When the locals want to hang out with friends, they often head for Cyrus Wathey Square. Enjoy some people-watching at this bustling place or make a few buddies of your own.

When you've spent a bit of time at this modern public area in Philipsburg, why not check out Maho Beach, Mullet Bay Beach, and Simpson Bay Beach? They're near Cyrus Wathey Square and also popular with many tourists.

Plan a trip to see Cyrus Wathey Square

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

Simpson Bay Resort, Marina & Spa

Pelican Key

$757

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,345 reviews)

This hotel out of the two was 100% the best! It was beautiful, comfortable, staff was excellent and the beach was great! Can’t wait to come back!

Reviewed on Sep 18, 2025

The Villas at Simpson Bay Resort

$885

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,241 reviews)

Plenty of walkable places nearby

Reviewed on Sep 18, 2025

La Playa Orient Bay

$1,065

per person

Nov 21 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.4/10 Exceptional! (590 reviews)

It was okay, could be better

Reviewed on Sep 15, 2025

Browse tours and tickets to explore Cyrus Wathey Square

Tours & day trips

See all 181 activities

Anguilla Getaway Cruise

Free cancellation available

Private & custom tours

See all 46 activities

St.Martin/St.Maarten Magical Tour

Free cancellation available

Water activities

See all 39 activities

Anguilla Getaway Cruise

Free cancellation available

Food, drink & nightlife

See all 16 activities

Tango Sunset Cruise with Caribbean Dinner & Open Bar

Free cancellation available

Wildlife & nature

See all 9 activities

Divi Little Bay Beach Day Package

Free cancellation available

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