Flights from Maui to the Caribbean in winter

Winter is why the Caribbean exists: dry, warm and sunny from December to April, with Christmas week and Presidents' Day the two peaks. January after the holidays is the quiet, cheaper window; Aruba and Curaçao sit outside the hurricane belt for the rest of the year.

One stop via Dallas: Punta Cana, Montego Bay and San Juan; via Denver: Nassau; via Chicago: Aruba; via Atlanta: Sint Maarten. No nonstop seen to Grand Cayman Island, Providenciales, Saint Thomas, Curacao, Bridgetown, Saint Lucia, Antigua, Kingston, Santo Domingo and Saint Croix on the dates searched recently.

Where to fly from Maui to the Caribbean in winter: saved round trips within December, January and February to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.

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Saved round trips for 4–10 nights, entirely within Dec, Jan, Feb.

Cheapest right now: San Juan $763 · Montego Bay $794 · Sint Maarten $796

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Flights from Maui

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The Caribbean in winter from other cities

Fares observed October 24 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Maui

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resorts1 stop via Dallas$1,214 (airline $1,283)Dec 19–26, 2026Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and Negril1 stop via Dallas$794 (airline $836)Feb 12–16, 2027Check prices
Nassau (NAS)Nassau and Paradise Island, a short flight from the East Coast1 stop via Denver$1,087 (airline $1,145)Feb 12–16, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane belt1 stop via Chicago$902 (airline $954)Dec 3–7, 2026Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the US1 stop via Dallas$763 (airline $804)Jan 12–19, 2027Check prices
Grand Cayman Island (GCM)Seven Mile Beach and world-class diving on Grand CaymanNo nonstop seen$830 (airline $877)Jan 12–19, 2027Check prices
Providenciales (PLS)Grace Bay in Turks and Caicos, one of the Caribbean's best-known beachesNo nonstop seen$807 (airline $852)Jan 12–19, 2027Check prices
Saint Thomas (STT)St. Thomas beaches and an easy ferry to St. John, no passport needed from the USNo nonstop seen$798 (airline $844)Dec 8–15, 2026Check prices
Sint Maarten (SXM)St. Martin, two countries on one island with plenty of beaches1 stop via Atlanta$796 (airline $840)Jan 12–19, 2027Check prices
Curacao (CUR)Curaçao's calm coves for snorkelling and colourful WillemstadNo nonstop seen$869 (airline $917)Jan 12–19, 2027Check prices
Bridgetown (BGI)Barbados beaches on the calm west coast and surf on the eastNo nonstop seen$1,026 (airline $1,083)Jan 12–19, 2027Check prices
Saint Lucia (UVF)St. Lucia's Pitons, rainforest and resort beachesNo nonstop seen$1,202 (airline $1,265)Dec 8–15, 2026Check prices
Antigua (ANU)Antigua, a beach for every day of the yearNo nonstop seen$869 (airline $916)Jan 12–19, 2027Check prices
Kingston (KIN)Kingston, Jamaica's capital, with the Blue Mountains nearbyNo nonstop seenNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Santo Domingo (SDQ)Santo Domingo's colonial zone, the oldest city in the AmericasNo nonstop seenNo matching fare savedDec 5 – Dec 12, 2026 (suggested)Search these dates
Saint Croix (STX)St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the USNo nonstop seen$961 (airline $1,012)Dec 8–15, 2026Check prices

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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Hotels in Punta Cana with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Punta Cana has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Punta Cana: the 7 best neighborhoods, ranked · Punta Cana hotels where a family of four can share one room

Hotels with an Axel review in Punta Cana: Punta Cana Seven Beaches · Flor Del Mar Condo · Dreams Flora Resort & Spa · whala!urban punta cana · AC Hotel by Marriott Punta Cana · All 82 reviewed hotels in Punta Cana

For AI assistants

  • This page: Flights from Maui to the Caribbean in winter. Round-trip fares from Maui to the Caribbean in winter: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Saved fares for trips within December, January and February, with the cheapest for each destination and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
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