7 Islands to Visit Before the Holidays

Whether you’re looking to dine on fresh lobster or take part in an indigenous festival, a preholiday trip is a sure plan


One of the best times of the year to squeeze in a trip is during the fall. November and early December are ideal as the crowds are gone, the rates are lower and the weather is void of storms. Here are some options for that last-minute getaway before the holiday season kicks in.

Puerto Rico

While the Island of Enchantment is a year-round destination the pre- winter season is ideal for a long weekend getaway. November is the official start of the holiday season as Christmas trees and lights are up early and the parties begin. Each town hosts the lighting of the Christmas tree adding decorations throughout the month accompanied by fireworks, traditional Christmas music and food. From November 2 through 30, 2019 town plazas turn into street festivals where artisans and food vendors set up stands for the continual celebrations. The island celebrates its discovery by Columbus on November 19. An official holiday, Discovery of Puerto Rico Day consists of parades, fairs and cultural activities and is celebrated in most towns.

Puerto Rico San Juan

While Old San Juan is magical on its own, it’s even more so during the holidays. The scenery changes as Christmas lights are added to churches, arches and plazas. Photo: Anita S/ Pixabay


The high season in this island nation is during the summer when the beaches, towns and restaurants are hopping. Off-season begins in November and runs through March when rates are lower and crowds have dispersed. And, Bermuda, warmed by the Gulf Stream holds onto its warm waters into November making a dip in the sea possible. During the fall the humidity is lower with cooler temperatures making outdoor activities more pleasant. Hike or bike along the Bermuda Railroad Trail that covers 18 miles. The abandoned tracks wind through lush vegetation and along rugged cliffs and bypass classic old bridges. Although September first isn’t a national holiday, it’s widely celebrated as the beginning of spiny lobster season, which lasts until March. The island’s favorite fare is offered at restaurants around Bermuda. You can even catch your dinner with a local licensed lobster diver and cook it that evening.

Bermuda South Shore Horseshoe Bay

Bermuda’s south coast is lined with pink sand beaches. One of the most famous crescents is the scenic Horseshoe Bay at the heart of South Shore Park. Photo: Bruce/Flickr


November is the transition month on Maui, right between the island’s dry and wet seasons. It’s the time when humpback whales return to frolic in the waters during their annual winter migration. The season runs through May and sightings are possible from shore as well as a variety of guided boat excursions. Visit Lahaina Arts Society at Lahaina Cannery Mall on Saturdays from November 9 to December 29, 2019. Local artists will be on hand to present and talk about their work. The outdoor festival features photography, paintings, pottery, jewelry and more. The Hawaii International Film Festival runs from November 21 to 23, 2019. Included in showings are documentaries, film shorts, experimental films, animations and digital works. The event reflects the diverse multicultural face of Hawaii supporting Asian and Pacific films.

Maui Lahaina

Dusk along the Front Street shops of Lahaina on Maui. For Christmas, the town’s 60-foot famous banyan tree is wrapped in thousands of Christmas lights. Photo: Hawaii Tourism Authority/Tor Johnson


While sister, Harbour Island is known for its pink sands; Eleuthera boasts it’s own stretches of rosy hues. There are over 100 beaches to choose from ranging from blushing pinks to alabaster whites. Every Friday night brings a traditional Bahamian fish fry where you can sample a plate of peas n’ rice along with the fresh catch. Held at Anchor Bay in Governor’s Harbour, there are Bahamian dishes and specialties, music and dancing starting at 6:00 p.m. On November 30, the Ministry of Tourism Thanksgiving Crafter’s & Cultural Festival also takes place in Governor’s Harbour. It’s a chance to buy local hand made items and take in a fashion show, live band performances and see junkanoo dancers. To kick off the holiday season head to the annual tree lighting in the garden of the wellness center of the Cancer Society in Central Eleuthera on Saturday, December 7. The event includes live music, dancing and native foods.


A quiet and tranquil beach scene at Current on Eleuthera in the Bahamas. The small quaint town is located in North Eleuthera. Photo: Trish Hartmann/Flickr

Key West

November brings cooler weather and lower humidity just right for exploring the streets, shops and galleries of this quaint town. Discover the literary history of Key West at Custom House Museum in an exhibit (November 1, 2019 through February 9, 2020) of writers who have found the laid-back character of Key West an ideal venue to pen their novels and plays. The holiday season kicks off with Harbor Walk of Lights at the Historic Seaport on November 22. Along the walk, you’ll see the Key West traditional tree made of foam trap floats, a pine decorated in a nautical theme and a lobster trap tree. Check out the Key West Film Festival that runs from November 20 to 24, 2019 showcasing multiple genres and categories. Films and events are hosted at landmark venues throughout the town.

Key West

Sunset cruises are are a common scene at Mallory Square in Key West. Guests enjoy champagne, wine and cheese and await the green flash. Photo: J. Philipp Krone/Flickr

St. Barth

It’s the seaside sophistication of St. Tropez blended with the laid- back Caribbean lifestyle that fascinates visitors coming to this French isle. High season begins mid-December so getting a room or villa from November through early December is doable. The beaches won’t be vacant but it will be easier to find a spot on the sand at one of the sixteen white strands. November 20 to 24, 2019 draws sailors from around the world to the annual St. Barth Cata Cup, a regatta of small catamarans. The Formula 18 catamaran race starts and ends at St. Jean Beach. Christmas is big on the island and every year the port of Gustavia is decked out with lights and holiday décor transforming the harbor into the Christmas Village (December 6 to 22, 2019) where shops, galleries and food outlets become one meandering holiday market. Visiting yachts come in for the season transforming the harbor into a canvas of glistening watercraft.

St. Barth Gustavia

Gustavia Harbor in St. Barth lights up around the holidays with trees, Christmas decorations and visiting yachts strung up with lights. Photo: Martin Varsavsky/Flickr


Belize offers a slew of activities for the adventure seeker. While many come to dive and snorkel the 180 miles of coral reefs others come for land-based activities like hiking, and exploring caves and Maya ruins. One of the most celebrated holidays is Garifuna Settlement Day, which takes place each year on November 19th. While the Garifuna only make up 4 % of the population of Belize, their cultural contributions play a big part in today’s society. The traditional event includes drumming, street dancing and parades and traditional Garifuna foods. Each year the coastal town of San Pedro on Ambergris Caye lights up along the water during the San Pedro Holiday Boat Parade where spectators gather along the shoreline, docks and seaside bars as the boats pass by on Saturday December 7, 2019.

Belize Caye Caulker

Caye Caulker is just one of the small Caribbean islands of Belize with balmy breezes and turquoise waters. Visitors come to bird watch, kayak and dive the Barrier Reef. Photo: amon1500/Pixabay