Make Your Next Trip Extraordinary

The Ideal Islands for Each Month of the Year

by Wendy Perrin | October 22, 2019

Figuring out the optimal time to travel to an island can be tricky. “Peak season” often does not mean the best time to go; it just means the most expensive time, based on when school’s out in the countries that send the most vacationers to that island. “Low season” might mean peaceful and lovely, with a brief and pleasantly cooling shower each afternoon, or it might mean that every restaurant and famous site shuts down entirely. In addition to seasonal changes in weather, most islands have limited lodging—which can drive rates to extortionate levels—and some island can get crowds that will overtax the small tourism infrastructure, especially when cruise ships stop there.

We’re here to help—by suggesting a few islands for each month of the year. These are the opportune moments when the destination is at its best yet, in most instances, offers shoulder-season pricing. Craving an island not listed below? Punch its name into the “Destinations” search box at top left; if we’ve got an Insider’s Guide for that island, you can read the best and worst times to go.

Seeking the right island or island-trip-planning specialist for your specific needs? You may ask us here.

January: Madeira, Portugal

This sub-tropical Portuguese island may be small, but it puts on a New Year’s Eve celebration and fireworks show that rivals the ones in Sydney, London, and Rio. (Book early!) Later in the month, the world-class hotels will be far more affordable, yet you can still enjoy virgin laurel forest, panoramic hiking, and great local gastronomy, including the island’s namesake wine.

Learn more in our Insider’s Guide to Portugal, and use our questionnaire to be marked as a VIP and get the best possible trip.

January: Mergui Archipelago, Myanmar

With a private yacht at your disposal, the Mergui archipelago is a veritable playground of diving and snorkeling sites full of rare underwater species, mangroves with crystal-clear water, and beaches where the only human footprints will be the ones you leave. In January, the weather is warm and sunny, and the seas are calm.

Ask Wendy who is the best Myanmar or yacht-charter specialist to plan your specific trip.

January: Raja Ampat, Indonesia

Located where the Pacific currents meet the Indian Ocean, this archipelago is a marine Eden with more than 1,300 species of fish and three-quarters of all the hard corals found in the world. Above the water line, the forested karst islands are home to fantastical creatures such as birds of paradise and tree kangaroos. October through April is Raja Ampat’s dry season; just after the holidays, prices drop considerably.

Ask Wendy who is the best Indonesia or cruise specialist to plan your specific trip.

February: Isla Palenque, Panama

Isla Palenque is an eco-friendly private-island resort off the Pacific coast of Panama.

Isla Palenque is an eco-friendly private-island resort off the Pacific coast of Panama.

A private-island resort off the Pacific coast of Panama, Isla Palenque offers both environmental sustainability and barefoot luxury. Just a 15-minute boat ride from the mainland, it’s easily combined with other parts of Panama or even Costa Rica, and you get seven different beaches, the surrounding Chiriqui National Marine Park, and a jungle full of monkeys and birds. February sees gorgeous weather—and with just eight thatch-roofed casitas and one villa on the 400-acre island, you’ll never encounter crowds.

Ask Wendy who is the best Panama specialist to plan your specific trip.

February: The Grenadines, Caribbean

The small, unspoiled islands of the Grenadines give you the feel of the old-world Caribbean. Explore by yacht and you can mingle with locals on tiny Bequia, snorkel in the Tobago Cays Marine Park, and rub elbows with high society on the private island of Mustique. The weather is excellent in February, with prices considerably lower than during the holidays.

Ask Wendy who is the best Caribbean or yacht-charter specialist to plan your specific trip.

February: Venice, Italy

All that is sumptuous and extravagant about Venice is kicked up several notches in February, thanks to Carnevale. A month’s worth of elaborate celebrations—marked by Baroque costumes, masked balls, sinful sweets, and general bacchanalian overindulgence—reach a fever pitch in the “Fat Days” preceding Martedì Grasso (Shrove Tuesday). Carnevale dates vary from year to year but always include at least part of February.

Learn more in our Insider’s Guide to Venice, and use our questionnaire to be marked as a VIP and get the best possible trip.

March: Crete, Greece

The island of Spinalonga, Crete, Greece. Photo: Blue Palace Resort and Spa

The island of Spinalonga, Crete, Greece. Photo: Blue Palace Resort and Spa

While many Greek islands go into hibernation in the winter, with resorts and restaurants shuttering for the season, Crete is large enough that it stays vibrant year-round. It’s also Greece’s most southern—and thus warmest—island. Not everything will be open in March, but it’s a great time to get a dose of local culture, and hotel rates are lower than you’ll find later in spring.

Use our questionnaire to be marked as a VIP and get the best possible trip.

March: Bermuda

The Reefs, Southampton, Bermuda

The Reefs, Southampton, Bermuda.

April is when the cruise ships start to arrive for the summer season, letting off up to 4,000 passengers at a time. A month earlier, hotel rates are half their summer peak, temps are in the low 70s (great for golf and tennis, if not bikinis), and there are free tours, lectures, and arts demonstrations all over the island.

Learn more in our Insider’s Guide to Bermuda, and ask Wendy who is the best Bermuda specialist to plan your specific trip.

March: Malta and Gozo

gozo island green hills scenery in Maltese archipelago

Gozo is smaller and more rural than its neighbor Malta.

March sees few of the cruise-ship visitors who arrive daily in Malta come summer. With highs in the mid-60s and a lush green coating on the hills brought out by winter rains, this is a particularly great time of year for countryside walks and cycling on neighboring Gozo, which is smaller and more rural than Malta.

Learn more in our Insider’s Guide to Malta, and use our questionnaire to be marked as a VIP and get the best possible trip.

April: The Azores

green fields on Flores island The Azores Portugal

The Azores are known for breathtaking natural beauty. Photo: Visit the Azores

You won’t find ultra-luxe resorts and 24-hour concierge service in the Azores, but you will find whale- and dolphin-watching (sightings of migrating cetaceans peak in April), breathtaking natural beauty, and locals who are genuinely happy to see tourists at this time of year. For a slower-paced trip, stay just on the main island of São Miguel; if you prefer to see a bit more, base yourself on Faial and take day trips by ferry to Pico and São Jorge.

Learn more in our Insider’s Guide to Portugal, and use our questionnaire to be marked as a VIP and get the best possible trip.

April: The Maldives

person swimming in clear blue water at Cheval Blanc Randheli resort in the Maldives

The Maldives. Photo: Cheval Blanc Randheli.

April (after Easter) is when you’ll find a sweet spot of lower hotel rates and ideal weather: Temperatures are consistently in the high 80s year-round, but in April there is almost no rain or wind, so the water is calm for snorkeling and diving.

Learn more in our Insider’s Guide to The Maldives, and use our questionnaire to be marked as a VIP and get the best possible trip.

May: Santorini, Greece

Oia town on Santorini island, Greece. Traditional and famous houses and churches with blue domes over the Caldera, Aegean sea

Oia town, on Santorini. Photo: Shutterstock

May weather is warm but not hot, and hotel rates are lower than from mid-June through September. The crowds are less too, which has the added benefit of ensuring the service will be better. During the hectic summer months, when hordes of cruise-ship passengers invade the island, service suffers; you can barely even find an available taxi.

Ask Wendy who is the best Greek Islands specialist to plan your specific trip.

May: Capri, Italy

Capri, Amalfi Coast, Italy

Capri, Amalfi Coast, Italy. Photo: IC Bellagio

Mild spring temperatures make it pleasant to explore this legendary island, which is still in a state of tranquility before the mad crush invades in June. The orange and jasmine flowers in bloom lend wonderful scents and colors; it’s also the time of year for many sailing events, as well as the annual celebration of the island’s Patron Saint San Costanzo.

Learn more in our Insider’s Guide to the Amalfi Coast, and use our questionnaire to be marked as a VIP and get the best possible trip.

May: Corsica, France

aerial view of Corsica island France

Corsica is great for hiking in May. Photo: Philip Haslett

While summer is high season, May and June are hard to beat: The temperatures are a bit lower, the crowds fewer, and the hotels don’t impose minimum-stay requirements. It’s a great time for the hiking, cycling, and canyoning that Corsica is known for—but if you want to spend a lot of time in the water, you’re better off waiting until September.

Ask Wendy who is the best Corsica specialist to plan your specific trip.

May: Oahu, Hawaii

View from the Makapuu Point Lookout, Oahu Hawaii

View from the Makapuu Point Lookout, Oahu. Photo: Hawaii Tourism Authority (HTA) / Mark Kushimi

Oahu’s temps are consistently pleasant year-round (usually between 78 and 82 degrees). The reason May is ideal—except for the Japanese holiday of Golden Week, at the start of the month— is that airfare is less expensive and crowds are fewer.

Learn more in our Insider’s Guide to Oahu, and use our questionnaire to be marked as a VIP and get the best possible trip.

June: Bali

Green rice fields on Bali island Indonesia

Green rice fields on Bali island. Photo: Shutterstock

June has the most reliably pleasant weather in Bali—daytime temps in the 80s and gentle breezes to keep the sun from feeling too hot—and better prices: High-season hotel rates don’t kick in until July.

Learn more in our Insider’s Guide to Bali, and use our questionnaire to be marked as a VIP and get the best possible trip.

June: Sri Lanka

eautiful Tropical Beach In Kalpitiya, Sri Lanka. These boats used to take people to watch dolphins

Kalpitiya beach, Sri Lanka. Photo: Shutterstock

Sri Lanka’s east coast, stretching from the quiet beaches of Trincomalee to the surf paradise of Arugam Bay, bursts with life this month. Compared to the better-known beaches in the south, those along this coast are more secluded, with a calmer and shallower sea—perfect for whale watching, snorkeling, diving, and fishing. After Easter and before summer vacation, visitors are fewer and the prices are easier on the wallet.

Learn more in our Insider’s Guide to Sri Lanka, and use our questionnaire to be marked as a VIP and get the best possible trip.

June: Spitsbergen, Norway

Spitsbergen, the largest island in the Svalbard Archipelago, is one of the world’s best places to see polar bears. While Arctic voyages set sail throughout the summer, going early in the season maximizes your chances of seeing these magnificent animals before the sea ice recedes.

Learn more in our Insider’s Guide to the Arctic, and use our questionnaire to be marked as a VIP and get the best possible trip.

June: Mallorca and Menorca, Spain

Beautiful traditional boathouses, apartments and beach at Playa Santanyi, located in the south east of Mallorca.

Find beautiful traditional boathouses, apartments and beaches at Playa Santanyi, located in the south east of Mallorca.Photo: Bespoke Travel Spain and Portugal

Early in the month, you’ll find great weather without the crowds of beachgoers who invade in summertime. Mallorca is a golfer’s dream, with a wide range of hotels, while Menorca is off the typical tourist circuit and ideal for those who want to relax by the sea and enjoy life as the locals do.

Ask Wendy who is the best Spain specialist to plan your specific trip.

June: Yakushima, Japan

This sub-tropical island, located in the waters just south of Kyushu, is ideal for intrepid travelers: Its mountains and vast forest of ancient cedar trees are crisscrossed by a network of hiking trails, from easy walks to challenging ascents. June signals the end of the rainy season, so you’ll find stunning waterfalls along the trails; it’s also when endangered loggerhead sea turtles return to Yakushima’s beaches to nest.

Ask Wendy who is the best Japan specialist to plan your specific trip.

July: Vanuatu

This Melanesian chain of roughly 80 islands that stretch across 800 miles is a remote and undeveloped paradise. You won’t find five-star resorts, but you will find crystal-clear waters, coral reefs, gorgeous beaches, active volcanoes, and warm and hospitable locals. July and August are a drier, cooler time of year in this tropical island nation.

Ask Wendy who is the best South Pacific or boat-charter specialist to plan your specific trip.

July: Aeolian Islands, Italy

Italy in July, you say? Isn’t it jam-packed? Not in this chain of islands—some of the most pristine left in Europe—that are just a short sail from Sicily and a UNESCO World Heritage Site in their entirety. While the mainland is mobbed, charter a yacht with a captain who was born on the islands and who can show you beautiful and lush Salina; the jet-setters’ getaway of Panarea; and magnificent Stromboli, where volcanic eruptions frequently light up the night sky.

Use our questionnaire to be marked as a VIP and get the best possible trip.

July: Tahiti

Heiva group dancing contest in Tahiti

Heiva group dancing contest. Photo: Tahiti Tourism

French Polynesia’s “Heiva” festival falls during July, with the culmination of ceremonies in Papeete, Tahiti, around the 20th. Heiva is a celebration of life and all things Polynesian. The outer islands hold local contests—in everything from outrigger racing to stone carrying and spear throwing, traditional dancing and singing to tifaifai (quilt) making—and the best go to Tahiti for the main festival. It’s a great time weather-wise as well; the trade winds keep temps in the low 80s and the humidity low.

Learn more in our Insider’s Guide to Tahiti and French Polynesia, and use our questionnaire to be marked as a VIP and get the best possible trip.

July: Zanzibar

July is a perfect time to cap off a safari with a few days on Zanzibar’s gorgeous white-sand beaches. It’s one of the island’s driest and sunniest months, with daytime temperatures in the low 80s and not much humidity. Plus, the Great Migration is usually in Tanzania’s northern Serengeti in early July, with the enormous herds of wildebeest and zebra crossing the Mara River into Kenya’s Masai Mara by mid-month.

Ask Wendy who is the best Zanzibar specialist to plan your specific trip.

August: Faroe Islands, Denmark

Gásadalur on Vagar Island, Faroe Islands. Photo: Tina Thorman

There is great hiking on the Faroe Islands, and more sheep than humans. Photo: Tina Thorman

The weather in the Faroe Islands is notoriously dramatic and unpredictable—but your surest chance of warm and sunny days comes in the summer. There is great hiking on the islands, more sheep than there are humans, and a rustic charm and sense of welcome that could have you sharing a home-cooked meal with a local family. Luxury here is not in the bathroom fixtures or the thread count of the sheets, but in the time and space to clear your mind and recenter your soul.

Use our questionnaire to be marked as a VIP and get the best possible trip.

August: Great Barrier Reef Islands, Australia

Great Barrier Reef aerial view

Great Barrier Reef, Australia. Photo: Shutterstock

August brings warm weather, good visibility for divers and snorkelers, and calm seas (the wind dies down at the end of July). It’s also the best time to view whales—dwarf minke whales visiting the northern reefs and humpbacks on their annual migration to Antarctica. Every August, Hamilton Island also hosts Race Week, a sailing regatta with festivities on and off the water.

Learn more in our Insider’s Guide to the Great Barrier Reef, and use our questionnaire to be marked as a VIP and get the best possible trip.

August: Madagascar

Ring-tailed lemur looks directly at the camera in Madagascar

Ring-tailed lemur, Madagascar

August is deep enough into the dry season that the wildlife viewing is very good (the lush foliage of rainy season makes it hard to see the animals) yet it also precedes the peak season of September and October, when the parks are more crowded (and the weather hotter).

Learn more in our Insider’s Guide to Madagascar, and use our questionnaire to be marked as a VIP and get the best possible trip.

August: Ionian Islands, Greece

If August is your only time to travel to Greece and you don’t love crowds, charter a yacht in the Ionians. Many of the smaller islands in this group are accessible only by boat, so you’ll be free of the swarms that plague Santorini and Mykonos this month. Instead, you’ll find a temperate climate, spectacular beaches, lush vegetation, beautiful mountains, and the true flavor of Greece when you disembark from your boat and head into a tiny town for a meal at a local taverna.

Ask Wendy who is the best Greek Islands or yacht-charter specialist to plan your specific trip.

September: Ibiza

Bay with sailboats in Cala d Hort IBIZA Spain

In September, it’s not nearly as crowded at Ibiza’s beach clubs, restaurants, and nightclubs

Come September, it’s not nearly as crowded at the beach clubs, restaurants, and nightclubs (or on the roads). Rates for hotels and private boating excursions drop, but the weather is still lovely, and it’s warm enough to swim (with ideal air temperatures for hiking and biking as well) right up until the hot spots’ closing parties in early October.

Use our questionnaire to be marked as a VIP and get the best possible trip.

September: Hvar, Croatia

aerial view of Hvar island and surrounding sea Croatia

On Hvar in September, it’s still swimsuit season but the party crowds have gone. Photo: Exeter International

It’s still swimsuit season, but the atmosphere is much more laid-back than in July and August, and the travelers are more sophisticated than the summer party crowds. Croatia is known for its excellent wine, and September also coincides with the grape harvest. Later in the month, hotel rates drop.

Ask Wendy who is the best Croatia specialist to plan your specific trip.

September: San Juan Islands

Lime Kiln Point Lighthouse, Haro Straight, San Juan Islands, Washington

Lime Kiln Point Lighthouse, Haro Straight, San Juan Islands, Washington. Photo: Shutterstock

The weather in the San Juans (and the Olympic Peninsula) is usually still very nice in September, and there are fewer tourists than you’ll find in July and August. (The best time to see the resident orca whales, though, is June.)

Learn more in our Insider’s Guide to the San Juan Islands, and use our questionnaire to be marked as a VIP and get the best possible trip.

September: Lofoten Islands, Norway

Reine, Lofoten, Norway. The village of Reine under a sunny, blue sky, with the typical rorbu houses. View from the top

The village of Reine in Lofoten, Norway. Photo: Shutterstock

In September and October, the crowds are gone, the weather is still pleasant, and the days are long enough to enjoy hiking, kayaking, fishing, and other activities—but with enough darkness that you stand a good chance of seeing the Northern Lights.

Ask Wendy who is the best Norway specialist to plan your specific trip.

October: Sicily

coast of Cefalu, Palermo Sicily Italy

The coast of Cefalu, Palermo, in Sicily. Photo: Shutterstock

October is one of the most colorful and flavorful months in Sicily. It is the season of the harvest, which means fresh olives, almonds, chestnuts, wild mushrooms, prickly pears, and carob complement the usual variety of culinary offerings. Air and sea temperatures are still warm and inviting, the ancient cultural sites are bathed in a crisp autumn light, and flights and hotels are less expensive than during the summer..

Learn more in our Insider’s Guide to Sicily, and use our questionnaire to be marked as a VIP and get the best possible trip.

October: The Seychelles

Anse Louis, Seychelles

Anse Louis, Seychelles. Photo: Maia Luxury Resort.

October brings calm winds and beautiful temperatures, but it’s not a popular time for Europeans to travel—so rates are lower than usual. It’s also the best month for spotting whale sharks.

Ask Wendy who is the best Seychelles specialist to plan your specific trip.

October: Hawaii’s Big Island

Wai'pio Valley Lookout, Hawaii

Wai’pio Valley Lookout, Big Island, Hawaii.

October is one of the Big Island’s driest months, with daytime temps hovering around 85 degrees.  It’s also a month for deals, given that so few families are traveling.

Learn more in our Insider’s Guide to the Big Island, and use our questionnaire to be marked as a VIP and get the best possible trip.

October: Newfoundland

berry picking on Fogo Island Newfoundland Canada

Berry picking on Fogo Island, Newfoundland.

This month brings out the island’s culinary delights: You’ll find locals foraging for wild berries, delicious food festivals, and restaurants blessed with abundant harvests and the freshest seafood.

Learn more in our Insider’s Guide to Newfoundland, and use our questionnaire to be marked as a VIP and get the best possible trip.

November: Ambergris Caye, Belize

sunset in Belize at Ambergris Caye

Ambergris Caye. Photo: Absolute Belize

Before Thanksgiving, hotel rates are at their lowest. The days are hot, but the humidity is dropping, and the evenings are cool and breezy. November 19 is Garifuna Settlement Day and is best spent on mainland Belize in either Dangriga or Hopkins, where the Garifuna people celebrate—with drumming, dancing, and parades—the arrival of their Afro-indigenous ancestors more than 200 years ago.

Learn more in our Insider’s Guide to Belize, and use our questionnaire to be marked as a VIP and get the best possible trip.

November: The Galapagos Islands

Blue-footed booby, Galapagos Islands.

Blue-footed booby, Galapagos Islands. Photo: Pixabay/Peter Stuart Miller

The Galapagos is a magnet for families with kids during summer and other school vacations; if you’re looking for a quieter time, think November (except Thanksgiving). Blue whales, humpback whales, and whale sharks—the largest fish in the sea, growing up to 40 feet in length and weighing as much as 40,000 pounds—are most likely to be spotted in the Galapagos from June through November.

Learn more in our Insider’s Guide to the Galapagos, and use our questionnaire to be marked as a VIP and get the best possible trip.

November: Papua New Guinea

Milne Bay is home to the most varied scuba diving in Papua New Guinea: Here you’ll find coral structures, exotic creatures hiding in the sandy bottom, and WWII wrecks to explore. The diving in Milne Bay is at its best from November through January, which is the dry season for this part of the country.

Learn more in our Insider’s Guide to Papua New Guinea, and use our questionnaire to be marked as a VIP and get the best possible trip.

November: South Georgia Island

King penguins, South Georgia Island. Photo: ExpeditionTrips

King penguins, South Georgia Island. Photo: ExpeditionTrips

A jewel in the Southern Ocean, South Georgia Island will appeal to anyone interested in wildlife, wild places, or the history of Antarctic exploration. The season here runs roughly from late October through early March, but what makes November special—in addition to the king penguins stretching as far as the eye can see—is the plethora of elephant seals and fur seals on shore.

Learn more in our Insider’s Guide to Antarctica Cruises, and use our questionnaire to be marked as a VIP and get the best possible trip.

November: St. Barts

Hotel Christopher, St. Barts

Hotel Christopher, St. Barts. Photo: Hotel Christopher

Come November, many resorts, boutiques, and restaurants that closed during the height of hurricane season have reopened, and everything feels fresh and new. The Saint Barth Gourmet Festival also takes place this month, attracting star chefs from France and elsewhere. Plus, hotel and villa rates don’t jump up until mid-December.

Learn more in our Insider’s Guides to St. Barts Beach Vacations and St. Barts Villa Vacations, and use Wendy’s trip request form to be marked as a VIP and get the best possible trip.

December: The Caribbean

Idyllic tropical beach with white sand, turquoise ocean water and blue sky at Antigua island in Caribbean

Antigua island in the Caribbean. Photo: Shutterstock

From just after Thanksgiving until just before Christmas, you have lovely weather and can enjoy savings of up to 40% off peak-season rates. (Peak season starts just before Christmas and lasts till just after Easter).

Learn more in our Insider’s Guide to Finding Your Perfect Caribbean Island Resort, and use our questionnaire to be marked as a VIP and get the best possible trip.

December: Fiji

Villa at the Taveuni Palms Resort, Fiji

A villa overlooking the ocean at the Taveuni Palms Resort in Fiji. Photo: Taveuni Palms

At the start of cyclone season, you’ll find tropical afternoon showers but also great resort deals: free nights, free massages, even free domestic airfares. The Yasawa and Mamanuca islands are your best bet for dry days at this time of year.

Learn more in our Insider’s Guide to Fiji, and use our questionnaire to be marked as a VIP and get the best possible trip.

Be a smarter traveler: Read real travelers’ reviews of Wendy’s WOW List and use it to plan your next trip. You can also follow her on Facebook, Twitter @wendyperrin, and Instagram @wendyperrin, and sign up for her weekly newsletter to stay in the know.

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