Have questions? We're here.
Sunset over Philipsburg

Philipsburg Small Ship Cruises

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Filter (17 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Philipsburg
Relax on the beaches of St. Maarten
from $2,010
EXPLORE

Antigua Roundtrip

Roundtrip St. John - 8 Day Itinerary aboard Star Clipper
  • Hike St. Kitts rainforests
  • Tour Basseterre colonial history
  • Shop Philipsburg Dutch bargains
  • Explore Tortola to see Soper's Hole
Starts / Ends
St. John's / St. John's
Activities
Snorkeling
Activity Level
Variable
Experience an 8-day round-trip cruise from St. John's, Antigua, aboard the Star Clipper, visiting destinations like St. Barts, the British Virgin Islands, and St. Maarten. Enjoy duty-free shopping, stunning beaches, and historic sites before concluding your journey in Antigua.
Cruise Details
0
Explore the famous rock formations of the baths
from $6,295
Save $150
EXPLORE

Eastern Caribbean with St. Barths

Bridgetown - Philipsburg - 8 Day Itinerary aboard Emerald Sakara
  • Explore Bridgetown rich heritage
  • Enjoy Soufriere sulfur springs
  • See St. John's Nelson's Dockyard
  • Experience Gustavia Creole cuisine
Starts / Ends
Bridgetown / Philipsburg
Activity Level
Variable
Set sail on an 8-day Eastern Caribbean cruise from Bridgetown on Emerald Sakara, visiting St. Lucia's mud baths, Antigua's Nelson's Dockyard, and the stunning beaches of Iles des Saintes. End your journey in Philipsburg, the lively capital of Dutch Sint Maarten.
Cruise Details
0
Lush green forests and clear blue waters of the Caribbean
from $13,340
Save $150
EXPLORE

Discover Eastern Caribbean & Grenadines

Philipsburg - Bridgetown - 15 Day Itinerary aboard Emerald Sakara
  • Discover Virgin Gorda The Baths
  • Wander Gustavia wooden houses
  • Visit St. John's Nelson's Dockyard
  • See Soufriere volcanic domes
Starts / Ends
Philipsburg / Bridgetown
Activity Level
Variable
Set sail on a 15-day Caribbean cruise from Philipsburg on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Visit charming islands like Virgin Gorda, Saint Barthelemy, and Bequia for stunning beaches, local cuisine, and water activities amidst breathtaking views.
Cruise Details
0
Relax on the pristine beaches of the Virgin Islands
from $13,390
Save $150
EXPLORE

Discover Eastern Caribbean & Grenadines

Bridgetown - Philipsburg - 15 Day Itinerary aboard Emerald Sakara
  • Visit Bequia Island sandy beaches
  • See Mayreau Island ocean views
  • Admire Soufriere hot sulfur springs
  • Tour Iles des Saintes Fort Napoleon
Starts / Ends
Bridgetown / Philipsburg
Activities
Archaeological Site Visits
Activity Level
Variable
Join a 15-day Caribbean cruise from Bridgetown on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Experience local culture in Speightstown, enjoy water sports in Kingstown, and relax in natural hot springs in Soufriere before returning to Barbados.
Cruise Details
0
Visit Las Palmas’ Santa Ana Cathedral, a central landmark in the city
from $13,695
EBD 30%
EXPLORE

Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Philipsburg - 17 Day Itinerary aboard Sea Cloud Spirit
  • Experience Transatlantic Crossing
  • See the Gran Canaria landscapes
  • Explore Las Palmas old town
  • Climb rigging and set sails
Starts / Ends
Las Palmas / Philipsburg
Activities
Village Visits, Small Ship Sailing
Activity Level
Variable
Experience 17 days aboard Sea Cloud Spirit on a transatlantic crossing from Las Palmas to Philipsburg. Relax on deck, enjoy wellness programs, and explore Gran Canaria’s landscapes before arriving in the Caribbean.
Cruise Details
0
13-17 of 17 Results
  • 1
  • 2

We do the homework for you.

Talk with an expert trip planner 1.800.344.6118

Plan My Trip
Jeff Rottschafer Adventure Life employee profile
Jeff R.
Sunset over Philipsburg
Caribbean

Chat Philipsburg with a specialist

Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.

Let's Chat
1.800.344.6118

Where is your next adventure?

Contact Chat Call

Why Travel With Us?

Seamless Trip Planning

We guide you through every detail beyond the cruise—from flights to pre- and post-trip stays—so your journey feels effortless.

Advocacy That Matters

You're backed by a team that knows the industry and has strong relationships—helping ensure you're prioritized and well taken care of every step of the way.

Unbiased Cruise Expertise

We're not tied to any one cruise line, so you receive honest guidance on the best ship and itinerary for you—not a sales pitch.

As Featured In

USA Today
Los Angeles Times
Travel Weekly
Outside
National Geographic Traveler
The New York Times
Travel + Leisure
Condé Nast Traveler
National Geographic

How it Works

Connect

No cost, no commitment. Talk with our experts about your dream trip.

Plan

Share your travel style—we match you with the right itinerary or create one just for you.

Book

Lock in knowing every detail is handled and you’re fully supported.

Travel

Enjoy a seamless journey—and unlock 5% off your next adventure.

Jeff Rottschafer Adventure Life employee profile
Jeff R
Plan My Trip
We love travel, talk with an expert 1.800.344.6118