Plan a trip to see Windward Islands

Price found within the past 48 hours. Click for updated prices.

El Colonial - Adults Only

Old San Juan

per person

Jun 24 - Jun 28

Roundtrip non-stop flight included

Newark (EWR) to San Juan (SJU)

9.6/10 Exceptional! (863 reviews)

Staff was very attentive, and nice. Clean, good service and you can walk all Viejo San Juan from here. I totally recommend.

Reviewed on May 17, 2024

Nando's Place

San Juan Antiguo

per person

Jul 5 - Jul 11

Roundtrip flight included

Newark (EWR) to San Juan (SJU)

8.8/10 Excellent! (36 reviews)

Nando’s place is in a great location. Ty he communication with the staff was outstanding the check in/out process was easy. Would definitely stay here again

Reviewed on Apr 6, 2024

Riu Palace Paradise Island - Adults Only - All Inclusive

per person

Jul 21 - Jul 25

Roundtrip non-stop flight included

Newark (EWR) to Nassau (NAS)

8/10 Very Good! (2,452 reviews)

Great place swimming up bar was great

Reviewed on May 16, 2024

Browse tours and tickets to explore Windward Islands

Tours & day trips

See all 441 activities

Tout Bagay Catamaran Cruise & Tour to Soufriere

Free cancellation available

Private & custom tours

See all 186 activities

Saint Lucia Sulphur Springs Rejuvenating Mud Bath Tour

Free cancellation available

Wildlife & nature

See all 35 activities

Rainforest Hike & Waterfall Safari

Free cancellation available

Classes & workshops

See all 17 activities

Project Chocolat Bean to Bar Experience from Hotel Chocolat

Free cancellation available

Shopping & fashion

See all 9 activities

Adventure and beach tour

Free cancellation available

Popular places to visit

Falls of Baleine

4/5(3 reviews)

Commune with nature and explore the great outdoors at Falls of Baleine during your travels in Prospect. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.

Friendship Bay

4.5/5(6 reviews)

Commune with nature and explore the great outdoors at Friendship Bay during your travels in Prospect. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Bamboo Church

Learn about the local history of Prospect when you take a trip to Bamboo Church. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Montreal Gardens

4.5/5(6 reviews)

Enjoy an outing to Montreal Gardens during your stay in Prospect. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Botanical Gardens

4.5/5(27 reviews)

Explore the great outdoors at Botanical Gardens, a lovely green space in Kingstown. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Fort Charlotte

4.5/5(26 reviews)

Find out about the history of Kingstown when you spend time at Fort Charlotte. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.