reykjavik, Iceland

Why go in 2026: Continued interest in short Arctic escapes and the rise of cheaper midweek European connections make Iceland accessible for long weekend trips.

Points strategy: Use Avios for short connections from the U.S. east coast to Iceland on select transatlantic carriers; Aeroplan also offers good routing rules for stopovers — sometimes cheaper to book two one‑ways. Expect one-way economy awards 20k–40k; business from 60k up. Use IHG or Marriott points for Reykjavik hotels; consider a cash rental car for Golden Circle day trips (if you’re planning to power small devices or charge cameras on the go, check portable power options like the comparison of portable power stations for RV or flight trips) and bring compact camping lights for any outdoor detours.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Arrive KEF, pick up car, drive Golden Circle — Þingvellir, Geysir, Gullfoss (08:00–15:00).
• Day 1 Night: Reykjavik downtown dinner and hot springs/Blue Lagoon option (18:00).
• Day 2 AM: Hallgrímskirkja church, coastal walk and local cafes (09:00–12:00).
• Day 2 PM: Museum or whale‑watching trip, evening flight home (13:00–18:00).

4. Tbilisi, Georgia

Why go in 2026: Emerging culinary and wine scene, friendly visa rules for many countries and lower prices for hotels make Tbilisi a top off‑radar pick.

Points strategy: Transferable points to Turkish Airlines Miles&Smiles or Aeroflot partners (where still useful) can be a sweet spot; check Star Alliance options through Lufthansa/LOT/Swiss via Aeroplan/United. Expect long-haul awards to Tbilisi to vary widely — look for routing via major European hubs. For in‑city stays, use Hyatt and boutique hotels; low nightly cash rates make saving points for flights sensible.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Arrive, check into Old Town guesthouse; walk Meidan, sulfur baths (09:00–13:00).
• Day 1 PM: Wine bar crawl in the evening in the Sololaki district (14:00–22:00).
• Day 2 AM: Day trip to Kakheti wine region or a hiking valley (08:00–17:00).

5. Cartagena, Colombia

Why go in 2026: Caribbean beaches plus colonial charm make Cartagena perfect for a winter weekend; more direct flights from U.S. gateways launched in 2025.

Points strategy: Use Avianca LifeMiles (no fuel surcharges) or Iberia Avios for intra‑Caribbean routing; short‑haul awards are often inexpensive off‑peak. Hotels are affordable — use Marriott or Hyatt points sparingly and save for pricier stays.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Arrive, walled-city walking tour and lunch in Getsemaní (09:00–14:00).
• Day 1 PM: Sunset drinks on city walls, street food (17:00–21:00).
• Day 2 AM: Rosary Islands boat trip (08:00–14:00). PM: Relax, fly home (15:00–20:00).

6. Azores (Ponta Delgada), Portugal

Why go in 2026: Nature-rich, fewer crowds than mainland Europe and improved mid‑Atlantic connectivity make the Azores an all‑season escape.

Points strategy: Use Avios or Aeroplan for transatlantic positioning via Lisbon, or book low-expense cash flights from the U.S. East Coast. Hotels in Ponta Delgada are generally reasonable — use points if you find a promotion, otherwise save points for long‑haul flights.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Arrive PDL, head to Sete Cidades viewpoint (08:00–13:00).
• Day 1 PM: Thermal baths, coastal dinner (14:00–20:00).
• Day 2 AM: Whale watching or hiking around Furnas (07:00–14:00).

7. Vancouver, Canada

Why go in 2026: Outdoor access plus city comforts — ideal for winter sports or a spring urban break.

Points strategy: Use Aeroplan for good routing and lower surcharges; Air Canada award charts and dynamic pricing still offer solid sweet spots for West Coast flyers. Westin/Hyatt properties in downtown offer good cash+points options for 48‑hour stays.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Capilano Suspension Park and Grouse Mountain (08:00–14:00).
• Day 1 PM: Gastown + waterfront stroll (15:00–19:00).
• Day 2 AM: Stanley Park bike loop, Granville Island market (08:00–13:00).

8. Seoul, South Korea

Why go in 2026: Nightlife, food culture and improved midweek award availability post-2025 expansion make Seoul an excellent short-break choice.

Points strategy: Transfer Amex or Chase to Korean Air SKYPASS, Asiana or to partners via Air Canada Aeroplan. Off‑peak one-way awards can be 35k–70k in economy and 80k–140k in business depending on promotions. Use hotel loyalty programs downtown (Myeongdong/Jongno) or consider boutique stays booked with cash if points redemptions are poor value.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Gyeongbokgung palace and Bukchon Hanok Village (09:00–13:00).
• Day 1 PM: Insadong, street food and evening in Hongdae (14:00–22:00).
• Day 2 AM: DMZ half-day tour or Seoul Tower and Namdaemun market (08:00–15:00).

9. Buenos Aires, Argentina

Why go in 2026: Strong value for money and renewed flight options from U.S. hubs make Buenos Aires a 48‑hour cultural treat.

Points strategy: Transferable points to LATAM or use AAdvantage for off‑peak routes; keep an eye on Avianca LifeMiles promos for partner awards. One-way economy can be 25k–45k; business seats vary widely. Balance points on flights and spend cash on local boutique hotels and experiences.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Recoleta cemetery and café culture (09:00–13:00).
• Day 1 PM: La Boca and San Telmo, tango show at night (14:00–23:00).
• Day 2 AM: Palermo parks and boutique shopping (09:00–14:00).

10. Marrakech, Morocco

Why go in 2026: An affordable long weekend that feels like another world — flights from European hubs got more frequent in 2025, improving award access.

Points strategy: Use Avios or Aeroplan for Europe-to-Marrakech legs; occasionally a transfer bonus to Iberia makes business-class sweet spots possible. Book riads with cash if nightly rates are low; save points for higher-cost hotels elsewhere.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Arrive Menara, relax and lunch in Medina (10:00–14:00).
• Day 1 PM: Jemaa el-Fnaa square at sunset, rooftop dinner (17:00–22:00).
• Day 2 AM: Bahia Palace + souk tours (08:00–13:00). Note the lively night markets and arrival-zone strategies for after-hours shopping and food stalls.

11. Split, Croatia

Why go in 2026: Post-season quiet and better direct seasonal links from Europe make Split a great short Adriatic getaway.

Points strategy: Fly into Split through Star Alliance partners via Zagreb or connect from major European hubs. Use Marriott/Hyatt points for waterfront stays if availability aligns; otherwise book cash and use points for bigger legs of the trip.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Diocletian’s Palace and old town walking tour (09:00–14:00).
• Day 1 PM: Ferry to a nearby island (Hvar/Brac) for sunset (15:00–22:00).
• Day 2 AM: Beach time or Marjan Hill hike (08:00–13:00).

12. Oslo, Norway

Why go in 2026: Compact city with outdoor access — great for cultural and fjord day trips. More award seats appeared on transatlantic routes in late 2025.

Points strategy: UK‑to‑Scandinavia Avios and Aeroplan sweet spots are valuable. Expect higher cash rates in peak season — use points to lock hotel value. Domestic Norway rail/bus passes are cheap in cash; don’t waste points on short local transfers.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Viking Ship Museum + Akershus Fortress (09:00–13:00).
• Day 1 PM: Aker Brygge waterfront dinner (14:00–20:00).
• Day 2 AM: Day fjord cruise or rail to nearby towns (08:00–16:00).

13. San Juan, Puerto Rico

Why go in 2026: No passport required for U.S. travelers, great value, beach + city culture in a long weekend.

Points strategy: Domestic award sweet spots via AA/United (often 7.5k–17.5k one-way) make short island hops cost‑efficient. Use Marriott or Hyatt for beachfront stays; low taxes and fees compared to international long-haul awards.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Old San Juan walk and Castillo San Felipe del Morro (09:00–14:00).
• Day 1 PM: Condado beachfront and evening salsa club (15:00–23:00).
• Day 2 AM: El Yunque mini-hike and waterfall, fly home late (07:00–18:00).

14. New Orleans, USA

Why go in 2026: Food and music capital that’s easy to reach for U.S. travelers — perfect for a jam-packed 48 hours.

Points strategy: Domestic award charts remain stable — use United or American for cheap one‑way redemptions. Hotels in the French Quarter can be expensive; consider Hilton or Marriott Points & Cash options in nearby neighborhoods.

48-hour itinerary (Fri–Sun):

• Day 1 AM: French Quarter and beignets at Café du Monde (09:00–12:00).
• Day 1 PM: Steamboat Natchez cruise, evening jazz on Frenchmen Street (13:00–23:00).
• Day 2 AM: Garden District streetcar + Lafayette Cemetery tour (08:00–13:00).

15. Melbourne, Australia

Why go in 2026: Strong café culture, art and accessible day trips make Melbourne a superb city-break anchor in the southern hemisphere shoulder seasons.

Points strategy: Use Qantas, Virgin Australia via Velocity, or partner awards (Air Canada Aeroplan) to reach Melbourne. Business awards from the U.S. are subject to dynamic pricing; look for positioning to Asia hubs for lower costs. Book hotels with Hilton Honors or Marriott for points stays in CBD.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Queen Victoria Market and laneway coffee crawl (08:00–12:00).
• Day 1 PM: National Gallery + Southbank dinner (13:00–20:00).
• Day 2 AM: Great Ocean Road day trip (05:00–18:00).

16. Funchal, Madeira (Portugal)

Why go in 2026: Year-round mild climate, hiking and levada trails — Madeira is a top slow-travel pick that fits a long weekend.

Points strategy: Position through Lisbon with Avios or TAP; local hotels are affordable — spend points strategically on flights rather than hotels.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Morning arrival, Funchal market, cable car to Monte (09:00–13:00).
• Day 1 PM: Levada walk and local seafood dinner (14:00–20:00).
• Day 2 AM: Pico do Arieiro sunrise hike, return late (04:00–15:00).

17. Tallinn, Estonia

Why go in 2026: Compact medieval charm, tech-friendly services and easy budget connections from Europe make Tallinn great for a short cultural escape.

Points strategy: Use Avios or SAS/EU partner awards through Scandinavia; cheap cash flights from European hubs often beat points in late‑season sales. Boutique hotels are wallet-friendly — use cash and save points for transatlantic legs.

48-hour itinerary (Fri–Sun):

• Day 1 AM: Walk Old Town and Town Hall Square (09:00–13:00).
• Day 1 PM: Kalamaja neighborhood and Telliskivi Creative City (14:00–19:00).
• Day 2 AM: Kadriorg Park and museums, late flight home (09:00–17:00).

Advanced ways to stretch points in 2026

• Search one-way awards first: Mix carriers or cabins to shave points and open more routing options.
• Use transfer bonuses: Keep a watchlist — targeted 20–40% transfer bonuses (Amex/Chase/Capital One) are still the fastest way to supercharge an award booking in 2026.
• Book positioners smartly: A cheap cash flight to a major alliance hub can unlock much cheaper long-haul award space — pairing that with smart arrival-zone tactics can save time and money (see arrival-to-street strategies).
• Leverage companion and elite perks: Companion certificates and free checked bags cut cash costs and increase award value.
• Cash+points where value is poor: Don’t burn 50k hotel points for a $150 night — use Points & Cash or save points for nights where value per point is >0.5¢.

Practical booking workflow (do this in under 90 minutes)

1. Pick three target dates (flex ±2 days) and two nearby airports.
2. Use Google Flights to find cash availability and approximate times; note the carrier and flight numbers.
3. Check award inventory on alliance websites and aggregators (United, Aeroplan, ExpertFlyer, AwardNexus).
4. If award space exists, confirm partner transfer times. If a transfer bonus is active, move points immediately (do not transfer unless award space is bookable and instant).
5. Book one‑ways separately to build mixed itineraries. Hold hotels with free cancellation where possible for price flexibility.
6. Set calendar reminders for ticket change/cancel windows and check bag/pcr/vaccine rules if relevant.

Packing checklist for 48-hour city breaks

• Carry-on only: versatile layers, travel-sized toiletries, power adapter, lightweight rain jacket.
• Electronics: phone + battery pack, noise-canceling earbuds, eSIM or local SIM plan if needed (local-first 5G trends make eSIMs more useful in cities).
• Documents: digital copies of passport/ID and award confirmations in screenshot form.
• Health & safety: small first‑aid, medications, travel insurance card (esp. for international trips).
• Points & cards: primary travel card, backup card with no foreign transaction fee, program numbers in notes app.

Budgeting cheat sheet (example weekend)

Sample 48‑hour budget ranges (per person) — costs in 2026 USD, excluding award flights:

• Low-cost city (Tbilisi, Tallinn): $120–$300 (2 nights midrange hotel, food, transit, one tour).
• Mid-range city (Lisbon, Split, Vancouver): $300–$700 (centrally-located hotel, dining, tours).
• High-cost city (Melbourne, Kyoto): $700–$1,500 (long-haul positioning, nicer lodging, day trips).

Quick decision checklist before you hit "transfer points"

• Do I have confirmed award space that books immediately after transfer?
• Is there a transfer bonus that makes this value-positive?
• Do I have flexible dates if the carrier re-prices dynamically?
• Have I held hotels with free cancellation and double-checked visa/entry rules?

Pro tip: “Book one‑way awards and stitch them with low-cost cash flights when it saves points. Flexibility usually beats hoarding.” — Your local points strategist

2026 trends to watch (late 2025 to early 2026)

• More targeted transfer bonuses tied to regional promotions — subscribe to email alerts from Chase/Amex/Capital One and points blogs.
• Greater award-seat transparency from some carriers — use real-time tools to monitor inventory instead of waiting for monthly releases.
• Regional carrier growth: more midweek routes reduce business-class award premiums on certain routes.

Final takeaways

If you have limited time, the biggest wins come from flexibility: nearby airports, shifting one travel day and mixing cash + points. Start with one of the 17 destinations above, follow the booking workflow and use the packing checklist — you’ll be surprised how many “someday” trips convert to a booked weekend in under an hour.

Call to action

Ready to book? Download our free 90‑minute booking worksheet and printable 48‑hour packing checklist (PDF). Want a tailored award-search plan for one of the 17 destinations above? Sign up for a 15‑minute planning consult and we’ll map the fastest award route and hotel option for your points balance.

Related Reading

• Airport & Travel Scheduling: The New Rules for Loyalty, Fast Pickup, and Carry-On Timelines (2026 Playbook)
• Case Study & Review: NomadPack 35L — Travel Kits for Judges on the Road
• Jackery HomePower 3600 vs EcoFlow DELTA 3 Max: which power station should you bring on an RV or flight trip?
• The Evolution of Ultralight Backpacking Kits in 2026: Advanced Strategies for Minimalist Campers
• From Gate to Street: Pop‑Up Strategies for Arrival Zones and Night Markets in 2026
• DIY 3D Food Molds: From Phone Scans to Custom Cookie Cutters
• Identity Verification for Declarations: Closing the $34B Gap Banks Are Missing
• Detecting and Blocking Suspicious Password Resets at Scale
• Build a Privacy-First Local Browser Plugin: Lessons from Puma and Local AI
• Wristbands vs Thermometers: How Reliable Are Wearables for Fertility Tracking?