Warm Vacation Spots: The Ultimate List

Chicago-based travel blog Bows & Sequins shares a luxurious list of reader favorite warm winter destinations. It's a mix of hotels and resorts with a few homes and VRBOs, too.

I started looking for warm vacation spots a few months ago and was a bit overwhelmed with where to start. The islands and resorts in the Caribbean are seemingly endless. Mexico, too. And then my head really started to spin once I added in Florida and Hawaii, or even destinations overseas. Where to begin?!

Dave and I have always hoped to plan a warm weather winter vacation the last few years, but have always lost track of time somehow. A few months ago, we actually decided to get ahead on planning a 2024 winter getaway and I’m so glad we did.

We’re going on our Caribbean vacay next week and it could not be more perfectly timed! Yes, we do go on a lot of trips, but it’s quite rare to take an actual vacation. I’m not sure the last time I took one, TBH. Between stress at work and wedding planning, we both need it. Not to mention, Chicago’s cold weather and lack of sunshine has been taking it’s yearly toll!

But where to go? Out of all of the warm vacation spots to choose, which one?!

Caneel Bay on St. John

In my mind, all I could picture was Caneel Bay on St. John in the US Virgin Islands. I’ve been dying to go back ever since I first visited in 2015! Unfortunately, the luxury resort has never reopened after the hurricanes in 2017.

Caneel Bay was absolutely magical. Relaxed, a little bit rustic, but luxe at the same time! For starters, the property didn’t have phones or TVs. It was like stepping back in time, in the best way possible. You can see some more snaps herehereherehereherehere, and here.

For this trip, since Caneel Bay wasn’t an option, we wanted somewhere where we wouldn’t necessarily need to leave the property all weekend. A warm weather vacation where we could just relax, eat, and drink. Somewhere with good drinks, great food, and even better vibes!

We decided to only go for a long weekend (four nights) and, shockingly, Dave has somehow never been to the Caribbean?! So that’s how we settled on that. We actually chose a place that’s not on this list at all, though! So I’ll be reporting back on how it was when we return in February.

Chicago travel blogger Jessica Sturdy of Bows & Sequins shares a coveted list of luxury travel destinations throughout the Caribbean, Mexico, and more.

Your Favorite Warm Vacation Spots

Luckily, I have all of you on Instagram to help me out when I need some advice! I asked for your favorite warm vacation spots and y’all sent in so many recommendations and travel tips for me to check out. I also got an overwhelming amount of messages to SHARE the list. So that’s what you’ll find below!

My hope is that this list of warm weather destinations will be a valuable resource as you’re trying to pick a place for your next vacay! Bookmark it, share it, spread the love.

It might serve as a brief geography and history lesson, too. Had to do some major research for this one to understand exactly where I was sharing a lot of these recommendations. 🙂

Some of your recommendations were for islands or places themselves, others were for specific hotels or resorts. And forewarning, most of these properties are LUXE! Y’all know how to travel and travel well.

The Caribbean

For a quick refresher, the Caribbean, also referred to as the West Indies, includes more than 7,000 islands! Of those, 13 are independent island countries, and some are dependencies or overseas territories of other nations.

In geographical terms the Caribbean area includes the Caribbean Sea and all of the islands located to the southeast of the Gulf of Mexico, east of Central America and Mexico, and to the north of South America.

Overall the Caribbean is a very pretty place of palm trees, pristine beaches, turquoise waters and sunshine, all blessed with a climate that consistently offers a much-needed break for those stuck in the cold weather winters of the north. White sand beaches, too! The average winter temperatures in the Caribbean are in the low 80s (degrees Fahrenheit). Plus, most locations are a pretty easy flight from the Midwest or East Coast!

The Caribbean’s hurricane season techinically spans from June 1 through November 30, but the highest risk is from mid-August through early October. Rains can come as early as May, which makes December to April the high season! You really can’t go wrong during the winter months. If you’re looking for warm vacation spots in December, warm vacation spots in January, or warm vacation spots in February, you can’t go wrong with the Caribbean.

I sincerely hope you have a warm winter vacation planned before you start looking at all of these properties. You’re about to have some serious wanderlust!


Anguilla is a British overseas territory in the Eastern Caribbean. One reader said she loves the Meads Bay Side (which is the West End), specifically the Four Seasons or Frangipani Beach Resort.

Cap Juluca (a Belmond property, also on the West End) came recommended in Anguilla, too!


Antigua is one of the two major islands that make up the Caribbean nation of Antigua and Barbuda.

In Antigua, Hammock Cove (adults-only and all-inclusive) and Jumby Bay both came recommended.


Barbados is an eastern Caribbean island and an independent British Commonwealth nation.

Sandy Lane came recommended and it’s apparently known as ‘the most iconic address in the Caribbean.’ Cobblers Cove was also recommended as family run, super stylish, and friendly!

British Virgin Islands

The British Virgin Islands, part of a volcanic archipelago in the Caribbean, is a British overseas territory. Comprising 4 main islands and many smaller ones, it’s known for its reef-lined beaches and as a yachting destination.

Cooper Island

Cooper Island is a small island of the BVIs. There are five privately owned properties on the island, plus a small beach club resort called Cooper Island Beach Club.

Guana Island

Guana Island is a private island in the Caribbean, off the northern end of Virgin Gorda. It’s mostly natural preserve, along with a small resort, the Guana Island resort“The most unspoiled jewel of the British Virgin Islands.”

Scrub Island

Scrub Island of the BVIs is home to the Scrub Island Resort Marina and Spa.


Tortola is the largest of the BVI’s and also home to the capital, Road Town, as well as the rainforest-filled Sage Mountain National Park. On Tortola, Sugar Mill Hotel came recommended.

Virgin Gorda

Virgin Gorda is BVI’s third-largest island and a number of hotels were recommended. Rosewood Little Dix Bay, Bitter End Yacht Club, and Saba Rock (a tiny private island off the coast of Virgin Gorda).


Dominica is a mountainous Caribbean island nation with natural hot springs and tropical rainforests. Secret Bay was specifically recommended!

Grand Cayman

Grand Cayman is the largest of the Cayman Islands, a British Overseas Territory in the Caribbean. A few girlfriends have recently gone there (stayed in both houses and hotels) and absolutely loved it. Palm Heights and the Westin were both recommended readers!


Jamaica, a Caribbean island nation, is the third largest in the Caribbean Sea! Half Moon Resort, Jamaica Inn, and Round Hill (designed by Ralph Lauren) all came recommended.

Mustique Island

Mustique is a private island in the Caribbean archipelago nation of St. Vincent and the Grenadines. A specific property wasn’t named, but you can browse the top hotels here.


Nevis is the smaller of the 2 islands comprising the nation of Saint Kitts and Nevis in the Caribbean. The Four Seasons came recommended.


Roatán is an island in the Caribbean, about ~40 miles off the northern coast of Honduras. On Roatán, the largest of Honduras’ Bay Islands, Hotel Ibagari came recommended.

St Barts

Saint Barthelemy, a French-speaking Caribbean island commonly known as St. Barts, is known for its white-sand beaches and designer shops. Le Sereno came recommended.

St John (USVI)

I absolutely adored St John in the United States Virgin Islands, as that’s where Caneel Bay was. Lovango Cay is a private island (118 acres) one mile northwest of the island of St. John, and Lovango Resort + Beach Club is the property on the island.

Saint Lucia

Saint Lucia is an Eastern Caribbean island nation with a pair of dramatically tapered mountains, the Pitons, on its west coast.

On Saint Lucia, Sugar Beach Viceroy and Anse Chastanet came recommended.

St Maarten

St. Maarten is known as the smallest landmass to consist of two nations. Sint Maarten, part of the Kingdom of the Netherlands, is a country on the southern part of a Caribbean island shared with Saint Martin, a French overseas collectivity. La Samanna, a Belmond property, on St Martin came recommended!


Aruba, officially known as the Country of Aruba, is a constituent country within the Kingdom of the Netherlands, situated in the south of the Caribbean Sea. It’s ~18 miles north of the Venezuelan peninsula and ~50 miles northwest of Curaçao. Bucuti & Tara was recommended!


The Bahamas is the fastest flight from New York City to the Caribbean at just three hours. However, even though the Bahamas is considered to be part of the Caribbean, it is not geographically in the Caribbean Sea. The Bahamian islands are actually located in the Atlantic Ocean! The more you know…

Harbour Island, known for the long pink sand beaches on it’s eastern shore, lies just northwest of Eleuthera Island in the Bahamas. On Harbour Island, The Dunmore came recommended, and I also know friends who have stayed at Coral House.

Treasure Cay is a parcel of land connected to Great Abaco Island in the Bahamas. A specific hotel wasn’t named, but you can browse some resorts here and VRBOs here.

On the northside Bahamian island Andros Island, Small Hope Bay came recommended.

Exuma is a district of The Bahamas, consisting of over 365 islands and cays. The largest of the islands is Great Exuma, which is 37 mi in length and joined to another island, Little Exuma, by a small bridge. Kahari Resort (which came recommended) is a boutique resort seculed on Great Exuma’s pristine barrier island, Stocking Island.

Baha Mar (which came recommended as a destination itself) is a 1,000-acre resort complex on the island of New Providence in The Bahamas, not far from The Atlantis. Within Baha Mar, there’s the Grand HyattRosewood, and SLS.


Belize is a country on the north-eastern coast of Central America. It is bordered by Mexico to the north, the Caribbean Sea to the east, and Guatemala to the west and south. It also shares a water boundary with Honduras to the southeast.

Cayo Espanto, A Private Island, has come highly recommended! It’s definitely on my travel bucket list. Great spot for a honeymoon or anniversary!


Bermuda is a British Overseas Territory in the North Atlantic Ocean. The closest land outside the territory is North Carolina, about ~650 miles to the northwest. The Hamilton Princess, a Fairmont-managed hotel, came recommended.

Punta Cana

Punta Cana, the easternmost tip of the Dominican Republic, abuts the Caribbean Sea and the Atlantic Ocean. Melia was the resort recommended.

Turks and Caicos

A common misconception is that the Turks and Caicos is part of the Caribbean. This is technically not true, as it’s considered to be part of the Lucayan Archipelago along with the Bahamian island chain, adjacent to the north of the Caribbean. 🗺️

A few resorts came recommended in Turks and Caicos… Como Parrot Cay, Alexandra Resort, and Seven Stars Resort & Spa.

Costa Rica & Puerto Rico

These two didn’t come reader recomended, but they’re worth looking into for their rich history and outdoor activities. Lots of surfing in Costa Rica! 


Mexico is quite large with so many fabulous destinations, but overall, it’s one of the warmest vacation spots in December through March. It can get HOT and HUMID into April and May, though!


I’ve been to Cabo (on the southern tip of Mexico’s Baja California peninsula) at least three times, maybe four?? I’ve stayed at the Paradisus by Melia, which you can read more about here. Absolutely loved it! The other two hotels I wouldn’t necessarily recommend. Dave has stayed at the Esperanza (an Auberge property) and really enjoyed it. Las Ventanas is at the top of my list – lots of friends have stayed there and raved about it! Grand Velas, Viceroy, Montage, Pueblo Bonito Pacifica, and Zadún all came recommended.

Isla Holbox

Isla Holbox (pronounced ol-bach) is a laidback island north of Mexico’s Yucatán Peninsula. It’s car-free and only allows golf carts on the island. Sandy roads, people without shoes, you get the idea. I actually had our entire trip planned here (staying at Punta Caliza, which came recommended), but Dave strongly preferred more of a resort where we wouldn’t have to leave the premises. With my research, I also liked the idea of El Corazon or Ser Casasandra. (Sometimes I really think I should be a travel agent… Nothing I love more than planning out trips.)


Mayakoba is a 500+ acre development ~35 minutes south of Cancun in Playa del Carmen. On one side of Mayakoba is the Caribbean Sea, on the other, a series of lagoons and canals wend their way through mangrove forests. There are four hotels within the Mayakoba property.

I’ve been to the Fairmont Mayakoba and loved it! You can read more about that trip here. The Rosewood in Mayakoba came recommended this time around, and I know some people who say you’ll never vacation anywhere else after you stay there!

Playa Mujeres

Playa Mujeres is located just north of Cancun on the north eastern coast side of the Yucatan peninsula facing the Caribbean Ocean. Excellence was recommended, as was Atelier multiple times!

Punta Mita

Punta Mita is located on the north end of Banderas Bay in the western Mexican state of Nayarit, about 10 miles north of Puerto Vallarta, Jalisco on Mexico’s Pacific coast. In Punta de Mita, the Four Seasons came recommended.

Riviera Maya

The Riviera Maya is a stretch of Caribbean coastline on Mexico’s northeastern Yucatán Peninsula. Excellence was recommended, as well as Secrets Moxche in Playa del Carmen.

Todos Santos

Todos Santos is a town on the Pacific coast of Mexico’s Baja California Peninsula, backed by the Sierra de la Laguna mountain range. It’s supposedly low key with an epic food scene! A friend of mine has stayed at Paradero Todos Santos and loved it. Hotel San Cristobal came recommended. “Cerritos” was also recommended so I’m not sure exactly which hotel they recommended. You can browse more available hotels here.


Tulum is a town on the Caribbean coastline of Mexico’s Yucatán Peninsula. The TRS Yucatán was recommended.

Best US Vacation Spots

Between Hawaii, California, and Florida, there are many US coastlines to discover during the winter. I wanted to leave a few links to resorts that came recommended.


Muana Kea (Big Island)

Four Seasons (Lanai)

The 1 Hotel (Kauai)

I grew up going to Hawaii with my Aunt & Uncle who live in Alaska. You can see a few snaps from my last trip in 2012 here!

Key West, Florida

Sunset Key

French Polynesia

French Polynesia is an overseas collectivity of France and its sole overseas country. It comprises 121 geographically dispersed islands and atolls stretching over more than 1,200 miles in the South Pacific Ocean. This was obviously a bit too far for a weekend trip, but two properties came recommended: the Hilton on Moorea Island and the St Regis Bora Bora.


For the following FAQs, I don’t really have the answers to all of these, so I’d love to open them up to you all! Please chime in in the comment section below.

1. What are good vacation spots in the US?

2. Where is the cheapest warm place to vacation?

3. What are some good vacation spots for families?

4. What are some underrated warm vacation spots?

5. What are some warm vacation spots near Texas?

6. What are some warm vacation spots near California?

I know people say great things about San Diego, but I’m not sure exactly where to stay!

I’d love to know… Where are some of your favorite warm vacation spots around the world? Bonus points if they’re warm winter destinations like all of these above. 🙂

xx jess

Both pictures above taken in Miami last year!

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Chicago based travel blogger shares 40 warm weather vacation destinations throughout the Caribbean and Mexico
Chicago based travel blogger shares 40 warm weather vacation destinations throughout the Caribbean
Chicago based travel blogger shares 20 warm weather vacation destinations in Mexico

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