Easy Caribbean Getaways

These eight island destinations are just a quick flight away from major North American cities. Start packing.


You’ve had it with the day-to-day. It’s time to fly to St. Somewhere and wiggle your toes in the sand. But what if your time is in short supply? Relax, with a bit of planning, you can still reach the beach for a long weekend without spending the majority of your getaway in transit lounges or taxi cabs. It’s all about picking a destination that’s a reasonable nonstop away, and a resort that’s not too far from where you land. To inspire you, we’ve created some sample arrivals, based on currently available nonstop flights and average transit times from arrival gateway to resort. Each of these properties was chosen not only for convenience to the airport, but also because they provide the Caribbean vacation experience you crave.

Atlanta to St. Lucia (ATL-UVF)

St Lucia Coconut Bay waterslide, caribbean getaways

St. Lucia’s Coconut Bay Resort has an adults-only wing, but grownups are free to cut loose as well. Photo: Richard Hallman/Coconut Bay Resort

 Depart at 9:51 a.m. / 4 hr. 24 min. flight time / 5 min. shuttle to Coconut Bay Resort / Check in at 3:25 p.m.

Travel Notes: After four hours on the plane, you’ll be ready to hit the beach, not spend another hour-plus on winding roads to reach one of the resorts on St. Lucia’s west-central coast. Coconut Bay is a well liked and reasonably-priced all-inclusive on the island’s southeastern corner, with separate wings for adults and families. It sits beachfront on the Atlantic, with a dedicated adult pool and spa, five restaurants, six bars, plenty of on-property water sports and short drive times to many of the island’s best day-trip adventures.

Boston to St. Thomas (BOS-STT)

St Thomas Ritz Carlton, Sailing Catamaran

The sailing catamaran Lady Lynsey cruises near the Ritz-Carlton on Great Bay, St. Thomas. Photo: Don Riddle/Ritz-Carlton

Depart at 8:57 a.m. / 4 hr. 2 min. flight time / 25-30 min. van ride to the Ritz-Carlton / Check in at 3:30 p.m.

Travel Notes: Getting to the majority of St. Thomas’ beachfront properties requires a run through downtown Charlotte Amalie. And once you are free of the traffic on Veteran’s Drive, it’s worth investing a few extra minutes of taxi time to go all the way to the island’s east end. The Ritz-Carlton sits on a quiet strand of beach known as Turtle Cove, overlooking Great Bay and St. John to the east. You’ll have plenty of time for a refreshing dip and a relaxing libation at the Coconut Cove bar before showering up for dinner. 

Charlotte to Barbados (CTL-BGI)

Coral reef club Barbados

The elegant Coral Reef Club commands prime beachfront real estate on Barbados’ calmer west coast. Photo: Mike Toy/Coral Reef Club

Depart at 10 a.m. / 4 hr. 32 min. flight time / 15 min. taxi ride to Ocean Two / Check in at 4:30 p.m.

Travel Notes: Located on calm Dover Beach, on the island’s south coast, Ocean Two offers easier access to the airport than resorts north of Bridgetown. Those willing to invest an additional 20 minutes of cab time to the west-central coast should consider the Coral Reef Club for a taste of gentile West Indies elegance.

Chicago to Jamaica (ORD-MBJ)

Jamaica Sandals Resort

Jamaica resorts such as Sandals at Montego Bay give couples a chance to enjoy private time together. Photo: Sandals Resort Montego Bay

Depart at 7:40 a.m. / 3 hr. 50 min. flight time / 10 min. shuttle to Sandals Royal Caribbean / Check in at 1:30 p.m.

Travel Notes: Arrival in Montego Bay couldn’t be easier. Once you clear customs, go right to a dedicated check-in desk for Sandals, then chill out in the on-site lounge while their staff takes care of your luggage transfers. From there, it’s a quick ride to the property, where a welcome drink awaits. To get the most out of a short stay, book a mid-afternoon return and enjoy a couple extra hours of morning beach time at the resort. The front desk will hold your bags after checkout, and there are facilities for a rinse and change before the flight. 

Cleveland to Puerto Rico (CLE-SJU)

La Concha Resort, Puerto Rico

The spectacular infinity pool at Puerto Rico’s La Concha resort overlooks blue ocean waters. Photo: La Concha

Depart at 8:45 a.m. / 4 hr. 15 min. flight time / 15 min. taxi to La Concha Resort / Check in at 2:30 p.m.

Travel Notes: There are no customs or immigration stops when flying to Puerto Rico, and once bags are in hand, you’ll have no problem flagging a taxi. Mid-day traffic should be reasonable, and the location of the La Concha couldn’t be better. The hotel sits smack in the middle of the upscale Condado district, overlooking an excellent stretch of beach that is right next door to the green spaces and lively activities of the Ventana del Mar square. Avenida Ashford is ideal for strolling and people watching, and just a mile away are the scenic streets of Old San Juan. 

New York to Bermuda (JFK-BDA)

Bermuda Hamilton Harbor

An intra-island ferry runs from Hamilton Harbour to destinations around the island nation of Bermuda. Photo: Verena Mathew/iStock

Depart at 7:30 a.m. / 2 hr. 10 min. flight / 25 min. taxi to Coco Reef Resort / Check in at 11:45 a.m.

Travel Notes: Bermuda is an easy hop from New York, but with the airport at the far north of the connected group of islands that comprise the nation of Bermuda, it can take an hour to reach the most distant resorts on the island’s southwest point. Split the distance by staying at Coco Reef Resort. It’s not the island’s fanciest or priciest, but it does sit on one of the most spectacular beaches, with direct ocean views from many rooms. 

Philadelphia to St. Martin (PHL-SXM)

St Maarten Philipsburg

St. Maarten’s capital, Philipsburg, sits beachside on a spit of land between a salt pond and Great Bay. Photo: iStock

Depart at 9:40 a.m. / 4 hr. flight time / 5 min. taxi to Azure Hotel / Check in at 3:15 p.m.

Travel Notes: You can reach most any part of the half-Dutch, half-French island of Sint Maarten/St. Marten in less than a half hour from the airport, so selecting a hotel is really about preferences: Dutch or French, leeward or windward, upscale or value-priced. One popular option that puts you within a few paces of the clear waters of Simpson Beach is the Azure Hotel. The decor is attractive, and kitchenettes allow you to dine in when you feel like it. You’ll be reminded of your proximity to the airport each time a plane takes off, but the immediate beach access can’t be beat. 

Washington, D.C. to Nassau (DCA-NAS)

Compass Point Resort, New Providence, Bahamas

Admiring the view of Love Beach from a balcony at Compass Point Resort, New Providence Island, Bahamas. Photo: Julian Bajzert/Bahamas Tourist Office

Depart at 8:40 a.m. / 2 hr. 50 min. flight time / 10 min. taxi to Compass Point Resort / Check in at 12:30 p.m.

Travel Notes: When you arrive at Lynden Pindling International Airport, you have choices. It’s about 15 minutes to the resorts on Cable Beach, which one day soon will include the ambitious Bahama Mar development, or a half hour ride through Nassau to Paradise Island. As an alternative, you could take a left on West Bay Street and arrive at one of the island’s favorite and most colorful getaways: Compass Point Beach Resort, where brightly-painted huts perch on the seawall overlooking turquoise waters. You may need to book well in advance, because this place has become one of the Bahama’s worst-kept secrets, but remains one of its best experiences.