Charters & Cruises

Nantucket Charter

Enjoy direct access from the Inn’s private dock to Nantucket, reaching the island in just about an hour for a full-day experience designed around your schedule. Stroll charming cobblestone streets, explore local shops and galleries, and dine at one of the Grey Lady’s many seaside restaurants.

• Primarily offered as private charters aboard Starlight, Starbright, or Starlight Express (Valhalla V-46)
• Guests choose their own departure time, allowing for a fully customized day on the water
• Ideal for full-day island escapes, combining scenic coastal cruising with time to explore ashore

Charter Options:

• Private Nantucket Charter (Full Day): The most popular option, offering more flexibility
• Shared Nantucket Charter (Select Days): Up to 6 guests with set departure times, ideal for those seeking a more structured day trip

Martha's Vineyard Charter

Experience a seamless, full-day escape to Martha’s Vineyard departing directly from the Inn’s private dock, where pristine beaches, dramatic clay cliffs, and a rich mix of cultural attractions, dining, and boutiques create the perfect island day trip.

• Available exclusively as a private charter aboard Starlight, Starbright, or Starlight Express (Valhalla V-46)
• Ideal for guests seeking a more private, elevated island experience

Boston Charter

Travel from Chatham Bars Inn’s private dock to Boston aboard Starlight Express, our custom-built Valhalla V-46, for a seamless and unforgettable day on the water. Cruise along the Cape’s scenic coastline before arriving in Boston Harbor, where the city’s iconic landmarks, world-class dining and cultural experiences await.

Designed around your schedule, this private charter offers the flexibility to create your perfect day in Boston. Explore historic neighborhoods, visit renowned galleries and museums, enjoy waterfront dining or simply take in the energy of the city before returning to Chatham by boat.

Exclusively offered aboard Starlight Express (Valhalla V-46)

• Private, customizable full-day charter experience
• Depart directly from the Inn’s private dock at a time that works best for your itinerary
• Combine coastal cruising with a personalized day exploring Boston Harbor

Newport Charter

Set out from Chatham Bars Inn’s private dock aboard Starlight Express, our custom-built Valhalla V-46, for a scenic coastal journey to Newport, Rhode Island. Cruise past iconic shorelines and historic harbors before arriving in one of New England’s most celebrated seaside destinations.

Designed entirely around your schedule, this private charter allows you to experience Newport at your own pace. Explore the city’s charming waterfront, visit legendary Gilded Age mansions, browse local boutiques and galleries or enjoy a leisurely meal overlooking the harbor before returning to Chatham by boat.

Exclusively offered aboard Starlight Express (Valhalla V-46)

• Private, customizable full-day charter experience
• Depart directly from the Inn’s private dock at a time that works best for your itinerary
• Combine scenic coastal cruising with time to explore Newport’s historic charm and waterfront attractions

Morning Seal Cruise

Begin your day with a relaxing cruise through Aunt Lydia's Cove and along the Chatham coastline. Explore one of the region's most active wildlife habitats, home to hundreds of gray and harbor seals. Observe seals basking on sandbars at low tide or playing in the water at high tide while learning about their feeding and migratory habits. Along the way, enjoy views of Tern Island, Chatham Lighthouse and the Chatham Fish Pier.

Vessel: bartender

Shared Ride: Up to 18 passengers | 1 hour

Evening Harbor Cruise

End the day with a peaceful cruise through Aunt Lydia's Cove and along the picturesque Chatham coastline. Pass Chatham Lighthouse, North Beach Island and the Chatham Fish Pier as the soft light of golden hour illuminates the shoreline, creating a memorable evening on the water.

Vessel: BarTender

Shared Ride | Up to 18 Guests | 1 Hour