Escape Winter at the Perfect Island for You

The hardest part is choosing where to go. We cover the top islands to escape to this winter, and why.

Posted: November 12, 2018 03:17 PM ET

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Deciding to go on a tropical vacation is the easy part. It’s choosing the right island that can be overwhelming (in a good way!). Here, we break down the top destinations, where to stay and why—whether you’re bringing the little ones along or going sans enfants.

Get away from it all in Puerto Rico

Reason to go: The island culture is vibrant, and the tourism industry is starting to regain momentum after the hurricane.

Where to stay: El San Juan Hotel, Curio Collection by Hilton

Why: Newly refreshed guest rooms put you right on a two-mile stretch of Isla Verde Beach, close to the historic attractions of Old San Juan. The hotel is accepting reservations for select rooms, suites and even beachfront villas in advance of its grand reopening this winter. Spend the day on the pristine beach or lounge around one of the four pools, all surrounded by 15 acres of lush gardens.

Claim to fame: Two evening hot spots: the recently redesigned Brava nightclub and the intimate, speakeasy-inspired Chico Cabaret

Live island-life bliss in Jamaica

Reason to go: Aside from the obvious draws, like warm weather and stunning beaches, Jamaica has a lot of personality and culture. You’ll experience the unique flavours of the local cuisine, the thrills of the landscape—from climbing Blue Mountain to hiking up to Dunn’s River Falls—and the chill rhythm of the reggae soundtrack.

Where to stay:

Hilton Rose Hall Resort & Spa, Montego Bay

Why: The newly designed resort sits on a legendary estate—private beach included—and it’s just a short complimentary shuttle ride from Montego Bay, an energetic city that’s worth exploring. You could also easily spend the entire time on the resort. Get pampered at the spa, lounge around one of the three pools, hang out the swim-up bar and dine at one of seven restaurants.

Kid appeal: The on-site water park (including a lazy river)

Where to stay (without the kids):

Jewel Dunn’s River Beach Resort & Spa, Ocho Rios

Why: This all-inclusive adults-only resort has everything, right down to butler-serviced suites if you feel so inclined. Plus, the location is ideal: Dunn’s River Falls is five minutes away, and nearby Dolphin Coast is surrounded by a tropical rainforest.

Claim to fame: An 18-hole championship golf course and Dive-in Movies, where you watch a flick as you float in the pool

Where to stay and really splurge:

Jewel Paradise Cove Resort & Spa, Runaway Bay

Why: With a health and wellness focus, this adults-only oceanfront resort offers a premium experience, from upscale dining to complimentary golf and up to three incredible excursions included in the price of your stay. Go horseback riding, zip line, see Konoko Falls, visit Margaritaville, learn all about Bob Marley in Nine Mile where he was born, plus much more.

Claim to fame: The excursions—this is the Jewel Resorts’ most inclusive all-inclusive

Unplug in Aruba

Reason to go: The beachy island is small but has it all: shopping, nightlife, great cuisine, historic architecture, even a national park.

Where to stay: Hilton Aruba Caribbean Resort & Casino

Why: The newly renovated resort has a beachfront spa offering staple treatments, and you can enjoy world-class dining at five restaurants. (In-room dining is also available if you’re looking for a quiet night.)

Claim to fame: The huge casino and the diving lessons with PADI Dive Center experts

Kid appeal: The Kids Club and on-site playground

Discover the charm of Barbados

Reason to go: The tiny island packs a punch, promising a depth of culture with British, West African and Caribbean influences and unique historical landmarks, including a sugar mill and 17th-century fort, all against a tropical backdrop—turquoise waters included.

Where to stay: Hilton Barbados Resort

Why: With private en-suite balconies, a sprawling pool complex and a beach that spans the serene peninsula of Needham’s Point, you’ll have no problem unwinding. And when you’ve had enough relaxing (if that’s even a thing), there’s a tennis court and a fitness centre, plus a scuba, snorkelling and watersports centre.

Claim to fame: A chartered submarine takes tourists to coral gardens and sunken ships

Kid appeal: The Kidz Paradise children’s program

Live that luau life in Hawaii

Reason to go: The epitome of the island getaway, Hawaii offers breathtaking vistas, lush tropical flora, lots of adventure, wildlife, culture and beauty—all well worth the travel time.

Where to stay on Oahu:

Hilton Hawaiian Village Waikiki Beach Resort

Why: Explore the beautiful thriving coastal city of Honolulu while staying at an incredible oceanfront resort on Oahu that boasts five pools and the best waterslides in Waikiki.

Claim to fame: Elvis Presley’s Blue Hawaii was filmed at the resort in 1961.

Kid appeal: The Hawaiian adventures at Camp Penguin, including a visit to the Honolulu Zoo

Where to stay on the Big Island:

Hilton Waikoloa Village

Why: This amazing resort on the Big Island’s Kohala Coast has its own four-acre lagoon perfect for watersports. You can swim with dolphins, play two championship golf courses and get around the resort on mahogany boats that take you through canals.

Claim to fame: The very popular luau Legends of Hawaii

Kid appeal: The 175-foot waterslide

Need one more reason to take a vacation?

CAA Members get up to 15% off at participating Hilton family hotels and resorts. Click here to book your stay!

Image credit: El San Juan Hotel, Hilton Rose Hall Resort & Spa, Playa Hotels & Resorts/Jewel Dunn’s River Beach Resort & Spa, Playa Hotels & Resorts/Jewel Paradise Cove Resort & Spa, Hilton Aruba Caribbean Resort & Casino, Hilton Barbados Resort, Hilton Hawaiian Village^® Waikiki Beach Resort and Hilton Waikoloa Village