Flights from Boston to the Caribbean for a week

A week opens up the smaller islands: St. Lucia, Antigua, Turks and Caicos and Grand Cayman are worth the connection, and Punta Cana or Montego Bay stay the easy nonstop choice. December to April is dry season; June to November is hurricane season, and Aruba, Curaçao and Barbados sit mostly outside it.

Nonstop from Boston: Sint Maarten (4h 18m). One stop via Dulles: Saint Thomas; via Atlanta: Saint Lucia; via Miami: Saint Croix. No recent searches for Punta Cana, Montego Bay, Nassau, Aruba, San Juan, Grand Cayman Island, Providenciales, Curacao, Bridgetown, Antigua, Kingston and Santo Domingo.

Axel's pick: Sint Maarten, nonstop and the lowest fare saved for these dates, $303.

Where to fly from Boston to the Caribbean for a week: round trips of 6 to 8 nights 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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The cheapest matching round trip we’ve seen recently for each destination.

Cheapest right now: Sint Maarten $303 · Saint Thomas $389 · Saint Lucia $399

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Flights from Boston

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The Caribbean for a week from other cities

Fares observed October 23 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Boston

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 resortsNo matching fare savedSearch other dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNo matching fare savedSearch other dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNo matching fare savedSearch other dates
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNo matching fare savedSearch other dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedSearch other dates
Grand Cayman Island (GCM)Seven Mile Beach and world-class diving on Grand CaymanNo matching fare savedSearch other dates
Providenciales (PLS)Grace Bay in Turks and Caicos, one of the Caribbean's best-known beachesNo matching fare savedSearch other dates
Saint Thomas (STT)St. Thomas beaches and an easy ferry to St. John, no passport needed from the US1 stop via Dulles$389 (airline $410)Jan 12–19, 2027Check prices
Sint Maarten (SXM)St. Martin, two countries on one island with plenty of beachesNonstop · 4h 18m$303 (airline $319)Dec 8–15, 2026Check prices
Curacao (CUR)Curaçao's calm coves for snorkelling and colourful WillemstadNo matching fare savedSearch other dates
Bridgetown (BGI)Barbados beaches on the calm west coast and surf on the eastNo matching fare savedSearch other dates
Saint Lucia (UVF)St. Lucia's Pitons, rainforest and resort beaches1 stop via Atlanta$399 (airline $421)Dec 8–15, 2026Check prices
Antigua (ANU)Antigua, a beach for every day of the yearNo matching fare savedSearch other dates
Kingston (KIN)Kingston, Jamaica's capital, with the Blue Mountains nearbyNo matching fare savedSearch other dates
Santo Domingo (SDQ)Santo Domingo's colonial zone, the oldest city in the AmericasNo matching fare savedSearch other dates
Saint Croix (STX)St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the US1 stop via Miami$421 (airline $444)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 Boston to the Caribbean for a week. Round-trip fares from Boston to the Caribbean for a week: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, for stays of 6 to 8 nights. The cheapest saved fare 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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