When to Go — Best Months by Destination

Nassau & the Out Islands

Bahamas

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M

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Go then: Mid-December through April — dry, breezy and warm without the humidity.
Best value: Late April to mid-June still delivers the same water at lower rates, before the season turns.
Worth knowing: Atlantic hurricane season runs June 1 to November 30 and peaks August through October. I book those months only with the right insurance and a flexible rate.

Plan Nassau & the Out Islands with me

Punta Cana

Dominican Republic

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M

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M

J

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D

Go then: December to April for dry, sunny beach weather — the classic all-inclusive window.
Best value: May and early June are the sweet spot for families watching a budget: warm sea, thinner crowds, softer pricing.
Worth knowing: Hurricane season June–November, most active August–October. Resorts stay open, but I'd want a flexible booking.

Plan Punta Cana with me

Montego Bay

Jamaica

J

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M

A

M

J

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D

Go then: December through April — the driest stretch and the reason the north coast fills up.
Best value: Late April to early June: rates drop noticeably and the sea is at its warmest.
Worth knowing: Two rainier peaks (May and October) and hurricane season June–November, peaking August–October.

Plan Montego Bay with me

Bridgetown

Barbados

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M

A

M

J

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D

Go then: December to April, when the calm west coast is at its most swimmable.
Best value: May and June before the wet season settles in — same water, quieter beaches.
Worth knowing: Wet season June–November, hurricane risk peaking August–October. Crop Over festivities run through July into early August.

Plan Bridgetown with me

Soufrière

St. Lucia

J

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M

A

M

J

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D

Go then: December through April for honeymoons — dry, clear views of the Pitons, calm sea.
Best value: May and early June: villa rates ease and the island feels like yours.
Worth knowing: Rainy season June–November with the highest hurricane risk August–October. The Pitons hold cloud more in the wet months.

Plan Soufrière with me

Providenciales

Turks & Caicos

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M

A

M

J

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D

Go then: December to April — Grace Bay at its calmest and clearest.
Best value: May and June, before the heat and the storm window, at a real discount to February.
Worth knowing: Hurricane season June–November, peaking September. Some restaurants and villas close for maintenance in September.

Plan Providenciales with me

Oranjestad

Aruba

J

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M

A

M

J

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D

Go then: January through April, though Aruba's weather is the steadiest in the Caribbean.
Best value: September and October — genuinely quiet and well priced, with far less storm exposure than the islands to the north.
Worth knowing: Aruba sits at the southern edge of the hurricane belt and is rarely hit directly, which is why I recommend it for late-summer travel. Trade winds are constant year-round.

Plan Oranjestad with me

St. Thomas

Charlotte Amalie, USVI

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Go then: December through April — dry season, and no passport needed for U.S. travellers.
Best value: May and June: cruise traffic thins and hotel rates fall before the storm window.
Worth knowing: Hurricane season June–November, peaking August–October. Cruise-ship days make Charlotte Amalie much busier — worth planning around.

Plan St. Thomas with me

St. John

Cruz Bay, USVI

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M

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D

Go then: December to April for the national-park beaches at their driest and clearest.
Best value: Late spring — May into early June — for villa value with the same snorkelling.
Worth knowing: Hurricane season June–November. Villas book far ahead for the Christmas and New Year weeks.

Plan St. John with me

St. Croix

Christiansted, USVI

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M

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Go then: December through April — the quietest of the three U.S. islands in high season.
Best value: May and June, and again early November, for noticeably lower rates.
Worth knowing: Hurricane season June–November, peaking September. Crucian Christmas Festival runs late December into early January.

Plan St. Croix with me

New York City

United States

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M

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Go then: Late April to June, and September through early November — the two windows the city is built for.
Best value: January and February are the cheapest weeks of the year for hotels, if you can take the cold.
Worth knowing: July and August are hot and humid. December is festive but the most expensive fortnight of the year; book well ahead.

Plan New York City with me

Maui

Hawaii, United States

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M

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M

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Go then: April to early June and September to mid-October — the shoulder seasons, and the best weather-to-crowd ratio of the year.
Best value: Those same shoulder months are when resort rates and airfare are at their most reasonable.
Worth knowing: Humpback whales are offshore roughly December to April — spectacular, and the busiest, priciest window. Winter brings more rain and bigger north-shore surf.

Plan Maui with me

Banff

Alberta, Canada

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M

A

M

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Go then: Late June through September for hiking and the lakes — Moraine and Louise are fully thawed and turquoise by late June.
Best value: January to March for skiing at lower rates than the summer peak; May and October are quiet but many trails and roads are still closed.
Worth knowing: Shoulder weeks (late April–May, November) see lifts and hiking both shut. Parks Canada now runs shuttles and vehicle restrictions for Moraine Lake — that needs planning, not luck.

Plan Banff with me

Mexico City

Mexico

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M

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Go then: March to May for warm dry days, and October to November for the clearest light of the year.
Best value: June to September is the rainy season — mornings are usually fine and afternoons wash out, and prices reflect it.
Worth knowing: Día de Muertos (November 1–2) is extraordinary and books out months ahead. The altitude is 2,240m — plan a gentle first day.

Plan Mexico City with me

El Nido

Palawan, Philippines

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M

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D

Go then: December through April, with January to April the most reliable for island hopping.
Best value: Late November and early December, before the Christmas rush lifts rates.
Worth knowing: July to September is the wet season, when boat trips are cancelled for days at a time. Palawan sees fewer typhoons than the eastern islands but is not immune.

Plan El Nido with me

Boracay

Western Visayas, Philippines

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Go then: December to April — the Amihan season, when White Beach is calm and glassy.
Best value: May and late November: warm water, far fewer people, better rates.
Worth knowing: The Habagat monsoon (roughly June–October) brings surf and seaweed to White Beach. Typhoon risk runs June through November.

Plan Boracay with me

Cebu

Central Visayas, Philippines

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Go then: January to April for diving, whale sharks and Kawasan Falls at their clearest.
Best value: May and June sit between the crowds and the rain, with better dive-resort pricing.
Worth knowing: Typhoon season June–November; the Visayas are more exposed than Palawan. Sinulog Festival packs Cebu City in mid-January.

Plan Cebu with me

Munich

Bavaria, Germany

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Go then: May to early October for beer gardens, the Alps within reach and long evenings.
Best value: March and April, and early November, are quiet and well priced between the two peaks.
Worth knowing: Oktoberfest runs the last two weeks of September into the first Sunday of October — hotel rates double or triple and sell out a year ahead. December is Christmas-market season, which is its own reason to come.

Plan Munich with me

Berlin

Germany

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Go then: May through September — the city lives outdoors, and the museums are still there when it rains.
Best value: March, April and November: cheap flights, cheap hotels, empty galleries.
Worth knowing: January and February are grey and cold, though Berlin handles winter better than most. Christmas markets run through December.

Plan Berlin with me

Heidelberg & the Rhine

Baden-Württemberg, Germany

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Go then: May, June and September for the castle, the river and the vineyards without the summer heat.
Best value: April and late October, when river cruises are running but the towns are quiet.
Worth knowing: Rhine river cruising generally runs April to October. Wine festivals cluster in September; Christmas markets in December. Winter is genuinely closed-feeling.

Plan Heidelberg & the Rhine with me

Paris

Île-de-France

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M

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Go then: April to June and September to October — the light Paris is famous for, and terrace weather without August's heat.
Best value: January to March: the lowest hotel rates of the year and no queue at the Louvre.
Worth knowing: August is hot, and many owner-run restaurants and shops close for the month. December brings the Christmas windows and higher rates.

Plan Paris with me

Provence

The South of France

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Go then: May, June and September — markets, hill towns and long dinners outside.
Best value: April and October are quieter and cheaper, with everything still open.
Worth knowing: Lavender blooms roughly mid-June to mid-July on the Valensole plateau, and that fortnight is busy. August is hot and full of French holidaymakers; November to March, much of rural Provence closes.

Plan Provence with me

The French Riviera

Nice & Cap Ferrat

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M

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M

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D

Go then: May, June and September — swimmable sea, open beach clubs, and room to move.
Best value: April and October for the coast at half the price, with warm days and cooler water.
Worth knowing: July and August are the busiest and most expensive weeks in Europe. The Cannes Film Festival (May) and the Monaco Grand Prix (late May) take over hotel availability for the whole coast.

Plan The French Riviera with me

The Amalfi Coast

Campania, Italy

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M

A

M

J

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D

Go then: May to June and September — warm sea, open terraces and a coast road you can still drive.
Best value: Late April and early October, either side of the crowds, at markedly lower rates.
Worth knowing: August is peak Italian holiday season: gridlocked and expensive. Many hotels and restaurants close from November to March, and ferry services wind down with them.

Plan The Amalfi Coast with me

Tuscany

Florence & the Val d'Orcia

J

F

M

A

M

J

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S

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N

D

Go then: May to June and September to October — the countryside at its greenest, then its most golden.
Best value: March, April and November for Florence without the queues and villas at winter prices.
Worth knowing: July and August are hot in the city and busy everywhere. The wine harvest runs September into October — wonderful to witness, and agriturismi book out early.

Plan Tuscany with me

Lake Como

Lombardy, Italy

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M

A

M

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N

D

Go then: May to June and September — gardens in bloom or turning, ferries running, mountains clear.
Best value: Late April and early October, when the lake is quiet and hotels are still open.
Worth knowing: July and August bring heavy day-trip traffic on a road built for far less. Many hotels, including the grand ones, close from November to March.

Plan Lake Como with me

The right month is half the trip.