Warm Weather Getaways

By David Barclay | June 5, 2024

Although I’m writing this blog post at the same time I’m sending out my newsletter on winter holiday travel options, these warm weather getaways are perfect for any fall/winter/spring travel.  They can be a great option for spring break trips, and traveling outside of the very popular holiday season (roughly Dec 15-Jan 5 each year) can result in meaningfully lower nightly rates compared to the peak holiday season rates.

All-Inclusive vs. Room Only

I’ll devote another blog post to the pros and cons of each of these accommodation option, and how the evolution and expansion of luxury all-inclusive options have changed the vacation option landscape. 

Both options exist in many of the suggested vacationing locations below.  When trying to decide between these two options, there are a few quick questions you can ask yourself to help decide:

• Are you looking to fly & flop and don’t expect to leave your resort, or do you want to experience several off-property restaurants?
  • If you want to stay on Grace Bay in Turks and Caicos, you will likely want to wander over to a few neighboring resorts and try their restaurants, in which case you likely don’t want to invest in an all-inclusive option.

• Are you traveling with kids or extended family members?
  • If you will cringe at a half-finished soda or don’t want the awkwardness of having to split up the dining bills among family members, an all-inclusive can be a good option.  You won’t see dollar bills floating away with every half-consumed food item and you won’t care if your cousin Jimmy dines on lobster and steak each night while the majority of the family has chicken and pasta dishes.

• Do you want to know your full vacation cost upfront and not have to budget for extras
  • In this case an all-inclusive is a must-have.  While most all-inclusives offer some extra activities for an additional fee, generally speaking you can have a great experience with the included services and activities and don’t have to spend more while on your vacation.

Mexico

Mexico is a very popular destination for Americans, as there are many direct flights from the U.S. and the country is very receptive to visitors from its northern neighbor.

Riviera Maya

The Cancun area is a very popular destination and there are many nice luxury resorts south of Cancun along the Riviera Maya.  In addition to beautiful beaches and plenty of water activities, visitors can travel inland to see the ruins at Chichén Itzá.

Mayakoba is a well-known property that brings together four resorts (Rosewood, Banyan Tree, Andaz, and Fairmont).  Each resort delivers its unique brand experience and combined they offer a range of price options to fit the budgets of a broad spectrum of luxury travelers.  Guests can dine at any of the 20 restaurants sprinkled across the four resorts and have the meals charged to their room accounts. 

For all-inclusive resorts, the relatively new Hilton Tulum is a great option for both couples and families.  Situated next to the Conrad Tulum, guests can use the Conrad’s highly regarded spa.  For one of the best all-inclusive experiences in Mexico, look no further than the Grand Velas Riviera Maya.

Cabo San Lucas

Cabo is a great option for couples looking to get away for a long weekend or even a full week.  Properties tend to have gorgeous views of the ocean, but many beaches can be rocky (hard to walk on without good water shoes) and are potentially unswimmable.  Combined with the fact that many resorts have a more mature vibe, Cabo may not be the best option for families with younger children and is better for those with older teens/20s.

Both the Waldorf Astoria Los Cabos Pedregal and Las Ventanas Al Paraiso, A Rosewood Resort are wonderful options with large rooms, beautifully groomed properties, large well-trained staffs, and the gorgeous views Cabo is known for.  If you are looking for an all-inclusive option, you can’t go wrong with the Grand Velas Los Cabos.

Punta Mita & Riviera Nayarit

About 10 miles north of Puerto Vallarta, the private peninsula of Puna Mita is home to a number of wonderful resorts.  While guests can travel into Puerto Vallarta, most tend to stay on property, relaxing and enjoying the warm weather.  Both the Four Seasons Punta Mita and St. Regis Punta Mita are well-know properties on this luxury resort reserve. 

Given the popularity of Punta Mita, One&Only recently opened a property on the undeveloped coastline along the Riviera Nayarit, the One&Only Mandarina.  One of my colleagues appropriately described this property as “Costa Rica and Mexico had a baby” since it combines jungle and beach experiences.

Caribbean

Turks & Caicos

A popular destination for travelers from the East Coast and Midwest, it is an archipelago of 40 low-lying coral islands in the Atlantic Ocean southeast of the Bahamas.  Guests arrive on the main island of Providenciales and most will stay there.  The very popular Grace Bay is home to many wonderful resorts, including Grace Bay Club, The Shore Club, and The Palms.  Many of the best resorts on Grace Bay are within easy walking distance of each other, allowing guests to easily dine off property.  Resorts on the eastern end of Grace Bay also offer easy walking to the small town for shopping.

For those willing to travel a little farther to their destination, Ambergris Cay offers the perfect combination of luxury and seclusion.  A private island to the southeast of Providenciales, it has just 17 bungalows and 9 villas and offers a luxurious all-inclusive experience. 

Jamaica

While Jamaica is well known for its all-inclusive resorts, it offers a variety of experiences to suit the needs of most travelers.  Guests can fly into Kingston or Montego Bay and then head to their beach resort of choice.  Half Moon Resort on Montego Bay is an excellent option, offering rooms in both the original Founders Cove and the newer Eclipse at Half Moon (which offers extra like butler service and a pillow menu).  Also coming this fall, Half Moon is adding 19 villas. 

Those looking for a villa for a larger group might also look at The Tryall Club, which offers a variety of villas on its 2,200 acres.

Puerto Rico

While Puerto Rico is frequently overlooked as a warm weather destination in the Caribbean, this U.S. territory has a lot to offer.  As a U.S. territory, there are no customs/passport control to pass through after arrival, meaning guests can head to their resorts minutes after collecting their luggage.  Puerto Rico offers a variety of beach/water activities and visitors will want to visit Old San Juan, to tour the colorful lanes, get in a little shopping, and tour the Castillo San Felipe del Morro (the Spanish fort built in the 1500’s).  Visitors can also take a kayaking adventure in the bioluminescent bay, plan a trip to the El Yunque Rain Forest, or visit the nearby islands of Culebra and Vieques.

Guests looking for a truly luxurious experience will want to stay at Dorado Beach, a Ritz-Carlton Reserve, on the north side of Puerto Rico, about a 30 minutes drive west of Old San Juan.  From one-bedroom suites to 5-bedroom villas, this resort is perfect for both couples and multi-gen family trips.  Another good option is the St. Regis Bahia Beach Resort, on the northeastern shores of Puerto Rico. 

The Lesser Antilles

The Lesser Antilles can offer a great experience with a strong Caribbean vibe and uncrowded beaches, for those who don’t need a direct flight to their destination (travelers will likely require a layover in Miami or San Juan). 

For those wishing to visit the British Virgin Islands, the Rosewood Little Dix Bay on Virgin Gorda is a perfect choice.  Nestled in 500 acres of untamed natural gardens, it provides the private island experience without needing to go to a private island. 

For an intimate experience with great food & beverage and lots to do, the Park Hyatt St Kitts is a great pick.  Or consider the Four Seasons Nevis on the nearby island of Nevis. 

For a pampered all-inclusive experience, Jumby Bay Island, off the coast of Antigua, has a lot to offer visitors.  The 300-acre private island resort offers 1-bedroom suites, 2-5 bedroom villas, and 4-11 bedroom private residences.  Many complimentary activities are included, as well as all food and beverages.  Special activities include themed dinners three nights per week and snorkeling excursions around the island every Monday, Wednesday and Friday.

Caribbean Cruise

For travelers wishing to explore the Caribbean, Mexico & Central America coastline but also wanting a 5-star resort experience, consider a Caribbean cruise on one of the luxury cruise lines.  These resorts on the sea are mostly all-inclusive, offer wonderful dining venues and plenty of activities both on and off the ship.  During the winter months, lines such as Seabourn, Silversea, Explora Journeys, Regent Seven Seas & the Ritz-Carlton Yacht Collection have multiple ships sailing the warm waters of the Caribbean.