10 Perfect Pre-Holiday Island and Coastal Escapes

Get away, enjoy the sun, and beat the crowds at these ideal destinations and resorts.

Quivira Los Cabos
A quick jaunt to Pueblo Bonito Pacifica Resort and Spa in Los Cabos is a great way to usher in the holidays. Quivira Los Cabos

The weeks leading up to both Thanksgiving and Christmas offer an excellent opportunity to get away for a relaxing or reinvigorating island stay before the annual shopping and cookie-baking frenzy kicks into high gear. Not only will you avoid holiday and high-season crowds, but by playing around with dates (especially for mid-week stays) you can also score great deals on airfare and hotel rates in destinations where prices skyrocket in the weeks afterward. 

So, if you’re feeling the need for a pre-holiday beach escape, here are 10 destinations to consider.

Key West, Florida

So close by—and yet with a vibe that feels far away from the U.S. mainland—Key West is the perfect pre-holiday playground for couples or families craving a mix of historic architecture, water-centric activities like boating and fishing, fresh seafood, fabulous sunsets and a unique ambience that’s laidback by day and lively after dark. It’s also a drive-to destination for those who live in the southeast, while others can fly to Miami or Fort Lauderdale and drive the scenic 113-mile Overseas Highway or connect to Key West International Airport via regional hubs.

Accommodations range from charming B&Bs to luxury resorts and rates in November and December start at under $300/night. Options include Parrot Key Hotel & Villas, offering oceanfront rooms, suites and villas that are a free shuttle ride away from Old Town; Kimpton Winslow’s Bungalows, a boutique inn in the historic district; The Capitana Key West, a breezy option with bay views; and Margaritaville Beach House Key West, located on the beach a short distance from Old Town.  

Los Cabos, Mexico

Desert-meets-ocean scenery, tequila tastings, activities from golf to deep-sea fishing and indulgent spa treatments are all part of the relaxation formula in coastal Los Cabos at the tip of the Baja Peninsula. Here, where the Pacific Ocean meets the Sea of Cortez, couples and families can spend lazy days by their resort pool or active hours enjoying all that Cabo San Lucas and neighboring San Jose del Cabo have to offer. Whale watching? Check. Horseback riding or ATV adventures? Yes. Fresh seafood and creative cocktails? Of course!

During November and December, you can expect to pay $250-to-$500/night for a four- or five-star accommodation, such as Pueblo Bonito Pacifica Resort & Spa, a tranquil adults-only all-inclusive; Marquis Los Cabos, another upscale adults-only all-inclusive; Nobu Hotel Los Cabos, a strikingly modern property that’s Nobu’s first hotel in Mexico; and Hilton Los Cabos Beach & Golf Resort, a hacienda-inspired resort set on one of Cabo’s most-swimmable beaches.

Jamaica

New Caribbean Hotels 2019 - S Hotel Jamaica
The main pool at S Hotel Jamaica, a popular hotel located on Doctor’s Cave Beach. S Hotel Jamaica

Jamaica’s main resort areas—Montego Bay, Negril and Ocho Rios—each deliver a relaxing Caribbean getaway filled with sun, legendary beaches and calm aquamarine water, all set to the happy rhythms of the island’s renowned reggae scene. Adventurous pursuits, such as waterfall climbs, zip-line and bobsled runs, cliff jumps and assorted watersports, offer adrenaline rushes to counterbalance the cocktail-centric beach and pool vibe. 

Jamaica’s many all-inclusive resorts make the island ideal for those seeking value while its boutique properties offer a mix of classic and contemporary design. Terrific pre-holiday options for November and December can be booked for $250-to-$400/night, including Jamaica Inn, a nostalgic property on a lovely beach in Ocho Rios; The Cliff Hotel, set on a five-acre bluff in Negril; Couples Tower Isle, an adults-only all-inclusive in Ocho Rios; and S Hotel Jamaica, a boutique all-inclusive in Montego Bay.

Riviera Maya, Mexico

Just to the south of Cancun, a lengthy stretch of beach communities known as Riviera Maya is a mecca for couples and families who love the ease and affordability of all-inclusive resorts and the soft lap of the western Caribbean against white-sand beaches backed by lush green jungle. Add easy access to Mayan ruins such as Coba and Tulum, and an escape here mixes carefree relaxation with fascinating history and insights into both ancient and modern Maya civilization and culture.

With ample flights into Cancun from major U.S. air hubs and November and December pre-holiday room rates of $200-to-$400/night at all-inclusive resorts, Riviera Maya is an easy choice for both couples and families. Options to consider include Excellence Riviera Cancun, an adults-only all-inclusive near Puerto Morelos; Royal Hideaway Playacar, another adults-only property close to lively Playa del Carmen; Bahia Principe Riveria Maya, which offers four distinct resorts within its sprawling beachfront setting; and El Dorado Royale by Karisma, an adults-only resort with swim-up suites.

Belize

From one of the planet’s most impressive coral reefs (plus the Great Blue Hole, a gigantic underwater sinkhole) to vivid-green rainforest sheltering remarkable Mayan cities (including Caracol and Lamanai), Belize offers visitors abundant access to nature, wildlife and ancient mysteries. Spot manatees in the shallows (Belize is home to as many as 1,000 of these gentle, endangered creatures), go birding (500 local species range from hummingbirds to toucans) as howler monkeys provide a soundtrack lifted from a National Geographic documentary, explore a cave holding the skeleton of a sacrificed Mayan maiden and snorkel amid Technicolor reef fish off Ambergris Caye. 

Rooms in November and December can be booked for under $300/night—at options that include Alaia Belize, Autograph Collection, a new resort in San Pedro on Ambergris Caye; Mahogany Bay Resort & Beach Club, Curio Collection by Hilton, also in San Pedro and offering access to a private beach club; Copal Tree Lodge, a farm-to-table eco-resort in southern Punta Gorda; and Matachica Resort & Spa, a secluded resort featuring private casitas on Ambergris Caye.

St. Lucia

Marigot Bay pool
Grab a cabana and enjoy the poolside serenity at Marigot Bay Resort and Marina. Marigot Bay Resort and Marina

Known for its landmark twin Piton peaks rising from the Southern Caribbean and for the colorful cottages and flavorful cuisine of its Creole heritage, St. Lucia offers a vacation that’s equal parts immersion in nature (you can climb one of the peaks and St. Lucia has a volcano and chocolate farms, too). The island is setting for a delightful, low-key escape offering insights into local culture, but also is home to top spots for sailing, snorkeling, diving, mountain biking, zip-lining and more. 

Accommodations can be booked for $250 to $400/night for pre-holiday stays in November and December and some top options include The Royalton St. Lucia, an Autograph Collection Resort, a family-friendly all-inclusive close to Rodney Bay; Marigot Bay Resort & Marina, a secluded resort with spacious private residences; Villa Beach Cottages, an intimate villa-style property near Castries; and Windjammer Landing Villa Beach Resort, a hillside all-inclusive offering panoramic sea views.

Barbados

As the Caribbean’s most southeasterly island, Barbados has a dual personality: The golden-sand beaches of its south and west coasts are lapped by the warm turquoise Caribbean while its wild and rugged eastern shoreline features dramatic boulder-strewn beaches and thunderous waves rolling in from the Atlantic Ocean. In between lies centuries of British-colonial heritage (Barbados ended 400 years of British rule and became a republic in November 2021), atmospheric great houses, several rum distilleries, manicured golf courses and even a spectacular cave.

While Barbados resort rates are known to be pricey in high season, during pre-holiday periods rooms can be booked for as little as $200-to-$400/night at properties that include Little Good Harbor, a hillside boutique hotel known for its beachfront The Fish Pot restaurant; The Crane Resort, a sprawling property overlooking a pink-sand beach in the southeast coast; Waves Hotel & Spa by Elegant Hotels, an all-inclusive boutique wellness hotel; and Sugar Bay Barbados, an all-inclusive resort within walking distance of Bridgetown’s South Coast Boardwalk.

Costa Rica

The Pacific Coast of Costa Rica attracts a mix of surfers and adventure enthusiasts seeking to embrace the country’s “pura vida” spirit while spotting sleepy sloths, several monkey species, majestic blue morpho butterflies and endangered sea turtles. Twenty six percent of the country’s land is protected—its 30 national parks include Manuel Antonio, Corcovado and Guanacaste—and it shelters 5 percent of the world’s biodiversity despite occupying just .03 percent of Earth’s land mass. While relaxing on the beach is an option, Costa Rica’s volcanoes (such as Arenal and Rincon de la Vieja) and abundant rainforests (including Monteverde) are ideal for hiking, zip-lining, horseback riding and other outdoor activities.

Top coastal accommodations during November and December (the beginning of dry season) can be booked for $250-to-$400/night at properties that include Gaia Hotel & Reserve, an eco-friendly luxury resort perched amid the rainforest near Manuel Antonio; Punta Islita, Autograph Collection, an eco-conscious retreat on the beach in Guancaste; Villa Caletas, a luxury boutique hotel set 1,150 feet above the Pacific; and Los Altos Resort, a luxury resort with a secluded beach near Manuel Antonio.

St. Kitts and Nevis

Golden Rock Inn
One of the most unique resorts in Nevis, if not the entire Caribbean, Golden Rock Inn seems like it exists on its own island. Golden Rock Inn

Known for its 18th century sugar plantations, rolling green golf courses and mischievous vervet monkeys, this dual-island Caribbean nation is ideal for both couples or families seeking a low-key getaway. St. Kitts has a laid-back ambience with plenty of open spaces for hiking, horseback riding and zip-lining (along with resort casinos and a scenic railway that’s the last remaining railroad in the Caribbean), while tiny Nevis is known for historic Charlestown (birthplace of Alexander Hamilton), photogenic stone churches, four-mile Pinney’s Beach (home to the famous Sunshine’s beach bar) and lush green Nevis Peak, which rises 3,232 feet above this 36-square-mile island.

For under $300/night during the pre-holiday weeks, you can enjoy a stay at the St. Kitts Marriott Resort & Royal Beach Casino, featuring several pools and a championship golf course; Koi Resort St. Kitts, Curio Collection, a new resort with Zen-inspired decor; Montpelier Plantation, a historic and romantic hillside inn on Nevis with a private beach club; and the Golden Rock Inn, an atmospheric boutique hotel on Nevis set amid beautiful gardens.

Grand Cayman

If relaxing days spent relaxing near or floating in some of the Caribbean’s most spectacular blue water is your idea of vacation bliss, Grand Cayman should be on your list of pre-holiday escape islands. Famous for resort-lined Seven Mile Beach (where watersports such as parasailing, wave runners and wakeboarding are popular) and the offshore sandbar Stingray City (where gentle Southern Stingrays gather for feeding and photo-ops with willing visitors), this island also has a good selection of duty-free shops in the capital, Georgetown, and the Cayman Turtle Centre, home to lagoons full of marine life.

Accommodations for pre-holiday stays can be booked for $300-to-$500/night at Grand Cayman Marriott Beach Resort, located directly on Seven Mile Beach; The Westin Grand Cayman Seven Mile Beach Resort & Spa, featuring a swim-up bar and several restaurants; Regal Beach Club, a condo resort featuring two- and three-bedroom villas and multiple swimming pools; and Hampton by Hilton Grand Cayman Seven Mile Beach, located steps from the beach and the shopping and dining at Camana Bay.

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