17 Places to Go in 2026 — Customized Itineraries for Families, Solo Travelers, and Adventure Seekers

Make 2026 your year of purpose-driven travel — without guessing about prices, seasons or award availability

Planning a big trip in 2026 feels great until you hit the usual pain points: which season is best, how to stretch points and miles for a family of four, hidden hotel fees, or whether a destination is safe and family-friendly right now. This guide cuts through the noise. Using The Points Guy’s 2026 picks as inspiration, we deliver 17 destination-specific itineraries—each with quick family, solo and adventure versions, practical seasonal timing, and actionable points-and-miles strategies you can use today.

How to use this guide (fast):

• Scan the destination list for what matches your travel type.
• Check the "Best season" and recommended trip length to lock a booking window.
• Use the points tips (transferable currencies + hotel chains) to estimate award options.
• Book refundable fares or travel insurance for families and last-minute solo trips.

2026 travel trends to plan around (late 2025–early 2026 context)

Before we jump into destinations, here are trends shaping travel this year:

• Dynamic award pricing is more common — lock in awards early, monitor alerts, and consider mixed-cabin splits for long-haul flights.
• Secondary city routes expanded — airlines added more seasonal nonstop links in late 2025, opening cheaper positioning options.
• Remote-work and long-stay offers continue to drive value in off-peak seasons; many hotels now offer weekly rates or workspace packages. Read up on portable power and the economics of charging while remote: The Hidden Costs and Savings of Portable Power.
• Sustainable travel and carbon-offset add-ons are mainstream in loyalty programs — prioritize brands with transparent policies.
• Digital visa and longer tourist stays are rolling out in regions courting long-stay visitors (check official government sites before booking).

Quick booking playbook (actionable)

1. Set award alerts with tools like ExpertFlyer, Point.me or airline loyalty notifications. For tactics on tracking fares and AI tools that find cheap routings, see Cheap Flight Hacks for 2026.
2. Transfer flexible points (AmEx MR, Chase UR, Capital One, Citi TY) to partner airlines or hotels within 7–30 days of booking to reduce volatility.
3. For families, prioritize refundable or changeable fares and book seats at the same time you secure award inventory.
4. Use hotel points for 3–4 night stays in pricey cities—save cash for experiences and transfers.
5. Always check baggage, resort fees and infant/child policies before completing a points booking.

17 Places to Go in 2026 — tailored itineraries

1. Kyoto, Japan

• Best season: March–April (cherry blossom) and October–November (fall color)
• Recommended nights: 4–6 in Kyoto + 1–2 in Osaka or Tokyo
• Family itinerary: Nijo Castle, Arashiyama bamboo grove, tea ceremony for kids, Kyoto Railway Museum; slower mornings and a private transfer for luggage.
• Solo itinerary: Temple-hopping, early-morning market walks, a day trip to Nara for deer and quieter temple time, evening izakaya crawl in Gion.
• Adventure itinerary: Hike the Kurama–Kibune trail, bike the Sagano countryside, and overnight in a ryokan with an onsen (check onsen rules for tattoos).
• Points & miles tip: Look for transpacific award space via ANA (transferable from AmEx/Marriott) or JAL partners. Consider positioning via Tokyo if nonstop availability is tight.

2. Lisbon, Portugal

• Best season: April–June and September–October
• Recommended nights: 3–5 + 1–2 for Sintra
• Family: Tram 28, Oceanário de Lisboa aquarium, day trip to Cascais and Estoril beaches.
• Solo: Fado houses, rooftop cafés, co-working day and evening food markets like Time Out Market.
• Adventure: Surfing lessons in Ericeira or Algarve, and cliff hikes near Cabo da Roca.
• Points tip: Iberia/Avios can yield good short-haul redemptions across Europe. Transfer UR or Avios into Iberia/BA for Iberian routes; use hotel points for boutique stays in Alfama.

3. Reykjavik & Iceland

• Best season: June–September for midnight sun; winter for northern lights (Nov–Mar)
• Recommended nights: 3–5 in Reykjavík with 2–3 nights for a south-coast or Westfjords loop
• Family: Golden Circle, secret lagoons, whale watching and easy glacier walks with guided operators that provide child equipment.
• Solo: Road-trip loop in a compact rental, stop at hot pools, book guided glacier or ice-cave tours for safety and company.
• Adventure: Multi-day glacier trekking, ice-cave exploration or kayaking among fjords (seasonal).
• Points tip: Look for seasonal award space on North Atlantic carriers; use AmEx or Chase transfers to partner airlines or hotels. Consider redeeming hotel points in Reykjavík in July–August well ahead of peak demand.

4. Dubai, UAE

• Best season: November–March
• Recommended nights: 3–5
• Family: Theme parks (IMG Worlds, Dubai Parks), desert safari with a reputable operator, aquarium at Dubai Mall.
• Solo: Skyline dining, art districts like Alserkal Avenue, and a dhow cruise for social evenings.
• Adventure: Sandboarding, morning quad biking, and camping under desert stars (pack sunscreen and hydration gear).
• Points tip: Emirates Skywards award space still shows value for premium cabins; transfer AmEx or Marriott points for upgrade possibilities. Watch fuel surcharges on certain award routings and compare cash+points options.

5. Vancouver & British Columbia, Canada

• Best season: May–September for outdoor activities; coastal winters for storm watching
• Recommended nights: 3–7 depending on road trips
• Family: Capilano Suspension Bridge Park, science world, day trip to Whistler or Victoria (ferry)
• Solo: Stanley Park bike loop, food truck scene, craft breweries and a day hike like Lynn Canyon.
• Adventure: Backcountry kayaking, coastal hiking, and sea-to-sky climbs; consider guided mountain excursions.
• Points tip: Use Air Canada Aeroplan for transborder and domestic awards (transfer from AmEx/Marriott/Capital One). For hotels, leverage Marriott Bonvoy and Hyatt for family-friendly suites.

6. Oaxaca, Mexico

• Best season: October–May (dry season; Day of the Dead in early Nov is a highlight)
• Recommended nights: 3–5
• Family: Cooking classes for kids, textile workshops, Mezcal museum visits with non-alcoholic learning options.
• Solo: Market tours, boutique guesthouses, and mezcal bar evenings; take a pottery or weaving workshop.
• Adventure: Hike Monte Albán and hierarchical valley trails; combine with Sierra Norte mountain biking or eco-camping.
• Points tip: Use Avios or U.S. carrier award space into Mexico City, then regional carriers or bus for the final leg. Consider boutique hotels booked via points or cash for small-group excursions.

7. Cape Town, South Africa

• Best season: October–April (southern hemisphere spring/summer)
• Recommended nights: 4–7 with a wine-region day trip
• Family: Table Mountain cable car, Boulders Beach penguins, scenic coastal drives along Chapman’s Peak.
• Solo: Hike Lion’s Head, explore street art and markets, join small-group township tours led by local guides.
• Adventure: Shark-cage diving, coastal surf, and trails in the Cape Peninsula. Use reputable operators and check seasonal conditions.
• Points tip: Look for award space via Star Alliance carriers through Johannesburg or direct seasonal flights. Use hotel points for comfortable family stays to reduce local costs.

8. Amalfi Coast, Italy

• Best season: May–June and September–early October
• Recommended nights: 4–6 based in Positano or Amalfi with a day trip to Capri
• Family: Slow boat trips, beach days with toddler-friendly coves, and flexible ferries for easy returns.
• Solo: Early-morning hikes on the Path of the Gods, late lunches in hilltop towns and off-peak ferry rides.
• Adventure: Sea-kayaking, cliff hikes and guided night sea tours. Travel lighter — many towns have stairs and limited car access.
• Points tip: Use Avios/Amex transfers for intra-Europe flights or trains. Hotel points can be more useful if you need a central base with family amenities.

9. South Island, New Zealand

• Best season: December–March (summer)
• Recommended nights: 7–12 for a loop from Christchurch to Queenstown
• Family: Wildlife sanctuaries, glowworm caves, Milford Sound cruises that accept kids.
• Solo: Backpack trails, bungee jumping in Queenstown, lakeside work-and-play days.
• Adventure: Multi-day tramps (hikes), heli-hiking, and glacier walks—book certified guides.
• Points tip: Look for transpacific awards to Auckland/Christchurch with partner carriers; consider long-term car rentals booked with points for freedom to explore remote spots.

10. Petra & Wadi Rum, Jordan

• Best season: March–May and September–November
• Recommended nights: 3–4 (base in Wadi Musa and a desert night)
• Family: Short guided Petra trails, camel rides for kids and safe, family-oriented desert camps.
• Solo: Sunrise at the Treasury, a night under the stars in Wadi Rum with Bedouin hosts, and relaxed cafés in Amman.
• Adventure: Multi-day canyon treks and jeep expeditions; hire certified guides and check weather for flash-flood risk in colder months.
• Points tip: Use Star Alliance awards to Amman or mix cash with local short-haul award flights. Redeem hotel points at larger Amman hotels for reliable family amenities.

11. Costa Rica (Guanacaste & Monteverde)

• Best season: December–April (dry season); green season has fewer crowds and lower rates
• Recommended nights: 5–10 split between beach and cloud-forest
• Family: Wildlife refuges, canopy bridges with kids-friendly operators, and beach days with easy snorkeling.
• Solo: Surf-friendly hostels and guided nature tours; pack insect repellent and reef-safe sunscreen.
• Adventure: White-water rafting, ziplining, volcano hikes and multi-day surfing trips.
• Points tip: Look at U.S.-based carrier awards with short regional connections; use hotel points or boutique ecolodges for higher sustainability standards.

12. Athens & Greek Islands

• Best season: Late May–June and September
• Recommended nights: 3–4 in Athens + 3–7 on islands
• Family: Acropolis with a private guide, ferry to less-crowded islands for safe swimming, and family cooking classes.
• Solo: Taverna nights, island-hopping by ferry, and photography walks at sunset.
• Adventure: Kayaking between islets, windsurfing in Paros, and hiking in Naxos.
• Points tip: Redeem Avios or Star Alliance partners to Athens; intra-Greece ferry discounts can be found with hotel packages or combined offers—book early for summer.

13. Barcelona, Spain

• Best season: April–June and September–October
• Recommended nights: 3–5
• Family: Park Güell, beach time and interactive museums like CosmoCaixa.
• Solo: Tapas bar crawl, Gaudí architecture off-peak, and late-night music venues.
• Adventure: Day trips for hiking in Montserrat or Costa Brava sea-kayaking.
• Points tip: Use Avios or transferable points for intra-Europe flights; book hotels with points for central locations to minimize transit with kids.

14. Alaska (Inside Passage & Denali)

• Best season: May–September (peak wildlife and long daylight)
• Recommended nights: 5–8 with a cruise or rail component
• Family: Wildlife cruises, interpretive hikes, and short rail journeys; pick family-friendly cruise lines with kids programs.
• Solo: Photography-focused days, guided fishing trips and backcountry days with permits.
• Adventure: Glacier trekking, sea-kayaking and multi-day wilderness treks—book certified guides and appropriate permits.
• Points tip: Seasonal award space on U.S. carriers and Alaska Airlines can offer value; redeem hotel points in gateway cities for quieter pre- or post-cruise stays.
• If you’re packing for snow or powder conditions on an Alaska or mountain trip, check a local packing guide like Packing for a Powder Day for essentials locals never forget.

15. Marrakech, Morocco

• Best season: March–May and September–October
• Recommended nights: 3–5 with a desert extension
• Family: Palace tours with private guides, garden visits and kid-friendly cooking classes in riads.
• Solo: Explore souks at dawn, hammams with trusted providers, and evening cultural shows.
• Adventure: Atlas Mountains hikes, overnight desert camps and camel treks—book local guides and acclimatize.
• Points tip: Redeem Avios or other European award currencies for Maroc connectivity; boutique riads often have few rooms—use points early or secure refundable bookings.

16. Medellín, Colombia

• Best season: Year-round spring-like climate; drier months Dec–Mar
• Recommended nights: 3–5
• Family: Cable car rides to Parque Arví, interactive museums and day trips to coffee farms with family activities.
• Solo: Nightlife in El Poblado, street art tours in Comuna 13, and café workdays in Laureles.
• Adventure: Paragliding, hiking in nearby páramo ecosystems and multi-day coffee region treks.
• Points tip: Use U.S. airline awards to Medellín or nearby hubs, then short domestic awards or buses. Redeem hotel points for upgraded stays with pool access for families.

17. Singapore

• Best season: Year-round (watch for occasional monsoon bursts)
• Recommended nights: 3–5
• Family: Gardens by the Bay, Universal Studios Sentosa, and kid-friendly science museums; many hotels offer family rooms and child care.
• Solo: Hawker-centre tasting tours, city gardens, design districts and a seamless public-transport experience.
• Adventure: Night safaris, Pulau Ubin cycling and offshore island snorkeling trips.
• Points tip: SIA KrisFlyer has good regional award availability; use transferable points or partner awards for long-haul premium flights. Consider redeeming points at luxury properties for stays with dining credits.

Practical notes across destinations (safety, cancellations, families)

• Booking windows: For peak-season international travel in 2026, start searching 6–12 months out for award travel; 3–6 months for shoulder seasons.
• Refundable vs. nonrefundable: Families should prioritize refundable fares or flexible awards. Solo travelers can take advantage of lower nonrefundable cash fares if plans are firm — see tips on fare-finding and flexible booking in Cheap Flight Hacks for 2026.
• Insurance: Get trip cancellation coverage with a “cancel for any reason” rider when traveling with larger groups; check pandemic, evacuation and medical limits.
• Local restrictions: Always confirm visa, vaccination and entry requirements directly with official government resources—policies updated frequently into 2026.

Advanced points strategies for 2026

• Micro-transfers: Transfer small amounts of flexible points to several partners to hold short-term award space while you confirm dates. See broader loyalty trend thinking in Loyalty 2.0 for the Frequent Traveler.
• Cash+points: When dynamic awards spike, use cash+points to lock seats and preserve miles.
• Sweet-spot hunting: Identify short-haul partner awards (e.g., intra-Europe, regional Asia) where fixed pricing still exists and book with bank transfers.
• Upgrade paths: Buying a cheap premium transcontinental fare and using miles for an upgrade can outperform outright premium award pricing in 2026’s market.

Actionable next steps (checklist)

1. Choose 1–2 destinations from this list and block travel dates.
2. Set award and fare alerts for those dates and airports.
3. Decide refundable vs nonrefundable based on group size and trip flexibility.
4. Transfer a small starter amount of points to one airline/hotel partner while you confirm your itinerary.
5. Book local experiences with vetted providers that offer free cancellation windows when traveling with kids. If you want a short gear checklist for shorter trips and carry-on efficiency, check these travel gadgets: 10 Small Gadgets That Make Flights and Layovers Less Miserable.

"Use your points this year—don’t hoard them for ‘someday.’ With 2026’s expanded routes and flexible hotel offers, the best value often appears early if you’re ready to act."

Key takeaways

• Match season to travel goals: Beaches and sun in summer; cultural festivals in shoulder seasons.
• Families need flexibility: Refundable awards and points-redemptions at family-friendly hotels reduce stress. See practical host upgrades and room tech that matter: Room Tech That Guests Actually Notice.
• Solo travelers: Leverage small-group experiences and local guides to add security and social options.
• Adventurers: Book certified guides for high-risk activities and pack appropriate gear for seasonal weather.
• Points & miles: Transfer flexible currencies wisely, set alerts and be ready to move quickly in 2026’s dynamic-award environment.

Ready to plan?

Pick a destination above, set your dates, and start alerting on award space now. For families, secure refundable options first; solo travelers can capitalize on last-minute deals. Want a custom itinerary tailored to your dates and points balance? Contact our travel concierge or sign up for alerts to get notified when awards and deals open for your chosen destination.

Related Reading

• Cheap Flight Hacks for 2026: AI Fare-Finders, Ethics and Booking Multi-City Trips
• Loyalty 2.0 for the Frequent Traveler: Predictive Perks & Tokenized Upgrades (2026 Playbook)
• Room Tech That Guests Actually Notice: A Host’s Guide to Meaningful Upgrades
• 10 Small Gadgets That Make Flights and Layovers Less Miserable
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• Packing for Destination Weddings in Italy: Airline Baggage Fees, Dress Bags and Timing Your Flights Right
• Microcation Kits for 2026: Building a Lightweight Weekend System That Pays Back
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