Make Your Next Trip Extraordinary

The Ideal Island for Each Month of the Year

Wendy Perrin | April 23, 2015

Figuring out the optimal time to travel to an island can be tricky, what with the limited accommodations and the crowds that can overtax the local infrastructure. 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 nearby countries. So I thought I’d help by suggesting an island (or archipelago) for each month of the year. These are 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. If you’re seeking the right travel agent to plan an island trip you have in mind, ask me here.

January: Sri Lanka

Beautiful Sunset at Tangalle, Sri Lanka

Beautiful Sunset at Tangalle, Sri Lanka. Photo: Sri Lanka in Style

The last two weeks of January bring delightful weather to Sri Lanka (spring-like temperatures and blue skies) and fall after the busy New Year’s period but before February, when many travelers come on half-term or over the Lunar New Year from Singapore, Hong Kong, Bangkok, Dubai, and other parts of Asia. —Miguel Cunat, Wendy’s Trusted Travel Expert for Sri Lanka

Read Miguel’s Insider’s Guide to Sri Lanka, and reach out to Miguel to plan the best possible trip.

February: Venice

Carnevale in Venice, Italy

Carnevale in Venice, Italy. Photo: armelle76/Pixabay

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—reaches 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. —Maria Landers and Brian Dore, Wendy’s Trusted Travel Experts for Italy

Read Maria and Brian’s Insider’s Guide to Venice, and reach out to them to plan 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. —Vicky McGlynn, Wendy’s Trusted Travel Expert for Bermuda

Read Vicky’s Insider’s Guide to Bermuda, and reach out to Vicky to plan the best possible trip.

April: The Maldives

Beach views from Gili Lankanfushi, Maldives

Beach views from Gili Lankanfushi, Maldives. Photo: Gili Lankanfushi

Late 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 late April there is almost no rain or wind, so the water is calm for snorkeling and diving. —Lindsey Wallace, Wendy’s Trusted Travel Expert for the Maldives

Read Lindsey’s Insider’s Guide to The Maldives, and reach out to Lindsey to plan the best possible trip.

May: Santorini

Astra Suites Hotel, Santorini

Astra Suites, Santorini. Photo courtesy of TrueGreece

May weather is warm but not hot, and hotel rates are more competitive than during the summer. The crowds are thinner too, which has the added benefit of ensuring the service will also be better (during the hectic summer months, service suffers). —Christos Stergiou, Wendy’s Trusted Travel Expert for Greece

Read Christos’ Insider’s Guide to Santorini, and reach out to Christos to plan the best possible trip.

June: Bali

Uma by Como, Ubud, Bali

Uma by Como, Ubud, Bali. Courtesy Como Resorts

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 decent prices: High-season hotel rates don’t kick in until July. —Diane Embree, Wendy’s Trusted Travel Expert for Bali

Read Diane’s Insider’s Guide to Bali, and reach out to Diane to plan the best possible trip.

July: Mykonos

beach chairs by the pool Myconian Villa Collection Myconian Villa Collection in Mykonos Greece

Mykonos. Photo: Myconian Villa Collection

From mid-June to mid-July, you get the best of both shoulder and peak seasons: It’s lively but not crowded, warm but not scorching, and hotel rates aren’t sky-high. Mykonos is always windy, so bring a light sweater for evenings. —Christos Stergiou, Wendy’s Trusted Travel Expert for Greece

Read Christos’s Insider’s Guide to Mykonos, and reach out to him to plan the best possible trip.

August: Great Barrier Reef islands, Australia

Lizard Island, Great Barrier Reef Australia

Lizard Island, Great Barrier Reef, Queensland. Photo: Delaware North Companies/Tourism Australia

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. —Stuart Rigg, Wendy’s Trusted Travel Expert for Australia

Read Stuart’s Insider’s Guide to the Great Barrier Reef, and reach out to him to plan the best possible trip.

September: San Juan Islands

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.) —Sheri Doyle, Wendy’s Trusted Travel Expert for the Pacific Northwest

Read Sheri’s Insider’s Guide to the San Juan Islands, and reach out to Sheri to plan the best possible trip.


October: Sicily


October is one of the most colorful and flavorful months in Sicily. It is the season of the harvest, which means fresh olives, almonds, and chestnuts—not to mention wild mushrooms, prickly pears, and carob—complement the island’s always-bountiful variety of culinary offerings. The air and sea temperatures are still warm and inviting, while the breathtaking array of ancient cultural sites are bathed in a crisp autumn light. Both flights and accommodations are less expensive than during the summer, and the fewer tourists mean you get a more intimate experience with the people of Sicily. —Marcello Baglioni, Wendy’s Trusted Travel Expert for Sicily

Read Marcello’s Insider’s Guide to Sicily, and reach out to him to plan the best possible trip.

November: Papua New Guinea

Komoa Beach guesthouse, Tufi, Papua New Guinea

Komoa Beach Guesthouse, Tufi, Papua New Guinea. Photo courtesy Lynette Wilson.

There are only two months that do not fall within the country’s two monsoon seasons: November and April. That’s when it’s the least rainy and the trade winds blow. If you want to do the 60-mile Kokoda Trek, though, arrive in October, when it’s still “dry season.” —Lynette Wilson, Wendy’s Trusted Travel Expert for Papua New Guinea

Read Lynette’s Insider’s Guide to Papua New Guinea, and reach out to her to plan the best possible trip.

December: Caribbean Islands

Hermitage Bay, Antigua

Ocean views at the Hermitage Bay Resort in Antigua. Photo: Hermitage Bay Resort

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).

Read Lindsey Epperly’s Insider’s Guide to the Caribbean, and reach out to her to plan the best possible trip.


Be a smarter traveler: Read real travelers’s 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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