Sidewalk Sailings
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Cruise-Style Weekends On Land

Land Cruise Frequently Asked Questions

  • What is Sidewalk Sailings?

    Sidewalk Sailings is a cruise-style weekend on land—hotel included, hosted itinerary, and curated “ports of call” in each destination.

  • Is the hotel included?

    Yes. Your booking includes a 2-night hotel stay (availability varies by departure and destination)

  • How does transportation work?

    We provide shuttle transportation for scheduled itinerary stops so guests can relax and enjoy the weekend without planning logistics.

  • What’s included vs. not included?

    Inclusions vary by departure, but typically include hotel, transportation, and hosted excursions. Personal purchases, incidentals, and gratuities are not included unless stated.

  • Are these trips family-friendly?

    Some departures are all-ages and some are adults-focused. The waitlist is the best way to get the right options for your group.

  • Hotel Included
  • Shuttle included
  • curated ports of call
  • 3 Day Trip
  • 3-Star hotel
  • Curated Activities
  • City Tours
  • 3 Day Trip
  • 3-Star hotel upgraded Room
  • Curated Activities
  • City Tours
  • 3 Day Trip
  • 3-Star hotel
  • Curated Activities
  • City Tours
  • upgrade to private room

Hosted, Not Hectic


Clear schedules, a dedicated host, and a smooth guest flow.

Essentials Included


Hotel + transportation are bundled into one booking—no spreadsheet vacations.

Clear Inclusions


What’s included (and what’s not) is clearly listed for each departure.

Ports of Call, On Land


Handpicked stops with reserved timing when available.

Why Travel Sidewalk Sailings?

We work with local partners and group-ready venues to deliver a seamless weekend experience.