Top Coastal Destinations from the 'Where to Go in 2026' List — Book These Beach Trips with Points

Hook: Turn points anxiety into beachfront action — book 2026's best coastal trips with miles

Struggling to translate your stash of credit card points and frequent-flier miles into a real seafront vacation? You're not alone. Travelers and aspiring coastal homeowners tell us the same things: confusing award charts, dynamic pricing, and unclear hotel redemption value make beachfront bookings feel impossible. In 2026, with programs evolving and more transfer bonuses circulating, you can still get exceptional value — if you know where to aim and how to pull the trigger. If you're planning a longer stay or remote work trip, the long-stay hotel strategies playbook is a useful companion for planning points use and cash tradeoffs.

The 2026 coastal shortlist: water lovers’ picks from The Points Guy’s list

We filtered The Points Guy’s “Where to Go in 2026” list for destinations that prioritize ocean, bays, or island experiences. Below are the coastal spots water lovers should prioritize — each followed by a step‑by‑step points-and-miles strategy, seasonality, and smart booking windows.

• Amalfi Coast, Italy
• Azores, Portugal
• Cartagena, Colombia
• Cape Town, South Africa
• Dubrovnik & Croatia’s Dalmatian Coast
• Maldives (atolls & resorts)
• Costa Rica — Guanacaste & Nicoya Peninsula
• Okinawa, Japan

Why 2026 is a sweet (and strategic) year to book coastal travel with points

Two big forces shaped award travel heading into 2026:

• More dynamic award pricing — carriers and hotels continued expanding dynamic redemptions through late 2025, but we also saw more consistent transfer-philanthropy-style bonuses from bank programs (Amex, Chase, Capital One) making targeted transfers lucrative. Keep an eye on airline structural shifts including new entrants and changing fleet strategies — developments such as rising niche carriers and freight-led operator strategies are worth watching (cargo-first airline trends).
• Work-from-anywhere demand stabilized — longer stays and midweek award availability improved for many coastal spots as travelers stagger trips to avoid peak crowds. For planning extended beachside work trips, the microcation resorts guide has useful product ideas and timing considerations.

Pro tip: dynamic awards mean peak-date inventory is expensive — focus on shoulder seasons (spring/fall) and midweek departures for the best points value.

How to read this guide

For each destination we provide:

1. A concise itinerary hub and transfer gateway
2. Step-by-step award flight strategy (programs, transfer partners, likely redemption ranges)
3. Hotel & lodging redemption advice (chain options, alternative strategies)
4. Best time to book and seasonal tips to save points and money

1) Amalfi Coast, Italy — luxury seaside towns, steep cliffs, and ferry hops

Hub & gateway

Fly into Naples (NAP) or Rome (FCO) and connect — for service and award availability, Rome is often easier for transatlantic redemptions. If you want smoother ground-to-hotel logistics near Rome, check recent reviews of airport-adjacent hotels and transit strategies for inspiration (many coastal planners use airport-night buffers to reduce missed-connection risk).

Award flight strategy — step by step

1. Search transatlantic award space to Rome or Naples on major alliances (Star Alliance for United/Lufthansa/ITA; SkyTeam for Delta/Air France/KLM; oneworld for American/Japan/IB).
2. Use transferable currencies: Chase Ultimate Rewards (transfer to United or Air France/KLM Flying Blue), Amex Membership Rewards (transfer to Air France/KLM, British Airways Avios for short hops), or Capital One (transfer to Avianca LifeMiles for Star Alliance redemptions).
3. Typical redemption: economy 40k–70k roundtrip; premium economy 90k–160k; business 115k–220k (varies with dynamic pricing). Look for promos or transfer bonuses to shave points off the ticket.
4. For Rome→Naples or Amalfi surface travel, use low-cost carriers or regional trains; redeem Avios or Flying Blue for short intra‑Europe hops when award pricing is favorable.

Hotel points strategy

• Large chains on the Amalfi Coast are limited; consider using Marriott (few properties nearby) and Hilton options in Sorrento/Positano. Also use hotel points for stays in Naples or Salerno and spend on local day trips to Amalfi/Positano.
• Alternative: convert points to Airbnb credits via card portal offers or use points for elite status benefits to access partner boutique hotels.

Best time to book

Shoulder seasons: late April–June and September–October. Book flights 4–6 months out for the best award availability; hotels can require 6–9 months in high demand spots (Positano in summer).

2) Azores, Portugal — rugged islands, whale watching, and volcanic coasts

Hub & gateway

Ponta Delgada (PDL) on São Miguel is the usual entry point. Transatlantic flights often route via Lisbon (LIS).

Award flight strategy — step by step

1. Book a transatlantic award to Lisbon. Transfer Chase UR to United or Air France/KLM from Amex for economy/premium cabin availability.
2. For Lisbon→Ponta Delgada use SATA/Azores Airlines; book paid flights when award space is poor and use points for hotels instead. LifeMiles sometimes offers bargain intra‑Europe options on partner carriers.
3. Example: 60k–90k Chase UR points for roundtrip economy to Lisbon; add 10k–20k for intra‑Europe if award seats match.

Hotel & stays

Use points at boutique hotels and try converting bank points to local B&B credits or to short-term rental platforms that accept points-based payment. The Azores reward availability is generally strong outside peak summer.

Best time to book

Late spring through early autumn (May–September) is best for whale watching. Book flights 3–5 months out; hotels often offer early-book discounts in winter months for 2026 travel.

3) Cartagena, Colombia — Caribbean vibes and colonial walls

Hub & gateway

Cartagena (CTG) is well served from Miami (MIA) and connecting U.S. hubs.

Award flight strategy — step by step

1. Look for American/Delta award space from U.S. hubs. Chase UR transfers to United (if routing via partners) or use Amex MR to Air France/KLM for connections via Europe if combining with a European itinerary.
2. Typical redemptions: 25k–45k roundtrip economy from the U.S., 50k+ for premium cabins when available.
3. Consider positioning flights into Miami or Fort Lauderdale — both have frequent low-cost and award options to Cartagena; use Avios for short regional flights when pricing is attractive.

Hotels & rentals

Cartagena has a strong market for boutique hotels. Use Hilton and Marriott points for branded stays, or convert bank points to Airbnb credits for colonial homes inside the old city.

Best time to book

Dry season December–April is peak; to save points, target May or late November. Book 2–4 months out for best award fares from the U.S.

4) Cape Town, South Africa — dramatic coastline and Atlantic surf

Hub & gateway

Cape Town (CPT) is a primary international hub. U.S. flyers typically connect via European or Middle Eastern carriers.

Award flight strategy — step by step

1. Search Star Alliance availability to Johannesburg (JNB) or direct to Cape Town on partners. United and Air Canada via London or Frankfurt can be useful.
2. Transferable points: Amex MR to Air France/KLM for Paris/Amsterdam connections; Chase UR to United or Singapore KrisFlyer for Star Alliance itineraries.
3. Sample redemption: economy 70k–110k roundtrip; business class 160k–300k (varies greatly with season and dynamic pricing). If you find business award space via Turkish Miles&Smiles or Singapore KrisFlyer, it can be a sweet spot.

Hotels & villas

Use hotel points at larger Cape Town properties (Hilton, Marriott) or book private villas via points-convertible platforms. Consider long-stay discounts in shoulder season (Apr–May, Sep–Nov).

Best time to book

South Africa’s summer (Nov–Mar) is warmest and busiest. For better value, book April–May or September–November. Allow 4–6 months for award space/dream dates.

5) Dubrovnik & Croatia’s Dalmatian Coast — islands, old towns, and bluewater

Hub & gateway

Fly into Dubrovnik (DBV) or Split (SPU) via European hubs (Zagreb, Vienna, Frankfurt).

Award flight strategy — step by step

1. Book awards to major European gateways (London, Paris, Frankfurt) and use low-cost carriers or short award hops to DBV/SPU.
2. Transfer points: Amex MR or Chase UR to Flying Blue or United to reach Europe; use Avios for short regional flights inside Europe.
3. Typical fares: 50k–90k UR/Amex points roundtrip to Europe; short intra‑Europe awards often fluctuate — book 1–3 months in advance for the best pricing post-2025.

Hotel & ferry strategy

Use points for stays in Dubrovnik’s historic core where boutique hotels are expensive in cash. For island-hopping, pay cash for local ferries (they’re cheap) and use saved points on premium nights in city centers.

Best time to book

Shoulder seasons May–June and September–October avoid peak cruise crowds. Book hotels 3–6 months out; look for weekday ferry schedules for quieter beaches.

6) Maldives — private atolls and overwater bungalows

Hub & gateway

Male (MLE) is the international entry point; seaplane or speedboat transfers to resorts are common. For operators and resort design ideas focused on short-stay products and transfer logistics, the microcation resorts guide has relevant thinking for island operators.

Award flight strategy — step by step

1. Book international award to Male on premium partners (Emirates, Qatar, SriLankan, Singapore). Transfer Amex MR to Qatar Avios or Capital One to Qatar Privilege Club when transfer bonuses appear.
2. Redeem: economy 60k–100k roundtrip; business 160k+ depending on carrier. Keep an eye out for seasonal promos from Gulf carriers in late 2025–2026.
3. For seaplane transfers, many resorts package the transfer into the cash rate — negotiate using points for the room and pay transfer separately if it reduces cash outlay.

Hotel points strategy

• Big chains: Marriott Bonvoy, Hilton Honors, and smaller luxury programs offer excellent redemptions for overwater bungalows if booked early or via Points + Cash.
• Look for resort reward availability in shoulder season (April–May, September–November). Some properties publish limited standard award rooms — set alerts and be ready to transfer points.

Best time to book

Best value: post-monsoon shoulder months (late April–May and September–November). Book awards 6–9 months ahead for high-end resorts; last-minute availability can appear but is risky.

7) Costa Rica — Guanacaste & Nicoya Peninsula (Pacific beaches)

Hub & gateway

Liberia (LIR) for Guanacaste, San José (SJO) for southern coasts. Direct flights from U.S. gateways are common.

Award flight strategy — step by step

1. Use United, American, or Delta award space from U.S. hubs. Transferable points can be useful for positioning flights.
2. Typical redemptions: 20k–40k roundtrip economy from the U.S.; premium cabins less common but occasionally available on connections.
3. Consider positioning with low-cost carriers into Liberia to access Guanacaste resorts — often cheaper cash fares; use points for hotels instead.

Hotel & eco-lodge tips

Redeem Hilton or Marriott points for beachfront resorts, or convert points to vacation-rental credits for longer stays. Eco-lodges sometimes accept partial payment with points via partner programs.

Best time to book

Dry season December–April is peak; shoulder seasons May and November offer green-season deals and lower points rates.

8) Okinawa, Japan — subtropical beaches and unique island culture

Hub & gateway

Naha (OKA) is the main Okinawa gateway, usually connecting through Tokyo or international hubs in Asia.

Award flight strategy — step by step

1. Book awards to Tokyo (NRT/HND) then book a separate domestic award to Naha. Use ANA (transfer from Amex or Chase) or Japan Airlines (Avios transfers from Amex).
2. Typical redemptions: transpacific economy 70k–120k UR/Amex roundtrip; domestic add-on 5k–15k for economy with domestic award promotions.
3. Watch for Japan-focused transfer promotions in late 2025 that sometimes reduce total points cost for multi-leg itineraries.

Hotels & long stays

Use points at international chains in main cities and convert points for local ryokan-style stays. For long remote stays, convert points to rental credits or use Points + Cash to limit cash outlay. If you need packing help for compact island travel, see the 48‑hour packing checklist.

Best time to book

Spring (March–May) and autumn (September–November) offer great weather and fewer typhoons. Book awards 5–7 months ahead for spring travel.

Actionable booking checklist (use before you transfer points)

1. Confirm award space — never transfer bank points before identifying confirmed award availability for your exact dates.
2. Compare transfer partners — for each route check at least two partners (e.g., Chase→United vs Amex→Air France) for better taxes/fees or lower mileage cost.
3. Set price/availability alerts — use award search tools (ExpertFlyer, airline alerts) to be notified when premium award seats open. Consider services and field tools used by professionals and events teams; airport micro-events and hub activity can influence local inventory patterns (airport micro‑events & operations).
4. Leverage transfer bonuses — late 2025 and early 2026 saw targeted transfer bonuses; sign up for bank offers and stack them when they align with your trip.
5. Use Points + Cash — if an award is too expensive, combine cash and points to save points for future trips. For strategies converting short trips into repeatable products, see the microcation design guide.
6. Check resort fees & transfers — many coastal resorts add mandatory transfers or resort fees; factor those cash costs into your redemption decision.

Real-world example: booking Amalfi Coast with Chase UR + Marriott points (a case study)

In November 2025 a traveler wanted Positano in May 2026. Strategy used:

1. Found United saver economy space to Rome for 60k RT in March — held dates.
2. Transferred 60k Chase UR to United the same day and ticketed.
3. Used 55k Marriott Bonvoy points for 4 nights in a Sorrento property (transferred from 70k Chase UR at a previous transfer rate and topped with targeted Marriott offer).
4. Saved cash by taking the Circumvesuviana train and local ferry for day trips rather than paying for seafront hotels in Positano.

Outcome: Business-class would have cost 180k–220k points; the economy + points-for-hotel strategy gave substantial savings while maintaining beachfront access via day trips.

2026 trends and predictions to plan for now

• More transfer bonuses — expect continued targeted bonuses from Amex, Chase, and Capital One; they’ll be decisive for expensive coastal redemptions.
• Increased Points + Cash flexibility — hotels and some airlines will expand hybrid redemption options to convert last‑minute cash deals into partial‑points bookings.
• Short-stay award sweet spots — as travelers prefer micro-getaways, airlines may continue offering better midweek award inventory for shorter trips. If you favour quick weekend escapes, see our weekend micro‑adventures playbook for timing ideas.
• Climate-driven season shifts — some traditional peak windows will shift; be flexible and monitor historical weather trends for seaside destinations.

Quick reference: Best time-to-book cheat sheet (coastal edition)

• International peak beach season: book 4–9 months ahead for awards (business 6–12 months).
• European coasts (Amalfi/Dalmatia/Azores): 3–6 months in shoulder seasons, 6–9 months for summer weeks.
• Maldives/high-end island resorts: 6–9 months for award rooms.
• Caribbean & Central America: 2–4 months if flexible; 4–6 months for holiday windows.

Final checklist — before you click "transfer"

• Confirm award availability and total taxes/fees.
• Compare cash vs points — sometimes a sale on cash fares + keep points is a smarter long-term play.
• Have a backup date or airport in case your preferred award seat disappears during transfer processing.
• Keep at least a cushion of points after booking (don’t zero out primary accounts if you have upcoming renewals or elite status requirements).

Takeaways — book smarter: timing, partners, and flexibility

In 2026, coastal award travel rewards flexible planners who act when transfer bonuses and award space align. Focus on shoulder-season travel, verify award seats before transferring points, and combine chain hotel points with boutique stays to maximize beachfront experiences. Use the destination-specific steps above to map exact transfer partners and booking windows. If you want logistics and airport-to-hotel strategies for sensitive connection windows, the field report on airport micro-events and operational practices is helpful.

Call to action

Ready to turn points into sand between your toes? Start with three minutes: pick your top coastal destination from this list, search for award space on your preferred dates, and set a transfer-alert for your rewards program. If you want a personalized redemption plan for one of the destinations above, request a tailored points strategy — tell us your home airport, points balances, and travel window and we’ll map the exact transfers and booking timeline. For quick packing guidance for short beach trips, don't miss the packing light checklist.

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