There are two ways to reach the Azores on points. Fly Azores Airlines nonstop from Boston, or fly TAP Air Portugal to Lisbon and connect. The second one is easier to pay for with points, because TAP sits inside Star Alliance and takes transfers from Capital One at 1:1.
That single fact is what makes the Azores a realistic 2027 award trip rather than a nice idea. Here is the full picture, including the parts where points do not help and cash is simply the answer.
Why the Azores, and why plan it a year out
Nine islands, four and a half to five hours from the US East Coast, in the middle of the Atlantic. It is the kind of trip a shoulder-season redemption playbook is built for. Volcanic craters, hot springs, whale watching and hiking, with almost none of the crowding that has made mainland European summers unpleasant.
The awards back it up. The Azores won Best Adventure Destination in the World at the 2023 World Travel Awards and Europe's Best Adventure Destination in 2024, and Condé Nast Traveler readers put the archipelago in their top ten European islands in 2024.
The reason to plan it now rather than next spring is structural, not fashionable. Award seats on thin routes open roughly eleven months ahead and go quickly, the summer window is short, and inter-island flights sell out around Portuguese holidays. A trip you book in September 2026 for summer 2027 has a genuinely better inventory picture than the same trip booked in March.
Route one: Boston to Ponta Delgada nonstop
Azores Airlines flies from Boston to Ponta Delgada. It is the shortest way in from the United States and it lands you on São Miguel, the largest island and the one most people start with.
The cash benchmark, as advertised on Azores Airlines' own site on August 31, 2026, was from $688.93 round trip in economy for Boston to Ponta Delgada. Hold that number, because it is what any award has to beat.
The problem is the currency. Azores Airlines runs its own loyalty program, SATA IMAGINE, with Bluesky, Silversky and Goldsky tiers. It has an extensive partner list, but the partners are overwhelmingly Azorean and Portuguese businesses: hotels, restaurants, opticians, rent-a-car firms, even a construction materials supplier. Earning rates run around 1 euro to 1 or 2 miles.
That is a fine program if you live in the Azores. It is close to unusable as a way for an American to accumulate a transatlantic award, because there is no major US bank transfer partner feeding it.
There is also a fee to plan for. SATA IMAGINE charges a service fee on award tickets: 16 euros on inter-island flights, 25 euros on domestic Portuguese flights and 100 euros on European flights. Those are per the program's published fare conditions.
Route two: TAP to Lisbon, then onward
This is the practical answer for most readers, and it is the one worth building a plan around.
TAP Air Portugal is a Star Alliance member. It flies to Ponta Delgada and Terceira, and it operates a large transatlantic network into Lisbon and Porto from the United States. So the trip breaks into two bookable pieces: get to Lisbon on Star Alliance metal, then take the short hop out to the islands.
Both halves can be paid for with points, and they do not have to come from the same program.
The transfer partners that actually reach TAP
TAP Miles&Go publishes its bank partners, and two of them matter to a US reader.
Capital One transfers at 1:1. Venture, VentureOne, Spark Miles and Spark Miles Select cardholders can move miles into TAP Miles&Go, where 1,000 Capital One miles becomes 1,000 Miles&Go miles. The minimum transfer is 1,000 miles, the account names have to match exactly, and TAP states plainly that all reward transfers are final and cannot be reversed.
HSBC transfers at 1:1. One HSBC Reward Point becomes one TAP Miles&Go mile, for HSBC Premier World Mastercard and Elite World Elite Mastercard holders. TAP says points typically post within five days, though some programs take up to fourteen.
There is also a TAP Miles&Go American Express Credit Card for direct earning.
Miles&Go itself is a Star Alliance currency. Miles earned on TAP or on Star Alliance members count as Status Miles toward Silver and Gold, and the program sells award tickets on any Star Alliance member as well as a round-the-world product.
Using other Star Alliance programs instead
You do not have to hold Miles&Go. TAP is a Star Alliance member, which means every other Star Alliance program can sell you a seat on TAP metal, priced under its own rules.
That is the same mechanic covered in our guide to partner flights and how the same seat costs fewer points, and it applies squarely here. Price the Lisbon leg in two or three Star Alliance programs before you transfer anything, because the spread on transatlantic economy and business is wide and the cheapest program is rarely the obvious one.
Two of the programs worth pricing are covered in detail already: Aeroplan against United MileagePlus is the comparison that decides most transatlantic bookings, and Turkish Miles and Smiles has Star Alliance sweet spots that beat both on specific routes.
The short Lisbon to Ponta Delgada leg is a different calculation. It is cheap in cash, from 205 to 217 euros round trip as advertised on Azores Airlines' site on August 31, 2026, and short awards rarely represent good value per point. Paying cash for that leg and saving your miles for the ocean crossing is usually the right split.
Island hopping, and what it costs
The archipelago is nine islands and you will want more than one.
Azores Airlines runs the inter-island network out of Ponta Delgada to Terceira, Pico, Horta on Faial, and Flores, among others. Advertised round-trip fares on August 31, 2026 ran from 113 euros to Pico, 129 euros to Terceira and 161 euros to Horta and Flores.
Those are cash prices, and they are the right way to pay. An award ticket carrying a 16 euro service fee against a 113 euro cash fare is a bad trade unless your miles are otherwise stranded.
Azores Airlines also sells an Azores Air Pass for multi-island itineraries, which is worth pricing against individual tickets if you are visiting three or more islands.
The TAP Stopover, which is the trick most people miss
TAP runs a Stopover program, and it is built for exactly this trip.
You can stop in Lisbon or Porto for up to 10 days between your connecting flights at no additional airfare cost. It works on one-way, return and multi-city tickets, and you can take it on the outbound or the return.
Then the part that matters here: Stopover participants get a 25% discount on connecting flights within Portugal, and TAP names Ponta Delgada and Terceira on that list alongside Faro, Funchal and Porto Santo.
So the shape of the trip becomes: cross the Atlantic on points, spend a few days in Lisbon for free, then take a quarter off the island hop. TAP also bundles a partner catalog of restaurant, hotel, tour and attraction discounts, and Global Traveler readers have voted it the best stopover program in the world for eight consecutive years.
Two conditions to note. The discount applies only to flights taken during the Stopover period, and it cannot be combined with other promotions.
Hotels, and why your hotel points will not help much
This is the part of the trip where a points strategy runs out of road, and it is better to know that in advance.
The Azores is not chain territory. The archipelago's hotels are overwhelmingly independent and regional operators rather than the big four loyalty programs. A useful proxy is Azores Airlines' own partner list, which is dense with Azorean hospitality names such as Azoris Hotels and Leisure, Bensaude Hotels and Aldeia da Fonte Hotel, and thin on anything you can book with Bonvoy, Honors or World of Hyatt points.
The practical consequence is that a Marriott or Hilton balance is close to dead weight here. Budget cash for accommodation and do not build the trip around a free night certificate you will not be able to use.
The consolation is that the cash cost is low by European standards, and the independent properties are the better stay anyway. Guesthouses and small hotels on São Miguel and Pico are the character of the place, not a compromise you make because a chain has not arrived.
What points genuinely save you here
Be honest about the shape of the saving, because it is lopsided.
The transatlantic leg is where points do the work. A Lisbon or Porto crossing in economy or business is the expensive part of the trip and the part with real award pricing spread between programs.
The Azores themselves are not expensive. Inter-island flights are cheap, and accommodation across the islands runs well below what the same quality costs in mainland Europe in summer. This is not a destination where you need points to make the trip possible. It is one where points make the crossing free and let you spend the cash budget on the ground.
That is a better outcome than it sounds. Most award strategies fail because the traveler optimises the cheap leg and pays cash for the expensive one.
How to Build the Azores Trip on Points
Here is the sequence that works.
- Decide the islands first. São Miguel for craters, hot springs and the easiest arrival. Pico for the mountain and the wine. Faial for Horta and the marina. Terceira for Angra do Heroísmo. Flores for the waterfalls and the least infrastructure.
- Price the crossing in three Star Alliance programs on your dates, in miles and cash, before transferring anything anywhere.
- Transfer only after you see the seat. Capital One and HSBC transfers into Miles&Go are final.
- Book the inter-island legs in cash unless you have stranded Miles&Go balances.
- Leave real connection time in Lisbon. A separately ticketed Lisbon to Ponta Delgada leg has no protection if the transatlantic flight is late, and that is a common way to lose a day.
Point five is the one people learn the hard way. If the crossing and the island hop are on one ticket, the airline owns the connection. If you booked them separately to save miles, you own it.
When to Visit the Azores
Summer is the reliable window for weather and the busy one for prices and inventory. Late spring and early autumn trade some certainty for much better availability, both in award seats and in the small hotels that fill up in July and August.
Whale watching runs on its own calendar rather than the tourist one, and the resident and migratory species do not overlap, so check what is actually in the water for your dates before you fix them.
If you want one island and one week, take São Miguel in June. If you want the archipelago properly, give it two weeks and three islands, and book the inter-island legs the moment your dates are firm.
One planning note on the smaller islands. Flores sits at the far western end of the chain and its air links are thinner than the central group, so a Flores leg constrains the rest of the itinerary rather than slotting into it. Build the trip around that flight if you want it, or leave it for a second visit.
Weather in the Azores is Atlantic weather, which means it changes inside an afternoon on every island in every month. Plan hikes and crater viewpoints with a spare day rather than a fixed slot, because a clear morning at Sete Cidades is worth reorganizing a day for.
What I would do
Open a Capital One transfer relationship before you need it, because that is the cleanest path from US spending into a currency that reaches Portugal. Then price the crossing in Miles&Go, Aeroplan and one more Star Alliance program, and let the numbers pick the booking.
Pay cash for everything inside the archipelago. Save the points for the Atlantic. That is the whole strategy, and it is the reason the Azores is one of the few genuinely reachable long-haul destinations for someone with a modest points balance and a year of notice.
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