Where to Go in 2026: 5 Point-Based Weekend Itineraries From The Points Guy List

Where to Go in 2026: 5 Point-Based Weekend Itineraries From The Points Guy List

Feeling buried in scattered travel advice while your points sit unused? If you’ve been hoarding miles and hotel credits for “someday,” 2026 is the year to turn them into short, high-value getaways. Using The Points Guy’s Jan 2026 roundup of the 17 best places to travel as inspiration, I picked five standout destinations and built purpose-driven, 48-hour itineraries that prioritize reward-night value, transferable points, and credit-card perks. Each plan shows how to stretch miles and certificates to make a stress-free, budget-friendly weekend trip.

Why weekend redemptions matter in 2026

Short trips are the perfect use case for points in 2026. Award availability recovered across most carriers in late 2024–2025, but dynamic pricing and shorter booking windows mean high-value opportunities exist for weekend travel: off-peak hotel nights, intra-region short-haul awards, and targeted use of one-night free certificates. Combine smarter award searches with current credit-card perks — lounge access, free night certificates, and statement credits — and you can often turn a modest stash of points into a luxury 48-hour escape.

“Weekend trips let you realize immediate returns on your points without long-haul award complexity.” — Practical travel strategy

Quick planning checklist (before you book)

• Inventory points: Check Chase Ultimate Rewards, Amex Membership Rewards, Capital One Miles, airline programs, and hotel balances plus any free night certificates.
• Transfer options: Confirm transfer partners and current transfer bonuses (late 2025 saw frequent limited-time transfer bonuses — watch for similar ones in 2026).
• Search strategy: Use flexible date searches ±2–3 days and set award alerts for award seats and hotel dates.
• Leverage perks: Use lounge access to reduce day-one stress, Fine Hotels & Resorts (Amex) or Hyatt/Marriott benefits for room upgrades, and credit-card travel credits for incidentals.
• Book smart: If you have a free night certificate, pair it with a points or cash night to maximize tiered-value stays.

Itinerary 1 — Lisbon, Portugal (TPG pick): Culture, pastel streets, and an Avios sweet spot

Lisbon remains a top European weekend pick on TPG’s 2026 list for its walkable neighborhoods, food scene, and short flights from North American gateways. For points-savvy travelers, Lisbon is a great short-haul award and hotel-redemption market.

How to get there using points

• From the U.S. East Coast: Look for saver-level transatlantic awards on Iberia/Level/ANA partners or use British Airways Avios for off-peak redemptions (shorter peak surges apply). Transfer Chase or Amex points to a partner airline where you find availability.
• Intra-Europe / short hops: Use Avios for Lisbon-Porto or nearby Spanish cities at typically low point costs — great for multi-city micro-trips.

Where to stay (48 hours)

• Use a free night certificate at a city-center Marriott or use World of Hyatt points for boutique Hyatt properties — a single free night often covers a Friday or Saturday stay when combined with a points night on Thursday.
• If you hold Amex Platinum, explore Fine Hotels & Resorts for guaranteed noon check-in, $100 credit, and breakfast credit — those perks can beat standard reward nights when availability is tight.

Sample 48-hour plan

1. Day 1 (Afternoon): Land, take the Aeroporto metro to Baixa-Chiado, check in using a free night certificate + points combination. Stroll to Praça do Comércio and take a sunset tram ride.
2. Evening: Tap a statement dining credit (Amex or Chase dining offers) where possible. Reserve a tile-style small restaurant — Lisbon rewards walking and late dinners.
3. Day 2: Morning visit to Belém (pastéis de nata stop). Afternoon Fado show in Alfama. Use public transport with a 24-hour travel card to keep costs low.
4. Late evening: Use airport lounge access on return flight or Capital One Venture X lounge benefits for relaxed security and drinks before departure.

Value tips

• Search Avios and Iberia slots at 330–360 days out for the best transatlantic saver fares; otherwise transfer Chase/Amex points to book mid-range dynamic awards.
• Combine one free night certificate with a points night to reduce out-of-pocket cash substantially while using benefits like upgrade potential from elite status or FHR perks.

Itinerary 2 — Kyoto, Japan (TPG pick): Zen gardens, food alleys, and strategic award sweet spots

Kyoto tops many 2026 lists for cultural immersion. For a 48-hour recharge, focus on quality over quantity: efficient routing, a single centrally located hotel, and a few booked experiences.

How to get there using points

• Book premium economy or business using transferrable points (Chase/Amex/Capital One) to partners like ANA, Japan Airlines, or on partner programs that access JAL/ANA inventory.
• If you're based in Asia-Pacific, short domestic flights or shinkansen can be purchased with points through partnered transfer programs or by using travel portals (e.g., Chase travel portal).

Where to stay

• Use Hyatt or Marriott points for central Kyoto properties; if you have Hyatt Globalist or Marriott Platinum, expect late check-out and room upgrades for extra comfort on a short trip.
• Consider using an Amex Fine Hotels & Resorts booking for Ryokan-style hotels where available; the property credits and guaranteed benefits are useful on a short stay.

Sample 48-hour plan (efficient routing)

1. Day 1 (Afternoon): Arrive, check in, drop bags. Walk to Gion, book an early evening kaiseki dinner (pre-book popular spots with concierge help using card benefits).
2. Day 2 (Morning): Sunrise at Fushimi Inari. Midday visit to Kiyomizu-dera then Nishiki Market for lunch. Use a taxi for tight timing, and redeem a small number of transfer miles or points for a one-way private transfer if arriving late-night for convenience.
3. Night 2: Return via Kansai or Osaka (if flying out) and use airport lounge access via your premium card before the flight.

Value tips

• Kyoto reward rooms can be limited on peak weekends — book hotels as soon as you lock flights. Use points + cash if necessary to conserve certificates.
• For short Japan trips, prioritize experience bookings (tea ceremony, private guide) with a dedicated portion of points rather than upgrading to business — the in-country experience often yields higher perceived value for a weekend.

Itinerary 3 — Oaxaca City, Mexico (TPG pick): Food, markets, and cheap short-haul awards

Oaxaca is one of those 2026 heavy-hitter destinations for food and culture. It’s also a perfect points play from U.S. gateways: short transborder flights with reasonable award rates and many affordable hotel redemptions.

How to get there using points

• Use airline partners like Aeroméxico (subject to partnership availability) or short-haul awards on American/United. Capital One and Amex transferable points can often be moved to partners to cover short-haul tickets.
• Or book flights through card travel portals where earning extra points on the purchase can offset cash cost — sometimes the portal rate plus used miles is a better deal for last-minute travel.

Where to stay

• Oaxaca has boutique independent hotels that partner with major programs for award nights; use Marriott/Hyatt points if you prefer chain comforts, but consider booking one night cash at a boutique and one with a certificate to sample both.
• For food-focused trips, prioritize location over star rating — central hotels save taxi time and cost.

Sample 48-hour plan

1. Day 1 (Late afternoon): Check into central hotel using a points night. Evening food crawl with mole tasting and mezcal bar visits; reserve a mezcal tasting through your hotel concierge using a credit-card travel credit if available.
2. Day 2 (All day): Daytrip to Monte Albán in the morning (guided tours often accept card reservations and are easy to book with hotel help). Afternoon market shopping at Mercado 20 de Noviembre and a cooking class in the evening.

Value tips

• Short flights to Oaxaca can be very cheap on points if you’re flexible; set award alerts and be ready to book within 24–48 hours.
• Use small-business-friendly cards to earn bonus categories on food experiences; some cards in 2025–26 expanded dining partners and targeted credits.

Itinerary 4 — Reykjavik, Iceland (TPG pick): Geothermal relaxation and capital convenience

Iceland is still a 2026 standout for short-adventure weekends. Reykjavik’s compact downtown, easy access to Golden Circle tours, and plentiful hotel award options make it a great points-trip choice.

How to get there using points

• Look for transatlantic deals on Icelandair or partners; Chase/Amex transfers can access airline partners that publish saver-level seats for Reykjavik.
• For intra-Scandinavia hops, Avios and other regional currencies are often efficient.

Where to stay

• Use Marriott or Hilton free night certificates for Reykjavik hotels — Iceland hotels can be pricey, so certificates have outsized value.
• If you hold an Amex Platinum, use Fine Hotels & Resorts or Amex Offers for Icelandic properties offering breakfast and credits.

Sample 48-hour plan

1. Day 1 (Evening): Arrive, check in with a free night certificate if possible. Quick walk to a nearby geothermal spa or local hot pool for a genuine Icelandic experience.
2. Day 2 (Full day): Rent a car (or book a Golden Circle tour). Use Hertz/enterprise partner credits linked to your premium card to offset rental insurance and GPS. End the day with a visit to the Blue Lagoon (book in advance with card perks if any discounts apply) before an evening flight or late-night stay.

Value tips

• Because hotels are expensive in Iceland, a single free night certificate can save you more than the card’s annual fee in cash value — that’s high ROI for weekend travelers.
• Book car rentals with cards that include primary rental insurance to avoid expensive vendor add-ons.

Itinerary 5 — Medellín, Colombia (TPG pick): Year-round spring and big hotel award value

Medellín’s climate, cafes, and growing cultural calendar make it a TPG 2026 highlight. It’s also an incredibly friendly market for international award travelers: affordable award flights from U.S. hubs and excellent redemption value on regional hotels.

How to get there using points

• Book direct or one-stop awards with Avianca Lifemiles, United, or American using transferred points to reach the best inventory. Capital One and Amex transfer partners can provide flexibility if one carrier lacks seats.
• Short regional connections within South America can be covered with lower-cost awards or by purchasing inexpensive intra-regional tickets when award space is limited.

Where to stay

• Use Marriott Bonvoy points for boutique properties in El Poblado or Laureles — the value per point in Medellín often exceeds the average global redemption.
• Hilton and Hyatt properties also present strong cash-vs-points sweet spots; use free night certificates or a one-night points booking with a cash night to maximize benefits.

Sample 48-hour plan

1. Day 1 (Evening): Arrive, check in using points. Dinner in El Poblado with nightlife walk — use mobile ride options to move at night safely and cheaply.
2. Day 2: Morning cable car ride to Parque Arví, then afternoon museum visits and rooftop coffee tastings. Use a credit-card dining/transport credit where applicable.

Value tips

• Medellín hotel redemptions often return 1.5–3x the base value of points compared to peak European cities — that’s a strong argument to spend hotel points here instead of saving them for a pricier destination.
• Keep an eye on airline promos in 2026 — leisure demand surges have led to intermittent award seat releases on South American routes, especially during local festivals.

Advanced strategies to squeeze more value (2026 updates)

Late 2025 and early 2026 saw several trends that impact weekend redemptions:

• More dynamic awards: Airlines continue to roll out dynamic pricing models. That means fewer “saver” seats but also more small inventory windows where you can get better value by booking exactly the right two days.
• Transfer bonuses remain tactical: Banks occasionally offered transfer bonuses in late 2025 — watch for repeat events in 2026. A 20–30% bonus to a hotel or airline partner can turn an average redemption into an outright steal.
• Passport-to-experience focus: Programs now emphasize experiential redemptions (food tours, local guides). For short trips, experience redemptions often deliver high perceived value and are typically easier to book with points than premium cabins.

Practical booking tips

• Always check both airline/hotel sites and transfer partners before moving points — it’s faster to transfer instant partners (Hyatt, Air Canada Aeroplan in some cases) than to risk a timed transfer.
• Split your redemptions: use points for the most expensive line item (usually hotels) and pay cash for cheap flights, or vice versa depending on cash price and award availability.
• Use credit-card travel portals when a portal sale or statement credit makes the cash option cheaper than burning points — portals can be surprisingly good on short-haul and last-minute itineraries.

Actionable checklist for booking your 48-hour points weekend

1. Decide which of the five destinations fits your travel window.
2. Inventory your points and free-night certificates.
3. Set award alerts and search across three different programs for both flights and hotels.
4. If seats appear, transfer just enough points needed if transfers are instant; if not instant, secure a hold with the airline or book a refundable cash fare and convert later.
5. Use hotel elite perks, concierge help, and card benefits to book experiences that add outsized value to a short trip.

Final takeaways

Weekend trips are an underused high-ROI strategy for points collectors in 2026. With award availability patterns shifting and hotel costs rising in many hotspots, targeted short trips unlock authentic experiences without the planning overwhelm. Pick one of TPG’s 17 best places — such as Lisbon, Kyoto, Oaxaca, Reykjavik, or Medellín — and combine a single free night certificate, some transferable points, and your card’s lounge and travel credits for a low-stress, high-value 48-hour getaway.

Ready to use those points?

Pick a destination, run the inventory checklist, and set award alerts tonight. If you want a tailored plan, sign up for our weekend-points planner — we’ll audit your balances and map a 48-hour itinerary around your exact certificates and travel dates.

Sources & context: This guide builds on The Points Guy’s Jan. 2026 “Where to go in 2026: The 17 best places to travel” roundup and recent late-2025 developments in airline and hotel loyalty programs. For real-time award availability and program rules, check your loyalty dashboards and follow transfer-bonus alerts.

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