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May is an underrated month for islands. The Caribbean is still in its dry season, hurricane season does not start until June 1, and the winter crowds have gone. Maui gets almost no rain. Fiji's cyclone season ends with April, and Bali is well into its dry season.
Curaçao leads, with a perfect 10 for May weather and the cheapest rooms in the top five. The list is also more spread out than in winter: the South Pacific, Bali, two US islands and Crete all appear.
Score = 55% this month's weather + 45% the island's other five factors. How we score
| # | Island | Score | High °F | Sea °F | Rain (in) |
|---|---|---|---|---|---|
| 1 | Curaçao | 9.1 | 87 | 82 | 1.1 |
| 2 | Maui | 9.0 | 82 | 79 | 0.7 |
| 3 | Martinique | 8.9 | 86 | 83 | 2.4 |
| 4 | Barbados | 8.9 | 85 | 84 | 2.5 |
| 5 | Oahu | 8.8 | 81 | 78 | 1.8 |
| 6 | Fiji (Viti Levu and the Mamanucas) | 8.5 | 85 | 85 | 3.6 |
| 7 | Bali | 8.5 | 85 | 85 | 3.1 |
| 8 | Hilton Head Island | 8.0 | 83 | 77 | 4.4 |
| 9 | Crete | 7.7 | 77 | 68 | 1.3 |
| 10 | Key West | 7.6 | 81 | 83 | 3.9 |
1Curaçao scores a perfect 10 for May weather: highs of 87°F (31°C), an 82°F (28°C) sea and 1.1 inches (29 mm) of rain. It is the cheapest island in the top five, at $62 a night in Willemstad on both dates we priced. It sits south of the main hurricane track, which matters more as summer approaches. The beaches are coves, so rent a car. Nonstops come from 6 US airports; you need a passport and the free Dicard.
2May is one of Maui's driest months: highs of 82°F (28°C), a 79°F (26°C) sea and 0.7 inches of rain, a perfect 10. It has the best beaches and most to do of the top three, a 9 for each, and needs no passport. It ranks second only on price: $296 in Kihei on January 13 and $216 on July 14, 2027. Drive the Hana road and Haleakala ($30 a car) while it is dry. Lahaina is still being rebuilt.
3Martinique's May weather scores 9.8: highs of 86°F (30°C), an 83°F (29°C) sea and 2.4 inches of rain. It has more culture than any other Caribbean island on this list: Creole food, rhum agricole distilleries and Mount Pelée. A room in Les Trois-Îlets was $82 on July 14, 2027. Access holds it at #3, as the only US nonstop is American from Miami. You will want a car and some French.
4Barbados makes the top five in May, with a 9.8 weather score: highs of 85°F (29°C), an 84°F (29°C) sea and 2.5 inches of rain. It is the low-effort option: calm west- and south-coast beaches, buses and nonstops from 8 US airports. A south-coast room fell from $140 on January 13 to $92 on July 14, 2027. Crowds keep it behind Martinique. Hikers should pick St. Lucia.
5Oahu's May weather scores 9.9: highs of 81°F (27°C), a 78°F (26°C) sea and 1.8 inches of rain. It is the easiest Hawaii trip, with nonstops from 28 US airports and Waikiki at $139 on January 13 and $169 on July 14, 2027. It ranks below Maui on crowds and beaches. No passport, no rental car needed, and Pearl Harbor is free.
6Fiji's cyclone season ends in April, and May's weather scores 9.0: highs of 85°F (29°C), an 85°F sea and 3.6 inches of rain. Value and crowds both score 10, with a Nadi room at $31 on January 13 and $39 on July 14, 2027. Fiji Airways flies nonstop from Los Angeles, San Francisco and Honolulu. Base yourself on a Mamanuca island for the beaches; the mainland ones near Nadi are average.
7Bali's May weather scores 9.5: highs of 85°F (29°C), an 85°F sea and 3.1 inches of rain as the dry season settles in. It has the most to do on this list, a 9.5: Ubud's temples and rice terraces, volcano hikes and diving. A 4-star Seminyak room was $22 on January 13 and $30 on July 14, 2027. Beaches score 6.5, and there are no US nonstops. Pay the $8 levy and $28 visa on arrival.
8Hilton Head is the closest island on this list, a drive for much of the East Coast, and Savannah has nonstops from 39 US airports. May's weather scores 8.6: highs of 83°F (29°C), a 77°F (25°C) sea and 4.4 inches of rain. A 3-star room was $85 with tax in January and $167 in July. The beaches are wide, flat and lifeguarded, but the water is brownish, not turquoise. It is a family pick, not a snorkel trip.
9Crete is the only European island in May's top ten, and its weather score is 7.4: highs of 77°F (25°C) and little rain, 1.3 inches, but a 68°F (20°C) sea. It qualifies on its other scores: beaches 9 and things to do 9.5. Use May for Knossos, Chania and hikes like Imbros Gorge; Samaria Gorge is closed until further notice. A Chania room was $59 on January 13, 2027. No US nonstop: fly via Athens.
10Key West's May weather scores 9.1: highs of 81°F (27°C), an 83°F (29°C) sea and 3.9 inches of rain. It ranks last here because its verdict is conditional and its beaches score 4. Come for Old Town, Mallory Square sunsets and the $260 Dry Tortugas ferry. No passport needed, with nonstops from 24 US airports or a drive down the Overseas Highway. A 3-star room was $197 in July.
In this guide
Each island's score is 55% its May weather and 45% our other scores: beaches, things to do, access from the US, hotel value and crowds. May weather combines the daytime high, sea temperature, rain and sunshine from ten years of data. Islands must score at least 7 for May weather, and no region takes more than three places. The formula is in how we score islands.
Both score a perfect 10 for May weather, and Curaçao wins by under a tenth of a point. The difference is cost: $62 a night in Willemstad against $216 to $296 in Kihei on our two dates. Maui has better beaches and more to do, a 9 for each, and needs no passport.
Pick Maui for a first Hawaii trip with Haleakala and the Hana road in dry weather. Pick Curaçao for reef snorkeling from shore and a real town, at a third of the price. Pick Barbados (#4) if you want calm beaches and buses instead of a rental car.
Grenada, Puerto Rico, Antigua, St. Martin, St. Lucia and Jamaica all score above 8.6 for May, higher than #8 Hilton Head, but the Caribbean already has three places. Puerto Rico is the no-passport choice with the most flights. Our Caribbean ranking for May lists them all.
Crete is the only European island to qualify, at #9, and only just: its May weather score is 7.4. The days are warm and dry, but the sea is still cool for most swimmers. May suits hiking, Knossos and Chania more than beach days. Sicily and Rhodes clear the weather bar but score lower overall, and Mallorca's May weather, 6.8, falls just short. See the best Greek island in May.
We priced hotels for Wednesday, January 13 and Wednesday, July 14, 2027, with taxes in; we did not price May itself. Hilton Head, Key West and Hawaii need no passport, only a REAL ID or other TSA-accepted ID. Fiji gives US citizens visa-free entry for up to four months. In Crete, you connect through Athens; Europe's Entry/Exit System has been fully live since April 10, 2026, and ETIAS is not yet in operation. See passport rules for US citizens.
It is short for the price and has no hotel pickup. A good option for non-swimmers who want to see the reef.
Rating as shown on Viator
Breakfast, a deli lunch and water are included; tips are not. It is a long day in a van on a narrow road, and the sign-up page lists pickup at hotels or a Kahului meeting point, so check which applies to you.
Rating as shown on Viator
Drinks and a fruit snack are included. Boarding is from Fort-de-France or Case-Pilote; check which when you book.
Rating as shown on GetYourGuide
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The Caribbean, Hawaii, Fiji, Bali and the southeastern US coast. On our data, May highs are 87°F (31°C) in Curaçao, 82°F on Maui, 85°F in Fiji and Bali, and 83°F on Hilton Head.
Yes. It is the end of the dry season, hurricane season does not begin until June 1, and five Caribbean islands score a perfect 10 for May weather on our data. Winter crowds have gone.
Yes. Maui's May weather scores a perfect 10, with 0.7 inches of rain, and Oahu's scores 9.9. Whale season is over, but it is one of the driest months of the year.
For the beach, a little. Crete's May weather scores 7.4: warm, dry days but a sea of 68°F (20°C) on our data. For swimming, June is the safer month.
Not the Andaman side. The southwest monsoon arrives around mid-May, so Phuket and Koh Lanta drop off this list. Koh Samui, on the Gulf, stays drier.
Further reading
