Winter Travel Advisory: Classic Vacations continues to actively monitor weather conditions that may impact advisors and their clients. For 24/7/365 in-travel support, call +1 (800) 243-6499, text +1 (408) 794-3499, chat at classicvacations.com/contact-us, or email customerservice@classicvacations.com. You may also book online.

Expert-Curated Offers

Warm Escapes

Trade Winter Blues for Tropical Hues

Bask in the glow of a sun-soaked Caribbean getaway with a hand-selected collection of Classic Preferred resorts. Think beachfront icons, tucked-away hideaways, and elevated stays designed for effortless luxury. 

Warm Escapes await — choose your island, then let Classic bring it all together.

Anguilla

Up to 40% Off 

Aurora Anguilla

4 nights from $2,819 per person

  • Acommodations as noted on itinerary
  • Welcome drink, upon arrival
  • Use of Fitness Center
  • Use of Bocce Ball and Tennis Courts, by appointment
  • Bottled Water in-room and at the Pool & Beach
  • Nightly Turn-Down Service
  • Wireless Internet
  • Island View Deluxe Room

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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antigua

$400 Savings Per Night 

Curtain Bluff

4 nights from $3,289 per person

  • Book Grond Floor Beachfront Deluxe and receive an upgrade to Ground Floor Beachfront Junior Suite. Subject to Availability at time of booking
  • All meals and drinks, including room service and mini-bar items
  • All watersports facilities and activities including swimming pools, twice daily snorkeling trips to Cades Reef, scuba diving (for certified divers only), waterskiing, wake-boarding, kayaking, windsurfing, Hobbie-cats
  • All land-based activities including tennis, squash, bocce, shuffleboard, basketball
  • Beach loungers, sun chaises, hammocks, and sun floats
  • Exercise facilities fully-equipped exercise room
  • Aerobics classes, Yoga and Pilates
  • Concierge service
  • All guests are offered the complimentary arrival meet and greet service (in order to be provided this information it is mandatory to provide incoming flight information). Guests are met after disembarkation by Signature Flight Support. Their agent holds a CURTAIN BLUFF SIGN, not a sign with the individual’s name. Guests are assisted through immigration and customs and out to the taxi area. The meet and greet service DOES NOT include the taxi transfer to hotel and is NOT personal for each guest. Must be booked separately and will be directed to where they meet their transfer
  • Junior Suite Beachfront Ground Floor

 

Book now to 02/20/26 for travel from 04/01/26 to 05/31/26 and 11/01/26 to 11/30/26*

*Blackout dates 11/21//26 to 11/28/26

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Antigua

25% Discounted Rate

Hermitage Bay

4 nights from $5,099 per person

  • Guests staying a minimum of 3 nights will receive accommodations as noted on itinerary
  • Breakfast, lunch, afternoon snack, dinner
  • Daily scheduled group wellness class
  • Freshly mixed cocktails
  • Premium brand drinks,
    soft drinks, water, poured house wine,
    French Champagne in high season, prosecco in summer
  • Evening canapes
  • Petit fours
  • Fully stocked mini-bar, replenished according to guests preference
  • Non-motorized watersports
  • Wi-Fi
  • Complimentary transfers for stays of 3 nights or more
  • Complimentary airport arrival fast track through Immigration and Customs with assistance for all guests. Flight details required
  • Hillside Garden Pool Villa

 

Book now to 03/31/26 for travel from now to 12/26/27

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Aruba

5% Off Best Available Rate

The ST. Regis aruba

4 nights from $1,669 per person

  • Accommodations as noted on itinerary
  • A resort fee of $90 USD plus tax per unit per night is to be paid direct upon checkout, subject to change without notice
  • Superior Ocean View Guest Room

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Bahamas

$200 in Added Value

Grand Hyatt Baha Mar

4 nights from $949 per person

  • $200 food & beverage credit – stays 4-nights or more
  • There is a mandatory daily resort fee of $76 USD per room, per night. The resort fee is not included in the room rate and is to be paid direct upon arrival. Tax and fees subject to change without notice
  • Daily access to Baha Bay Luxury Beachfront Waterpark for all registered guests
  • Non-motorized water sports: Single & Double Kayaks, Water hammocks, Water mats
  • ESPA fitness center access
  • Unlimited local calls
  • 2 bottles of water replenished daily
  • Sunscreen at all Hyatt towel huts
  • Hyatt beach and pool setup and seating with umbrellas
  • Self parking
  • Daily Flamingo Ambasador Parade
  • Aviary Sanctuary hands on experience
  • Coffee and teas in guestroom
  • Basketball, Bocce Ball, Croquet courts
  • Concierge Service
  • Fountain King View Room

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

Blackout dates 04/03/26 to 04/05/26

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Bahamas

25% Discounted Rate

Rosewood Baha Mar

4 nights from $3,389 per person

  • Early booking bonus
  • Accommodations as noted on itinerary
  • A reduced room rate
  • Access to Rosewood arrival lounge at Lynden Pindling International Airport
  • Bell Staff and Daily Housekeeping gratuities
  • Complimentary Wi-Fi throughout resort
  • Access to fitness center
  • Unlimited local calls
  • Bottled water replenished daily
  • Coffee and select teas
  • Complimentary sunscreen
  • Complimentary beach and pool setup and seating with umbrellas
  • Non-motorized water sports at Rosewood and Bah Mar Campus
  • Rates, taxes, service charges and fees are subject to change without prior notice
  • Garden View Room

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Barbados

45-55% Discounted Rate from Best Available Rate

O2 Beach Club

4 nights from $1,649 per person

  • Accommodations as noted on itinerary
  • All Inclusive Rates include:
    • All meals, premium beverages, and quality wines (some supplements may apply)
    • Organized pool and beach activities
    • Free property-wide Wi-Fi
    • Unique ‘How to’ experiences
    • Pool and beach towels
    • 24-hour gym
    • Games lounge
    • Books and games library
    • Dedicated guest services
    • All Junior Suites include upgraded furnishings and amenities, luxury bathrooms, and the added benefit of the Inclusions detailed below.
    • Daily pre-stocked mini-bar, nightly turn down service, and specialty coffee or espresso maker
  • Stay 5 nights or more and also receive:
    • USD $75 Spa credit per adult per stay (terms and conditions apply)
    • Complimentary beach bag, access to Sea Breeze Beach House during the day and dinner reservations (subject to availability and occupancy)
    • One game of 18-hole golf per person all year round. *Transfers NOT included
  • O2 Beach Hotel kindly requests that guests complete the online check-in for before arrival at: www.o2beachclubbarbados.com/advanced-checkin. This will allow guests to complete the arrival process at the hotel more quickly
  • Luxury Ocean View Junior Suite

Book now to 02/28/26 for travel from 04/01/26 to 06/03/26

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British Virgin Islands

28% Discount From Best Available Rate

Rosewood Little Dix Bay

4 nights from $3,689 per person

  • 4th Night free
  • Accommodations as noted on itinerary
  • Arrival drink
  • Daily full American breakfast for 2
  • Dedicated butler service
  • Snorkeling gear and lessons
  • Local beach drops and day trips to nearby islands
  • Use of Hobie Cat sailboats
  • Stand up paddleboards and sea kayaks
  • Sunfish sail boats and lessons
  • Guided snorkel tours
    Use of the fitness center and tennis and pickleball courts
  • Beginner tennis clinics and round robin tournaments
  • Garden tour and hiking trails
  • Twice daily housekeeping service
  • Complimentary Wi-Fi throughout the resort.
  • There are no televisions in any guest room
  • The Sugar Mill, the fine dining restaurant welcomes children ages 12 and up for dinner service with their parents
  • Dress Code: During the daytime, a cover-up and footwear are appropriate in the dining room and public areas. After sunset, in the Pavilion gentlemen may wear dress shorts, a collared shirt and open shoes. Shorts, t-shirts, jeans, tennis shoes and beach sandals are not permitted. Ladies may wear suitable evening attire. During the winter season, from Christmas until Easter, gentlemen are requested to wear long slacks, a collared shirt and closed-toe shoes. At the Sugar Mill, throughout the year, gentlemen are required to wear long slacks, a collared shirt and closed-toe shoes. Jackets and ties are not necessary. Ladies may wear suitable evening attire
  • Ocean View Cottage

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Cayman Islands

$100 Savings Per Day

Kimpton Seafire

4 nights from $2,889 per person

  • Exclusive breakfast for 2
  • $100 resort credit
  • Upgrade upon arrival based on availability
  • Premium Ocean Front Room

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Dominican Republic

5% Savings

Sanctuary Cap Cana

4 nights from $1,179 per person

  • Accommodations as noted on itinerary
  • Gourmet meals
  • Unlimited selection of Domestic and Imported Drinks
  • Set Activities and Entertainment Program
  • Tax and Service charge
  • Junior Suite Ocean View

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Dominican Republic

53% Savings

Casa De Campo

4 nights from $1,149 per person

  • Early Booking Bonus
  • Accommodations as noted on itinerary
  • Gourmet meals
  • Unlimited selection of Domestic and Imported Drinks
  • Set Activities and Entertainment Program
  • Tax and Service charge
  • Superior Casita

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Jamaica

$150 in Added Value

Round Hill

4 nights from $1,689 per person

  • $150 Food and Beverage credit for stay of 4-nights or more
  • A reduced room rate
  • Twice daily housekeeping service
  • In-room tablet
  • Bottled spring water at turndown
  • Wi-Fi
  • Use of the Pineapple Kids Club
  • Jogging and walking path with FitTrail exercise workstations
  • Use of tennis courts (day & night)
  • Guided garden tour (Fridays)
  • Snorkeling, paddle boats, kayaks, glass bottom boat ride (scheduled)
  • Daily afternoon tea
  • Welcome drink on arrival
  • Use of fitness centre/gym with instructor (complimentary 30-min stretch class 4pm daily, except Tuesdays)
  • Premium Ocean View Double Room

 

Book now to 02/28/26 for travel from now to 10/31/26

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PUERTO RICO

$175 in Added Value

El Conquistador Resort

4 nights from $899 per person

  • No Passport Required (U.S. Citizens Only)
  • $175 Food and Beverage Credit
  • Marina Ocean View Room

Book now to 03/08/26 for travel from 05/01/26 to 06/30/26

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PUERTO RICO

$100 in Added Value

San Juan Marriott Resort and Stellaris Casino

4 nights from $979 per person

  • No Passport Required (U.S. Citizens Only)
  • $100 Food and Beverage Credit
  • 20% off Spa (once during stay)
  • Guest Room Ocea View Cabana Building

Book now to 02/28/26 for travel from 04/14/26 to 12/17/26 (blackout dates 11/04/26 -11/08/26 & 11/22/26 – 11/28/26)

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St. Maarten

32% Off Standard Rate

Sonesta Ocean Point

4 nights from $1,479 per person

  • Accommodations as noted on itinerary
  • A Reduced Room Rate
  • Welcome drink and cold towel upon check-in
  • Full breakfast, lunch, dinner each day at Azul; light bites throughout the day; dinner on select evenings at Bluefin and Portofino
  • Unlimited international and domestic premium beer, wine and spirits, fruit drinks and soft drinks at all of the exclusive bars at Sonesta Ocean Point Resort
    Mini-bar, refreshed daily with soft drinks, bottled water, spirits and beer; and pods for Nespresso machine
  • Resort-wide Free Wi-Fi
  • Fitness Center
  • 24-hr room service, Pool Service
  • Concierge service and Butler Service in the 25 top category suites Stay at One, Play at Two offering full access to all facilities, dining, and bars at the adjacent family resort Sonesta Maho Beach Resort
  • All hotel taxes, utility and service fees
  • Junior Suite King

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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St. Lucia

$100 in Added Value

Sugar Beach

4 nights from $4,259 per person

  • $100 resort credit
  • Accommodations as noted on itinerary
  • A reduced room rate
  • Daily Breakfast Buffet in Terrace Restaurant – 2 adults per room
  • Grand Luxury Villa

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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St. Lucia

$700 in Added Value

Cap Maison

5 nights from $3,779 per person

  • Bed & Breakfast Meal Plan PLUS enjoy:
    • Complimentary luxury car, boat, or helicopter transfer on arrival at Hewanorra International Airport
    • Luxury car for your return journey
  • 1 Bedroom Oceanview Villa with Pool

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Turks & Caicos

42% Discount From Best Available Rate

Grace Bay

4 nights from $2,189 per person

  • Beach Escapes
  • Accommodations as noted on itinerary
  • Daily Full Breakfast in the restaurant
  • Wi-Fi
  • Non-motorized water sports
  • Villas Junior Suite

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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Turks & Caicos

30% Discount From Standard Rate

Seven Stars

4 nights from $1,639 per person

  • Spring Offer w/Breakfast
  • A Reduced Room Rate
  • A Welcome Cocktail
  • Complimentary Buffet Breakfast
  • Complimentary use of non-motorized water sports equipment
  • Health Club admission
  • Wi-Fi
  • Island View Junior Suite

 

Book now to 02/28/26 for travel from 04/12/26 to 06/30/26

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Turks & Caicos

30% Discount From Standard Rate

The Shore Club

4 nights from $1,989 per person

  • Early Booking Bonus w/breakfast
  • Guests staying a minimum of 3 nights will receive:
    • Accommodations as noted on itinerary
    • A reduced room rate
    • Daily Full American Breakfast Buffet from 7:00am – 10:30am at the Almond Tree
    • Welcome amenity
    • Free long distance phone calls to USA and Canada
    • High-speed wireless internet
    • Use of bicycles
    • Use of business center
    • Use of resort owned non-motorized water sports equipment
    • Use of fitness center and tennis court
  • Junior Suite Garden View

 

Book now to 02/28/26 for travel from 04/01/26 to 06/30/26

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U.s. virgin islands

$100 in Added Value

Buoy Haus Beach Resort St. Thomas, Autograph Collection

4 nights from $1,309 per person

  • No Passport Required (U.S. Citizens Only)
  • $100 Resort Credit
  • Garden View Guest Room

Book now to 03/30/26 for travel from 03/01/26 to 10/31/26

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U.s. virgin islands

$100 in Added Value

The Buccaneer Beach & Golf Resort

5 nights from $1,609 per person

  • No Passport Required (U.S. Citizens Only)
  • $100 Resort Credit
  • Daily breakfast for two
  • Guest House Ocean View

Book now to 02/28/26 for travel from now to 06/30/26

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U.s. virgin islands

$100 in Added Value

The Westin St. Thomas Beach Resort & Spa

4 nights from $939 per person

  • No Passport Required (U.S. Citizens Only)
  • $100 Resort Credit
  • Garden View Guest Room

Book now to 03/30/26 for travel from 03/01/26 to 10/31/26

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BOOK ONLINE NOW OR CALL +1 (800) 221-3949

Promotion may be discontinued at any time. Classic Vacations offers customers access to vacation packages, which are provided by separate and independent vendors of travel services. Classic Vacations does not operate, control, or otherwise provide the services of the independent travel vendors.  Offers are valid on new bookings only and cannot be applied to existing reservations.  Prices shown are per person, land-only, based on double occupancy, and do not include optional excursions or other optional items unless expressly stated otherwise.  Obvious errors and misprints are not binding.  Offers are subject to availability at the time of booking and may be modified, replaced, or discontinued without prior notice.  Prices are subject to change until full payment is received.  Blackout dates, minimum night stays, air booking requirements, seasonal surcharges, resort fees (if applicable), and other restrictions may apply.  Customers are responsible for purchasing travel insurance.  Some offers may require the purchase of Classic Vacations’ Travel Smart Plan or a travel waiver for eligibility.  Customers are responsible for paying any cancellation fees.  Offers are not valid for Group Travel unless explicitly stated.  Booking and travel dates may vary by offer.  Additional promotions and alternative departure dates may be available, potentially resulting in different pricing or hotel inclusions.  Customers are responsible for all applicable taxes and fees associated with a booking, including those associated with complimentary nights at hotels, where applicable.  For properties where Classic Vacations offers dynamic pricing rates, prices are subject to change based on market conditions and external factors beyond Classic Vacations’ control.  Additional terms and conditions may apply to specific offers. Please refer to the individual offer details for full terms. California Seller of Travel # 2079429.  Registration as a seller of travel does not constitute approval by the State of California.