Best Caribbean Tours & Trips
The Caribbean is an archipelago of thousands of islands and cays defined by its mountainous rainforests and volcanic peaks. The region serves as a crossroads of African, European, and Indigenous traditions, creating a cultural landscape where every island has a distinct identity. Iconic cities such as Havana, Old San Juan, Santo Domingo, and Willemstad function as open-air museums. Visitors can explore 16th-century Spanish forts, admire Dutch colonial architecture, or visit the oldest cathedrals in the Americas. Beyond the cities, the geography supports a wide range of activities. In Jamaica, travelers hike the Blue Mountains or climb Dunn’s River Falls, while the volcanic Pitons in Saint Lucia provide a backdrop for sailing. The region is also a global hub for music and festivals.
Show All
21 Results
Filters
Places
Dates & Length
4.9
( 12 reviews )
Tour Code: 720222Start / End City
Lima, Cusco
Duration
13.0 Days
City & Attractions
Lima, Paracas, Nazca
+14 more
Languages
English Live, Spanish Live
Group Type
Small Group
Tour Audience
Mixed International Travelers
Operator
Lima Tours
Save 15%
From $2,478.06
$2,106.35
4.6
( 83 reviews )
Tour Code: 692121Start / End City
Mexico City
Duration
9.0 Days
City & Attractions
Mexico City, Patzcuaro, Morelia
+10 more
Languages
English Live, Spanish Live
Group Type
Standard Group
Operator
Europamundo Vacaciones
Save 5%
From $1,171.00
$1,112.45
5.0
Tour Code: 681534Start / End City
Santiago, Buenos Aires
Duration
9.0 Days
City & Attractions
Santiago, Vina del Mar, Puerto Varas
+17 more
Languages
English Live
Group Type
Standard Group
Save 15%
From $2,169.60
$1,844.16
4.8
( 11 reviews )
Tour Code: 737214Start / End City
Mexico City
Duration
8.0 Days
City & Attractions
Mexico City, Taxco, Acapulco
+4 more
Languages
English Live, Spanish Live
Group Type
Standard Group
Operator
Europamundo Vacaciones
Save 5%
From $1,232.00
$1,170.40
5.0
( 5 reviews )
Tour Code: 716511Start / End City
New York, Oranjestad
Duration
11.0 Days
City & Attractions
New York, Philadelphia, Washington D.C.
+29 more
Languages
Chinese Live, English Live
Group Type
Standard Group
Tour Audience
Primarily Mandarin-Speaking Travelers
From
$1,998.00
5.0
( 8 reviews )
Tour Code: 738270Start / End City
Mexico City, Playa del Carmen
Duration
14.0 Days
City & Attractions
Mexico City, Oaxaca, Puebla
+10 more
Languages
English Live
Group Type
Small Group
Tour Audience
Mixed International Travelers
From
$3,008.10
4.9
( 5 reviews )
Tour Code: 715443Start / End City
Cusco, Rio de Janeiro
Duration
18.0 Days
City & Attractions
Cusco, Aguas Calientes, Machu Picchu Town
+11 more
Languages
English Live
Group Type
Standard Group
Tour Audience
Primarily English-Speaking Travelers
Operator
The Travel Corporation (TTC)
From
$5,274.00
5.0
( 5 reviews )
Tour Code: 714942Start / End City
Lima
Duration
14.0 Days
City & Attractions
Lima, Arequipa, Puno
+14 more
Languages
English Live
Group Type
Standard Group
Tour Audience
Primarily English-Speaking Travelers
Operator
The Travel Corporation (TTC)
From
$3,445.00
4.9
( 5 reviews )
Tour Code: 715440Start / End City
Cusco, Rio de Janeiro
Duration
18.0 Days
City & Attractions
Cusco, Aguas Calientes, Machu Picchu Town
+11 more
Languages
English Live
Group Type
Standard Group
Tour Audience
Primarily English-Speaking Travelers
Operator
The Travel Corporation (TTC)
From
$5,689.00
5.0
Tour Code: 584311Start / End City
Kingston in Jamaica, Negril
Duration
3.0 Hours
City & Attractions
Negril
Languages
English Live
Group Type
Standard Group
From
$161.25
4.9
( 5 reviews )
Tour Code: 714939Start / End City
Lima
Duration
14.0 Days
City & Attractions
Lima, Arequipa, Puno
+14 more
Languages
English Live
Group Type
Standard Group
Tour Audience
Primarily English-Speaking Travelers
Operator
The Travel Corporation (TTC)
Save 10%
From $4,155.84
$3,740.26
5.0
Tour Code: 450142Start / End City
Punta Cana
Duration
1.0 Day
City & Attractions
Languages
English Live, Spanish Live
Group Type
Standard Group
From
$139.00
4.1
( 40 reviews )
Tour Code: 715653Start / End City
Lima, Cusco
Duration
11.0 Days
City & Attractions
Lima, Puno, Cusco
+6 more
Languages
English Live
Group Type
Standard Group
Tour Audience
Primarily English-Speaking Travelers
Operator
The Travel Corporation (TTC)
From
$2,477.00
4.1
( 41 reviews )
Tour Code: 715656Start / End City
Lima, Cusco
Duration
11.0 Days
City & Attractions
Lima, Puno, Cusco
+6 more
Languages
English Live
Group Type
Standard Group
Tour Audience
Primarily English-Speaking Travelers
Operator
The Travel Corporation (TTC)
From
$2,087.00
4.9
( 5 reviews )
Tour Code: 747426Start / End City
Lima, Cusco
Duration
4.0 Days
City & Attractions
Lima, Cusco, Huaca Pucllana
+3 more
Languages
English Live
Group Type
Standard Group
From
$1,301.00
1
2
Why book with Tours4fun?
Best Price Guarantee Transparent Pricing Travel Safety Assurance 24/7 Multilingual Support
Best Time to Visit Caribbean
Summer
2026
Summer in the Caribbean brings hotter temperatures, with daytime highs ranging between 85°F (29°C) and 95°F (35°C), making it the season for sun-lovers. Coastal regions and islands such as the Cayman Islands and Aruba benefit from refreshing trade winds, which help temper the heat. While this is the most popular season for tourists, it can also be a time to find exciting deals and discounts, especially in popular spots like the Virgin Islands or the Bahamas. Water-based activities like surfing, windsurfing, and deep-sea fishing are top choices for thrill-seekers, while families can enjoy excursions to water parks and cultural attractions. The summer months also mark the beginning of the Caribbean’s hurricane season, so travelers should be aware of weather conditions and plan accordingly. Although the risk of a hurricane is low, it's a good idea to stay informed on forecasts during your visit.
Show All
Autumn
2026
Autumn in the Caribbean sees a drop in temperatures as the region begins to transition into the cooler months. Expect highs between 80°F (27°C) and 85°F (29°C). It’s an off-peak period, making it a great time for budget-conscious travelers to visit. Many of the islands, such as Saint Lucia and Barbados, offer significant discounts on accommodations and activities. While the hurricane season is still in effect, most of the storms occur later in the season, and many islands experience pleasant weather during this time. This is the best time for those seeking tranquility, with fewer crowds on the beaches and popular attractions. Autumn also brings rich cultural experiences like Jamaica’s Jamaica Carnival, providing a colorful backdrop to any visit. Enjoy scenic hiking trails, such as those in the Dominican Republic’s Pico Duarte, and visit historic forts and plantations for a glimpse into the Caribbean’s storied past.
Show All
Winter
2026/2027
Winter in the Caribbean offers a welcome escape from the cold northern climates, with average temperatures ranging from 70°F (21°C) to 80°F (27°C). The dry season makes this the peak time for travel, particularly from December to February, as visitors flock to destinations like the Bahamas, Puerto Rico, and Cuba. It’s perfect for exploring the islands, as the weather is consistently sunny and pleasant. Winter is a prime time for beach relaxation, with pristine white sands and crystal-clear waters ideal for swimming and sunbathing. This is also the best season for water activities such as snorkeling, diving, and sailing, with calm seas and excellent visibility. Winter also brings major events like the Saint Kitts Music Festival and Carnival in Trinidad and Tobago, where visitors can experience the vibrant energy of Caribbean music and dance. Despite the increase in tourist numbers, the Caribbean still offers a range of luxury and boutique options for a more personalized vacation.
Show All
Spring
2027
Spring in the Caribbean is characterized by warm temperatures and gentle breezes. During this time, average highs range from 75°F (24°C) to 85°F (29°C), offering perfect weather for beachgoers and outdoor enthusiasts alike. Popular destinations like Jamaica, the Bahamas, and the Dominican Republic are particularly inviting, with clear skies and calm seas perfect for water activities. Spring is an ideal time for snorkeling, scuba diving, and island-hopping, with vibrant marine life visible around the coral reefs. Festivals like the Barbados Reggae Festival and Puerto Rico’s La Calle San Sebastián create an electric atmosphere, providing an authentic cultural experience for visitors. While it's a great time for sightseeing, the region is less crowded than in peak summer, allowing for a more relaxed and intimate experience.
Show All
Browse Caribbean Tour Types
Explore Popular Caribbean Itineraries
Insider Travel Offers
Sign up for early access to new tours, limited-time offers & travel perks.